Condensed cyclic compound, light emitting device including same, and electronic device including light emitting device

Abstract

Disclosed are a fused ring compound represented by Formula 1, a light-emitting device including the same, and an electronic device including the light-emitting device. In Formula 1, Ar0 is a group represented by Formula 2, and at least one of Z3 in number b3 is a C1-C60 alkyl group which is unsubstituted or substituted by deuterium,-F, cyano, or any combination thereof. Formula 1 satisfies at least one of conditions 1 and 2: Condition 1: b1 is 1 or more, and at least one of Z1 in number b1 includes a carbazole group; and Condition 2: b2 is 1 or more, and at least one of the Z2 in number b2 includes a carbazole group. The remaining groups and various variables in Formula 1 are as described in the specification. Formula 1 # imgabs 0 # and formula 2 # imgabs 1 #

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application is based on and claims the benefit of priority from Korean Patent Application No. 10-2023-0099834 filed in the Korean Intellectual Property Office on July 31, 2023, the contents of which are incorporated herein in their entirety by reference. Technical Field

[0003] The present disclosure relates to a condensed ring compound, a light emitting device including the same, and an electronic device including the same. Background Art

[0004] Among the light-emitting devices, the organic light-emitting device is a self-emitting device having a wide viewing angle, a high contrast ratio, a short response time, and excellent characteristics in terms of brightness, driving voltage, and response speed compared to devices in the art, and can produce full-color images.

[0005] In an example, an organic light emitting device includes an anode, a cathode, and an intermediate layer disposed between the anode and the cathode and including an emission layer. A hole transport region may be provided between the anode and the emission layer, and an electron transport region may be provided between the emission layer and the cathode. Holes provided from the first electrode move toward the emission layer through the hole transport region, and electrons provided from the second electrode move toward the emission layer through the electron transport region. Holes and electrons recombine in the emission layer to generate excitons. Excitons may transition from an excited state to a ground state, thereby generating light. Summary of the invention

[0006] Provided are a novel condensed-ring compound, a light-emitting device comprising the same, and an electronic device comprising the light-emitting device.

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

[0008] According to one aspect of the present disclosure, a fused ring compound represented by Formula 1 is provided:

[0009] Formula 1

[0010]

[0011] Wherein, in Formula 1, Ar 0 is a group represented by Formula 2,

[0012] Formula 2

[0013]

[0014] Wherein, in formula 1 and 2,

[0015] Ring Y 1 To Ring Y 3 Each independently is C 5 -C 60 Carbocyclic group or C 3 -C 60 Heterocyclic group, W 1 For single bonds, O, S, N (Ar 1 )、N(T 11 )、C(T 12 )(T 13 ), or Si(T 12 )(T 13 ), W 2 For single bonds, O, S, N (Ar 2 )、N(T 21 )、C(T 22 )(T 23 ), or Si(T 22 )(T 23 ), n1 and n2 are each independently 0 or 1,

[0016] When n1 is 0, *-(W 1 ) n1 -*' does not exist,

[0017] When n2 is 0, *-(W 2 ) n2 -*' does not exist,

[0018] The sum of n1 and n2 is 1 or greater,

[0019] Ar 1 and Ar 2 Each is a group represented by Formula 2,

[0020] R 0 for

[0021] hydrogen, deuterium, -F, or cyano, or

[0022] C unsubstituted or substituted by deuterium, -F, cyano, or any combination thereof 1 -C 60 alkyl,

[0023] R 1 -R 4 Each independently

[0024] hydrogen, deuterium, -F, or cyano,

[0025] C unsubstituted or substituted by deuterium, -F, cyano, or any combination thereof 1 -C 60 Alkyl, or

[0026] Unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 Aryl, or any combination thereof substituted C 6 -C 60 Aryl,

[0027] a1 is an integer from 0 to 3,

[0028] a2 and a4 are each independently an integer of 0-4,

[0029] a3 and m are each independently an integer of 0-5,

[0030] The * in Formula 2 represents the binding site with Formula 1,

[0031] Z 1 -Z 3 , T 11 -T 13 , and T 21 -T 23 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 1 -C 60 Alkylthio, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 2 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60heteroaryl, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -N(Q 1 )(Q 2 )、-Si(Q 3 )(Q 4 )(Q 5 )、-Ge(Q 3 )(Q 4 )(Q 5 )、-B(Q 6 )(Q 7 )、-P(=O)(Q 8 )(Q 9 )、-P(Q 8 )(Q 9 ), or a group represented by formula 2,

[0032] b1 and b2 are each independently an integer of 0-10,

[0033] b3 is an integer from 1 to 5,

[0034] Formula 1 satisfies at least one of conditions 1 and 2:

[0035] Condition 1

[0036] b1 is 1 or greater, and the number of Z is b1 1 At least one of includes a carbazole group; and

[0037] Condition 2

[0038] b2 is 1 or greater, and the number of Z is b2 2 at least one of which comprises a carbazole group,

[0039] Z with quantity b3 3 At least one of which is unsubstituted or substituted with deuterium, -F, cyano, or any combination thereof. 1 -C 60 alkyl,

[0040] Z 1 , Z 2 , Z 3 , T 11 , T 12 , T 13 , T 21 , T 22 and T 23 Two or more of are optionally linked together to form a substituted or unsubstituted C 5 -C 30 A carbocyclic group or a substituted or unsubstituted C 1 -C 30 Heterocyclic groups,

[0041] Substituted C 5 -C 30 Carbocyclic groups, substituted C 1 -C 30 Heterocyclic groups, substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 1 -C 60 Alkylthio, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 2 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 At least one substituent of the heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group is:

[0042] Deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, or C 1 -C 60 Alkylthio,

[0043] Each of C is substituted by 1 -C60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, or C 1 -C 60 Alkylthio: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 11 )(Q 12 )、-Si(Q 13 )(Q 14 )(Q 15 )、-Ge(Q 13 )(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 )、-P(=O)(Q 18 )(Q 19 )、-P(Q 18 )(Q 19 ), or any combination thereof,

[0044] Each C is unsubstituted or substituted as follows 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 1 -C 60 Alkylthio, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 21 )(Q 22 )、-Si(Q 23 )(Q 24 )(Q 25 )、-Ge(Q 23 )(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 )、-P(=O)(Q 28)(Q 29 )、-P(Q 28 )(Q 29 ), or any combination thereof,

[0045] -N(Q 31 )(Q 32 )、-Si(Q 33 )(Q 34 )(Q 35 )、-Ge(Q 33 )(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 )、-P(=O)(Q 38 )(Q 39 ), or -P(Q 38 )(Q 39 ),or

[0046] Any combination of these, and

[0047] Q 1 -Q 9 , Q 11 -Q 19 , Q 21 -Q 29 , and Q 31 -Q 39 are each independently hydrogen, deuterium, -F, or C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 1 -C 60 Alkylthio, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60Heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, cyano, C 1 -C 60 Alkyl, C 6 -C 60 aryl, or any combination thereof.

[0048] According to another aspect of the present disclosure, a light emitting device includes a first electrode, a second electrode, and an intermediate layer disposed between the first electrode and the second electrode and including an emission layer, wherein the intermediate layer includes at least one of the condensed ring compounds.

[0049] According to another aspect of the present disclosure, an electronic device includes the light emitting device. BRIEF DESCRIPTION OF THE DRAWINGS

[0050] From the combination Figure 1 The above and other aspects, features, and advantages of some embodiments of the present disclosure will become more apparent upon consideration of the following description. Figure 1 is a schematic cross-sectional view of a light emitting device according to an embodiment. DETAILED DESCRIPTION

[0051] Embodiments will now be described in detail, examples of which are illustrated in the accompanying drawings, wherein the same reference numerals refer to the same elements throughout. In this regard, the present embodiments may have different forms and should not be construed as being limited to the descriptions set forth herein. Therefore, embodiments are described below only by reference to the accompanying drawings to illustrate aspects.

[0052] It will be understood that when an element is referred to as being “on” another element, it can be directly on the other element or intervening elements may be present therebetween. In contrast, when an element is referred to as being “directly on” another element, there are no intervening elements present.

[0053] It will be understood that although the terms "first", "second", "third", etc. may be used herein to describe various elements, components, regions, layers and / or parts, these elements, components, regions, layers and / or parts should not be limited by these terms. These terms are only used to distinguish one element, component, region, layer or part from another element, component, region, layer or part. Therefore, without departing from the teachings herein, the "first element", "component", "region", "layer" or "part" discussed below may be referred to as a second element, component, region, layer or part.

[0054] The terms used herein are only used for the purpose of describing specific embodiments and are not intended to be limiting. As used herein, "a (kind) (indefinite article) (a, an)", "the (the)" and "at least one (kind)" do not represent a limit of quantity, and are intended to cover both the singular and the plural, unless the context clearly indicates otherwise. For example, "element" has the same meaning as "at least one element", unless the context clearly indicates otherwise.

[0055] Expressions such as “at least one of,” when preceding or following a list of elements, modify the entire list of elements and do not modify the individual elements of the list.

[0056] "Or" means "and / or". As used herein, the term "and / or" includes any and all combinations of one or more of the relevant listed items. It will be further understood that the terms "comprise" or "include" when used in this specification indicate the presence of the stated features, regions, integers, steps, operations, elements, and / or components, but do not exclude the presence or addition of one or more additional features, regions, integers, steps, operations, elements, components, and / or their collections.

[0057] In addition, relative terms such as "lower" or "bottom" and "upper" or "top" may be used herein to describe the relationship of one element to another element as shown in the figure. It will be understood that in addition to the orientation depicted in the figure, relative terms are also intended to include different orientations of the device. For example, if the device in one of the figures is turned over, the element described as being on the "lower" side of the other element will be oriented on the "upper" side of the other element. Therefore, depending on the specific orientation of the figure, the exemplary term "lower" can cover both "lower" and "upper" orientations. Similarly, if the device in one of the figures is turned over, the element described as "below" or "below" the other element will be oriented "above" the other element. Therefore, the exemplary terms "below..." or "below..." can cover both "above..." and "below..." orientations.

[0058] As used herein, "about" or "approximately" is inclusive of the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art taking into account the measurement in question and the errors associated with the measurement of the particular quantity (i.e., the limitations of the measurement system). For example, "about" can mean within one or more standard deviations, or within ±10% or 5% relative to the stated value.

[0059] Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which the present disclosure belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning consistent with their meaning in the context of the present disclosure and the relevant art, and will not be interpreted in an idealized or overly formal sense, unless clearly so defined herein.

[0060] Exemplary embodiments are described herein with reference to cross-sectional views as schematic diagrams of idealized embodiments. Thus, deviations from the shapes of the figures as a result of, for example, manufacturing techniques and / or tolerances are to be expected. Therefore, the embodiments described herein should not be construed as being limited to the specific shapes of the regions as illustrated herein, but rather include deviations in shape caused by, for example, manufacturing. For example, a region illustrated or described as flat may typically have rough and / or nonlinear features. Moreover, the illustrated sharp corners may be rounded. Therefore, the regions shown in the figures are schematic in nature and their shapes are not intended to illustrate the precise shapes of the regions and are not intended to limit the scope of the claims.

[0061] As used herein, the term "X group substituted with an A group, a B group, or any combination thereof" may cover the following: an X group substituted with an A group; an X group substituted with a B group; an X group substituted with an A group at one site and with a B group at another site; an X group substituted with an A group, which is further substituted with a B group; and an X group substituted with a B group, which is further substituted with an A group.

[0062] Description of fused ring compounds

[0063] The fused ring compounds provided herein can be represented by Formula 1:

[0064] Formula 1

[0065]

[0066] Wherein, in Formula 1, Ar 0 It may be a group represented by Formula 2,

[0067] Formula 2

[0068]

[0069] The detailed description of Formula 2 may be the same as described herein.

[0070] In Formula 1, ring Y 1 To Ring Y 3 Can be independently C 5 -C 60 Carbocyclic group or C3 -C 60 Heterocyclic group.

[0071] In an embodiment, ring Y 1 To Ring Y 3 Each of them may independently be a benzene group, a naphthyl group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a quinoline group, an isoquinoline group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group, a dibenzosilole group, an azadibenzofuran group, an azadibenzothiophene group, an azacarbazole group, an azafluorene group, or an azadibenzosilole group.

[0072] In one or more embodiments, ring Y 1 To Ring Y 3 Each of them may independently be a benzene group, a naphthalene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group, or a dibenzosilole group.

[0073] In formula 1, W 1 Can be single bond, O, S, N(Ar 1 )、N(T 11 )、C(T 12 )(T 13 ), or Si(T 12 )(T 13 ), and W 2 Can be single bond, O, S, N(Ar 2 )、N(T 21 )、C(T 22 )(T 23 ), or Si(T 22 )(T 23 ). Here, Ar 1 and Ar 2 Each may be a group represented by Formula 2, and T 11 -T 13 and T 21 -T 23 Each may be the same as described herein.

[0074] In Formula 1, n1 and n2 can each independently be 0 or 1, wherein when n1 is 0, *-(W 1 ) n1 -*' may not exist, and when n2 is 0, *-(W 2 ) n2 -*' may not exist, wherein the sum of n1 and n2 may be 1 or greater.

[0075] For example, in Formula 1,

[0076] i) n1 may be 1, and n2 may be 0;

[0077] ii) n1 may be 0, and n2 may be 1; or

[0078] iii) n1 and n2 may each be 1.

[0079] In an embodiment, in Formula 1, n1 may be 1, and W 1 Can be N(Ar 1 ) or N(T 11 ).

[0080] In one or more embodiments, in Formula 1, n2 may be 1, and W 2 Can be N(Ar 2 ) or N(T 21 ).

[0081] In one or more embodiments, in Formula 1, n1 may be 1, and W 1 Can be N(Ar 1 ), where Ar 0 and Ar 1 Can be the same as each other.

[0082] In one or more embodiments, in Formula 1, n1 may be 1, and W 1 Can be N(Ar 1 ), where Ar 0 and Ar 1 Can be different from each other.

[0083] In one or more embodiments, in Formula 1, n2 may be 1, and W 2 Can be N(Ar 2 ), where Ar 0 and Ar 2 Can be the same as each other.

[0084] In one or more embodiments, in Formula 1, n2 may be 1, and W 2 Can be N(Ar 2 ), where Ar 0 and Ar 2 Can be different from each other.

[0085] In formula 2,

[0086] R 0 Can be:

[0087] hydrogen, deuterium, -F, or cyano; or

[0088] C unsubstituted or substituted by deuterium, -F, cyano, or any combination thereof 1 -C 60 Alkyl, and

[0089] R 1-R 4 Can be independently:

[0090] hydrogen, deuterium, -F, or cyano;

[0091] C unsubstituted or substituted by deuterium, -F, cyano, or any combination thereof 1 -C 60 Alkyl; or

[0092] Unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 60 Alkyl, C 1 -C 60 Aryl, or any combination thereof substituted C 6 -C 60 Aryl.

[0093] For example, in Formula 2,

[0094] R 0 Can be:

[0095] hydrogen, deuterium, -F, or cyano; or

[0096] C unsubstituted or substituted by deuterium, -F, cyano, or any combination thereof 1 -C 20 Alkyl, and

[0097] R 1 -R 4 Can be independently:

[0098] hydrogen, deuterium, -F, or cyano;

[0099] C unsubstituted or substituted by deuterium, -F, cyano, or any combination thereof 1 -C 20 Alkyl; or

[0100] Unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 20 Alkyl, phenyl, or phenyl substituted with any combination thereof.

[0101] In formula 2, a1-a4 and m represent R 1 -R 4 and the number of phenylene groups, wherein a1 may be an integer of 0-3, a2 and a4 may each independently be an integer of 0-4, and a3 and m may each independently be an integer of 0-5. When a1 is 2 or more, two or more R 1 may be the same as or different from each other. When a2 is 2 or greater, two or more R 2 may be the same as or different from each other. When a3 is 2 or greater, two or more R 3may be the same as or different from each other, and when a4 is 2 or greater, two or more R 4 For example, m may be 0 or 1.

[0102] In Formula 2, * represents a binding site with Formula 1.

[0103] In an embodiment, in Formula 2, a2 ​​may be 1, R 2 It can be unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 20 Alkyl, phenyl, or phenyl substituted with any combination thereof.

[0104] In this manual, C 1 -C 60 Alkyl or C 1 -C 20 Examples of the alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, and the like.

[0105] In formula 1, Z 1 -Z 3 , T 11 -T 13 , and T 21 -T 23 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 1 -C 60 Alkylthio, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 2 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -N(Q 1 )(Q 2 )、-Si(Q 3 )(Q 4 )(Q 5 )、-Ge(Q 3 )(Q 4 )(Q 5 )、-B(Q 6 )(Q 7 )、-P(=O)(Q 8 )(Q 9 )、-P(Q 8 )(Q 9 ), or a group represented by Formula 2.

[0106] For example, Z 1 -Z 3 , T 11 -T 13 , and T 21 -T 23 Can be independently:

[0107] hydrogen, deuterium, -F, or cyano;

[0108] Each C is unsubstituted or substituted as follows 1 -C 20 Alkyl, phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, or dibenzothioyl: deuterium, -F, cyano, C 1 -C 20 Alkyl, phenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, dibenzothioyl, or any combination thereof; or

[0109] -N(Q 1 )(Q 2 ),and

[0110] Q 1 and Q 2 may be each independently unsubstituted or substituted by C 1 -C 20 Alkyl, phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, or dibenzothioyl: deuterium, -F, cyano, C 1 -C 20Alkyl, phenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, dibenzosilyl, or any combination thereof.

[0111] In formula 1, b1-b3 represent Z 1 -Z 3 wherein b1 and b2 may each independently be an integer of 0-10, and b3 may be an integer of 1-5. When b1 is 2 or greater, two or more Z 1 may be the same as or different from each other. When b2 is 2 or greater, two or more Z 2 may be the same as or different from each other, and when b3 is 2 or greater, two or more Z 3 For example, b1-b3 can each independently be 0, 1, or 2.

[0112] Formula 1 may satisfy at least one of conditions 1 and 2:

[0113] Condition 1

[0114] b1 is 1 or greater, and b1 Z 1 At least one of includes a carbazole group; and

[0115] Condition 2

[0116] b2 is 1 or greater, and b2 Z 2 At least one of the compounds includes a carbazole group.

[0117] In an embodiment, Formula 1 may satisfy both Conditions 1 and 2.

[0118] In one or more embodiments, in Formula 1, b1 and b2 may each be 1 or greater, and Z 1 and Z 2 At least one of Z may be a group represented by Formula 3, for example, 1 and Z 2 Each may be independently a group represented by Formula 3:

[0119] Formula 3

[0120]

[0121] Among them, in formula 3,

[0122] Z 11 -Z 18 Can be independently:

[0123] hydrogen, deuterium, -F, or cyano;

[0124] C unsubstituted or substituted by deuterium, -F, cyano, or any combination thereof 1 -C 20 Alkyl; or

[0125] Unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 20 Alkyl, phenyl, or phenyl substituted by any combination thereof, and

[0126] * indicates the binding site with Formula 1.

[0127] In one or more embodiments, Z in Formula 3 11 -Z 18 Each may be hydrogen or deuterium.

[0128] In one or more embodiments, Z in Formula 3 13 and Z 16 At least one (e.g., Z 13 and Z 16 Both) can be:

[0129] C unsubstituted or substituted by deuterium, -F, cyano, or any combination thereof 1 -C 20 Alkyl (eg, unsubstituted or deuterium-substituted tert-butyl); or

[0130] Unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 20 Alkyl, phenyl, or phenyl substituted with any combination thereof.

[0131] In one or more embodiments, Z in Formula 3 11 -Z 18 At least one of may be independently: deuterium; or Group 4 (Group 4) substituted with at least one deuterium, wherein Group 4 may be:

[0132] C unsubstituted or substituted by -F, cyano, or any combination thereof 1 -C 20 Alkyl; or

[0133] Unsubstituted or substituted by -F, cyano, C 1 -C 20 Alkyl, phenyl, or phenyl substituted with any combination thereof.

[0134] As used herein, the term "group 4 substituted with at least one deuterium" refers to a substituent in which at least one hydrogen in group 4 is replaced with deuterium. For example, "group 4 substituted with at least one deuterium" may be -CD 3 、-CD 2 H.-CDH 2 、-CD 2 F, -C(CD 3 ) 3 , -C 6 D 5, -C 6 D 2 H 3 , -C 6 D 4 (CH 3 ),-C 6 H 4 (CD 3 ),-C 6 D 4 (CD 3 ),-C 6 F 4 (CD 3 ),-C 6 D 4 (C 6 H 5 ) etc. The terms "Group 1 substituted by at least one deuterium (Group 1)", "Group 2 substituted by at least one deuterium (Group 2)", and "Group 3 substituted by at least one deuterium (Group 3)" can also be understood in the same manner.

[0135] In one or more embodiments, in Formula 1, b1 and b2 may each be 1, and Z 1 and Z 2 Each may be unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 20 An N-carbazolyl group substituted with an alkyl group, a phenyl group, or any combination thereof.

[0136] The term "N-carbazolyl" as used herein refers to a monovalent group in which H is separated from N of a carbazole group so that the N can be bonded to another group, and can be Indicates (where * indicates the binding site with the adjacent atom).

[0137] In formula 1, the quantity Z is b3 3 At least one of the C 1 -C 60 Alkyl (e.g., C 1 -C 20 alkyl).

[0138] In an embodiment, the number of Z in Formula 1 is b3 3 At least one of may be a tert-butyl group which is unsubstituted or substituted with at least one deuterium.

[0139] In one or more embodiments, in Formula 1, b3 may be 1, and Z 3 C may be unsubstituted or substituted with deuterium, -F, cyano, or any combination thereof 1 -C 20Alkyl (eg, tert-butyl unsubstituted or substituted with at least one deuterium).

[0140] In one or more embodiments, the group represented by Formula 2 may be a group represented by one of Formulas 2-1 to 2-3:

[0141]

[0142] Among them, in formulas 2-1 to 2-3,

[0143] R 0 can be the same as described in this article,

[0144] R 11 -R 13 Can be respectively related to R 1 Same as described,

[0145] R 21 -R 24 Can be respectively related to R 2 Same as described,

[0146] R 31 -R 35 Can be respectively related to R 3 Same as described, and

[0147] * indicates a binding site to Formula 1 (eg, nitrogen in Formula 1).

[0148] For example, Formulas 2-1 to 2-3 may each satisfy Conditions 3 to 5:

[0149] Condition 3

[0150] 3a)R 11 -R 13 each is hydrogen or deuterium,

[0151] 3b)R 12 is unsubstituted or substituted by deuterium, -F, cyano, or any combination thereof 1 -C 20 alkyl (e.g., unsubstituted or deuterium-substituted tert-butyl), or

[0152] 3c)R 11 -R 13 At least one of each independently is: deuterium; or Group 1 substituted with at least one deuterium, wherein Group 1 comprises:

[0153] C unsubstituted or substituted by -F, cyano, or any combination thereof 1 -C 20 Alkyl; or

[0154] Unsubstituted or substituted by -F, cyano, C 1 -C20 Alkyl, phenyl, or phenyl substituted by any combination thereof; Condition 4

[0155] 4a)R 21 -R 24 each is hydrogen or deuterium,

[0156] 4b)R 22 is unsubstituted or substituted by deuterium, -F, cyano, or any combination thereof 1 -C 20 alkyl (e.g., unsubstituted or deuterium-substituted tert-butyl), or

[0157] 4c)R 22 is unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 20 Alkyl, phenyl, or phenyl substituted by any combination thereof,

[0158] 4d)R 24 is unsubstituted or substituted by deuterium, -F, cyano, or any combination thereof 1 -C 20 Alkyl (e.g., unsubstituted or deuterium-substituted tert-butyl),

[0159] 4e)R 24 is unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 20 Alkyl, phenyl, or phenyl substituted by any combination thereof, or

[0160] 4f)R 21 -R 24 At least one of each independently is: deuterium; or Group 2 substituted with at least one deuterium, wherein Group 2 comprises:

[0161] C unsubstituted or substituted by -F, cyano, or any combination thereof 1 -C 20 Alkyl; or

[0162] Unsubstituted or substituted by -F, cyano, C 1 -C 20 Alkyl, phenyl, or phenyl substituted with any combination thereof; and

[0163] Condition 5

[0164] 5a)R 31 -R 35 each is hydrogen or deuterium,

[0165] 5b)R 31 is unsubstituted or substituted by deuterium, -F, cyano, or any combination thereof 1 -C 20Alkyl (e.g., unsubstituted or deuterium-substituted tert-butyl),

[0166] 5c)R 31 is unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 20 Alkyl, phenyl, or phenyl substituted by any combination thereof,

[0167] 5d)R 32 is unsubstituted or substituted by deuterium, -F, cyano, or any combination thereof 1 -C 20 Alkyl (e.g., unsubstituted or deuterium-substituted tert-butyl),

[0168] 5e)R 32 is unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 20 Alkyl, phenyl, or phenyl substituted by any combination thereof,

[0169] 5f)R 33 is unsubstituted or substituted by deuterium, -F, cyano, or any combination thereof 1 -C 20 alkyl,

[0170] 5g)R 33 is unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 20 Alkyl, phenyl, or phenyl substituted by any combination thereof,

[0171] 5h)R 32 and R 34 Each independently is:

[0172] C unsubstituted or substituted by deuterium, -F, cyano, or any combination thereof 1 -C 20 Alkyl (eg, unsubstituted or deuterium-substituted tert-butyl); or

[0173] Unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 20 Alkyl, phenyl, or phenyl substituted by any combination thereof, or

[0174] 5i)R 31 -R 35 At least one of each independently is: deuterium; or Group 3 substituted with at least one deuterium, wherein Group 3 includes:

[0175] C unsubstituted or substituted by -F, cyano, or any combination thereof 1 -C 20 Alkyl; or

[0176] Unsubstituted or substituted by -F, cyano, C 1 -C 20 Alkyl, phenyl, or phenyl substituted with any combination thereof.

[0177] In one or more embodiments, the number of benzene groups included in the group represented by Formula 2 (e.g., benzene groups included in the group represented by Formula 2, not fused to each other, and connected to each other by a single bond) may be 4 or greater, for example, 4, 5, or 6.

[0178] In one or more embodiments, the group represented by Formula 2 may be a group represented by Formula 2-1(1):

[0179]

[0180] Among them, in formula 2-1(1),

[0181] R 0 can be the same as described in this article,

[0182] R 11 -R 13 Can be respectively related to R 1 Same as described,

[0183] R 21 , R 23 , and R 24 Can be respectively related to R 2 Same as described,

[0184] R 31 -R 35 Can be respectively related to R 3 Same as described, and

[0185] R 25 -R 29 Can be independently:

[0186] hydrogen, deuterium, -F, or cyano; or

[0187] C unsubstituted or substituted by deuterium, -F, cyano, or any combination thereof 1 -C 20 Alkyl, and

[0188] * indicates the binding site with Formula 1.

[0189] For example, Formula 2-1(1) may satisfy conditions 3 and 5 as described above with respect to Formula 2-1 and the following conditions 6 and 7:

[0190] Condition 6

[0191] 6a)R 21 , R 23 , and R24 each is hydrogen or deuterium,

[0192] 6b)R 23 is unsubstituted or substituted by deuterium, -F, cyano, or any combination thereof 1 -C 20 Alkyl (e.g., unsubstituted or deuterium-substituted tert-butyl),

[0193] 6c)R 21 , R 23 , and R 24 At least one of each independently is: deuterium; or Group 5 substituted with at least one deuterium, wherein Group 5 includes:

[0194] C unsubstituted or substituted by -F, cyano, or any combination thereof 1 -C 20 Alkyl; or

[0195] Unsubstituted or substituted by -F, cyano, C 1 -C 20 Alkyl, phenyl, or phenyl substituted with any combination thereof; and

[0196] Condition 7

[0197] 7a)R 25 -R 29 each is hydrogen or deuterium,

[0198] 7b)R 25 is unsubstituted or substituted by deuterium, -F, cyano, or any combination thereof 1 -C 20 Alkyl (e.g., unsubstituted or deuterium-substituted tert-butyl),

[0199] 7c)R 25 is unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 20 Alkyl, phenyl, or phenyl substituted by any combination thereof,

[0200] 7d)R 26 is unsubstituted or substituted by deuterium, -F, cyano, or any combination thereof 1 -C 20 Alkyl (e.g., unsubstituted or deuterium-substituted tert-butyl),

[0201] 7e)R 26 is unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 20 Alkyl, phenyl, or phenyl substituted by any combination thereof,

[0202] 7f)R 27is unsubstituted or substituted by deuterium, -F, cyano, or any combination thereof 1 -C 20 alkyl,

[0203] 7g)R 27 is unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 20 Alkyl, phenyl, or phenyl substituted by any combination thereof, or

[0204] 7h)R 26 and R 28 Each independently is:

[0205] C unsubstituted or substituted by deuterium, -F, cyano, or any combination thereof 1 -C 20 Alkyl (eg, unsubstituted or deuterium-substituted tert-butyl); or

[0206] Unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 20 Alkyl, phenyl, or phenyl substituted by any combination thereof,

[0207] 7i)R 25 -R 29 At least one of each independently is: deuterium; or Group 6 substituted with at least one deuterium, wherein Group 6 includes:

[0208] C unsubstituted or substituted by -F, cyano, or any combination thereof 1 -C 20 Alkyl; or

[0209] Unsubstituted or substituted by -F, cyano, C 1 -C 20 Alkyl, phenyl, or phenyl substituted with any combination thereof.

[0210] In one or more embodiments, R in Formula 2-1(1) 31 and R 25 Can be independently:

[0211] C unsubstituted or substituted by deuterium, -F, cyano, or any combination thereof 1 -C 20 Alkyl (eg, unsubstituted or deuterium-substituted tert-butyl); or

[0212] Unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 20 Alkyl, phenyl, or phenyl substituted with any combination thereof.

[0213] In one or more embodiments, R in Formula 2-1(1) 32and R 26 Can be independently:

[0214] C unsubstituted or substituted by deuterium, -F, cyano, or any combination thereof 1 -C 20 Alkyl (eg, unsubstituted or deuterium-substituted tert-butyl); or

[0215] Unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 20 Alkyl, phenyl, or phenyl substituted with any combination thereof.

[0216] In one or more embodiments, R in Formula 2-1(1) 33 and R 27 Can be independently:

[0217] C unsubstituted or substituted by deuterium, -F, cyano, or any combination thereof 1 -C 20 Alkyl (eg, unsubstituted or deuterium-substituted tert-butyl); or

[0218] Unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 20 Alkyl, phenyl, or phenyl substituted with any combination thereof.

[0219] In formula 1, Z 1 , Z 2 , Z 3 , T 11 , T 12 , T 13 , T 21 , T 22 and T 23 Two or more of may be optionally linked together to form a substituted or unsubstituted C 5 -C 30 A carbocyclic group or a substituted or unsubstituted C 1 -C 30 Heterocyclic group.

[0220] In an embodiment, in Formula 1, Z 1 , Z 2 , Z 3 , T 11 , T 12 , T 13 , T 21 , T 22 and T 23 Two or more of may be linked together to form a substituted or unsubstituted C 5 -C 30 A carbocyclic group or a substituted or unsubstituted C 1 -C30 As a result, the condensed ring compound can be represented by, for example, Formula 1-1, 1-2, or 1-3:

[0221]

[0222]

[0223] Wherein, in Formulas 1-1, 1-2, and 1-3,

[0224] Ar 0 , Ring Y 1 , Ring Y 3 , W 1 , W 2 、n1、n2、Z 1 , Z 3 , b1, and b3 may each be the same as described herein,

[0225] Ring Y 21 and Ring Y 22 Can be independently C 5 -C 60 Carbocyclic group or C 3 -C 60 Heterocyclic groups,

[0226] W 3 Can be single bond, O, S, N(Ar 3 )、N(T 31 )、C(T 32 )(T 33 ), or Si(T 32 )(T 33 ),

[0227] W 4 Can be single bond, O, S, N(Ar 4 )、N(T 41 )、C(T 42 )(T 43 ), or Si(T 42 )(T 43 ),

[0228] W 5 Can be single bond, O, S, N(Ar 5 )、N(T 51 )、C(T 52 )(T 53 ), or Si(T 52 )(T 53 ),

[0229] n3-n5 can be 0 or 1 independently.

[0230] When n3 is 0, *-(W 3 ) n3 -*' may not exist,

[0231] When n4 is 0, *-(W 4 ) n4 -*' may not exist,

[0232] When n5 is 0, *-(W 5 ) n5 -*' may not exist,

[0233] The sum of n1 and n2 in formulas 1-1 and 1-2 may be 1 or greater.

[0234] The sum of n3, n4, and n5 in Formula 1-1 may be 1 or greater,

[0235] The sum of n3 and n4 in formulas 1-2 and 1-3 may be 1 or greater.

[0236] Ar 3 -Ar 5 Each may be a group represented by Formula 2,

[0237] Z 20 -Z 22 Can be respectively with respect to Z 2 Same as described,

[0238] b21 and b22 may each independently be an integer from 0 to 5, and

[0239] Formulas 1-1, 1-2, and 1-3 may each satisfy at least one of conditions 1A and 2A:

[0240] Condition 1A

[0241] b1 is 1 or greater, and b1 Z 1 At least one of includes a carbazole group; and

[0242] Condition 2A

[0243] Satisfies at least one of a), b), and c):

[0244] a) b21 is 1 or greater, and b21 Z 21 at least one of which comprises a carbazole group,

[0245] b) Z 20 including a carbazole group, and

[0246] c) b22 is 1 or greater, and b22 Z 22 At least one of the compounds includes a carbazole group.

[0247] Ring Y 21 and Ring Y22 Each of them can be related to the ring Y 1 Same as described.

[0248] In an embodiment, the condensed ring compound represented by Formula 1 may include at least one deuterium, at least one tert-butyl group, or any combination thereof. For example, the condensed ring compound represented by Formula 1 may include at least one tert-butyl group and optionally at least one deuterium.

[0249] In one or more embodiments, the condensed ring compound represented by Formula 1 may have a symmetrical structure.

[0250] In one or more embodiments, the condensed ring compound represented by Formula 1 may have an asymmetric structure.

[0251] In one or more embodiments, the fused ring compound may be represented by Formula 1A:

[0252] Formula 1A

[0253]

[0254] Wherein, in Formula 1A,

[0255] W 1 Can be O, S, N (Ar 1 )、N(T 11 )、C(T 12 )(T 13 ), or Si(T 12 )(T 13 ),

[0256] Ar 0 ,Ar 1 , and T 11 -T 13 may each be the same as described herein,

[0257] Z 11 and Z 12 can be respectively compared with the Z 1 Same as described,

[0258] Z 21 and Z 22 Can be respectively with respect to Z 2 Same as described,

[0259] Z 11 , Z 12 , Z 21 , and Z 22 At least one of may be unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 20 an N-carbazolyl group substituted with an alkyl group, a phenyl group, or any combination thereof, and

[0260] Z 3 C may be unsubstituted or substituted with deuterium, -F, cyano, or any combination thereof 1 -C 20 Alkyl (eg, unsubstituted or deuterium-substituted tert-butyl).

[0261] In an embodiment, in Formula 1A, Z 11 and Z 21 Each may be unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 20 alkyl, phenyl, or any combination thereof substituted N-carbazolyl, and Z 12 and Z 22 Each may be hydrogen or deuterium.

[0262] In one or more embodiments, in Formula 1A, Z 12 and Z 22 Each may be unsubstituted or substituted with deuterium, -F, cyano, C 1 -C 20 alkyl, phenyl, or any combination thereof substituted N-carbazolyl, and Z 11 and Z 21 Each may be hydrogen or deuterium.

[0263] In one or more embodiments, the condensed ring compound may be a multiple resonance thermally activated delayed fluorescence material.

[0264] In one or more embodiments, the fused ring compound may be one of compounds 1 to 782:

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305]

[0306]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317]

[0318]

[0319]

[0320]

[0321]

[0322]

[0323] In formula 1, Ar 0 It can be a group represented by Formula 2, and the number of Z is b3 3 At least one of the C 1 -C 60Alkyl. In addition, Formula 1 may satisfy at least one of Conditions 1 and 2. Therefore, the condensed ring compound represented by Formula 1 may have a relatively large absolute value of the highest occupied molecular orbital (HOMO) energy level and a relatively large absolute value of the lowest unoccupied molecular orbital (LUMO) energy level, as shown in Table 1. The HOMO and LUMO energy levels shown in Table 1 are evaluated according to Evaluation Example 1. In addition, the condensed ring compound may emit blue light having a relatively large oscillator strength and a relatively narrow half width (FWHM), and therefore an electronic device including the condensed ring compound, such as a light-emitting device, may have an improved driving voltage, an improved external quantum efficiency, and an improved lifespan characteristic.

[0324] Table 1

[0325]

[0326]

[0327] In embodiments, the FWHM of the emission spectrum of the fused ring compound may be in a range of about 5 nanometers (nm) to about 30 nm, for example, about 10 nm to about 25 nm.

[0328] In one or more embodiments, the emission peak wavelength (ie, maximum emission wavelength or peak emission wavelength) of the emission spectrum of the fused ring compound may be in the range of about 400 nm to about 500 nm, for example, about 440 nm to about 470 nm.

[0329] In one or more embodiments, the singlet state (S 1 ) energy level may be in the range of about 2.4 eV to about 3.1 eV.

[0330] In one or more embodiments, in the singlet state (S 1 ) energy level and triplet state (T 1 ) energy levels may be in the range of about 0 eV to about 1 eV.

[0331] In one or more embodiments, the absolute value of the HOMO energy level of the fused ring compound may be in the range of about 4.0 eV to about 6.5 eV.

[0332] The synthesis method of the condensed ring compound can be recognized by those skilled in the art with reference to the synthesis examples which will be described later.

[0333] Light-emitting devices

[0334] The condensed ring compound may be suitable for use as an intermediate layer of a light-emitting device, for example, as a material for an emission layer in the intermediate layer. In this regard, another aspect of the present disclosure provides a light-emitting device comprising: a first electrode; a second electrode; and an intermediate layer disposed between the first electrode and the second electrode and comprising an emission layer, wherein the intermediate layer comprises at least one condensed ring compound represented by Formula 1.

[0335] Such a light-emitting device is provided with an intermediate layer including at least one type of the aforementioned condensed ring compound. In this regard, the light-emitting device may be able to emit blue light with a relatively narrow FWHM, and may have improved driving voltage, improved external quantum efficiency, improved luminous efficiency, and / or improved life characteristics.

[0336] The condensed ring compound may be used between the electrode pairs of the light emitting device. For example, the condensed ring compound may be included in the emission layer. Here, the emission layer may further include a host. The amount (weight) of the host may be greater than the amount (weight) of the condensed ring compound. The emission layer may emit red light, green light, or blue light. For example, the emission layer may emit blue light.

[0337] In embodiments, the CIEy value of light emitted from the emission layer may be in a range of about 0.040 to about 0.170, about 0.050 to about 0.170, about 0.060 to about 0.170, about 0.040 to about 0.165, about 0.050 to about 0.165, or about 0.060 to about 0.165.

[0338] In one or more embodiments, the peak emission wavelength of light emitted from the emission layer may be in the range of about 440nm to about 470nm, about 445nm to about 470nm, about 450nm to about 470nm, about 455nm to about 470nm, about 460nm to about 470nm, about 440nm to about 465nm, about 445nm to about 465nm, about 450nm to about 465nm, about 455nm to about 465nm, or about 460nm to about 465nm.

[0339] The emission layer may further include a body. A detailed description of the body may be the same as described herein.

[0340] The first electrode may be an anode as a hole injection electrode, and the second electrode may be a cathode as an electron injection electrode; or the first electrode may be a cathode as an electron injection electrode, and the second electrode may be an anode as a hole injection electrode.

[0341] For example, in the light-emitting device, the first electrode may be an anode, the second electrode may be a cathode, and the intermediate layer may further include a hole transport region arranged between the first electrode and the emission layer and an electron transport region arranged between the emission layer and the second electrode, wherein the hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, an auxiliary layer, or any combination thereof, and the electron transport region may include a buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0342] The term "intermediate layer" as used herein refers to a single layer or a plurality of layers disposed between the first electrode and the second electrode of the light emitting device. In addition to the organic compound, the "intermediate layer" may also include an organic metal complex including a metal, and the like.

[0343] For example, the emission layer may include the first embodiment or the second embodiment:

[0344] First embodiment

[0345] The emission layer may include at least one condensed ring compound represented by Formula 1, and the condensed ring compound may be used as an emitter such as a delayed fluorescent emitter. That is, the condensed ring compound may be an emitter. For example, among the total luminescent components in the emission layer, the luminescent components obtained from the condensed ring compound may account for 80% or more, 85% or more, 90% or more, or 95% or more. The light emitted from the condensed ring compound may be blue light. The emission layer may further include a sensitizer, and the sensitizer and the condensed ring compound may be different from each other. The sensitizer may be an organic metal compound, a delayed fluorescent material, an instantaneous fluorescent material, or any combination thereof. The amount (weight) of the sensitizer may be from about 0.01 parts by weight to about 10 parts by weight per 100 parts by weight of the emission layer.

[0346] Second embodiment

[0347] The emission layer may include at least one condensed ring compound, and the condensed ring compound may be used as a sensitizer or an auxiliary dopant. That is, the condensed ring compound may be a sensitizer or an auxiliary dopant. The emission layer may further include an emitter. The sensitizer or auxiliary dopant may effectively transfer excitons from the host to the emitter. The emitter may be different from the condensed ring compound. The emitter may be an organic metal compound, an instantaneous fluorescent material, a delayed fluorescent material, or any combination thereof.

[0348] In the present specification, the emitter may be a material that receives excitons from a host, a sensitizer, and / or an auxiliary dopant and emits light by transition of the excitons to a ground state.

[0349] In the first and second embodiments, the amount of the condensed cyclic compound may be about 0.01 to about 40 parts by weight, about 0.1 to about 20 parts by weight, or about 1 to about 20 parts by weight per 100 parts by weight of the emission layer.

[0350] In the first and second embodiments, the organometallic compound may include a transition metal and n ligands bonded to the transition metal, wherein n may be an integer of 1-4.

[0351] In an embodiment, the transition metal in the organometallic compound may be platinum (Pt) or palladium (Pd), n may be 1, and the ligand may be a tetradentate ligand. The tetradentate ligand may include, for example, a carbene moiety bonded to the transition metal.

[0352] In one or more embodiments, the organometallic compound may include a transition metal and a tetradentate ligand bonded to the transition metal, wherein the transition metal may be Pt or Pd, and the tetradentate ligand may include a carbene moiety bonded to the transition metal.

[0353] In one or more embodiments, in the organometallic compound, the transition metal may be iridium (Ir) or osmium (Os), and n may be 3, wherein at least one ligand among the n ligands may be: a bidentate ligand including -F, a cyano group, or a combination thereof; or a bidentate ligand including a carbene moiety bonded to the transition metal. For example, the bidentate ligand may further include an imidazole group or a triazole group.

[0354] In one or more embodiments, the organometallic compound may be an organometallic compound represented by Formula 30 and / or an organometallic compound represented by Formula 5. Detailed descriptions of Formulas 30 and 5 will be provided below.

[0355] In the first and second embodiments, the delayed fluorescent material may be, for example, a thermally activated delayed fluorescent material. In one or more embodiments, the delayed fluorescent material may be a multi-resonance thermally activated delayed fluorescent material.

[0356] The multiple resonance thermally activated delayed fluorescent material may be a polycyclic compound that i) does not include a transition metal, and ii) includes two or more C 3 -C 60 The core of the cyclic groups is fused to each other. Here, the two C 3 -C 60 The cyclic groups may be fused to each other while sharing (commonly) boron or nitrogen.

[0357] In an embodiment, the delayed fluorescent material may be a polycyclic compound represented by Formula 4. A detailed description of Formula 4 will be provided below.

[0358] In the first and second embodiments, the instantaneous fluorescent material may be a compound containing an amino group, a compound containing a styrene group, etc. For example, the instantaneous fluorescent material may include a naphthyl group, a fluorene group, a spirobifluorene group, a benzofluorene group, a dibenzofluorene group, a phenanthrene group, an anthracene group, a fluoranthene group, a benzo[9,10]phenanthrene group, a pyrene group, group, tetraphenyl group (i.e., tetraphenyl group), A group, a perylene group, a pentaphene group, an indenoanthracene group, a group represented by one of Formulae 501-1 to 501-21, or any combination thereof:

[0359]

[0360] In one or more embodiments, the transient fluorescent material may include a compound represented by Formula 501A or 501B:

[0361]

[0362] Wherein, in Formulas 501A and 501B,

[0363] Ar 501 It can be a naphthyl group, a fluorene group, a spirobifluorene group, a benzofluorene group, a dibenzofluorene group, a phenanthrene group, an anthracene group, a fluoranthene group, a benzo[9,10]phenanthrene group, a pyrene group, Group, tetraphenyl group, group, a perylene group, a pentaphene group, an indenoanthracene group, a bianthracene group, or a group represented by one of Formulae 501-1 to 501-21,

[0364] R 511 It may be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, or -Si(Q 501 )(Q 502 )(Q 503 ),

[0365] xd5 can be an integer from 0 to 10.

[0366] L 501 -L 503 Can be independently:

[0367] Single bond; and

[0368] Each C is unsubstituted or substituted as follows 3 -C 10 Cycloalkylene, C 1 -C 10 Heterocycloalkylene, C 3 -C 10 Cycloalkenylene, C 1 -C 10 Heterocycloalkenylene, C 6 -C 60 Arylene, C 1 -C 60 heteroarylene group, a divalent non-aromatic condensed polycyclic group, or a divalent non-aromatic condensed heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, hydroxyl, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si(Q 501 )(Q 502 )(Q 503 ), or any combination thereof,

[0369] xd1-xd3 can each independently be 1, 2, or 3,

[0370] R 501 and R 502 Each of them may be independently unsubstituted or substituted phenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, a pyridyl group, a pyrazyl group, a pyrimidyl group, a pyridazinyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a carbazole group, a triazine group, a dibenzofuranyl group, a dibenzothiophenyl group, or a dibenzosilyl group: deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si(Q 501 )(Q 502 )(Q 503 ), or any combination thereof,

[0371] Z 11 may be C each unsubstituted or substituted as follows1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, monovalent non-aromatic condensed polycyclic group, or monovalent non-aromatic condensed heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, hydroxyl, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si(Q 501 )(Q 502 )(Q 503 ), or any combination thereof,

[0372] xd4 can be 1, 2, 3, 4, 5, or 6, and

[0373] Q 501 -Q 503 can be independently hydrogen, C 1 -C 60 Alkyl, C 1 -C 60 Alkoxy, C 6 -C 60 Aryl, C 1 -C 60 a heteroaryl group, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group.

[0374] In one or more embodiments, the transient fluorescent material may include a compound represented by Formula 501A or 501B, wherein xd4 in Formula 501A may be 1, 2, 3, 4, 5, or 6, and xd4 in Formula 501B may be 2, 3, or 4.

[0375] Description of the subject

[0376] The emission layer may include m1 host, and the m1 host may include a hole transport compound, an electron transport compound, a bipolar compound, or any combination thereof. m1 may be an integer of 1 to 3. The host may not include a transition metal.

[0377] For example, in the emission layer, m1 may be 2, and two hosts in the emission layer may include a hole transport compound and an electron transport compound, wherein the hole transport compound and the electron transport compound may be different from each other.

[0378] In an embodiment, the hole transport compound may include at least one π-electron-rich C 3 -C 60 The cyclic group may not include an electron transporting group. Examples of the electron transporting group may include a cyano group, a fluorine group (—F), a cyclic group containing π-electron-deficient nitrogen, a phosphine oxide group, a sulfoxide group, and the like.

[0379] As used herein, the term "cyclic group containing π-electron-deficient nitrogen" refers to a C-type ring group including at least one *-N=*' moiety as a ring-forming part. 1 -C 60 Heterocyclic group. Examples of the cyclic group containing π-electron-deficient nitrogen may include a triazine group, an imidazole group, and the like.

[0380] As used herein, the term "π-electron-rich C 3 -C 60 "Cyclic group" refers to a C-type group that does not include the *-N=*' moiety as a ring-forming part. 3 -C 60 Cyclic group. π-electron-rich C3 -C 60 Examples of the cyclic group may include a benzene group, a naphthyl group, a benzo[9,10]phenanthrene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, an indoledibenzofuran group, an indoledibenzothiophene group, an indolecarbazole group, a naphthobenzofuran group, a naphthobenzothiophene group, a benzocarbazole group, a phenanthrobenzofuran group, a phenanthrobenzothiophene group, a naphthocarbazole group, a dinaphthofuran group, a dinaphthothiophene group, a dibenzocarbazole group, and the like.

[0381] For example, the hole transport compound may include two or more carbazole groups.

[0382] In one or more embodiments, the electron transport compound may be a compound including at least one electron transport group. Examples of the electron transport group may include a cyano group, a fluorine group, a C 1 -C 60 A cyclic group, a phosphine oxide group, a sulfoxide group, or any combination thereof. In an embodiment, the electron transport compound may include a triazine group.

[0383] For example, the electron transport compound may include at least one electron transport group (eg, a triazine group) and at least one π-electron-rich C 3 -C 60 A cyclic group (for example, a benzene group, a naphthyl group, a benzo[9,10]phenanthrene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, an indoledibenzofuran group, an indoledibenzothiophene group, an indolecarbazole group, a naphthobenzofuran group, a naphthobenzothiophene group, a benzocarbazole group, a phenanthrobenzofuran group, a phenanthrobenzothiophene group, a naphthocarbazole group, a dinaphthofuran group, a dinaphthothiophene group, a dibenzocarbazole group, or any combination thereof).

[0384] In an embodiment, the hole transport compound may be a compound represented by Formula 6:

[0385] Formula 6

[0386]

[0387] Among them, in formula 6,

[0388] L 61 and L 62 may be each independently unsubstituted or substituted with a π-electron-rich C 3 -C 60 Cyclic groups: deuterium, C 1 -C 20 Alkyl, deuterated C 1 -C 20Alkyl, phenyl, deuterated phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, (C 1 -C 20 Alkyl)biphenyl, -Si(Q 33 )(Q 34 )(Q 35 ), or any combination thereof,

[0389] e61 and e62 can each independently be an integer of 1-6,

[0390] R 61 -R 64 Can be independently:

[0391] Hydrogen, deuterium, C 1 -C 20 Alkyl, or deuterated C 1 -C 20 alkyl;

[0392] Unsubstituted or substituted π-electron-rich C 3 -C 60 Cyclic groups: deuterium, C 1 -C 20 Alkyl, deuterated C 1 -C 20 Alkyl, phenyl, deuterated phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, (C 1 -C 20 Alkyl)biphenyl, -Si(Q 33 )(Q 34 )(Q 35 ), or any combination thereof; or

[0393] -Si(Q 3 )(Q 4 )(Q 5 ),and

[0394] a63 and a64 may each independently be an integer of 0-7.

[0395] Q 3 -Q 5 and Q 33 -Q 35 Each may be the same as described herein.

[0396] In one or more embodiments, the hole transport compound may be a compound represented by Formula 6-1, 6-2, or 6-3:

[0397] Formula 6-1

[0398]

[0399] Formula 6-2

[0400]

[0401] Formula 6-3

[0402]

[0403] Among them, in formulas 6-1 to 6-3, L 61 , L 62 , R 61 -R 64 , e61, e62, a63, a64 may each be the same as described herein.

[0404] In one or more embodiments, the hole transport compound may be one of compounds HTH1 to HTH6:

[0405]

[0406] In one or more embodiments, the electron transport compound may be a compound represented by Formula 7:

[0407] Formula 7

[0408]

[0409] Among them, in formula 7,

[0410] X 74 Can be C(R 74 ) or N, X 75 Can be C(R 75 ) or N, X 76 Can be C(R 76 ) or N, and X 74 -X 76 At least one of may be N,

[0411] L 71 -L 73 may be each independently unsubstituted or substituted by C 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic groups: deuterium, -F, cyano, C 1 -C 20 Alkyl, deuterated C 1 -C 20 Alkyl, fluorinated C 1 -C 20 Alkyl, phenyl, deuterated phenyl, fluorophenyl, (C1 -C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorophenyl, (C 1 -C 20 Alkyl)biphenyl, -Si(Q 33 )(Q 34 )(Q 35 ), or any combination thereof,

[0412] e71-e73 can each independently be an integer of 1-10,

[0413] R 71 -R 76 Can be independently:

[0414] hydrogen, deuterium, -F, or cyano;

[0415] C unsubstituted or substituted by deuterium, -F, cyano, or any combination thereof 1 -C 20 alkyl;

[0416] Each C is unsubstituted or substituted as follows 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic groups: deuterium, -F, cyano, C 1 -C 20 Alkyl, deuterated C 1 -C 20 Alkyl, fluorinated C 1 -C 20 Alkyl, phenyl, deuterated phenyl, fluorophenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorophenyl, (C 1 -C 20 Alkyl)biphenyl, -Si(Q 33 )(Q 34 )(Q 35 ), or any combination thereof; or

[0417] -Si(Q 3 )(Q 4 )(Q 5 ).

[0418] Q 3 -Q 5 and Q 33 -Q 35 Each may be the same as described herein.

[0419] In one or more embodiments, X in Formula 7 74 -X 76 Each can be N.

[0420] In one or more embodiments, L in Formula 7 71 -L 73 and phenyl, naphthalene, benzo[9,10]phenanthrene, dibenzofuran, dibenzothiophene, carbazole, indoledibenzofuran, indoledibenzothiophene, indolecarbazole, naphthobenzofuran, naphthobenzothiophene, benzocarbazole, phenanthrobenzofuran, phenanthrobenzothiophene, naphthocarbazole, dinaphthofuran, dinaphthothiophene, or dibenzocarbazole, each of which is unsubstituted or substituted with: deuterium, -F, cyano, C 1 -C 20 Alkyl, deuterated C 1 -C 20 Alkyl, fluorinated C 1 -C 20 Alkyl, phenyl, deuterated phenyl, fluorophenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorophenyl, (C 1 -C 20 Alkyl)biphenyl, -Si(Q 33 )(Q 34 )(Q 35 ), or any combination thereof.

[0421] In one or more embodiments, in Formula 7, e71 L 71 At least one, e72 L 72 At least one, e73 L 73 At least one of the above, or any combination thereof, may be each independently a dibenzofuran group, a dibenzothiophene group, a carbazole group, an indole dibenzofuran group, an indole dibenzothiophene group, an indole carbazole group, a naphthobenzofuran group, a naphthobenzothiophene group, a benzocarbazole group, a phenanthrobenzofuran group, a phenanthrobenzothiophene group, a naphthocarbazole group, a dinaphthofuran group, a dinaphthothiophene group, or a dibenzocarbazole group, each of which is unsubstituted or substituted with: deuterium, -F, cyano, C 1 -C 20 Alkyl, deuterated C 1 -C 20 Alkyl, fluorinated C 1 -C 20 Alkyl, phenyl, deuterated phenyl, fluorophenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorophenyl, (C 1 -C 20 Alkyl)biphenyl, -Si(Q 33 )(Q34 )(Q 35 ), or any combination thereof.

[0422] In one or more embodiments, in Formula 7, e71 L 71 At least one, e72 L 72 At least one, e73 L 73 At least one of the above, or any combination thereof, may each independently include a carbazole group, an indolecarbazole group, a benzocarbazole group, a naphthoxycarbazole group, or a dibenzocarbazole group, wherein the nitrogen atom of the pyrrole group of the carbazole group, the indolecarbazole group, the benzocarbazole group, the naphthoxycarbazole group, or the dibenzocarbazole group may be connected to the pyrrole group by a single bond or an adjacent L 71 , L 72 , and / or L 73 Connect to the X in Equation 7 74 -X 76 A carbon atom of a 6-membered ring.

[0423] In one or more embodiments, in Formula 7, e71-e73 represent L 71 -L 73 , and can each independently be 1, 2, 3, 4, or 5.

[0424] In one or more embodiments, R in Formula 7 71 -R 76 Can be independently:

[0425] hydrogen, deuterium, -F, or cyano;

[0426] C unsubstituted or substituted by deuterium, -F, cyano, or any combination thereof 1 -C 20 alkyl;

[0427] a phenyl group, a naphthyl group, a benzo[9,10]phenanthrene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, an indoledibenzofuran group, an indoledibenzothiophene group, an indolecarbazole group, a naphthobenzofuran group, a naphthobenzothiophene group, a benzocarbazole group, a phenanthrobenzofuran group, a phenanthrobenzothiophene group, a naphthocarbazole group, a dinaphthofuran group, a dinaphthothiophene group, or a dibenzocarbazole group, each of which is unsubstituted or substituted with: deuterium, -F, cyano, C 1 -C 20 Alkyl, deuterated C 1 -C 20 Alkyl, fluorinated C 1 -C 20 Alkyl, phenyl, deuterated phenyl, fluorophenyl, (C 1 -C 20alkyl)phenyl, biphenyl, deuterated biphenyl, fluorophenyl, (C 1 -C 20 Alkyl)biphenyl, -Si(Q 33 )(Q 34 )(Q 35 ), or any combination thereof; or

[0428] -Si(Q 3 )(Q 4 )(Q 5 ).

[0429] In one or more embodiments, the electron transport compound may be one of compounds ETH1 to ETH7:

[0430]

[0431] Description of Formula 30

[0432] In the first and second embodiments, the organometallic compound may be an organometallic compound represented by Formula 30:

[0433] Formula 30

[0434]

[0435] Among them, in formula 30,

[0436] M 31 It can be a transition metal,

[0437] X 11 -X 14 can be independently C or N,

[0438] In X 11 and M 31 The key between X 12 and M 31 The key between X 13 and M 31 The keys between 14 and M 31 Two of the bonds between may each be coordinate bonds, and the other two bonds may each be covalent bonds,

[0439] Cyclo 31 To Ring CY 34 Can be independently C 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic groups,

[0440] T 31 Can be single bond, double bond, *-N(R35a )-*'、*-B(R 35a )-*'、*-P(R 35a )-*'、*-C(R 35a )(R 35b )-*'、*-Si(R 35a )(R 35b )-*'、*-Ge(R 35a )(R 35b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) 2 -*'、*-C(R 35a )=*'、*=C(R 35a )-*'、*-C(R 35a )=C(R 35b )-*', *-C(=S)-*', *-C≡C-*', unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic groups,

[0441] T 32 Can be single bond, double bond, *-N(R 36a )-*'、*-B(R 36a )-*'、*-P(R 36a )-*'、*-C(R 36a )(R 36b )-*'、*-Si(R 36a )(R 36b )-*'、*-Ge(R 36a )(R 36b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) 2 -*'、*-C(R 36a )=*'、*=C(R 36a )-*'、*-C(R 36a )=C(R 36b )-*', *-C(=S)-*', *-C≡C-*', unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C30 Heterocyclic groups,

[0442] T 33 Can be single bond, double bond, *-N(R 37a )-*'、*-B(R 37a )-*'、*-P(R 37a )-*'、*-C(R 37a )(R 37b )-*'、*-Si(R 37a )(R 37b )-*'、*-Ge(R 37a )(R 37b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) 2 -*'、*-C(R 37a )=*'、*=C(R 37a )-*'、*-C(R 37a )=C(R 37b )-*', *-C(=S)-*', *-C≡C-*', unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic groups,

[0443] T 34 Can be single bond, double bond, *-N(R 38a )-*'、*-B(R 38a )-*'、*-P(R 38a )-*'、*-C(R 38a )(R 38b )-*'、*-Si(R 38a )(R 38b )-*'、*-Ge(R 38a )(R 38b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) 2 -*'、*-C(R 38a )=*'、*=C(R 38a )-*'、*-C(R 38a )=C(R 38b )-*', *-C(=S)-*', *-C≡C-*', unsubstituted or substituted with at least one R 10a Substituted C 5-C 30 A carbocyclic group, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic groups,

[0444] n31-n34 may each independently be an integer of 0-5, and three or more of n31-n34 may each independently be an integer of 1-5,

[0445] When n31 is 0, T 31 It may not exist. When n32 is 0, T 32 It may not exist. When n33 is 0, T 33 may not exist, and when n34 is 0, T 34 But it doesn't exist.

[0446] When n31 is 2 or more, two or more T 31 may be the same as or different from each other. When n32 is 2 or greater, two or more T 32 may be the same as or different from each other. When n33 is 2 or greater, two or more T 33 may be the same as or different from each other, and when n34 is 2 or greater, two or more T 34 may be the same or different from each other,

[0447] R 31 -R 34 , R 35a , R 35b , R 36a , R 36b , R 37a , R 37b , R 38a , and R 38b can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 、-SF 5 , hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 2 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 7 -C 60 Arylalkyl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 heteroarylalkyl, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -N(Q 1 )(Q 2 )、-Si(Q 3 )(Q 4 )(Q 5 )、-Ge(Q 3 )(Q 4 )(Q 5 )、-B(Q 6 )(Q 7 )、-P(=O)(Q 8 )(Q 9 ), or -P(Q 8 )(Q 9 ),

[0448] a31-a34 can each independently be an integer of 0-20,

[0449] R with quantity a31 31 Two or more of may be optionally bonded together to form an unsubstituted or substituted group. 10a Substituted C 5 -C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic groups,

[0450] The number of R is a32 32Two or more of may be optionally bonded together to form an unsubstituted or substituted group. 10a Substituted C 5 -C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic groups,

[0451] R with quantity a33 33 Two or more of may be optionally bonded together to form an unsubstituted or substituted group. 10a Substituted C 5 -C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic groups,

[0452] R with quantity a34 34 Two or more of may be optionally bonded together to form an unsubstituted or substituted group. 10a Substituted C 5 -C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic groups,

[0453] R 31 -R 34 , R 35a , R 35b , R 36a , R 36b , R 37a , R 37b , R 38a , and R 38b At least two of may be optionally bonded to each other to form an unsubstituted or substituted R 10a Substituted C 5 -C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic groups, and

[0454] R 10a About R 31 Same as described,

[0455] * and *' each represent a binding site with an adjacent atom,

[0456] Substituted C 1 -C 60Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 2 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 7 -C 60 Arylalkyl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 Heteroaryl, substituted C 2 -C 60 The substituents of the heteroarylalkyl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be:

[0457] Deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, or C 1 -C 60 Alkoxy;

[0458] Each of C is substituted by 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, or C 1 -C 60Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 11 )(Q 12 )、-Si(Q 13 )(Q 14 )(Q 15 )、-Ge(Q 13 )(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 )、-P(=O)(Q 18 )(Q 19 )、-P(Q 18 )(Q 19 ), or any combination thereof;

[0459] C each unsubstituted or substituted with at least one of the following 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C1 -C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 21 )(Q 22 )、-Ge(Q 23 )(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 )、-P(=O)(Q 28 )(Q 29 )、-P(Q 28 )(Q 29 ), or any combination thereof;

[0460] -N(Q 31 )(Q 32 )、-Si(Q 33 )(Q 34 )(Q 35 )、-Ge(Q 33 )(Q 34 )(Q35 )、-B(Q 36 )(Q 37 )、-P(=O)(Q 38 )(Q 39 ), or -P(Q 38 )(Q 39 );or

[0461] Any combination of these, and

[0462] Q 1 -Q 9 , Q 11 -Q 19 , Q 21 -Q 29 , and Q 31 -Q 39 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, unsubstituted or substituted with deuterium, C 1 -C 60 Alkyl, C 6 -C 60 Aryl, or any combination thereof substituted C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, unsubstituted or substituted with deuterium, C 1 -C 60 Alkyl, C 6 -C 60 Aryl, or any combination thereof substituted C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group.

[0463] In an embodiment, M in Formula 3031 It can be Pt, Pd, or Au.

[0464] In an embodiment, M in Formula 30 31 It can be Pt or Pd.

[0465] In one or more embodiments, in Formula 30, in X 11 and M 31 The bond between them can be a coordination bond.

[0466] In one or more embodiments, in Formula 30, X 11 Can be C, and in X 11 and M 31 The bond between may be a coordination bond. That is, X in Formula 30 11 It may be C in the carbene part.

[0467] In one or more embodiments, ring CY in formula 30 31 To Ring CY 34 may each independently be i) a first ring, ii) a second ring, iii) a fused ring in which two or more first rings are fused to each other, iv) a fused ring in which two or more second rings are fused to each other, or v) a fused ring in which at least one first ring is fused to at least one second ring,

[0468] wherein the first ring can be a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a thiol group, an oxazole group, an isoxazole group, an oxadiazole group, an isoxadiazole group, an oxatriazole group, an isoxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiadiazole group, a thiatriazole group, an isothiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azathiol group, a diazathiol group, or a triazathiol group, and

[0469] The second ring may be an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a phenyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, an oxazine group, a thiazine group, a dihydropyrazine group, a dihydropyridine group, or a dihydroazasilane group.

[0470] In an embodiment, R 31 -R 34 , R 35a , R 35b , R 36a , R 36b , R 37a , R 37b , R 38a , and R 38b Can be independently:

[0471] Hydrogen, deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , cyano (CN), nitro, amino, C 1 -C 20 Alkyl, or C 1 -C 20 Alkoxy;

[0472] Each of the following C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , cyano, nitro, amino, and phenyl; or

[0473] cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, fluorenyl, phenanthryl, or anthracenyl, each unsubstituted or substituted with at least one of the following: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , cyano, nitro, amino, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, fluorenyl, phenanthryl, and anthracenyl.

[0474] In an embodiment, the organometallic compound represented by Formula 30 may be an organometallic compound represented by Formula 30-1 or an organometallic compound represented by Formula 30-2:

[0475] Formula 30-1

[0476]

[0477] Formula 30-2

[0478]

[0479] Wherein, in formula 30-1, between the carbon of the imidazole group and M 31 The bond between may be a coordination bond. That is, in Formula 30-1, the imidazole group may include a bond to M 31 The carbine part.

[0480] In formula 30-2, between the carbon and M of the benzimidazole group 31 The bond between may be a coordination bond. That is, in Formula 30-2, the benzimidazole group may include a bond to M 31 The carbine part.

[0481] Thus, the imidazole group bonded to M 31 Formula 30-1' wherein the carbon of the benzimidazole group is a carbene is the same as Formula 30-1, and wherein the bond to M in the benzimidazole group is 31 Formula 30-2', in which the carbon of the carbon is a carbene, is the same as Formula 30-2:

[0482] Formula 30-1'

[0483]

[0484] Formula 30-2'

[0485]

[0486] In equations 30-1 and 30-2,

[0487] M 31 CY 32 CY 33 CY 34 , X 12 , X 13 , X 14 , T 31 , T 32 , T 33 、n31、n32、n33、R 32 , R 33 , R 34 , a32, a33, and a34 may each be the same as described herein, and

[0488] R 311 -R 317 can be respectively compared with R in equation 30 31 Same as described.

[0489] In an embodiment, in Formulas 30-1 and 30-2,

[0490] R 311 -R 317 Can be independently:

[0491] Hydrogen, deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 、-SF 5 , hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, or phosphoric acid group or its salt;

[0492] Each C is unsubstituted or substituted as follows 1 -C 20 Alkyl or C 1 -C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 、-SF 5 , hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, or any combination thereof;

[0493] Each C is unsubstituted or substituted as follows 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 6 -C 60 Aryl, C 7 -C 60 Arylalkyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 Heteroarylalkyl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 、-SF 5 , hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C1 -C 20 Alkoxy, or any combination thereof; or

[0494] -N(Q 1 )(Q 2 )、-Si(Q 3 )(Q 4 )(Q 5 )、-Ge(Q 3 )(Q 4 )(Q 5 )、-B(Q 6 )(Q 7 )、-P(=O)(Q 8 )(Q 9 ), or -P(Q 8 )(Q 9 ).

[0495] In an embodiment, R in Formula 30-1 and 30-2 311 -R 317 At least one of the following may include C 1 -C 20 Alkyl, C 6 -C 60 Aryl, or C 7 -C 60 Arylalkyl: deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, phenyl, cumyl (cumyl), or any combination thereof.

[0496] According to an embodiment, the organic metal compound represented by Formula 30 may be an organic metal compound represented by Formula 30-1(1) or an organic metal compound represented by Formula 30-2(1):

[0497] Formula 30-1(1)

[0498]

[0499] Formula 30-2(1)

[0500]

[0501] In equations 30-1(1) and 30-2(1),

[0502] M 31 , X 12 , X 13 , X 14 , and T 31 each being the same as described herein,

[0503] R 311 -R317 Can be respectively related to R 31 Same as described,

[0504] R 321 -R 323 Can be respectively related to R 32 Same as described, and R 321 -R 323 Two or more of may be optionally bonded together to form an unsubstituted or substituted group. 10a Substituted C 5 -C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic groups,

[0505] R 331 -R 336 Can be respectively related to R 33 Same as described, and R 331 -R 336 Two or more of may be optionally bonded together to form an unsubstituted or substituted group. 10a Substituted C 5 -C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic groups, and

[0506] R 341 -R 344 Can be respectively related to R 34 Same as described, and R 341 -R 344 Two or more of may be optionally bonded together to form an unsubstituted or substituted group. 10a Substituted C 5 -C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic group.

[0507] Description of Formula 5

[0508] In the first and second embodiments, the organometallic compound may be an organometallic compound represented by Formula 5:

[0509] Formula 5

[0510] M 51 (L 51 ) n51(L 52 ) n52

[0511] Where M in Formula 5 51 It may be a transition metal.

[0512] In an embodiment, M 51 It can be a first row transition metal, a second row transition metal, or a third row transition metal of the periodic table.

[0513] In one or more embodiments, M 51 It may be iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).

[0514] In one or more embodiments, M 51 It may be Ir, Pt, Os, or Rh.

[0515] In one or more embodiments, M 51 It can be Ir or Os.

[0516] In formula 5, L 51 may be a ligand represented by Formula 5A, and L 52 It may be a ligand represented by Formula 5B:

[0517]

[0518] wherein Formulae 5A and 5B may each be the same as described herein.

[0519] In Formula 5, n51 may be 1, 2, or 3, wherein when n51 is 2 or greater, two or more L 51 Can be the same as or different from each other.

[0520] In Formula 5, n52 can be 0, 1, or 2, wherein when n52 is 2, the two L 52 Can be the same as or different from each other.

[0521] The sum of n51 and n52 in Formula 5 may be 2 or 3. For example, the sum of n51 and n52 may be 3.

[0522] In an embodiment, in Formula 5, i) M may be Ir, and n51+n52=3; or ii) M may be Pt, and n51+n52=2.

[0523] In one or more embodiments, in Formula 5, M may be Ir, and i) n51 may be 1, and n52 may be 2, or ii) n51 may be 2, and n52 may be 1.

[0524] L in Formula 551 and L 52 Can be different from each other.

[0525] In Formulas 5A and 5B, Y 51 -Y 54 can be independently C or N. For example, Y 51 and Y 53 Can be N, and Y 52 and Y 54 Can each be C.

[0526] Ring CY in Formula 5A and 5B 51 To Ring CY 54 Can be independently C 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic group.

[0527] For example, ring CY in Formula 5A and 5B 51 To Ring CY 54 may each independently include (or be) i) a third ring, ii) a fourth ring, iii) a condensed ring in which two or more third rings are condensed to each other, iv) a condensed ring in which two or more fourth rings are condensed to each other, or v) a condensed ring in which at least one third ring is condensed to at least one fourth ring,

[0528] wherein the third ring may be a cyclopentane group, a cyclopentene group, a furan group, a thiophene group, a pyrrole group, a thiole group, a borocyclopentadiene group, a phosphole group, a germanocyclopentadiene group, a selenophene group, an oxazole group, an oxadiazole group, an oxatriazole group, a thiazole group, a thiadiazole group, a thiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, or an azathiole group, and

[0529] The fourth ring may be an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a phenyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

[0530] In one or more embodiments, in Formulas 5A and 5B, ring CY 1 To Ring CY 4 can be independently a cyclopentane group, a cyclohexane group, a cyclohexene group, a phenyl group, a naphthalene group, an anthracene group, a phenanthrene group, a benzo[9,10]phenanthrene group, a pyrene group, group, 1,2,3,4-tetrahydronaphthalene group, cyclopentadiene group, pyrrole group, furan group, thiophene group, thiorrole group, boroheterocyclopentadiene group, phosphocyclopentadiene group, germanoheterocyclopentadiene group, selenophene group, indene group, indole group, benzofuran group, benzothiophene group, benzothiorrole group, benzoborole group, benzophosphocyclopentadiene group, benzogermanocyclopentadiene group, benzoselenophene group, fluorene group, carbazole group, dibenzofuran group, dibenzothiophene group, dibenzothiorrole group, dibenzoborole group, dibenzophosphocyclopentadiene group, dibenzogermanocyclopentadiene group, dibenzoselenophene group, benzofluorene group, benzocarbazole group, naphthobenzofuran group, naphthobenzothiophene group, naphthobenzo benzothiorrole group, naphthobenzoborole group, naphthobenzophosphole group, naphthobenzogermanol group, naphthobenzoselenophene group, dibenzofluorene group, dibenzocarbazole group, dinaphthofuran group, dinaphthothiophene group, dinaphthothiorrole group, dinaphthoborole group, dinaphthophosphole group, dinaphthogermanol group, dinaphthoselenophene group, indenophenanthrene group, indolephenanthrene group, phenanthrenyl group, phenanthrenylbenzofuran group, phenanthrenylbenzothiophene group, phenanthrenylbenzothiorrole group, phenanthrenylbenzoborole group, phenanthrenylbenzophosphole group, phenanthrenylbenzogermanol group, phenanthrenylbenzoselenophene group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, azaindene group, azaindole group, azabenzofuran group, azabenzothiophene group, azabenzosilole group, azabenzoborole group, azabenzophosphole group, azabenzogermanole group, azabenzoselenophene group, azafluorene group, azacarbazole group, azadibenzofuran group, azadibenzothiophene group, azadibenzosilole group, azadibenzoborole group, azadibenzophosphole group, azadibenzogermanole group, azadibenzoselenophene group, azafluorene group, azacarbazole group, azadibenzofuran group, azadibenzothiophene group, azadibenzosilole group, azadibenzoborole group, azadibenzophosphole group, azadibenzogermanole group, azadibenzoselenophene group, azabenzofluorene group, azabenzocarbazole group, azanaphthobenzofuran group, azanaphthobenzothiophene group, azanaphthobenzosilole group, azanaphtho aza-naphthobenzophosphoside group, aza-naphthobenzogermanoside group, aza-naphthobenzoselenophene group, aza-dibenzofluorene group, aza-dibenzocarbazole group, aza-dinaphthofuran group, aza-dinaphthothiophene group, aza-dinaphthothiorrole group, aza-dinaphthoborole group, aza-dinaphthophosphoside group, aza-dinaphthogermanoside group, aza-dinaphthoselenophene group, aza-indenophenanthrene group, aza-indolephenanthrene group, aza-phenanthrenebenzofuran group, aza-phenanthrenebenzothiophene group, aza-phenanthrenebenzothiorrole group, aza-phenanthrenebenzoborole group, aza-phenanthrenebenzophosphoside group, aza-phenanthrenebenzogermanoside group, aza-phenanthrenebenzogermanoside group group, an azaphenanthrobenzoselenophene group, an azadibenzothiophene 5-oxide group, an aza9H-fluorene-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a benzoquinoline group, a benzoisoquinoline group, a benzoquinoxaline group, a benzoquinazoline group, a phenanthroline group, a phenanthridine group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, an azathiorrole group, an azaborole group, an azaphosphole group, an azagermanole group, an aza selenophene group, benzopyrrole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzisoxazole group, benzothiazole group, benzisothiazole group, benzooxadiazole group, benzothiadiazole group, pyridopyrrole group, pyridopyrazole group, pyridoimidazole group, pyridooxazole group, pyridisoxazole group, pyridothiazole group, pyridisothiazole group, pyridooxadiazole group, pyridothiadiazole group, pyrimidopyrrole group, pyrimidopyrazole group, pyrimidoimidazole group, pyrimidooxazole group, pyrimidoisoxazole group, pyrimidothiazole group, pyrimidoisothiazole group, pyrimidooxadiazole group, pyrimidothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group, 5,6,7,8-tetrahydroisoquinoline group, 5,6,7,8-tetrahydroisoquinoline group, 5,6,7,8-tetrahydroisoquinoline group, 5,6,7,8-tetrahydroisoquinoline group, 5,6,7,8-tetrahydroisoquinoline group, 5,6,7,8-tetrahydroisoquinoline group, 5,6,7,8-tetrahydroisoquinoline group, 5,6,7,8-tetrahydroisoquinoline group,8-tetrahydroquinoline group, adamantane group, norbornane group, norbornene group, phenyl group condensed with cyclohexane group, phenyl group condensed with norbornane group, pyridine group condensed with cyclohexane group, or pyridine group condensed with norbornane group.

[0531] For example, ring CY in Formula 5A and 5B 51 and CY 53 Can be different from each other.

[0532] In one or more embodiments, ring CY in Formula 5A and 5B 52 and CY 54 Can be different from each other.

[0533] In one or more embodiments, ring CY in Formula 5A and 5B 51 To Ring CY 54 Can be different from each other.

[0534] R in Formula 5A and 5B 51 -R 54 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 1 -C 60 Alkylthio, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 2 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60heteroaryl, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -N(Q 51 )(Q 52 )、-Si(Q 53 )(Q 54 )(Q 55 )、-Ge(Q 53 )(Q 54 )(Q 55 )、-B(Q 56 )(Q 57 )、-P(=O)(Q 58 )(Q 59 ), or -P(Q 58 )(Q 59 ). Q 51 -Q 59 Each is the same as described in this specification.

[0535] In an embodiment, R in Formulas 5A and 5B 51 -R 54 Can be independently:

[0536] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, -SF 5 , C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, or C 1 -C 20 Alkylthio;

[0537] Each of C is substituted by 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, or C 1 -C 20 Alkylthio: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 10alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, (C 1 -C 20 alkyl)cyclopentyl, (C 1 -C 20 alkyl)cyclohexyl, (C 1 -C 20 alkyl)cycloheptyl, (C 1 -C 20 Alkyl)cyclooctyl, (C 1 -C 20 Alkyl) adamantyl, (C 1 -C 20 Alkyl) norbornyl, (C 1 -C 20 Alkyl) norbornene, (C 1 -C 20 alkyl)cyclopentenyl, (C 1 -C 20 alkyl)cyclohexenyl, (C 1 -C 20 alkyl)cycloheptenyl, (C 1 -C 20 alkyl)bicyclo[1.1.1]pentyl, (C 1 -C 20 alkyl)bicyclo[2.1.1]hexyl, (C 1 -C 20 alkyl) bicyclo[2.2.2]octyl, phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidinyl, or any combination thereof;

[0538] cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzo Thiphenyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl or azadibenzothiophenyl: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, (phenyl) C 1 -C 10 Alkyl, C 1 -C 20 alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, (C 1 -C 20 alkyl)cyclopentyl, (C 1 -C 20 alkyl)cyclohexyl, (C 1 -C 20 alkyl)cycloheptyl, (C 1 -C 20 Alkyl)cyclooctyl, (C 1 -C 20 Alkyl) adamantyl, (C 1 -C 20 Alkyl) norbornyl, (C 1 -C 20 Alkyl) norbornene, (C 1 -C 20 alkyl)cyclopentenyl, (C 1 -C 20 alkyl)cyclohexenyl, (C 1 -C 20 alkyl)cycloheptenyl, (C 1 -C 20alkyl)bicyclo[1.1.1]pentyl, (C 1 -C 20 alkyl)bicyclo[2.1.1]hexyl, (C 1 -C 20 alkyl) bicyclo[2.2.2]octyl, phenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, or any combination thereof; or

[0539] -N(Q 51 )(Q 52 )、-Si(Q 53 )(Q 54 )(Q 55 )、-Ge(Q 53 )(Q 54 )(Q 55 )、-B(Q 56 )(Q 57 )、-P(=O)(Q 58 )(Q 59 ), or -P(Q 58 )(Q 59 ),and

[0540] Q 51 -Q 59 Can be independently:

[0541] -CH 3 、-CD 3 、-CD 2 H.-CDH 2 、-CH 2 CH 3 、-CH 2 CD 3 、-CH 2 CD 2 H, -CH 2 CDH 2、-CHDCH 3 、-CHDCD 2 H, -CHDCDH 2 、-CHDCD 3 、-CD 2 CD 3 、-CD 2 CD 2 H, or -CD 2 CDH 2 ;or

[0542] n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, phenyl, biphenyl, or naphthyl, each unsubstituted or substituted with: deuterium, C 1 -C 10 Alkyl, phenyl, or any combination thereof.

[0543] In one or more embodiments, R 51 -R 54 Can be independently:

[0544] hydrogen, deuterium, -F, or cyano;

[0545] C is unsubstituted or substituted as follows 1 -C 20 Alkyl: deuterium, cyano, C 3 -C 10 Cycloalkyl, deuterated C 3 -C 10 Cycloalkyl, fluorinated C 3 -C 10 Cycloalkyl, (C 1 -C 20 Alkyl)C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, deuterated C 1 -C 10 Heterocycloalkyl, fluorinated C 1 -C 10 Heterocycloalkyl, (C 1 -C 20 Alkyl)C 1 -C 10 Heterocycloalkyl, phenyl, deuterated phenyl, fluorophenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorobiphenyl, (C 1 -C 20 alkyl) biphenyl, dibenzofuranyl, deuterated dibenzofuranyl, fluorodibenzofuranyl, (C 1-C 20 alkyl) dibenzofuranyl, dibenzothiophenyl, deuterated dibenzothiophenyl, fluorodibenzothiophenyl, (C 1 -C 20 alkyl)dibenzothienyl, or any combination thereof;

[0546] Each C is unsubstituted or substituted as follows 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, phenyl, or biphenyl: deuterium, cyano, C 1 -C 20 Alkyl, deuterated C 1 -C 20 Alkyl, fluorinated C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, deuterated C 1 -C 20 Alkoxy, fluorinated C 1 -C 20 Alkoxy, C 3 -C 10 Cycloalkyl, deuterated C 3 -C 10 Cycloalkyl, fluorinated C 3 -C 10 Cycloalkyl, (C 1 -C 20 Alkyl)C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, deuterated C 1 -C 10 Heterocycloalkyl, fluorinated C 1 -C 10 Heterocycloalkyl, (C 1 -C 20 Alkyl)C 1 -C 10 Heterocycloalkyl, phenyl, deuterated phenyl, fluorophenyl, (C 1 -C 20 alkyl)phenyl, biphenyl, deuterated biphenyl, fluorobiphenyl, (C 1 -C 20 alkyl) biphenyl, dibenzofuranyl, deuterated dibenzofuranyl, fluorodibenzofuranyl, (C 1 -C 20 alkyl) dibenzofuranyl, dibenzothiophenyl, deuterated dibenzothiophenyl, fluorodibenzothiophenyl, (C 1 -C 20 alkyl)dibenzothienyl, or any combination thereof; or

[0547] -Si(Q 53 )(Q 54 )(Q 55 ) or -Ge(Q 53 )(Q 54 )(Q 55 ).

[0548] In Formulae 5A and 5B, b51-b54 represent R 51 -R 54 When b51 is 2 or more, two or more R 51 may be the same or different from each other. When b52 is 2 or greater, two or more R 52 may be the same or different from each other. When b53 is 2 or greater, two or more R 53 may be the same as or different from each other, and when b54 is 2 or greater, two or more R 54 They may be the same as or different from each other. For example, b51-b54 may each independently be an integer of 0-8.

[0549] In an embodiment, in Formula 5A, Y 52 Can be C, in Y 52 and M 51 The bond between them can be a covalent bond, and the number of R is b52 52 At least one of may be cyano or -F.

[0550] In one or more embodiments, in Formula 5A, Y 51 Can be N, in Y 51 and M 51 The bond between them can be a coordination bond, CY 51 may be an imidazole group, a triazole group, a benzimidazole group, or a triazolopyridine group, and the number of R is b52 52 At least one of may be cyano or -F.

[0551] In one or more embodiments, in Formula 5A, Y 51 Can be C, and in Y 51 and M 51 The bond between them can be a coordination bond.

[0552] In one or more embodiments, in Formula 5A, Y 51 Can be C, in Y 51 and M 51 The bond between can be a coordination bond, and CY 51 It may be a benzimidazole group or an imidazopyrazine group.

[0553] Specific examples of the organometallic compound of formula 30 or 5

[0554] For example, the organometallic compound represented by Formula 30 or 5 may be one of the following compounds P1 to P52:

[0555]

[0556]

[0557]

[0558] Description of Formula 4

[0559] In the first and second embodiments, the delayed fluorescent material may be a polycyclic compound represented by Formula 4:

[0560] Formula 4

[0561]

[0562] Among them, in formula 4,

[0563] Z can be B or N,

[0564] Cyclo 41 To Ring CY 43 Can be independently C 5 -C 60 Carbocyclic group or C 1 -C 60 Heterocyclic groups,

[0565] Y 41 Can be a single bond, *-N(R 44 )-*'、*-B(R 44 )-*'、*-P(R 44 )-*'、*-C(R 44 )(R 45 )-*'、*-Si(R 44 )(R 45 )-*'、*-Ge(R 44 )(R 45 )-*', *-O-*', *-S-*', *-Se-*', *-C(=O)-*', or *-S(=O) 2 -*',

[0566] Y 42 Can be a single bond, *-N(R 46 )-*'、*-B(R 46 )-*'、*-P(R 46 )-*'、*-C(R 46 )(R 47)-*'、*-Si(R 46 )(R 47 )-*'、*-Ge(R 46 )(R 47 )-*', *-O-*', *-S-*', *-Se-*', *-C(=O)-*', or *-S(=O) 2 -*',

[0567] Y 43 Can be a single bond, *-N(R 48 )-*'、*-B(R 48 )-*'、*-P(R 48 )-*'、*-C(R 48 )(R 49 )-*'、*-Si(R 48 )(R 49 )-*'、*-Ge(R 48 )(R 49 )-*', *-O-*', *-S-*', *-Se-*', *-C(=O)-*', or *-S(=O) 2 -*',

[0568] b41-b43 can each independently be 0 or 1,

[0569] When b41 is 0, Y 41 Does not exist. When b42 is 0, Y 42 does not exist, and when b43 is 0, Y 43 does not exist,

[0570] R 41 -R 49 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10Cycloalkenyl, substituted or unsubstituted C 2 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 7 -C 60 Arylalkyl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 2 -C 60 Heteroarylalkyl, substituted or unsubstituted C 6 -C 60 aryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -N(Q 1 )(Q 2 )、-Si(Q 3 )(Q 4 )(Q 5 )、-Ge(Q 3 )(Q 4 )(Q 5 )、-B(Q 6 )(Q 7 )、-P(=O)(Q 8 )(Q 9 ), or -P(Q 8 )(Q 9 ),

[0571] a41-a43 can each independently be an integer of 0-20,

[0572] R with quantity a41 41 Two or more of may be optionally bonded together to form an unsubstituted or substituted group. 10b Substituted C 5 -C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10b Substituted C 1 -C 30 Heterocyclic groups,

[0573] R with quantity a42 42 Two or more of may be optionally bonded together to form an unsubstituted or substituted group. 10b Substituted C 5 -C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10b Substituted C 1 -C 30 Heterocyclic groups,

[0574] R with quantity a43 43 Two or more of may be optionally bonded together to form an unsubstituted or substituted group. 10b Substituted C 5 -C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10b Substituted C 1 -C 30 Heterocyclic groups,

[0575] R 41 -R 49 Two or more of may be optionally bonded together to form an unsubstituted or substituted group. 10b Substituted C 5 -C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10b Substituted C 1 -C 30 Heterocyclic groups,

[0576] R 10b Can be related to R 41 Same as described,

[0577] * and *' each represent a binding site with an adjacent atom,

[0578] Substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 2 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 7 -C 60 Arylalkyl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 Heteroaryl, substituted C 2-C 60 The substituents of the heteroarylalkyl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be:

[0579] Deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, or C 1 -C 60 Alkoxy;

[0580] Each of C is substituted by 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, or C 1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 11 )(Q 12 )、-Si(Q 13 )(Q 14 )(Q 15 )、-Ge(Q 13 )(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 )、-P(=O)(Q 18 )(Q 19 )、-P(Q 18 )(Q 19 ), or any combination thereof;

[0581] C each unsubstituted or substituted with at least one of the following 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 21 )(Q 22 )、-Ge(Q 23 )(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 )、-P(=O)(Q 28 )(Q 29 )、-P(Q 28 )(Q 29 ) or any combination thereof;

[0582] -N(Q 31 )(Q 32 )、-Si(Q 33 )(Q 34 )(Q 35 )、-Ge(Q 33 )(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 )、-P(=O)(Q 38 )(Q 39 ), or -P(Q 38 )(Q 39 );or

[0583] Any combination of these, and

[0584] Q 1 -Q 9 , Q 11 -Q 19 , Q 21 -Q 29 , and Q 31 -Q 39 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, unsubstituted or substituted with deuterium, C 1 -C 60 Alkyl, C 6 -C 60Aryl, or any combination thereof substituted C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, unsubstituted or substituted with deuterium, C 1 -C 60 Alkyl, C 6 -C 60 Aryl, or any combination thereof substituted C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group.

[0585] In an embodiment, cyclic CY 41 To Ring CY 43 may each independently be i) a phenyl group, or ii) two or more C 3 -C 30 A polycyclic group in which cyclic groups are fused to each other. Here, two C 3 -C 30 The cyclic groups may be fused to each other while sharing boron (B) or nitrogen (N).

[0586] In one or more embodiments, at least one of b41-b43 may be 1, or at least two of b41-b43 may each be 1. In one or more embodiments, two of b41-b43 may be 1, and the remaining one may be 0.

[0587] In one or more embodiments, R 41 -R 49 Can be independently:

[0588] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C 1 -C 20 Alkyl, or C 1 -C20 Alkoxy;

[0589] Each of the following C 1 -C 60 Alkyl or C 1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, phenyl, biphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, and or

[0590] cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, each unsubstituted or substituted by at least one of the following yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, or carbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, C 1 -C 60 Alkyl, C 1 -C 60 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, benzofuranyl, benzothiophenyl, benzisothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, and carbazolyl.

[0591] In one or more embodiments, the polycyclic compound represented by Formula 4 may be a polycyclic compound represented by one of Formulae 4-1 to 4-9:

[0592] Formula 4-1

[0593]

[0594] Formula 4-2

[0595]

[0596] Formula 4-3

[0597]

[0598] Formula 4-4

[0599]

[0600] Formula 4-5

[0601]

[0602] Formula 4-6

[0603]

[0604] Formula 4-7

[0605]

[0606] Formula 4-8

[0607]

[0608] Formula 4-9

[0609]

[0610] Among them, in formulas 4-1 to 4-9,

[0611] Z 1 -Z 3 may each be the same as described herein with respect to Z of Formula 4,

[0612] Y 41 and Y 42 can be the same as described in this article,

[0613] Y 44 -Y 47 Can be respectively with about Y 41 and Y 42 Same as described,

[0614] R 411 Can be related to R 41 Same as described, R 421 Can be related to R 42 Same as described, R 431 and R 432 Can be respectively related to R 43 Same as described, R 441Can be related to R 41 Same as described, R 451 Can be related to R 42 Same as described, and R 461 Can be related to R 43 Same as described,

[0615] a411 can be an integer from 0 to 4.

[0616] a421 can be an integer from 0 to 3.

[0617] a431 can be an integer from 0 to 4.

[0618] a441 can be an integer from 0 to 4.

[0619] a451 can be an integer from 0 to 3, and

[0620] a461 can be an integer from 0 to 3.

[0621] Specific examples of polycyclic compounds of formula 4

[0622] The polycyclic compound represented by Formula 4 may be selected from compounds D1 to D30:

[0623]

[0624]

[0625]

[0626] Figure 1 Description

[0627] Figure 1 FIG. 1 is a schematic cross-sectional view of an organic light-emitting device 10 according to an embodiment. Figure 1 A structure and a method of manufacturing the organic light emitting device 10 according to an embodiment are described.

[0628] exist Figure 1 In the embodiment, the organic light emitting device 10 includes a first electrode 11 , a second electrode 19 facing the first electrode 11 , and an intermediate layer 10A disposed between the first electrode 11 and the second electrode 19 .

[0629] The intermediate layer 10A includes the emission layer 15 , and may further include a hole transport region 12 disposed between the first electrode 11 and the emission layer 15 , and an electron transport region 17 disposed between the emission layer 15 and the second electrode 19 .

[0630] A substrate may be additionally disposed under the first electrode 11 or on the second electrode 19. For use as the substrate, a substrate generally used in an organic light-emitting device, for example, a glass substrate or a transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, easy handling (handling), and waterproofness may be used.

[0631] The first electrode 11

[0632] The first electrode 11 may be formed by, for example, depositing or sputtering a material for forming the first electrode 11 onto the substrate. The first electrode 11 may be an anode. The material for forming the first electrode 11 may include a material having a high work function to facilitate hole injection.

[0633] The first electrode 11 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. In an embodiment, when the first electrode 11 is a transmissive electrode, the material used to form the first electrode 11 may include indium tin oxide ("ITO"), indium zinc oxide ("IZO"), tin oxide (SnO 2 ), zinc oxide (ZnO), or any combination thereof. In one or more embodiments, when the first electrode 11 is a semi-transmissive electrode or a reflective electrode, the material used to form the first electrode 11 may include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.

[0634] The first electrode 11 may have a single-layer structure or a multi-layer structure including a plurality of layers.

[0635] Emission layer 15

[0636] The thickness of the emission layer 15 may be about to about For example to about When the thickness of the emission layer 15 is within these ranges, excellent light emitting characteristics can be obtained without a significant increase in driving voltage.

[0637] In an embodiment, the emission layer 15 may include the aforementioned condensed ring compound. The emission layer 15 may follow the first embodiment or the second embodiment.

[0638] The emission layer 15 may further include the host in addition to the condensed ring compound, the sensitizer, and the emitter.

[0639] Hole transport region 12

[0640] The hole transport region 12 may be disposed between the first electrode 11 and the emission layer 15 of the organic light emitting device 10 .

[0641] The hole transport region 12 may have a single-layer structure or a multi-layer structure.

[0642] For example, the hole transport region 12 may have a hole injection layer structure, a hole transport layer structure, a hole injection layer / hole transport layer structure, a hole injection layer / first hole transport layer / second hole transport layer structure, a hole injection layer / first hole transport layer / second hole transport layer / electron blocking layer structure, a hole transport layer / organic layer structure, a hole injection layer / hole transport layer / organic layer structure, a hole transport layer / electron blocking layer structure, or a hole injection layer / hole transport layer / electron blocking layer structure.

[0643] The hole transport region 12 may include any compound having hole transport properties.

[0644] For example, the hole transport region 12 may include an amine-based compound.

[0645] In an embodiment, the hole transport region 12 may include m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), a compound represented by one of Formulae 201 to 205, or any combination thereof:

[0646]

[0647] Formula 201

[0648]

[0649] Formula 202

[0650]

[0651] Formula 203

[0652]

[0653] Formula 204

[0654]

[0655] Formula 205

[0656]

[0657] Wherein, in Formulas 201 to 205,

[0658] L 201 -L 209 can be independently *-O-*', *-S-*', substituted or unsubstituted C 5 -C 60 A carbocyclic group, or a substituted or unsubstituted C 1 -C 60 Heterocyclic groups,

[0659] xa1-xa9 can each independently be an integer from 0 to 5, and

[0660] R 201 -R 206 may be independently substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 2 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, wherein R 201 -R 206 Two adjacent groups of may be optionally linked to each other via a single bond, a dimethyl-methylene group, or a diphenyl-methylene group.

[0661] For example, L 201 -L 209 and may be each independently unsubstituted or substituted by a phenyl group, a heptalene group, an indene group, a naphthyl group, an azulene group, an indacene group, an acenaphthene group, a fluorene group, a spirobifluorene group, a benzofluorene group, a dibenzofluorene group, a phenanthren group, an anthracene group, a fluoranthene group, a benzo[9,10]phenanthrene group, a pyrene group, Group, tetraphenyl group, group, perylene group, pentacene group, hexacenyl group, pentaphene group, rubine group, coronene group, ovobenzene group, pyrrole group, isoindole group, indole group, furan group, thiophene group, benzofuran group, benzothiophene group, benzocarbazole group, dibenzocarbazole group, dibenzofuran group, dibenzothiophene group, dibenzothiophene sulfone group, carbazole group, dibenzosilole group, indenocarbazole group, indolocarbazole group, benzofuranocarbazole group, benzothiophenocarbazole group, or triindolophenyl group: deuterium, C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, benzo[9,10]phenanthryl, biphenyl, terphenyl, quaterphenyl, -Si(Q 11 )(Q 12 )(Q 13 ), or any combination thereof,

[0662] xa1-xa9 can each independently be 0, 1, or 2,

[0663] R 201 -R 206 Each of the following may be independently unsubstituted or substituted phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, coronenyl, ovolophenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothioyl, pyridyl, indenocarbazolyl, indolcarbazolyl, benzofuranocarbazolyl, or benzothiophenocarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C 1 -C 10 Alkyl-substituted phenyl, -F-substituted phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenaltenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, phenyl, tetraphenyl, phenyl, peryl, pentaphenyl, hexaphenyl, pentacene, rubinyl, coronene, ovalene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 ), or any combination thereof,

[0664] Q 11 -Q 13 and Q 31 -Q 33 Can be independently C 1 -C 10 Alkyl, C 1 -C 10 alkoxy, phenyl, biphenyl, terphenyl, or naphthyl.

[0665] In one or more embodiments, the hole transport region 12 may include an amine-based compound including carbazole.

[0666] In one or more embodiments, the hole transport region 12 may include an amine-based compound containing carbazole and an amine-based compound not containing carbazole.

[0667] The amine-based compound containing carbazole may include, for example, a compound represented by Formula 201 including a carbazole group and further including at least one of the following: a dibenzofuran group, a dibenzothiophene group, a fluorene group, a spirobifluorene group, an indenocarbazole group, an indolecarbazole group, a benzofuranocarbazole group, and a benzothiophenocarbazole group.

[0668] The amine-based compound not containing carbazole may include, for example, a compound represented by Formula 201 that does not include a carbazole group and includes at least one of the following: a dibenzofuran group, a dibenzothiophene group, a fluorene group, a spirobifluorene group, an indenocarbazole group, an indolecarbazole group, a benzofuranocarbazole group, and a benzothiophenocarbazole group.

[0669] In one or more embodiments, the hole transport region 12 may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.

[0670] In one or more embodiments, the hole transport region 12 may include a compound represented by Formula 201-1, 202-1, or 201-2, or any combination thereof:

[0671] Formula 201-1

[0672]

[0673] Formula 202-1

[0674]

[0675] Formula 201-2

[0676]

[0677] Wherein, in Formulas 201-1, 202-1, and 201-2, L 201 -L 203 , L 205 ,xa1-xa3,xa5,R 201 and R 202 may each be the same as described herein with respect to Formulas 201 to 205, and R 211 -R 213 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, C 1 -C 10 Alkyl-substituted phenyl, -F-substituted phenyl, naphthyl, fluorenyl, spirobifluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzo[9,10]phenanthryl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, or pyridyl.

[0678] In an embodiment, the hole transport region 12 may include one of compounds HT1 to HT39 or any combination thereof:

[0679]

[0680]

[0681]

[0682]

[0683] In one or more embodiments, the hole transport region 12 of the organic light emitting device 10 may further include a p-dopant. When the hole transport region 12 further includes a p-dopant, the hole transport region 12 may have a matrix (e.g., at least one of the compounds represented by Formulae 201 to 205) and a p-dopant included in the matrix. The p-dopant may be uniformly or non-uniformly doped in the hole transport region 12.

[0684] In an embodiment, the p-dopant may have a LUMO energy level of -3.5 electron volts (eV) or less.

[0685] The p-dopant may include a quinone derivative, a metal oxide, a cyano group-containing compound, or any combination thereof.

[0686] For example, the p-dopant may include:

[0687] Quinone derivatives, such as tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanobenzoquinodimethane (F4-TCNQ), and F6-TCNNQ;

[0688] Metal oxides, such as tungsten oxide or molybdenum oxide;

[0689] 1,4,5,8,9,12-Hexaazabenzo[9,10]phenanthrene-hexanitrile (HAT-CN);

[0690] A compound represented by Formula 221; or

[0691] Any combination of:

[0692]

[0693] Formula 221

[0694]

[0695] Among them, in formula 221,

[0696] R 221 -R 223 may be independently substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 2 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C1 -C 60 heteroaryl, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, wherein R 221 -R 223 At least one substituent may be: cyano; -F; -Cl; -Br; -I; C substituted by -F 1 -C 20 Alkyl; C substituted by -Cl 1 -C 20 Alkyl; C substituted by -Br 1 -C 20 Alkyl; C substituted by -I 1 -C 20 or any combination thereof.

[0697] The compound represented by Formula 221 may include, for example, compound HT-D2:

[0698]

[0699] The hole transport region 12 may have a to about For example to about The emission layer 15 may have a thickness in the range of about to about For example to about When the thickness of each of the hole transport region 12 and the emission layer 15 is within these ranges, satisfactory hole transport characteristics and / or light emitting characteristics may be obtained without a significant increase in driving voltage.

[0700] The hole transport region 12 may further include an electron blocking layer. The electron blocking layer may include known materials, for example, mCP or DBFPO:

[0701]

[0702] Electron transport region 17

[0703] The electron transport region 17 is disposed between the emission layer 15 and the second electrode 19 of the organic light emitting device 10 .

[0704] The electron transport region 17 may have a single-layer structure or a multi-layer structure.

[0705] For example, the electron transport region 17 may have an electron transport layer, an electron transport layer / electron injection layer structure, a buffer layer / electron transport layer structure, a hole blocking layer / electron transport layer structure, a buffer layer / electron transport layer / electron injection layer structure, or a hole blocking layer / electron transport layer / electron injection layer structure. The electron transport region 17 may further include an electron control layer.

[0706] The electron transport region 17 may include a known electron transport material.

[0707] The electron transport region 17 (eg, a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a metal-free compound containing at least one C-containing π-electron-deficient nitrogen. 1 -C 60 The C containing nitrogen lacking π electrons 1 -C 60 The cyclic groups are the same as described herein.

[0708] For example, the electron transport region 17 may include a compound represented by Formula 601:

[0709] Formula 601

[0710] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 .

[0711] Wherein, in Formula 601,

[0712] Ar 601 and L 601 may be independently unsubstituted or substituted with at least one R 601a Substituted C 5 -C 60 A carbocyclic group, either unsubstituted or substituted with at least one R 601a Substituted C 1 -C 60 Heterocyclic groups,

[0713] xe11 can be 1, 2, or 3,

[0714] xe1 can be an integer from 0 to 5.

[0715] R 601a and R 601 may be independently substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 2 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 601 )(Q 602 )(Q 603 )、-C(=O)(Q 601 )、-S(=O) 2 (Q 601 ), or -P(=O)(Q 601 )(Q 602 ),

[0716] Q 601 -Q 603 Can be independently C 1 -C 10 Alkyl, C 1 -C 10 alkoxy, phenyl, biphenyl, terphenyl, or naphthyl, and

[0717] xe21 can be an integer from 1 to 5.

[0718] In an embodiment, the amount of Ar is xe11 601 and the number of R is xe21 601 At least one of the C 1 -C 60 Cyclic group.

[0719] In an embodiment, Ar in Formula 601 601 and L 601 Each of them may be independently unsubstituted or substituted by a benzene group, a naphthalene group, a fluorene group, a spirobifluorene group, a benzofluorene group, a dibenzofluorene group, a phenanthene group, a phenanthene group, an anthracene group, a fluoranthene group, a benzo[9,10]phenanthrene group, a pyrene group, Group, tetraphenyl group, group, perylene group, pentaphene group, indenoanthracene 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, naphthyridine group, quinoxaline group, quinazoline group, Cinoline group, phenanthridine group, acridine group, phenanthroline group, phenazine group, benzimidazole group, isobenzothiazole group, benzoxazole group, isobenzoxazole group, triazole group, tetrazole group, oxadiazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group, or azacarbazole group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q 31 )(Q 32 )(Q 33 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ), or any combination thereof, and

[0720] Q 31 -Q 33 Can be independently C 1 -C 10 Alkyl, C 1 -C 10 alkoxy, phenyl, biphenyl, terphenyl, or naphthyl.

[0721] When xe11 in Formula 601 is 2 or greater, two or more Ar 601 can be connected to each other via a single bond.

[0722] In one or more embodiments, Ar in Formula 601 601 It may be an anthracene group.

[0723] In one or more embodiments, the compound represented by Formula 601 can be represented by Formula 601-1:

[0724] Formula 601-1

[0725]

[0726] Among them, in formula 601-1,

[0727] X 614 Can be N or C(R614 ), X 615 Can be N or C(R 615 ), X 616 Can be N or C(R 616 ), and X 614 -X 616 At least one of may be N,

[0728] L 611 -L 613 Can be independently related to L 601 Same as described,

[0729] xe611-xe613 can be independently the same as described for xe1,

[0730] R 611 -R 613 Can be independently related to R 601 Same as described, and

[0731] R 614 -R 616 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 alkoxy, phenyl, biphenyl, terphenyl, or naphthyl.

[0732] In one or more embodiments, xe1 and xe611-xe613 in formulas 601 and 601-1 may each independently be 0, 1, or 2.

[0733] In one or more embodiments, R in Formula 601 and 601-1 601 and R 611 -R 613 Each of them may be independently unsubstituted or substituted phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinoline quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, or azacarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, peryl, pentaphenyl, hexaphenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothiophenyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl , pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, or any combination thereof; or

[0734] -S(=O) 2 (Q 601 ), or -P(=O)(Q 601 )(Q 602 ),and

[0735] Q 601 and Q 602 Each may be the same as described herein.

[0736] The electron transport region 17 may include one of compounds ET1 to ET36, or any combination thereof:

[0737]

[0738]

[0739]

[0740] In one or more embodiments, the electron transport region 17 may include 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq 3 , BAlq, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), NTAZ, DBFPO, or any combination thereof. For example, when the electron transport region 17 includes a hole blocking layer, the hole blocking layer may include BCP or Bphen:

[0741]

[0742] The thickness of the buffer layer, the hole blocking layer, and the electron control layer may be independently about to about For example to about When the thicknesses of the buffer layer, the hole blocking layer, and the electron control layer are within these ranges, excellent hole blocking characteristics or excellent electron control characteristics may be obtained without a significant increase in driving voltage.

[0743] The thickness of the electron transport layer may be about to about For example to about When the thickness of the electron transport layer is within these ranges, satisfactory electron transport characteristics may be obtained without a significant increase in driving voltage.

[0744] The electron transport region 17 (eg, an electron transport layer in the electron transport region 17 ) may further include a material containing a metal in addition to the foregoing materials.

[0745] The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The metal ions of the alkali metal complex may include Li ions, Na ions, K ions, Rb ions, Cs ions, or any combination thereof, and the metal ions of the alkaline earth metal complex may include Be ions, Mg ions, Ca ions, Sr ions, Ba ions, or any combination thereof. The ligand coordinated with the metal ions of the alkali metal complex or the alkaline earth metal complex may include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiphenyloxadiazole, hydroxydiphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.

[0746] For example, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (LiQ) or ET-D2:

[0747]

[0748] The electron transport region 17 may include an electron injection layer that facilitates injection of electrons from the second electrode 19. The electron injection layer may directly contact the second electrode 19.

[0749] The electron injection layer may have i) a single layer structure consisting of a single layer including a single material, ii) a single layer structure consisting of a single layer including a plurality of materials different from each other, or iii) a multilayer structure consisting of a plurality of layers including a plurality of materials different from each other.

[0750] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.

[0751] The alkali metal may include Li, Na, K, Rb, Cs, or any combination thereof. In an embodiment, the alkali metal may be Li, Na, or Cs. In one or more embodiments, the alkali metal may be Li or Cs.

[0752] The alkaline earth metal may include Mg, Ca, Sr, Ba, or any combination thereof.

[0753] The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.

[0754] The alkali metal compound, alkaline earth metal compound, and rare earth metal compound may include oxides and halides (e.g., fluorides, chlorides, bromides, or iodides) of the alkali metal, alkaline earth metal, and rare earth metal, or any combination thereof.

[0755] The alkali metal compound may include: an alkali metal oxide such as Li 2 O, Cs 2 O, K 2 O, etc.; an alkali metal halide such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI, etc.; or any combination thereof. In an embodiment, the alkali metal compound may include LiF, Li 2 O, NaF, LiI, NaI, CsI, KI, or any combination thereof.

[0756] The alkaline earth metal compound may include an alkaline earth metal compound such as BaO, SrO, CaO, Ba x Sr 1-x O (where 0 < x < 1), or Ba x Ca 1-x O (where 0 < x < 1), or any combination thereof. In an embodiment, the alkaline earth metal compound may include BaO, SrO, CaO, or any combination thereof.

[0757] The rare earth metal compound may include YbF 3 , ScF 3 , ScO 3 , Y 2 O 3 , Ce 2 O 3 , GdF 3 , TbF 3 , or any combination thereof. In an embodiment, the rare earth metal compound may include YbF 3 , ScF 3 , TbF 3 , YbI 3 , ScI 3 , TbI 3 , or any combination thereof.

[0758] The alkali metal complex, alkaline earth metal complex, and rare earth metal complex may include ions of the alkali metal, alkaline earth metal, and rare earth metal as described above, and the ligand coordinated with the metal ion of the alkali metal complex, alkaline earth metal complex, or rare earth metal complex may include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiphenyloxadiazole, hydroxydiphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.

[0759] The electron injection layer may be composed of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof as described above. In one or more embodiments, the electron injection layer may further include an organic material. When the electron injection layer further includes an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof may be uniformly or non-uniformly dispersed in a matrix including the organic material.

[0760] The thickness of the electron injection layer can be about to about For example to about When the thickness of the electron injection layer is within these ranges, satisfactory electron injection characteristics can be obtained without a significant increase in driving voltage.

[0761] The second electrode 19

[0762] The second electrode 19 is disposed on the aforementioned intermediate layer 10A. The second electrode 19 may be a cathode as an electron injection electrode, and in this regard, a material for forming the second electrode 19 may be selected from metals, alloys, conductive compounds, and combinations thereof having a relatively low work function.

[0763] The second electrode 19 may include Li, Ag, Mg, Al, Al-Li, Ca, Mg-In, Mg-Ag, ITO, IZO, or any combination thereof. The second electrode 19 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.

[0764] The second electrode 19 may have a single-layer structure having a single layer or a multi-layer structure including two or more layers.

[0765] Explanation of terminology

[0766] As used herein, the term "C 1 -C60 "Alkyl" refers to a straight chain or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and as used herein, the term "C 1 -C 60 "Alkylene" refers to a group having a C 1 -C 60 Alkyl is a divalent group of the same structure.

[0767] C 1 -C 60 Alkyl, C 1 -C 20 Alkyl, and / or C 1 -C 10 Examples of the alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl , or tert-decyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl, tert-decyl, or any combination thereof.

[0768] As used herein, the term "C 1 -C 60 "Alkoxy" refers to a 101 (A 101 C 1 -C 60 The term "C alkyl" as used herein is a monovalent group represented by a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, and the like. 1 -C 60 "Alkylthio" refers to -SA 101 (A 101 C 1 -C 60 The invention further comprises a monovalent group represented by an alkyl group, and examples thereof include a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a pentylthio group and the like.

[0769] As used herein, the term "C 2 -C 60 "Alkenyl" refers to a group consisting of 2 -C 60The term "C" as used herein refers to a hydrocarbon group formed by inserting at least one carbon-carbon double bond in the middle or at the terminal of an alkyl group, and examples thereof include vinyl, propenyl, butenyl, and the like. 2 -C 60 "Alkenylene" refers to a 2 -C 60 Alkenyl is a divalent group of the same structure.

[0770] As used herein, the term "C 2 -C 60 "Alkynyl" refers to a 2 -C 60 The term "C" as used herein refers to a hydrocarbon group formed by inserting at least one carbon-carbon triple bond in the middle or at the terminal of an alkyl group, and examples thereof include ethynyl, propynyl, and the like. 2 -C 60 "Alkyne" refers to a group having a C 2 -C 60 Alkynyl is a divalent group of the same structure.

[0771] As used herein, the term "C 3 -C 10 "Cycloalkyl" refers to a monovalent saturated hydrocarbon ring group having 3 to 10 carbon atoms as ring atoms, and the term "Cycloalkyl" as used herein 3 -C 10 "Cycloalkylene" refers to a cycloalkylene having a 3 -C 10 Cycloalkyl is a divalent group of the same structure.

[0772] C 3 -C 10 Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl (bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, and bicyclo[2.2.2]octyl.

[0773] As used herein, the term "C 1 -C 10 "Heterocycloalkyl" refers to a monovalent saturated cyclic group including at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring atom and 1 to 10 carbon atoms as ring atoms, and the term "C 1 -C 10 "Heterocycloalkylene" refers to a group having a C 1 -C 10 Heterocycloalkyl is a divalent group of the same structure.

[0774] C 1 -C 10Examples of heterocycloalkyl include silacyclopentyl, silacyclohexyl, tetrahydrofuranyl, tetrahydro-2H-pyranyl, tetrahydrothienyl and the like.

[0775] As used herein, the term "C 3 -C 10 The term "cycloalkenyl" as used herein refers to a monovalent hydrocarbon ring group which includes 3 to 10 carbon atoms as ring atoms and at least one carbon-carbon double bond in its ring and does not have aromaticity, and examples thereof include cyclopentenyl, cyclohexenyl, and cycloheptenyl. 3 -C 10 "Cycloalkenylene" refers to a 3 -C 10 Cycloalkenyl is a divalent group of the same structure.

[0776] As used herein, the term "C 2 -C 10 The term "heterocycloalkenyl" refers to a monovalent cyclic group having at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring atom, 2 to 10 carbon atoms as ring atoms, and at least one carbon-carbon double bond in its ring and having no aromaticity. 2 -C 10 Examples of heterocycloalkenyl include 2,3-dihydrofuranyl, 2,3-dihydrothienyl, and the like. 2 -C 10 "Heterocycloalkenylene" refers to a 2 -C 10 Heterocycloalkenyl is a divalent group of the same structure.

[0777] As used herein, the term "C 6 -C 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and as used herein, the term "C 6 -C 60 "Arylene" refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. 6 -C 60 Examples of aryl groups include phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, Ji et al. 6 -C 60 Aryl and C 6 -C 60 When the arylene groups each include two or more rings, the rings may be fused to each other.

[0778] As used herein, the term "C 1 -C 60The term “heteroaryl” refers to a monovalent group including a heterocyclic aromatic system having at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring atom and 1 to 60 carbon atoms as ring atoms, and the term “C 1 -C 60 The term "heteroarylene" refers to a divalent group including a heterocyclic aromatic system having at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring atom and 1 to 60 carbon atoms as ring atoms. 1 -C 60 Examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, and the like. 1 -C 60 Heteroaryl and C 1 -C 60 When the heteroarylene groups each include two or more rings, the rings may be fused to each other.

[0779] As used herein, the term "C 6 -C 60 "Aryloxy" means -OA 102 (A 102 C 6 -C 60 aryl), and as used herein, the term "C 6 -C 60 "Arylthio" means -SA 103 (A 103 C 6 -C 60 aryl).

[0780] The term "monovalent non-aromatic fused polycyclic group" as used herein refers to a monovalent group in which two or more rings are fused to each other, only carbon is used as a ring-forming atom (e.g., the number of carbon atoms may be 8-60), and the entire group is non-aromatic. An example of a monovalent non-aromatic fused polycyclic group is a fluorenyl group. The term "divalent non-aromatic fused polycyclic group" as used herein refers to a divalent group having the same structure as the monovalent non-aromatic fused polycyclic group described above.

[0781] The term "monovalent non-aromatic fused heteropolycyclic group" as used herein refers to a monovalent group having two or more rings fused to each other, having a heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom in addition to carbon atoms (e.g., having 1 to 60 carbon atoms), and having no aromaticity in terms of its entire molecular structure. Examples of monovalent non-aromatic fused heteropolycyclic groups include carbazolyl and the like. The term "divalent non-aromatic fused heteropolycyclic group" as used herein refers to a divalent group having the same structure as the monovalent non-aromatic fused heteropolycyclic group.

[0782] As used herein, the term "C 1 -C 60 A "cyclic group" refers to a cyclic group having 1 to 60 carbon atoms and including at least one *-N=*' (wherein * and *' each represent a binding site with an adjacent atom) as a ring-forming part. For example, a C-containing nitrogen lacking π electrons 1 -C 60 The cyclic group may be a) a first ring, b) a condensed ring in which at least two first rings are condensed, or c) a condensed ring in which at least one first ring and at least one second ring are condensed.

[0783] As used herein, the term "π-electron-rich C 3 -C 60 A "cyclic group" refers to a cyclic group having 3 to 60 carbon atoms and not including any *-N=*' (wherein * and *' each represent a binding site with an adjacent atom) as a ring-forming part. For example, a π-electron-rich C 3 -C 60 The cyclic group may be a) a second ring or b) a condensed ring in which at least two second rings are condensed.

[0784] As used herein, the term "C 5 -C 60 Carbocyclic group" and "C 5 -C 30 The "carbocyclic group" refers to a monocyclic or polycyclic group having only 5 to 60 or 5 to 30 carbon atoms as ring-forming atoms, respectively, and may be, for example, a) a tertiary ring or b) a condensed ring in which two or more tertiary rings are condensed to each other.

[0785] As used herein, the term "C 1 -C 60 Heterocyclic group" or "C 1 -C 30The term "heterocyclic group" refers to a monocyclic or polycyclic group having 1 to 60 or 1 to 30 carbon atoms and at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as ring-forming atoms, respectively, and may be, for example, a) a fourth ring, b) a condensed ring in which two or more fourth rings are condensed to each other, or c) a condensed ring in which at least one third ring is condensed to at least one fourth ring.

[0786] The “first ring” as used herein may be an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, or a thiadiazole group.

[0787] The "second ring" as used herein may be a benzene group, a cyclopentadiene group, a pyrrole group, a furan group, a thiophene group, or a silole group.

[0788] The “third ring” as used herein may be a cyclopentane group, a cyclopentadiene group, an indene group, an adamantane group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.1]heptane group (norbornane group), a bicyclo[2.2.2]octane group, a cyclohexane group, a cyclohexene group, or a phenyl group.

[0789] The “fourth ring” as used herein may be a furan group, a thiophene group, a pyrrole group, a thiol group, an oxazole group, an isoxazole group, an oxadiazole group, an isoxadiazole group, an oxatriazole group, an isoxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiadiazole group, a thiatriazole group, an isothitriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azathiol group, a diazathiol group, a triazathiol group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

[0790] For example, C containing π-electron-deficient nitrogen 1 -C 60The cyclic group may be an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, an acridine group, or a pyridopyrazine group.

[0791] For example, the π-electron-rich C 3 -C 60 The cyclic group can be a phenyl group, a heptadene group, an indene group, a naphthalene group, an azulene group, an indacene group, an acenaphthene group, a fluorene group, a spirobifluorene group, a benzofluorene group, a dibenzofluorene group, a phenanthene group, a phenanthrenene group, an anthracene group, a fluoranthene group, a benzo[9,10]phenanthrene group, a pyrene group, Group, tetraphenyl group, group, perylene group, pentacene group, hexacenyl group, pentaphene group, rubine group, coronene group, ovobenzene group, pyrrole group, furan group, thiophene group, isoindole group, indole group, indene group, benzofuran group, benzothiophene group, benzosilole group, naphthopyrrole group, naphthofuran group, naphthothiophene group, naphthosilole group, benzocarbazole group, dibenzocarbazole group, dibenzofuran group, dibenzothiophene group, A benzothiophene group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolecarbazole group, a benzofuranocarbazole group, a benzothienocarbazole group, a benzothioylcarbazole group, a triindolephenyl group, a pyrrolophenanthrene group, a furanophenanthrene group, a thiophenophenanthrene group, a benzonaphthofuran group, a benzonaphthothiophene group, an (indole)phenanthrene group, a (benzofurano)phenanthrene group, or a (benzothioyl)phenanthrene group.

[0792] For example, C 5 -C 60 Carbocyclic group or C 5 -C 30 The carbocyclic group may be a cyclopentane group, a cyclohexane group, a cyclohexene group, a phenyl group, a naphthalene group, an anthracene group, a phenanthrene group, an indene group, a benzo[9,10]phenanthrene group, a pyrene group, group, a 1,2,3,4-tetrahydronaphthalene group, a cyclopentadiene group, an indene group, a fluorene group, a 5,6,7,8-tetrahydroisoquinoline group, a 5,6,7,8-tetrahydroquinoline group, an adamantane group, a norbornane group, or a norbornene group.

[0793] For example, C 1 -C 60 Heterocyclic group or C 1 -C 30 The heterocyclic group may be a thiophene group, a furan group, a pyrrole group, a cyclopentadiene group, a thiol group, a borocyclopentadiene group, a phosphocyclopentadiene group, a selenophene group, a germanocyclopentadiene group, a benzothiophene group, a benzofuran group, an indole group, a benzothiol group, a benzoborole group, a benzophosphocyclopentadiene group, a benzoselenophene group, a benzogermanocyclopentadiene group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a dibenzo Silole group, dibenzoborole group, dibenzophosphole group, dibenzoselenophene group, dibenzogermanol group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, azabenzothiophene group, azabenzofuran group, azaindole group, azaindene group, azabenzosilole group, azabenzoborole group, azabenzophosphole group, aza ...thiophene group, azabenzoborole group, azabenzophosphole group, azabenzothiophene 5-oxide group, azabenzothiophene 5,5-dioxide group, azabenzothiophene group, azabenzofuran group, azaindole group, azaindene group, azabenzothiophene group, azabenzo heterobenzoselenophene group, azabenzogermanyl heterocyclopentadiene group, azadibenzothiophene group, azadibenzofuran group, azacarbazole group, azafluorene group, azadibenzosilole group, azadibenzoborolyl group, azadibenzophospholeyl group, azadibenzoselenophene group, azadibenzogermanyl heterocyclopentadiene group, azadibenzothiophene 5-oxide group, aza-9H-fluoren-9-one group, azadibenzothiophene 5,5 - a dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzooxadiazole group, or a benzothiadiazole group.

[0794] As used herein, the term "C 1 -C 60 Cyclic groups", "π-electron-rich C 3 -C 60 Cyclic group", "C 5 -C 60 Carbocyclic group", "C 5 -C 30 Carbocyclic group", "C1 -C 60 Heterocyclic group", and "C 1 -C 30 The "heterocyclic group" each refers to a part of a condensed ring or a monovalent, divalent, trivalent, tetravalent, pentavalent, or hexavalent group depending on the formula structure.

[0795] Substituted C containing π-electron-deficient nitrogen 1 -C 60 Cyclic groups, substituted π-electron-rich C 3 -C 60 Cyclic groups, substituted C 5 -C 60 Carbocyclic groups, substituted C 5 -C 30 Carbocyclic groups, substituted C 1 -C 60 Heterocyclic groups, substituted C 1 -C 30 Heterocyclic groups, substituted C 1 -C 60 Alkylene, substituted C 2 -C 60 Alkenylene, substituted C 2 -C 60 Alkynylidene, substituted C 3 -C 10 Cycloalkylene, substituted C 1 -C 10 Heterocycloalkylene, substituted C 3 -C 10 Cycloalkenylene, substituted C 2 -C 10 Heterocycloalkenylene, substituted C 6 -C 60 Arylene, substituted C 1 -C 60 Heteroarylene, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 2-C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 The substituents of the heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group may each independently be:

[0796] Deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, or C 1 -C 60 Alkylthio;

[0797] Each of C is substituted by 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, or C 1 -C 60 Alkylthio: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 11 )(Q 12 )、-Si(Q 13 )(Q 14 )(Q 15 )、-Ge(Q 13 )(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 )、-P(=O)(Q 18 )(Q 19 )、-P(Q 18 )(Q 19 ), or any combination thereof;

[0798] Each C is unsubstituted or substituted as follows 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 1 -C 60 Alkylthio, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 21 )(Q 22 )、-Si(Q 23 )(Q 24 )(Q 25 )、-Ge(Q 23 )(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 )、-P(=O)(Q 28 )(Q 29 )、-P(Q 28 )(Q 29 ), or any combination thereof;

[0799] -N(Q 31 )(Q 32 )、-Si(Q 33 )(Q 34 )(Q 35 )、-Ge(Q 33 )(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 )、-P(=O)(Q 38 )(Q 39 ), or -P(Q 38 )(Q 39 );or

[0800] Any combination thereof.

[0801] Q 1 -Q 9 , Q 11 -Q 19 , Q 21 -Q 29 , and Q 31 -Q 39 may be each independently hydrogen, deuterium, -F, or C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 1 -C 60 Alkylthio, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, cyano, C 1 -C 60 Alkyl, C 6 -C 60 aryl, or any combination thereof.

[0802] Unless otherwise defined, Q 1 -Q 9 , Q 11 -Q 19 , Q 21 -Q 29 , and Q 31 -Q 39 Can be independently, for example:

[0803] -CH 3 、-CD 3 、-CD 2 H.-CDH 2 、-CH 2 CH 3 、-CH 2CD 3 、-CH 2 CD 2 H, -CH 2 CDH 2 、-CHDCH 3 、-CHDCD 2 H, -CHDCDH 2 、-CHDCD 3 、-CD 2 CD 3 、-CD 2 CD 2 H, or -CD 2 CDH 2 ;or

[0804] n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, phenyl, biphenyl, or naphthyl, each unsubstituted or substituted with: deuterium, C 1 -C 10 Alkyl, phenyl, or any combination thereof.

[0805] The term "room temperature" as used herein refers to a temperature of about 25°C.

[0806] As used herein, the terms "biphenyl, terphenyl, and quaterphenyl" refer to a monovalent group in which two, three, or four phenyl groups are linked together via a single bond, respectively.

[0807] As used herein, the term "(C 1 -C 20 alkyl)X group" (e.g., (C 1 -C 20 Alkyl)phenyl) refers to a 1 -C 20 Alkyl substituted X groups (eg, phenyl).

[0808] Hereinafter, the compound and the organic light-emitting device according to the embodiment are described in detail with reference to the synthesis examples and the examples. However, the organic light-emitting device is not limited thereto. The phrase "using 'B' instead of 'A'" used in describing the synthesis examples means that the amount of 'A' used is the same as the amount of 'B' used in terms of molar equivalent.

[0809] Example

[0810] Synthesis Example 1 (Compound 1)

[0811]

[0812] Synthesis of Compound 1-2

[0813] N1,N3-di([1,1':3',1"-terphenyl]-2-yl)-5-(tert-butyl)benzene-1,3-diamine [15 g, 24.16 mmol], 1-bromo-3-iodobenzene (136.7 g, 483.3 mmol), CuI (0.46 g, 2.42 mmol), and K 2 CO 3 A mixture of (11.69 g, 84.56 mmol) was heated at 200°C for 24 hours in a nitrogen atmosphere, and then an aqueous ammonium chloride solution was added to the reaction mixture. The organic phase was extracted with dichloromethane and the resulting extract was washed with MgSO 4 The dried extract was then purified by column chromatography using dichloromethane (MC) and hexane (in a volume ratio of 1:3) to provide 12.94 g of Compound 1-2 (white solid).

[0814] Liquid chromatography-mass spectrometry (LCMS): with a calculated mass-to-charge ratio (m / z) of 930.83 grams / mole (g / mol), found: [M + ]931.720g / mol.

[0815] N1,N3-di([1,1':3',1"-terphenyl]-2-yl)-5-(tert-butyl)benzene-1,3-diamine is obtained by reaction scheme 1, wherein in reaction scheme 1 and reaction schemes 2 to 4 to be mentioned later, step A and step B can refer to the synthesis of compound 1075 (1) in US2020 / 0083458 and the synthesis of compound A1 in US2023 / 0232702, respectively:

[0816] <Reaction Scheme 1>

[0817]

[0818] Synthesis of compound 1-1

[0819] After the temperature was raised to 150° C., compound 1-2 (10.4 g, 11.17 mmol), 100 ml of 1,2-dichlorobenzene, and BI 3 A mixture of 1,4-dihydro-1,4-dihydro-2-nitropropene (6.56 g, 16.76 mmol) was stirred under nitrogen for 24 hours. The resulting solution was cooled to room temperature and Na 2 CO 3 The aqueous solution was added to the reaction mixture. The organic phase was extracted with dichloromethane and the extract was concentrated with MgSO 4 The dried extract was purified by column chromatography using MC and hexane (in a volume ratio of 1:3) to provide 3.03 g of Compound 1-1 (solid).

[0820] LCMS (m / z): calculated value: 938.61 g / mol, found value: [M + ]939.159g / mol.

[0821] Synthesis of compound 1

[0822] Compound 1-1 (1 g, 1.07 mmol), carbazole (0.35 g, 2.09 mmol), Pd 2 (dba) 3 (0.001 g, 0.001 mmol), S-Phos (0.008 g, 0.02 mmol), and NaOtBu (0.31 g, 3.21 mmol) were mixed with toluene, and the mixture was heated at 110° C. for 5 hours in a nitrogen atmosphere. The reaction mixture was cooled to room temperature and an aqueous ammonium chloride solution was added to the reaction mixture. The organic phase was extracted with dichloromethane and washed with MgSO 4 The dried extract was purified by column chromatography using MC and hexane (in a volume ratio of 1:2) to provide 0.49 g of Compound 1 (yellow solid).

[0823] LCMS (m / z): calculated value: 1111.21 g / mol, found value: [M + ]1110.11g / mol.

[0824] Synthesis Example 2 (Compound 121)

[0825]

[0826] Synthesis of compound 121-2

[0827] 5-(tert-butyl)-N1,N3-bis(5-(tert-butyl)-[1,1':3',1"-terphenyl]-2-yl)benzene-1,3-diamine (23 g, 31.37 mmol), 1-bromo-3-iodobenzene (177.53 g, 627.5 mmol), CuI (0.6 g, 3.14 mmol), and K 2 CO 3 A mixture of (15.17 g, 109.79 mmol) was heated at 200 °C for 24 h under nitrogen atmosphere, and then aqueous ammonium chloride solution was added to the reaction mixture. The organic phase was extracted with dichloromethane and washed with MgSO 4 The dried extract was then purified by column chromatography using MC and hexane (in a volume ratio of 1:3) to provide 23.05 g of compound 121-2 (white solid).

[0828] LCMS (m / z): calculated value: 1043.04 g / mol, found value: [M + ]1043.3024g / mol.

[0829] 5-(tert-butyl)-N1,N3-bis(5-(tert-butyl)-[1,1':3',1"-terphenyl]-2-yl)benzene-1,3-diamine is obtained by reaction scheme 2:

[0830] <Reaction Scheme 2>

[0831]

[0832] Synthesis of Compound 121-1

[0833] After the temperature was raised to 150°C, compound 121-2 (10 g, 9.59 mmol), 100 ml of 1,2-dichlorobenzene, and BI 3 A mixture of 5.63 g, 14.38 mmol) was stirred under nitrogen for 24 hours. The resulting solution was cooled to room temperature and Na 2 CO 3 The aqueous solution was added to the reaction mixture. The organic phase was extracted with dichloromethane and washed with MgSO 4 The dried extract was purified by column chromatography using MC and hexane (in a volume ratio of 1:3) to provide 3.03 g of compound 121-1 (solid).

[0834] LCMS (m / z): calculated value: 1050.83 g / mol, found value: [M + ]1050.159g / mol.

[0835] Synthesis of compound 121

[0836] Compound 121-1 (1.7 g, 1.61 mmol), carbazole (0.33 g, 1.97 mmol), Pd 2 (dba) 3 (0.014 g, 0.015 mmol), S-Phos (0.013 g, 0.032 mmol), and NaOtBu (0.46 g, 4.79 mmol) were mixed with toluene, and the mixture was heated at 110° C. for 5 hours in a nitrogen atmosphere. The reaction mixture was cooled to room temperature, and an aqueous ammonium chloride solution was added to the reaction mixture. The organic phase was extracted with dichloromethane and washed with MgSO 4 The dried extract was purified by column chromatography using MC and hexane (in a volume ratio of 1:2) to provide 1.2 g of Compound 121 (yellow solid).

[0837] LCMS (m / z): calculated: 1223.43 g / mol, found: [M + ]1223.31g / mol.

[0838] Synthesis Example 3 (Compound 576)

[0839]

[0840] Synthesis of Compound 576-2

[0841] Compound 576-2 was synthesized in the same manner as in the synthesis of Compound 1-2 in Synthesis Example 1, except that Compound 576-3 was used instead of N1,N3-di([1,1':3',1"-terphenyl]-2-yl)-5-(tert-butyl)benzene-1,3-diamine.

[0842] Compound 576-3 is obtained via reaction scheme 3:

[0843] <Reaction Scheme 3>

[0844]

[0845] Synthesis of Compound 576-1

[0846] Compound 576-1 was synthesized in the same manner as in the synthesis of Compound 1-1 in Synthesis Example 1, except that Compound 576-2 was used instead of Compound 1-2.

[0847] Synthesis of compound 576

[0848] Compound 576 (1.6 g, yellow solid) was synthesized in the same manner as in the synthesis of Compound 1 in Synthesis Example 1, except that Compound 576-1 was used instead of Compound 1-1, and 9H-carbazole-1,2,3,4,5,6,7,8-d 8 Replace carbazole.

[0849] LCMS (m / z): calculated value: 1615.022 g / mol, found value: [M + ]1616.027g / mol.

[0850] Synthesis Example 4 (Compound 516)

[0851]

[0852] Synthesis of Compound 516-2

[0853] Compound 516-2 was synthesized in the same manner as in the synthesis of Compound 1-2 in Synthesis Example 1, except that Compound 516-3 was used instead of N1,N3-di([1,1':3',1"-terphenyl]-2-yl)-5-(tert-butyl)benzene-1,3-diamine.

[0854] Compound 516-3 is obtained via reaction scheme 4:

[0855] <Reaction Scheme 4>

[0856]

[0857] Synthesis of Compound 516-1

[0858] Compound 516-1 was synthesized in the same manner as in the synthesis of Compound 1-1 in Synthesis Example 1, except that Compound 516-2 was used instead of Compound 1-2.

[0859] Synthesis of compound 516

[0860] Compound 516 (0.75 g, yellow solid) was synthesized in the same manner as in the synthesis of Compound 1 in Synthesis Example 1, except that Compound 516-1 was used instead of Compound 1-1, and 9H-carbazole-1,2,3,4,5,6,7,8-d 8 Replace carbazole.

[0861] LCMS (m / z): calculated value: 1278.77 g / mol, found value: [M + ]1278.757g / mol.

[0862] Comparative Synthesis Example 1 (Compound R3)

[0863]

[0864] Synthesis of compound R3-1

[0865] 1-Bromo-2,3-dichlorobenzene (1.25 g, 5.53 mmol), compound R3-2 (4.996 g, 12.17 mmol), Pd 2 (dba) 3 (0.504 g, 0.55 mmol), S-Phos (0.456 g, 1.11 mmol), and NaOtBu (1.86 g, 19.37 mmol) were mixed with 110 ml of xylene, and the mixture was refluxed for 30 minutes. Then, an aqueous ammonium chloride solution was added to the reaction mixture, and the organic phase was extracted with ethyl acetate and washed with MgSO 4The dried extract was then purified by column chromatography using MC and hexane (in a volume ratio of 1:3) to provide 4.3 g of compound R3-1 (white solid).

[0866] LCMS (m / z): calculated value: 928.333 g / mol, found value: [M + ]929.336g / mol.

[0867] Synthesis of compound R3

[0868] Compound R3-1 (3.26 g, 3.51 mmol) was dissolved in 87 ml of tert-butylbenzene, and the resulting solution was cooled to -78 ° C. Then, after t-BuLi (5.48 ml, 8.77 mmol) was added thereto, the temperature was raised to 60 ° C, and the resulting solution was stirred for one and a half hours. After the reaction mixture was cooled to 0 ° C, boron tribromide (1.76 ml, 7.01 mmol) was added and the reaction solution was stirred at room temperature for one and a half hours. The reaction mixture was cooled to 0 ° C and acetic acid N, N-diisopropylethylamine (1.19 ml, 7.01 mmol) was added thereto, and the reaction solution was stirred at 120 ° C for 4 hours. Then, sodium acetate aqueous solution (1.0 M) was added to the reaction mixture. The organic phase was extracted with ethyl acetate and MgSO 4 The dried extract was purified by column chromatography using MC and hexane (in a volume ratio of 1:4) to provide 0.6 g of Compound R3 (solid).

[0869] LCMS (m / z): calculated value: 902.368 g / mol, found value: [M + ]903.353g / mol.

[0870] Evaluation Example 1

[0871] For each of Compounds 1, 121, 576, 516, and R1 to R4, the HOMO level, LUMO level, singlet state (S) and R2 were evaluated by density functional theory (DFT) calculations using the Gaussian 16 program with structural optimization at the level of B3LYP / 6-31G (D, P). 1 ) energy level, triplet state (T 1 ) energy level, and △Est (in S 1 Energy Level and T 1 The absolute value of the difference between the energy level values) was calculated, and the results are shown in Table 2. Compounds R1, R2 and R4 can be obtained by the methods in Reference Synthesis Example and Comparative Synthesis Example 1.

[0872] Table 2

[0873]

[0874]

[0875] As shown in Table 2, Compounds 1, 121, 576, and 516 have electrical properties suitable for use in light-emitting devices.

[0876] Example 1

[0877] Formed thereon The glass substrate of thick ITO electrode (i.e., anode) was cut into a size of 50 millimeters (mm) × 50 mm × 0.5 mm, ultrasonically treated with acetone, isopropanol and pure water for 15 minutes each, and cleaned by ultraviolet-ozone radiation for 30 minutes. Then, the resulting glass substrate was loaded onto a vacuum deposition device.

[0878] Subsequently, m-MTDATA was deposited on the ITO electrode of the glass substrate to form a A hole injection layer having a thickness of , and α-NPD is deposited on the hole injection layer to form a The hole transport layer has a thickness of .

[0879] Next, compound 1 (emitter) and mCP (host) were co-deposited on the hole transport layer at a weight ratio of 10:90 to form a The thickness of the emission layer.

[0880] BAlq is deposited on the emission layer to form a The thickness of the hole blocking layer is Alq 3 deposited on the hole blocking layer to form a An electron transport layer having a thickness of An electron injection layer having a thickness of , and Al is vacuum deposited on the electron injection layer to form A second electrode (ie, cathode) having a thickness of , thereby completing the manufacture of a light-emitting device having the following structure: ITO / m-MTDATA / α-NPD / mCP+Compound 1 (10 weight percent (wt%)) / BAlq / Alq 3 / LiF / Al

[0881]

[0882] Examples 2 to 4 and Comparative Examples R1 to R3

[0883] Light-emitting devices were manufactured in the same manner as in Example 1, except that the compounds shown in Table 3 were each used instead of Compound 1 when forming the emission layer.

[0884] Evaluation Example 2

[0885] For each of the light-emitting devices of Examples 1 to 4 and Comparative Examples R1 to R3, the emission peak wavelength (i.e., maximum emission peak wavelength), half width (FWHM), driving voltage, external quantum efficiency at 1,000 nits (EQE at 1,000 nits), and lifetime (LT at 1,000 nits) of the electroluminescence (EL) spectrum were evaluated. 95 ), and the results are shown in Table 3. Based on the EL spectrum measured by using a luminance meter (Minolta Cs-1000A), the emission peak wavelength and FWHM of the EL spectrum were evaluated for each light-emitting device. The driving voltage and EQE were evaluated by using a current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A). Lifespan (LT at 1,000 nits) 95 ) is the time (hours) required for the brightness to reach 95% of the initial brightness of 100%, and is expressed by converting the measured time into a relative value (%).

[0886] Table 3

[0887]

[0888]

[0889] As shown in Table 3, the light emitting devices of Examples 1 to 4 emitting blue light have improved driving voltage, improved EQE, and improved lifespan characteristics compared to the light emitting devices of Comparative Examples R1 to R3.

[0890] According to the one or more embodiments, the condensed ring compound can emit blue light having a relatively large oscillator strength and a relatively narrow FWHM, and thus an electronic device including the condensed ring compound, such as a light-emitting device, can have improved driving voltage, improved external quantum efficiency, and improved lifespan characteristics.

[0891] It should be understood that the embodiments described herein should be considered in a descriptive sense only and not for limiting purposes. The description of features or aspects in each embodiment should typically be considered to be applicable to other similar features or aspects in other embodiments. Although one or more embodiments have been described with reference to the accompanying drawings, it will be understood by those of ordinary skill in the art that various changes in form and detail may be made therein without departing from the spirit and scope as defined by the appended claims.

Claims

1. A condensed ring compound represented by Formula 1: Formula 1 in, In Formula 1, Ar0 is a group represented by Formula 2, Formula 2 Wherein, in formula 1 and 2, Ring Y1 to Ring Y3 are each independently C5-C 60 Carbocyclic group or C1-C 60 Heterocyclic group, W1 is a single bond, O, S, N(Ar1), N(T 11 )、C(T 12 )(T 13 ), or Si(T 12 )(T 13 ), W2 is a single bond, O, S, N(Ar2), N(T 21 )、C(T 22 )(T 23 ), or Si(T 22 )(T 23 ), n1 and n2 are each independently 0 or 1, When n1 is 0, *-(W1) n1 -*' does not exist, When n2 is 0, *-(W2) n2 -*' does not exist, The sum of n1 and n2 is 1 or greater, Ar1 and Ar2 are each a group represented by Formula 2, R0 is: hydrogen, deuterium, -F, or cyano; or C1-C2-substituted or substituted by deuterium, -F, cyano, or any combination thereof 60 alkyl, R1-R4 are each independently: hydrogen, deuterium, -F, or cyano; C1-C2-substituted or substituted by deuterium, -F, cyano, or any combination thereof 60 Alkyl; or Unsubstituted or deuterated, -F, cyano, C1-C 60 Alkyl, C6-C 60 Aryl, or any combination thereof substituted C6-C 60 Aryl, a1 is an integer from 0 to 3, a2 and a4 are each independently an integer of 0-4, a3 and m are each independently an integer of 0-5, The * in Formula 2 represents the binding site with the compound of Formula 1, Z1-Z3, T 11 -T 13 , and T 21 -T 23 Each is independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C1-C 60 Alkylthio, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C2-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), -P(Q8)(Q9), or a group represented by Formula 2, b1 and b2 are each independently an integer of 0-10, b3 is an integer from 1 to 5, Formula 1 satisfies at least one of conditions 1 and 2: Condition 1 b1 is 1 or more, and at least one of the b1-numbered Z1 includes a carbazole group; and Condition 2 b2 is 1 or more, and at least one of the b2 number of Z2 includes a carbazole group, At least one of the b3 Z3 is a C1-C1-C2-substituted group which is unsubstituted or substituted with deuterium, -F, cyano, or any combination thereof. 60 alkyl, Z1, Z2, Z3, T 11 , T 12 , T 13 , T 21 , T 22 and T 23 Two or more of are optionally linked together to form a substituted or unsubstituted C5-C 30 Carbocyclic group or substituted or unsubstituted C1-C 30 Heterocyclic groups, Substituted C5-C 30 Carbocyclic groups, substituted C1-C 30 Heterocyclic groups, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkynyl, substituted C1-C 60 Alkoxy, substituted C1-C 60 Alkylthio, substituted C3-C 10 Cycloalkyl, substituted C1-C 10 Heterocycloalkyl, substituted C3-C 10 Cycloalkenyl, substituted C2-C 10 Heterocycloalkenyl, substituted C6-C 60 Aryl, substituted C6-C 60 Aryloxy, substituted C6-C 60 Arylthio, substituted C1-C 60 At least one substituent of the heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group is: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, or C1-C 60 Alkylthio; C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, or C1-C 60 Alkylthio: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C2-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 11 )(Q 12 )、-Si(Q 13 )(Q 14 )(Q 15 )、-Ge(Q 13 )(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 )、-P(=O)(Q 18 )(Q 19 )、-P(Q 18 )(Q 19 ), or any combination thereof; C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C2-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C2-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 21 )(Q 22 )、-Si(Q 23 )(Q 24 )(Q 25 )、-Ge(Q 23 )(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 )、-P(=O)(Q 28 )(Q 29 )、-P(Q 28 )(Q 29 ), or any combination thereof; -N(Q 31 )(Q 32 )、-Si(Q 33 )(Q 34 )(Q 35 )、-Ge(Q 33 )(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 )、-P(=O)(Q 38 )(Q 39 )、or -P(Q 38 )(Q 39 ); or Any combination of these, and Q1-Q9, Q 11 -Q 19 , Q 21 -Q 29 , and Q 31 -Q 39 are independently: hydrogen; deuterium; -F; or C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C2-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, cyano, C1-C 60 Alkyl, C6-C 60 aryl, or any combination thereof.

2. The fused ring compound of claim 1, wherein Ring Y1 to Ring Y3 are each independently a phenyl group, a naphthyl group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a quinoline group, an isoquinoline group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group, a dibenzosilole group, an azadibenzofuran group, an azadibenzothiophene group, an azacarbazole group, an azafluorene group, or an azadibenzosilole group.

3. The fused ring compound according to claim 1, wherein n1 is 1, and W1 is N(Ar1) or N(T 11 ).

4. The fused ring compound according to claim 1, wherein R0 is: hydrogen, deuterium, -F, or cyano; or C1-C2-substituted or substituted by deuterium, -F, cyano, or any combination thereof 20 Alkyl, and R1-R4 are each independently: hydrogen, deuterium, -F, or cyano; C1-C2-substituted or substituted by deuterium, -F, cyano, or any combination thereof 20 Alkyl; or Unsubstituted or deuterated, -F, cyano, C1-C 20 Alkyl, phenyl, or phenyl substituted with any combination thereof.

5. The fused ring compound according to claim 1, wherein a2 is 1, and R2 is unsubstituted or substituted with deuterium, -F, cyano, C1-C 20 Alkyl, phenyl, or phenyl substituted with any combination thereof.

6. The fused ring compound according to claim 1, wherein Z1-Z3, T 11 -T 13 , and T 21 -T 23 Each independently is: hydrogen, deuterium, -F, or cyano; C1-C 20 Alkyl, phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, or dibenzothioyl: deuterium, -F, cyano, C1-C 20 Alkyl, phenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, dibenzothioyl, or any combination thereof; or -N(Q1)(Q2), and Q1 and Q2 are each independently C1-C2 which is unsubstituted or substituted as follows: 20 Alkyl, phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, or dibenzothioyl: deuterium, -F, cyano, C1-C 20 Alkyl, phenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, dibenzosilyl, or any combination thereof.

7. The fused ring compound according to claim 1, wherein b1 and b2 are each 1 or greater, and At least one of Z1 and Z2 is a group represented by Formula 3: Formula 3 in, In formula 3, Z 11 -Z 18 Each independently is: hydrogen, deuterium, -F, or cyano; C1-C2-substituted or substituted by deuterium, -F, cyano, or any combination thereof 20 Alkyl; or Unsubstituted or deuterated, -F, cyano, C1-C 20 Alkyl, phenyl, or phenyl substituted by any combination thereof, and * indicates the binding site with Formula 1.

8. The condensed ring compound according to claim 1, wherein the group represented by Formula 2 is a group represented by one of Formulas 2-1 to 2-3: in, In formulas 2-1 to 2-3, R0 as defined in claim 1, R 11 -R 13 Each as defined in claim 1 for R1, R 21 -R 24 Each as defined in claim 1 for R2, R 31 -R 35 each as defined in claim 1 for R3, and * indicates the binding site with Formula 1.

9. The fused ring compound according to claim 1, wherein the group represented by Formula 2 is a group represented by Formula 2-1(1): in, In formula 2-1(1), R0 as defined in claim 1, R 11 -R 13 Each as defined in claim 1 for R1, R 21 , R 23 , and R 24 Each as defined in claim 1 for R2, R 31 -R 35 Each as defined in claim 1 for R3, R 25 -R 29 Each independently is: hydrogen, deuterium, -F, or cyano; or C1-C2-substituted or substituted by deuterium, -F, cyano, or any combination thereof 20 Alkyl, and * indicates the binding site with Formula 1.

10. The fused ring compound according to claim 1, wherein the fused ring compound is represented by Formula 1A: Formula 1A in, In Formula 1A, W1 is O, S, N(Ar1), N(T 11 )、C(T 12 )(T 13 ), or Si(T 12 )(T 13 ), Ar0, Ar1, and T 11 -T 13 Each as defined in claim 1, Z 11 and Z 12 as defined in claim 1 for Z1, Z 21 and Z 22 as defined in claim 1 for Z2, Z 11 , Z 12 , Z 21 , and Z 22 At least one of them is unsubstituted or substituted with deuterium, -F, cyano, C1-C 20 an N-carbazolyl group substituted with an alkyl group, a phenyl group, or any combination thereof, and Z3 is C1-C2 which is unsubstituted or substituted by deuterium, -F, cyano, or any combination thereof. 20 alkyl.

11. The fused ring compound of claim 1, wherein the fused ring compound comprises at least one deuterium, at least one tert-butyl group, or any combination thereof.

12. A light emitting device comprising: a first electrode; a second electrode; as well as an intermediate layer disposed between the first electrode and the second electrode and including an emission layer, The intermediate layer comprises at least one condensed ring compound as claimed in any one of claims 1 to 11.

13. The light emitting device of claim 12, wherein the at least one condensed-cyclic compound is included in the emission layer. The light emitting device of claim 13 , wherein light emitted from the emission layer has an emission peak wavelength within a range of 440 nm to 470 nm.

15. The light emitting device of claim 13, wherein the at least one condensed-cyclic compound included in the emission layer is an emitter. 16 . The light emitting device of claim 13 , wherein the emission layer further comprises a sensitizer, and the sensitizer and the condensed-cyclic compound are different from each other. 17 . The light emitting device of claim 16 , wherein the sensitizer is an organic metal compound, a delayed fluorescent material, a transient fluorescent material, or any combination thereof.

18. The light emitting device according to claim 17, wherein The organometallic compound includes a transition metal and a tetradentate ligand bonded to the transition metal, The transition metal is platinum or palladium, and The tetradentate ligand includes a carbene moiety bonded to the transition metal.

19. The light emitting device of claim 13, wherein the at least one condensed-cyclic compound included in the emission layer is a sensitizer.

20. An electronic device comprising the light emitting device according to any one of claims 12 to 19.

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