Light-emitting device including fused ring compound, electronic device including light-emitting device, and fused ring compound

Abstract

Embodiments provide a fused ring compound, a light-emitting device including the fused ring compound, and an electronic device including the light-emitting device. The light emitting device includes a first electrode, a second electrode facing the first electrode, and an interlayer between the first electrode and the second electrode and including an emission layer, wherein the interlayer includes a fused ring compound. The fused ring compound includes boron (B) atoms, the ratio of surface area to volume of the fused ring compound has a value less than or equal to about # imgabs0 #, and the molecular weight of the fused ring compound is greater than or equal to about 1,000 g / mol.

Description

[0001] Cross - reference to related applications

[0002] This application claims the priority and benefit of Korean Patent Application No. 10 - 2023 - 0197604, filed with the Korean Intellectual Property Office on December 29, 2023, the entire contents of which are incorporated herein by reference. Technical field

[0003] Embodiments relate to a light - emitting device including a polycyclic compound, an electronic device including the light - emitting device, and a polycyclic compound. Background art

[0004] Compared with the devices of the prior art, a light - emitting device is a self - emitting device having a wide viewing angle, high contrast, short response time, and excellent characteristics in terms of brightness, driving voltage, and response speed, and generates a full - color image.

[0005] A light - emitting device may have the following structure, in which a first electrode is located on a substrate, and a hole - transport region, an emission layer, an electron - transport region, and a second electrode may be sequentially formed on the first electrode. Holes provided from the first electrode may move through the hole - transport region toward the emission layer, and electrons provided from the second electrode may move through the electron - transport region toward the emission layer. Charge carriers, such as holes and electrons, recombine in the emission layer to generate excitons. These excitons may transition from an excited state to a ground state, thereby generating light.

[0006] It should be understood that this background - art section is intended in part to provide useful background for understanding the technology. However, this background - art section may also include ideas, concepts, or knowledge that were not known or understood by those skilled in the relevant art before the effective filing date of the corresponding application for the subject matter disclosed herein. Summary of the invention

[0007] Embodiments include: a light - emitting device including a polycyclic compound, an electronic device including the light - emitting device, and a polycyclic compound.

[0008] Additional aspects will be set forth in part in the following description, and in part will be obvious from the description, or may be learned by practice of the embodiments of the present disclosure.

[0009] According to an embodiment, a light - emitting device may include:

[0010] A first electrode, a second electrode facing the first electrode, and a laminate between the first electrode and the second electrode and including an emission layer, wherein

[0011] The laminate may include a polycyclic compound,

[0012] The polycyclic compound may include a boron (B) atom,

[0013] The ratio of the surface area to the volume of the polycyclic compound may be less than or equal to about a value, and

[0014] the molecular weight of the polycyclic compound may be greater than or equal to about 1,000 g / mol.

[0015] In an embodiment, the first electrode may be an anode; the second electrode may be a cathode; the interlayer may further include a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode; the hole transport region may include a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, or any combination thereof; and the electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0016] In an embodiment, the emission layer may include a polycyclic compound.

[0017] In an embodiment, the polycyclic compound in the emission layer may be a thermally activated delayed fluorescence (TADF) emitter; and the emission layer may emit delayed fluorescence.

[0018] In an embodiment, the light-emitting device may include: a first compound including a polycyclic compound; and a second compound including a group represented by Formula 20, a third compound including at least one π-deficient nitrogen-containing C1-C 60 cyclic group, a fourth compound including a transition metal, or any combination thereof, wherein

[0019] the first compound, the second compound, the third compound, and the fourth compound may be different from each other, and Formula 20 is explained below.

[0020] In an embodiment, the emission layer may include: a first compound including a polycyclic compound, and at least one of a second compound and a third compound; and the emission layer may optionally further include a fourth compound.

[0021] In an embodiment, the third compound may include a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, or any combination thereof.

[0022] According to an embodiment, the electronic device may include a light-emitting device.

[0023] In an embodiment, the electronic device may further include a thin film transistor, wherein the thin film transistor may include a source electrode and a drain electrode, and the first electrode of the light-emitting device may be electrically connected to the source electrode or the drain electrode.

[0024] According to an embodiment, the polycyclic compound may include: a nucleus including at least one cyclic group, the cyclic group including boron (B) atoms and nitrogen (N) atoms each as ring-forming atoms, wherein

[0025] The ratio of the surface area to the volume of the polycyclic compound may be less than or equal to about and

[0026] the molecular weight of the polycyclic compound may be greater than or equal to about 1,000 g / mol.

[0027] In an embodiment, the sublimation temperature of the polycyclic compound may be less than or equal to about 370 °C.

[0028] In an embodiment, at least one hydrogen atom of the nucleus of the polycyclic compound may be substituted with a substituent having a molecular weight of greater than or equal to about 153 g / mol.

[0029] In an embodiment, the nucleus may include at least two nitrogen (N) atoms, and at least one of the at least two nitrogen atoms may be linked to a substituent having a molecular weight of greater than or equal to about 153 g / mol.

[0030] In an embodiment, the substituent having a molecular weight of greater than or equal to about 153 g / mol may include a group represented by formula A, which is explained below.

[0031] In an embodiment, the nucleus may include a boron (B) atom and at least two nitrogen (N) atoms, and at least one of the at least two nitrogen (N) atoms may be linked to a substituent having a molecular weight of greater than or equal to about 153 g / mol and including two or more rings.

[0032] In an embodiment, among the above substituents, two or more rings may each independently be an unsubstituted or R 10a -substituted C6-C 60 aryl, an unsubstituted or R 10a -substituted C1-C 60 heteroaryl, an unsubstituted or R 10a -substituted non-aromatic fused polycyclic group or an unsubstituted or R 10a -substituted non-aromatic fused heteropolycyclic group, where R 10a is explained below.

[0033] In an embodiment, the polycyclic compound may be represented by formula 1, which is explained below.

[0034] In an embodiment, Ar2 may be a group represented by formula B, which is explained below.

[0035] In an embodiment, Ar 11 and Ar 12 may each independently be a C6-C 60 aryl, a C1-C 60 heteroaryl, a non-aromatic fused polycyclic group or a non-aromatic fused heteropolycyclic group.

[0036] In an embodiment, a1 to a3 may each independently be an integer selected from 1 to 10; at least one of R1 in the amount of a1 may not be hydrogen; at least one of R2 in the amount of a2 may not be hydrogen; and at least one of R3 in the amount of a3 may not be hydrogen.

[0037] It should be understood that the above embodiments are described only in a general and illustrative sense and not for the purpose of limitation, and the present disclosure is not limited to the above embodiments. BRIEF DESCRIPTION OF THE DRAWINGS

[0038] The accompanying drawings are included to provide a further understanding of the embodiments, and the accompanying drawings are incorporated in and constitute a part of this specification. The drawings illustrate embodiments of the present disclosure and their principles. By referring to the accompanying drawings, the above and other aspects and features of the present disclosure will become more apparent, wherein:

[0039] Figure 1 is a schematic cross-sectional view of a light-emitting device according to an embodiment;

[0040] Figure 2 is a schematic cross-sectional view of an electronic device according to an embodiment;

[0041] Figure 3 is a schematic cross-sectional view of an electronic device according to another embodiment;

[0042] Figure 4 is a schematic perspective view of an electronic apparatus including a light-emitting device according to an embodiment;

[0043] Figure 5 is a schematic perspective view of the exterior of a vehicle as an electronic apparatus including a light-emitting device according to an embodiment; and

[0044] Figures 6A to 6C are each a schematic view of the interior of a vehicle according to various embodiments. DETAILED DESCRIPTION OF THE EMBODIMENTS

[0045] The present disclosure will now be described more fully hereinafter with reference to the accompanying drawings, in which embodiments are shown. However, the present disclosure may be embodied in different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the scope of the present disclosure to those skilled in the art.

[0046] In the drawings, for ease of description and for clarity, the dimensions (e.g., thickness), ratios, and dimensions of elements may be enlarged. The same reference numerals and / or the same reference characters refer to the same elements throughout.

[0047] In the description, it will be understood that when an element (or region, layer, portion, etc.) is referred to as being "on", "connected to", or "coupled to" another element (or region, layer, portion, etc.), it can be directly on, connected to, or coupled to the other element (or region, layer, portion, etc.), or there can be one or more intervening elements (or regions, layers, portions, etc.) between them. In a similar sense, when an element (or region, layer, portion, etc.) is described as "covering" another element (or region, layer, portion, etc.), it can directly cover the other element (or region, layer, portion, etc.), or there can be one or more intervening elements (or regions, layers, portions, etc.) between them.

[0048] In the description, when an element is "directly on", "directly connected to", or "directly coupled to" another element, there is no intervening element. For example, "directly on" can mean that two layers or two elements are arranged with no additional element (such as an adhesive element) between them.

[0049] As used herein, expressions used in the singular form, such as "a", "an", and "the", are intended to also include the plural form, unless the context clearly indicates otherwise.

[0050] As used herein, the term "and / or" includes any and all combinations of one or more of the associated listed items. For example, "A and / or B" can be understood to mean "A, B, or A and B". The terms "and" and "or" can be used in a conjunctive or disjunctive sense and can be understood to be equivalent to "and / or".

[0051] In the specification and claims, for purposes of their meaning and interpretation, the term "at least one of..." is intended to include the meaning of "at least one selected from the group consisting of...". For example, "at least one of A, B, and C" can be understood to mean only A, only B, only C, or any combination of two or more of A, B, and C, such as ABC, ACC, BC, or CC. When following a list of elements, the term "at least one of..." modifies the entire list of elements, rather than individual elements of the list.

[0052] It will be understood that although terms such as first, second, etc. may be used herein to describe various elements, these elements should not be limited by these terms. These terms are only used to distinguish one element from another. Thus, without departing from the teachings of the present disclosure, the first element can be referred to as the second element. Similarly, without departing from the scope of the present disclosure, the second element can be referred to as the first element.

[0053] For ease of description, spatial relative terms such as "below", "beneath", "under", "above", or "over" may be used herein to describe the relationship between one element or component and another element or component as illustrated in the figures. It will be understood that the spatial relative terms are intended to encompass different orientations of the device in use or operation in addition to the orientation depicted in the figures. For example, if the device illustrated in the figures is turned over, a device that is "below" or "beneath" another device may be positioned "above" the other device. Accordingly, the illustrative term "below" can include both a lower position and an upper position. The device may also be oriented in other directions and thus the spatial relative terms may be interpreted differently depending on the orientation.

[0054] As used herein, the term "about" or "approximate" includes the recited value and means within an acceptable deviation range of the recited value as determined by one of ordinary skill in the art in view of the measurements discussed and the error associated with the measurement of the recited quantity (e.g., the limitations of the measurement system). For example, "about" can mean within one or more standard deviations of the recited value, or within ±20%, ±10%, or ±5% of the recited value.

[0055] It should be understood that the terms "comprise", "comprising", "include", "including", "have", "having", "contains", and "containing" and the like are intended to indicate the presence of the recited features, integers, steps, operations, elements, components, or any combination thereof in the present disclosure, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or any combination thereof.

[0056] Unless otherwise defined or implied herein, all terms (including technical and scientific terms) used have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure pertains. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the relevant art and should not be interpreted in an idealized or overly formal sense unless clearly defined in the specification.

[0057] In an embodiment, a light-emitting device (e.g., an organic light-emitting device) may include: a first electrode; a second electrode facing the first electrode; and a sandwich layer between the first electrode and the second electrode and including an emission layer, wherein the sandwich layer may include a polycyclic compound.

[0058] Hereinafter, the polycyclic compound will be described.

[0059] In an embodiment, the ratio of the surface area to the volume of the polycyclic compound may be less than or equal to about value

[0060] The value of the ratio of the surface area to the volume of the polycyclic compound can be calculated by using the program Material Studio 2018 with reference to the method for calculating the molecular surface area described in J. Appl. Cryst. (1983), 16, 548 - 558.

[0061] According to an embodiment, the ratio of the surface area to the volume of the polycyclic compound can be less than or equal to about value. For example, the ratio of the surface area to the volume of the polycyclic compound can be less than or equal to about value. For example, the ratio of the surface area to the volume of the polycyclic compound can be less than or equal to about value. For example, the ratio of the surface area to the volume of the polycyclic compound can be less than or equal to about value

[0062] In an embodiment, the molecular weight of the polycyclic compound can be greater than or equal to about 1,000 g / mol.

[0063] According to an embodiment, the molecular weight of the polycyclic compound can be greater than or equal to about 1,010 g / mol. For example, the molecular weight of the polycyclic compound can be greater than or equal to about 1,020 g / mol. For example, the molecular weight of the polycyclic compound can be greater than or equal to about 1,030 g / mol. For example, the molecular weight of the polycyclic compound can be greater than or equal to about 1,040 g / mol. For example, the molecular weight of the polycyclic compound can be greater than or equal to about 1,050 g / mol.

[0064] The smaller the value of the ratio of the surface area to the volume of the molecule (i.e., surface area divided by volume), the closer the shape of the molecule is to the form of a sphere. In an embodiment, the compound can have the following shape, where the substituents of the compound surround and protect the nucleus, such that, for example, when the nucleus of the compound includes a boron (B) atom, the substituents can protect the empty p - orbital of boron, thus increasing the stability of the compound.

[0065] In an embodiment, even when the ratio of the surface area to the volume of the compound has a small value, when the molecular weight of the compound is less than about 1,000 g / mol, the substituents of the compound are not large enough and the substituents do not exist at the protective positions of the nucleus, so the effect of the substituents protecting the nucleus is reduced.

[0066] The smaller the value of the ratio of the surface area to the volume of the molecule, the smaller the surface area of the molecule, which means that the distance between the central core and the outermost part of the molecule can be increased. As the surface area of the molecule decreases, the number of surrounding molecules that can interact with each other decreases, and as the distance between the central core and the outermost part of the molecule increases, the distance between the molecules also increases. Therefore, the interaction with adjacent molecules can be reduced, and thus π-π stacking and Dexter energy transfer (DET) between molecules can be reduced, and the sublimation temperature can also be reduced.

[0067] A light-emitting device including such a polycyclic compound may have improved luminous efficiency and lifetime characteristics.

[0068] In an embodiment, the sublimation temperature of the polycyclic compound may be less than or equal to about 370 °C.

[0069] The sublimation temperature of the polycyclic compound may be a value measured by sublimating 1 g of the polycyclic compound.

[0070] According to an embodiment, the sublimation temperature of the polycyclic compound may be less than or equal to about 370 °C. For example, the sublimation temperature of the polycyclic compound may be less than or equal to about 365 °C. For example, the sublimation temperature of the polycyclic compound may be less than or equal to about 360 °C. For example, the sublimation temperature of the polycyclic compound may be less than or equal to about 355 °C. For example, the sublimation temperature of the polycyclic compound may be less than or equal to about 350 °C.

[0071] In an embodiment, the polycyclic compound may include a boron (B) atom.

[0072] According to an embodiment, the polycyclic compound may include: a core including at least one cyclic group, the cyclic group including boron (B) atoms and nitrogen (N) atoms each as ring-forming atoms.

[0073] According to an embodiment, at least one hydrogen atom of the core of the polycyclic compound may be substituted with a substituent having a molecular weight of greater than or equal to about 153 g / mol.

[0074] According to an embodiment, the core may include at least two nitrogen (N) atoms, and at least one of the at least two nitrogen atoms may be connected to a substituent having a molecular weight of greater than or equal to about 153 g / mol.

[0075] According to an embodiment, the substituent having a molecular weight of greater than or equal to about 153 g / mol may include a group represented by formula A:

[0076] [Formula A]

[0077]

[0078] In formula A,

[0079] Ar 11and Ar 12 may each independently be a C3-C 60 carbocyclic group or a C1-C 60 heterocyclic group,

[0080] Z1 and Z2 may each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, an unsubstituted or at least one R 10a substituted C1-C 60 alkyl group, an unsubstituted or at least one R 10a substituted C2-C 60 alkenyl group, an unsubstituted or at least one R 10a substituted C2-C 60 alkynyl group, an unsubstituted or at least one R 10a substituted C1-C 60 alkoxy group, an unsubstituted or at least one R 10a substituted C1-C 60 alkylthio group, an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group, an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group, an unsubstituted or at least one R 10a substituted C6-C 60 aryloxy group, an unsubstituted or at least one R 10a substituted C6-C 60 arylthio group, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2),

[0081] Two or more adjacent groups among those of Z1 in number b1 may optionally bond to each other to form an unsubstituted or at least one R 10b substituted C5-C 30 carbocyclic group or an unsubstituted or at least one R 10b substituted C1-C 30 heterocyclic group,

[0082] Two or more adjacent groups among those of Z2 in number b2 may optionally bond to each other to form an unsubstituted or at least one R 10b substituted C5-C 30 carbocyclic group or an unsubstituted or at least one R 10b substituted C1-C 30 heterocyclic group,

[0083] Two or more adjacent groups of Z1 in the amount of b1 and Z2 in the amount of b2 may optionally be bonded to each other to form an unsubstituted or at least one R 10b substituted C5-C 30 carbocyclic group or an unsubstituted or at least one R 10b substituted C1-C 30 heterocyclic group,

[0084] b1 and b2 may each independently be an integer selected from 0 to 10,

[0085] * indicates the binding site to an adjacent atom, and

[0086] R 10a 、R 10b and Q1 to Q3 may each be the same as described herein.

[0087] According to another embodiment, the core may include a boron (B) atom and at least two nitrogen (N) atoms, and

[0088] at least one of the at least two nitrogen (N) atoms may be linked to a substituent that may have a molecular weight of greater than or equal to about 153 g / mol and may include two or more rings.

[0089] According to another embodiment, in the substituent, two or more rings may each independently be an unsubstituted or at least one R 10a substituted C6-C 60 aryl, an unsubstituted or at least one R 10a substituted C1-C 60 heteroaryl, an unsubstituted or at least one R 10a substituted non-aromatic fused polycyclic group or an unsubstituted or at least one R 10a substituted non-aromatic fused heteropolycyclic group. R 10a may be the same as described herein.

[0090] In an embodiment, in the substituent, two or more rings may each independently be each unsubstituted or at least one R 10aSubstituted phenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, pyrenyl, 1,2-benzophenanthryl, cyclopentadienyl, 1,2,3,4-tetrahydronaphthyl, thienyl, furyl, indolyl, benzoborolyl, benzophospholyl, indenyl, benzosilolyl, benzogermolyl, benzothienyl, benzoselenophenyl, benzofuryl, carbazolyl, dibenzoborolyl, dibenzophospholyl, fluorenyl, dibenzosilolyl, dibenzogermolyl, dibenzothienyl, dibenzoselenophenyl, dibenzofuryl, dibenzothiophen-5-oxide group, 9H-fluoren-9-one group, dibenzothiophene-5,5-dioxide group, azaindolyl, azabenzoborolyl, azabenzophospholyl, azaindenyl, azabenzosilolyl, azabenzogermolyl, azabenzothienyl, azabenzoselenophenyl, azabenzofuryl, azacarbazolyl, azadibenzoborolyl, azadibenzophospholyl, azafuorenyl, azadibenzosilolyl, azadibenzogermolyl, azadibenzothienyl, azadibenzoselenophenyl, azadibenzofuryl, azadibenzothiophen-5-oxide group, aza-9H-fluoren-9-one group, azadibenzothiophene-5,5-dioxide group, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, 5,6,7,8-tetrahydroisoquinolinyl or 5,6,7,8-tetrahydroquinolinyl.

[0091] According to an embodiment, at least one hydrogen of the polycyclic compound may be substituted with deuterium.

[0092] According to an embodiment, the polycyclic compound may be represented by Formula 1:

[0093] [Formula 1]

[0094]

[0095] In Formula 1, Ring CY1 to Ring CY3, Ar 11 and Ar 12 may each independently be a C3-C 60 carbocyclic group or a C1-C 60 heterocyclic group.

[0096] According to an embodiment, Ar 11 and Ar 12 may each independently be a C6-C 60 aryl group, a C1-C 60Heteroaryl, non-aromatic fused polycyclic group or non-aromatic fused heteropolycyclic group.

[0097] According to an embodiment, ring CY1 to ring CY3, Ar 11 and Ar 12 may each independently be phenyl, naphthyl, anthracenyl, phenanthryl, triphenylenyl, pyrenyl, 1,2-benzophenanthryl, cyclopentadienyl, 1,2,3,4-tetrahydronaphthyl, thienyl, furyl, indolyl, benzoborolyl, benzophospholyl, indenyl, benzosilolyl, benzogermolyl, benzothienyl, benzoselenophenyl, benzofuryl, carbazolyl, dibenzoborolyl, dibenzophospholyl, fluorenyl, dibenzosilolyl, dibenzogermolyl, dibenzothienyl, dibenzoselenophenyl, dibenzofuryl, dibenzothiophen-5-oxide group, 9H-fluoren-9-one group, dibenzothiophene-5,5-dioxide group, azaindolyl, azabenzoborolyl, azabenzophospholyl, azaindenyl, azabenzosilolyl, azabenzogermolyl, azabenzothienyl, azabenzoselenophenyl, azabenzofuryl, azacarbazolyl, azadibenzoborolyl, azadibenzophospholyl, azafuorenyl, azadibenzosilolyl, azadibenzogermolyl, azadibenzothienyl, azadibenzoselenophenyl, azadibenzofuryl, azadibenzothiophen-5-oxide group, aza-9H-fluoren-9-one group, azadibenzothiophene-5,5-dioxide group, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, 5,6,7,8-tetrahydroisoquinolinyl or 5,6,7,8-tetrahydroquinolinyl.

[0098] In formula 1, Ar2 may be an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group. R 10a may be the same as described herein.

[0099] According to an embodiment, Ar2 may each be unsubstituted or at least one R 10aSubstituted phenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, pyrenyl, 1,2-benzophenanthryl, cyclopentadienyl, 1,2,3,4-tetrahydronaphthyl, thienyl, furyl, indolyl, benzoborolyl, benzophospholyl, indenyl, benzosilolyl, benzogermanolyl, benzothienyl, benzoselenophenyl, benzofuryl, carbazolyl, dibenzoborolyl, dibenzophospholyl, fluorenyl, dibenzosilolyl, dibenzogermanolyl, dibenzothienyl, dibenzoselenophenyl, dibenzofuryl, dibenzothiophen-5-oxide group, 9H-fluoren-9-one group, dibenzothiophene-5,5-dioxide group, azaindolyl, azabenzoborolyl, azabenzophospholyl, azaindenyl, azabenzosilolyl, azabenzogermanolyl, azabenzothienyl, azabenzoselenophenyl, azabenzofuryl, azacarbazolyl, azadibenzoborolyl, azadibenzophospholyl, azafuorenyl, azadibenzosilolyl, azadibenzogermanolyl, azadibenzothienyl, azadibenzoselenophenyl, azadibenzofuryl, azadibenzothiophen-5-oxide group, aza-9H-fluoren-9-one group, azadibenzothiophene-5,5-dioxide group, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, 5,6,7,8-tetrahydroisoquinolinyl or 5,6,7,8-tetrahydroquinolinyl.

[0100] According to an embodiment, Ar2 may be a group represented by formula B:

[0101] [Formula B]

[0102]

[0103] In formula B,

[0104] Ar 13 and Ar 14 may each independently be a C3-C 60 carbocyclic group or a C1-C 60 heterocyclic group,

[0105] Z3 and Z4 may each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, an unsubstituted or at least one R 10a substituted C1-C 60 alkyl, an unsubstituted or at least one R 10a substituted C2-C 60Alkenyl, unsubstituted or substituted by at least one R 10a Substituted C2-C 60 Alkynyl, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Alkoxy, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Alkylthio, unsubstituted or substituted by at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted by at least one R 10a Substituted C6-C 60 Aryloxy, unsubstituted or substituted by at least one R 10a Substituted C6-C 60 Arylthio, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2),

[0106] Two or more adjacent groups in Z3 of number b3 may optionally be bonded to each other to form an unsubstituted or at least one R 10b Substituted C5-C 30 Carbocyclic group or unsubstituted or at least one R 10b Substituted C1-C 30 Heterocyclic group,

[0107] Two or more adjacent groups in Z4 of number b4 may optionally be bonded to each other to form an unsubstituted or at least one R 10b Substituted C5-C 30 Carbocyclic group or unsubstituted or at least one R 10b Substituted C1-C 30 Heterocyclic group,

[0108] Two or more adjacent groups in Z3 of number b3 and Z4 of number b4 may optionally be bonded to each other to form an unsubstituted or at least one R 10b Substituted C5-C 30 Carbocyclic group or unsubstituted or at least one R 10b Substituted C1-C 30 Heterocyclic group,

[0109] b3 and b4 can each independently be an integer selected from 0 to 10,

[0110] * indicates the binding site to the adjacent atom, and

[0111] R 10a 、R 10b and Q1 to Q3 can be the same as those described herein.

[0112] According to an embodiment, Ar 13 and Ar 14 can each independently be C6-C 60 aryl, C1-C 60 heteroaryl, non-aromatic fused polycyclic group or non-aromatic fused heteropolycyclic group.

[0113] In Formula 1, R1 to R3, Z1 and Z2 can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, unsubstituted or substituted by at least one R 10a substituted C1-C 60 alkyl, unsubstituted or substituted by at least one R 10a substituted C2-C 60 alkenyl, unsubstituted or substituted by at least one R 10a substituted C2-C 60 alkynyl, unsubstituted or substituted by at least one R 10a substituted C1-C 60 alkoxy, unsubstituted or substituted by at least one R 10a substituted C1-C 60 alkylthio, unsubstituted or substituted by at least one R 10a substituted C3-C 60 carbocyclic group, unsubstituted or substituted by at least one R 10a substituted C1-C 60 heterocyclic group, unsubstituted or substituted by at least one R 10a substituted C6-C 60 aryloxy, unsubstituted or substituted by at least one R 10a substituted C6-C 60 arylthio, unsubstituted or substituted by at least one R 10a substituted C7-C 60 aralkyl, -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2). R 10a and Q1 to Q3 can each be the same as those described herein.

[0114] According to an embodiment, R1 to R3, Z1 and Z2 can each independently be:

[0115] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C1-C 20 alkyl or C1-C20 alkoxy group;

[0116] C1-C each substituted with at least one of the following 20 alkyl group or C1-C 20 alkoxy group: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 10 alkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, naphthyl group, pyridyl group and pyrimidinyl group;

[0117] cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, 1,2,3,4-tetrahydronaphthyl group, phenyl group, biphenyl group, (C1-C 10 alkyl) phenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthryl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, 1,2-benzophenanthryl group, pyrrolyl group, thienyl group, furyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, carbazolyl group, phenanthrolinyl group, benzimidazolyl group, benzofuryl group, benzothienyl group, benzisothiazolyl group, benzoxazolyl group, benzisoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuryl group, dibenzothienyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridyl group, imidazopyrimidinyl group, azacarbazolyl group, azadibenzofuryl group, azadibenzothienyl group, azafuryl group or azadibenzosilolyl group, each unsubstituted or substituted with at least one of the following: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy group, cyano group, nitro group, C1-C 20 alkyl group, C1-C 20 alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, 1,2,3,4-tetrahydronaphthyl group, phenyl group, biphenyl group, (C1-C 10alkyl)phenyl, naphthyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2-benzophenanthryl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuryl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuryl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -P(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ) and -P(=O)(Q 31 )(Q 32 ); or

[0118] -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2), and

[0119] Q1 to Q3 and Q 31 to Q 33 can each independently be:

[0120] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H or -CD2CDH2; or

[0121] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, naphthyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or triazinyl, each unsubstituted or substituted by at least one of the following: deuterium, C1-C 10 alkyl, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl and triazinyl.

[0122] According to an embodiment, R1 to R3, Z1, and Z2 may each independently be:

[0123] hydrogen, deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, or C1-C 60 alkoxy; or

[0124] a group represented by any one of Formulae 9-1 to 9-61, Formulae 9-201 to 9-240, Formulae 10-1 to 10-129, and Formulae 10-201 to 10-355:

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134] In Formulae 9-1 to 9-61, Formulae 9-201 to 9-240, Formulae 10-1 to 10-129, and Formulae 10-201 to 10-355, * indicates a binding site to an adjacent atom, Ph may be a phenyl group, D may be a deuterium atom, TMS may be a trimethylsilyl group, and TMG may be a trimethylgermyl group.

[0135] In Formula 1, two or more adjacent groups among the a1 number of R1s may optionally bond to each other to form an unsubstituted or at least one R 10b substituted C5-C 30 carbocyclic group or an unsubstituted or at least one R 10b substituted C1-C 30 heterocyclic group.

[0136] In Formula 1, two or more adjacent groups in R2 with a quantity of a2 may optionally be bonded to each other to form an unsubstituted or at least one R 10b substituted C5-C 30 carbocyclic group or an unsubstituted or at least one R 10b substituted C1-C 30 heterocyclic group.

[0137] In Formula 1, two or more adjacent groups in R3 with a quantity of a3 may optionally be bonded to each other to form an unsubstituted or at least one R 10b substituted C5-C 30 carbocyclic group or an unsubstituted or at least one R 10b substituted C1-C 30 heterocyclic group.

[0138] In Formula 1, two or more adjacent groups in Z1 with a quantity of b1 may optionally be bonded to each other to form an unsubstituted or at least one R 10b substituted C5-C 30 carbocyclic group or an unsubstituted or at least one R 10b substituted C1-C 30 heterocyclic group.

[0139] In Formula 1, two or more adjacent groups in Z2 with a quantity of b2 may optionally be bonded to each other to form an unsubstituted or at least one R 10b substituted C5-C 30 carbocyclic group or an unsubstituted or at least one R 10b substituted C1-C 30 heterocyclic group.

[0140] In Formula 1, two or more adjacent groups in Z1 with a quantity of b1 and Z2 with a quantity of b2 may optionally be bonded to each other to form an unsubstituted or at least one R 10b substituted C5-C 30 carbocyclic group or an unsubstituted or at least one R 10b substituted C1-C 30 heterocyclic group.

[0141] R 10b may be the same as described herein.

[0142] In Formula 1, a1 to a3, b1, and b2 may each independently be an integer selected from 0 to 10.

[0143] According to an embodiment, in Formula 1, a1 to a3 may each independently be an integer selected from 1 to 10, and

[0144] At least one of R1 in the amount of a1 may not be hydrogen, at least one of R2 in the amount of a2 may not be hydrogen, and at least one of R3 in the amount of a3 may not be hydrogen.

[0145] According to an embodiment, the condensed ring compound may be represented by any one of Formula 1-1, Formula 1-2, and Formula 1-3:

[0146] [Formula 1-1]

[0147]

[0148] [Formula 1-2]

[0149]

[0150] [Formula 1-3]

[0151]

[0152] In Formulas 1-1 to 1-3,

[0153] Y1 may be O, S, or N(Ar3), and Y2 may be O, S, or N(Ar4),

[0154] Y3 may be O, S, or N(Ar5), and Y4 may be O, S, or N(Ar6),

[0155] Ar3 to Ar6 may each be unsubstituted or substituted with at least one R 10a substituted C3-C 60 carbocyclic group or unsubstituted or substituted with at least one R 10a substituted C1-C 60 heterocyclic group,

[0156] Ar2, Ar 11 、Ar 12 、Z1, Z2, b1, b2, R1 to R3, and R 10a may each be the same as described for Formula 1, and R4 to R7 may each independently be the same as described for R1 in Formula 1,

[0157] Two or more adjacent groups of R4 in the amount of a4 may optionally be bonded to each other to form an unsubstituted or R-substituted 10b substituted C5-C 30 carbocyclic group or unsubstituted or R-substituted 10b substituted C1-C 30 heterocyclic group,

[0158] Two or more adjacent groups of R5 in the amount of a5 may optionally be bonded to each other to form an unsubstituted or R-substituted 10b substituted C5-C30 a carbocyclic group or an unsubstituted or at least one R- 10b substituted C1-C 30 heterocyclic group,

[0159] Two or more adjacent groups among the a6 R6 groups may optionally be bonded to each other to form an unsubstituted or at least one R- 10b substituted C5-C 30 a carbocyclic group or an unsubstituted or at least one R- 10b substituted C1-C 30 heterocyclic group,

[0160] Two or more adjacent groups among the a7 R7 groups may optionally be bonded to each other to form an unsubstituted or at least one R- 10b substituted C5-C 30 a carbocyclic group or an unsubstituted or at least one R- 10b substituted C1-C 30 heterocyclic group,

[0161] R 10b may be the same as described for Formula 1,

[0162] In Formula 1-1, a1 and a2 may each independently be an integer selected from 0 to 4, and a3 may be an integer selected from 0 to 3,

[0163] In Formula 1-2, a1 may be 0 or 1, a2, a4 and a5 may each independently be an integer selected from 0 to 4, and a3 may be an integer selected from 0 to 3, and

[0164] In Formula 1-3, a1 and a7 may each independently be an integer selected from 0 to 4, a3 and a6 may each independently be an integer selected from 0 to 3, and a2 may be an integer selected from 0 to 2.

[0165] According to an embodiment, Y1 and Y2 in Formula 1-2 may be the same as each other.

[0166] According to an embodiment, Y1 and Y2 in Formula 1-2 may be different from each other.

[0167] According to an embodiment, Y3 and Y4 in Formula 1-3 may be the same as each other.

[0168] According to an embodiment, Y3 and Y4 in Formula 1-3 may be different from each other.

[0169] According to an embodiment, the fused-ring compound may be any one of Compound 1 to Compound 32:

[0170]

[0171]

[0172]

[0173] Those of ordinary skill in the art can identify the synthesis methods of polycyclic compounds by referring to the synthesis examples and / or embodiments provided below.

[0174] According to an embodiment,

[0175] The first electrode of the light-emitting device may be an anode,

[0176] The second electrode of the light-emitting device may be a cathode,

[0177] The interlayer may further include a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode,

[0178] The hole transport region may include a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, or any combination thereof, and

[0179] The electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0180] According to another embodiment, the polycyclic compound represented by Formula 1 may be included between the first electrode and the second electrode of the light-emitting device. Accordingly, the interlayer of the light-emitting device may include the polycyclic compound represented by Formula 1. For example, in an embodiment, the emission layer of the interlayer may include the polycyclic compound represented by Formula 1.

[0181] According to another embodiment, the polycyclic compound represented by Formula 1 in the emission layer may be a thermally activated delayed fluorescence (TADF) emitter, and the emission layer may emit delayed fluorescence. The emission layer may emit red light, green light, blue light, and / or white light. For example, the emission layer may emit blue light. The blue light may have a maximum emission wavelength in the range of about 400 nm to about 490 nm. For example, the blue light may have a maximum emission wavelength in the range of about 420 nm to about 480 nm. For example, the blue light may have a maximum emission wavelength in the range of about 430 nm to about 480 nm. The emission layer may further include a host, and the amount of the host may be greater than the amount of the polycyclic compound represented by Formula 1.

[0182] According to another embodiment, the light-emitting device may include a capping layer outside the first electrode and / or outside the second electrode.

[0183] For example, the light-emitting device may further include at least one of a first capping layer outside the first electrode and a second capping layer outside the second electrode, and at least one of the first capping layer and the second capping layer may include the polycyclic compound represented by Formula 1. The first capping layer and / or the second capping layer may be the same as those described herein.

[0184] As used herein, the phrase “(the interlayer and / or the capping layer) may include a polycyclic compound represented by Formula 1” can be understood as “(the interlayer and / or the capping layer) may include one kind of polycyclic compound represented by Formula 1 or two or more different kinds of polycyclic compounds each represented by Formula 1”.

[0185] In an embodiment, the interlayer and / or the capping layer may include only Compound 1 as the polycyclic compound represented by Formula 1. In an embodiment, Compound 1 may be present in the emission layer of the light-emitting device. In another embodiment, the interlayer may include Compound 1 and Compound 2 as the polycyclic compounds represented by Formula 1. In an embodiment, Compound 1 and Compound 2 may be present in the same layer (e.g., all of Compound 1 and Compound 2 may be present in the emission layer), or may be present in different layers (e.g., Compound 1 may be present in the emission layer and Compound 2 may be present in the electron transport region).

[0186] As used herein, the term “interlayer” refers to a single layer and / or multiple layers located between the first electrode and the second electrode of the light-emitting device.

[0187] According to an embodiment,

[0188] the emission layer in the light-emitting device may include:

[0189] a first compound including a polycyclic compound; and

[0190] a second compound including a group represented by Formula 20, a third compound including at least one π-deficient nitrogen-containing C1-C 60 cyclic group, a fourth compound including a transition metal, or any combination thereof, wherein

[0191] the first compound, the second compound, the third compound, and the fourth compound may be different from each other:

[0192] [Formula 20]

[0193]

[0194] In Formula 20,

[0195] ring CY 71 and ring CY 72 may each independently be a π-rich C3-C 60 cyclic group or a pyridyl group,

[0196] X 71 may be: a single bond; or a linking group including O, S, N, B, C, Si, or any combination thereof,

[0197] * indicates the binding site to an adjacent atom, and

[0198] CBP and mCBP can be excluded from the second compound:

[0199]

[0200] [Second compound to fourth compound]

[0201] According to an embodiment, the emission layer may include the first compound and at least one of the second compound and the third compound.

[0202] According to another embodiment, the emission layer may include the first compound and the fourth compound.

[0203] According to another embodiment, the emission layer may include the first compound, the second compound, the third compound, and the fourth compound.

[0204] According to another embodiment, when the emission layer includes the first compound, the second compound, the third compound, and the fourth compound,

[0205] Based on the total amount of the first compound to the fourth compound of 100 wt%, the amount of the first compound may be in the range of about 0.1 wt% to about 5 wt%. For example, based on the total amount of the first compound to the fourth compound of 100 wt%, the amount of the first compound may be in the range of about 0.5 wt% to about 4 wt%. For example, based on the total amount of the first compound to the fourth compound of 100 wt%, the amount of the first compound may be in the range of about 1 wt% to about 3 wt%.

[0206] Based on the total amount of the first compound to the fourth compound of 100 wt%, the amount of the second compound and the third compound (the sum of the second compound and the third compound) may be in the range of about 65 wt% to about 89.9 wt%. For example, based on the total amount of the first compound to the fourth compound of 100 wt%, the amount of the second compound and the third compound may be in the range of about 55 wt% to about 89 wt%. For example, based on the total amount of the first compound to the fourth compound of 100 wt%, the amount of the second compound and the third compound may be in the range of about 60 wt% to about 88 wt%.

[0207] Based on the total amount of the first to fourth compounds being 100 wt%, the amount of the fourth compound can be in the range of about 10 wt% to about 30 wt%. For example, based on the total amount of the first to fourth compounds being 100 wt%, the amount of the fourth compound can be in the range of about 11 wt% to about 28 wt%. For example, based on the total amount of the first to fourth compounds being 100 wt%, the amount of the fourth compound can be in the range of about 12 wt% to about 26 wt%. For example, based on the total amount of the first to fourth compounds being 100 wt%, the amount of the fourth compound can be in the range of about 13 wt% to about 24 wt%.

[0208] According to an embodiment, the second compound may include a compound represented by Formula 20-1, a compound represented by Formula 20-2, a compound represented by Formula 20-3, a compound represented by Formula 20-4, a compound represented by Formula 20-5, or any combination thereof:

[0209] [Formula 20-1]

[0210]

[0211] [Formula 20-2]

[0212]

[0213] [Formula 20-3]

[0214]

[0215] [Formula 20-4]

[0216]

[0217] [Formula 20-5]

[0218]

[0219] In Formulas 20-1 to 20-5,

[0220] Ring CY 71 to Ring CY 74 may each independently be an electron-rich C3-C 60 cyclic group or a pyridyl group,

[0221] X 82 may be a single bond, O, S, N[(L 82 ) b82 -R 82 , B[(L 82 ) b82 -R 82 , C(R 82a )(R 82b) or Si(R 82a )(R 82b ),

[0222] X 83 may be a single bond, O, S, N[(L 83 ) b83 -R 83 , B[(L 83 ) b83 -R 83 , C(R 83a )(R 83b ) or Si(R 83a )(R 83b ),

[0223] X 84 may be O, S, N[(L 84 ) b84 -R 84 , B[(L 84 ) b84 -R 84 , C(R 84a )(R 84b ) or Si(R 84a )(R 84b ),

[0224] X 85 may be C or Si,

[0225] L 81 to L 85 may each independently be a single bond, *-C(Q4)(Q5)-*', *-Si(Q4)(Q5)-*', an unsubstituted or at least one R 10a substituted π - electron rich C3 - C 60 cyclic group or an unsubstituted or at least one R 10a substituted pyridyl group, where Q4 and Q5 may each independently be the same as described herein for Q1,

[0226] b81 to b85 may each independently be an integer selected from 1 to 5,

[0227] R 71 to R 74 , R 81 to R 85 , R 82a , R 82b , R 83a , R 83b , R 84a and R 84b may each be the same as described herein,

[0228] a71 to a74 can each independently be an integer selected from 0 to 20, and

[0229] R 10a can be the same as described herein.

[0230] In an embodiment, the third compound can include a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, or any combination thereof.

[0231] According to an embodiment, the third compound can include a compound represented by Formula 30:

[0232] [Formula 30]

[0233]

[0234] In Formula 30,

[0235] L 51 to L 53 can each independently be a single bond, an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group,

[0236] b51 to b53 can each independently be an integer selected from 1 to 5,

[0237] X 54 can be N or C(R 54 ), X 55 can be N or C(R 55 ), X 56 can be N or C(R 56 ), and at least one of X 54 to X 56 can each be N,

[0238] R 51 to R 56 can each be the same as described herein, and

[0239] R 10a can be the same as described herein.

[0240] The fourth compound can include a compound represented by Formula 401:

[0241] [Formula 401]

[0242] M(L 401 ) xc1 (L 402 ) xc2

[0243] [Formula 402]

[0244]

[0245] In Formula 401 and Formula 402,

[0246] M can be a transition metal (e.g., iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), or thulium (Tm)),

[0247] L 401 can be a ligand represented by Formula 402, and xc1 can be 1, 2, or 3, where when xc1 is 2 or greater, two or more L 401 can be the same as or different from each other,

[0248] L 402 can be an organic ligand, and xc2 can be 0, 1, 2, 3, or 4, where when xc2 is 2 or greater, two or more L 402 can be the same as or different from each other,

[0249] X 401 and X 402 can each independently be nitrogen or carbon,

[0250] Ring A 401 and Ring A 402 can each independently be a C3-C 60 carbocyclic group or a C1-C 60 heterocyclic group,

[0251] T 401 can be a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 411 )-*', *-C(Q 411 )(Q 412 )-*',

[0252] *-C(Q 411 )=C(Q 412 )-*', *-C(Q 411 )=*' or *=C=*',

[0253] X 403 and X 404 can each independently be a chemical bond, O, S, N(Q 413 ), B(Q 413 ), P(Q 413 ), C(Q 413 )(Q 414 ) or Si(Q 413 )(Q 414 ),

[0254] R 401 and R 402 may each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, unsubstituted or substituted by at least one R 10a substituted C1-C 20 alkyl, unsubstituted or substituted by at least one R 10a substituted C1-C 20 alkoxy, unsubstituted or substituted by at least one R 10a substituted C3-C 60 carbocyclic group, unsubstituted or substituted by at least one R 10a substituted C1-C 60 heterocyclic group, -Si(Q 401 )(Q 402 )(Q 403 )、-N(Q 401 )(Q 402 )、-B(Q 401 )(Q 402 )、-C(=O)(Q 401 )、-S(=O)2(Q 401 ) or -P(=O)(Q 401 )(Q 402 ),

[0255] xc11 and xc12 may each independently be an integer selected from 0 to 10,

[0256] Q 411 to Q 414 and Q 401 to Q 403 may each independently be: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxy; cyano; nitro; or C1-C each unsubstituted or substituted by deuterium, -F, cyano, C1-C 60 alkyl, C1-C 60 alkoxy, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof substituted C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, C1-C 60 alkoxy, C1-C 60 alkylthio, C3-C 60 carbocyclic group, C1-C 60 heterocyclic group, C6-C 60 aryloxy, C6-C 60 arylthio, C7-C 60 aralkyl or C2-C 60 heteroaralkyl,

[0257] In Formula 402, each of * and *' indicates a binding site to M in Formula 401, and

[0258] R 10a may be the same as those described herein.

[0259] [Descriptions of Formula 20, Formulae 20-1 to 20-5, and Formula 30]

[0260] In an embodiment, the group represented by in Formulae 20-1 and 20-2 may be a group represented by one of Formulae CY71-1(1) to CY71-1(8), and / or

[0261] the group represented by in Formulae 20-1 and 20-3 may be a group represented by one of Formulae CY71-2(1) to CY71-2(8), and / or

[0262] the group represented by in Formulae 20-2 and 20-4 may be a group represented by one of Formulae CY71-3(1) to CY71-3(32), and / or

[0263] the group represented by in Formulae 20-3 to 20-5 may be a group represented by one of Formulae CY71-4(1) to CY71-4(32), and / or

[0264] the group represented by in Formula 20-5 may be a group represented by one of Formulae CY71-5(1) to CY71-5(8):

[0265]

[0266]

[0267]

[0268]

[0269] In Formulae CY71-1(1) to CY71-1(8), Formulae CY71-2(1) to CY71-2(8), Formulae CY71-3(1) to CY71-3(32), Formulae CY71-4(1) to CY71-4(32), and Formulae CY71-5(1) to CY71-5(8),

[0270] X 82 to X 85 、L 81 、b81、R 81and R 85 may each be the same as those described herein,

[0271] X 86 may be a single bond, O, S, N(R 86 ), B(R 86 ), C(R 86a )(R 86b ), or Si(R 86a )(R 86b ),

[0272] X 87 may be a single bond, O, S, N(R 87 ), B(R 87 ), C(R 87a )(R 87b ), or Si(R 87a )(R 87b ),

[0273] In Formulas CY71-1(2) to CY71-1(4), Formulas CY71-4(2) to CY71-4(4), Formulas CY71-4(10) to CY71-4(12), Formulas CY71-4(18) to CY71-4(20), and Formulas CY71-4(26) to CY71-4(28), X 86 and X 87 may not both be single bonds at the same time,

[0274] X 88 may be a single bond, O, S, N(R 88 ), B(R 88 ), C(R 88a )(R 88b ), or Si(R 88a )(R 88b ),

[0275] X 89 may be a single bond, O, S, N(R 89 ), B(R 89 ), C(R 89a )(R 89b ), or Si(R 89a )(R 89b ),

[0276] In Formulas CY71-2(2) to CY71-2(4), Formulas CY71-3(2) to CY71-3(4), Formulas CY71-3(10) to CY71-3(12), Formulas CY71-3(18) to CY71-3(20), Formulas CY71-3(26) to CY71-3(28), and Formulas CY71-5(2) to CY71-5(4), X88 and X 89 may each independently be a single bond, and

[0277] R 86 to R 89 、R 86a 、R 86b 、R 87a 、R 87b 、R 88a 、R 88b 、R 89a and R 89b may each independently be the same as those described herein for R 81 described.

[0278] In Formula 30, b51 to b53 respectively indicate the number of L 51 to L 53 and may each independently be an integer selected from 1 to 5. When b51 is 2 or greater, two or more L 51 may be the same as or different from each other, when b52 is 2 or greater, two or more L 52 may be the same as or different from each other, and when b53 is 2 or greater, two or more L 53 may be the same as or different from each other. For example, b51 to b53 may each independently be 1 or 2.

[0279] In an embodiment, in Formula 30, L 51 to L 53 may each independently be:

[0280] a single bond; or

[0281] Each unsubstituted or substituted phenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, pyrenyl, 1,2-benzophenanthryl, cyclopentadienyl, furyl, thienyl, silolyl, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, benzosilolyl, dibenzosilolyl, azafuranyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azadibenzosilolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, dibenzooxasilacyclohexanyl, dibenzothiasilacyclohexanyl, dibenzodihydroazasilacyclohexanyl, dibenzodihydrodisilacyclohexanyl, dibenzodihydrosilacyclohexanyl, dibenzo-1,4-dioxanyl, dibenzooxathiacyclohexanyl, dibenzoxazinyl, dibenzopyranyl, dibenzodithiolanyl, dibenzothiazinyl, dibenzothiopyranyl, dibenzocyclohexadienyl, dibenzodihydropyridyl or dibenzodihydropyrazinyl: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C1-C 20 alkyl, C1-C 20 alkoxy, phenyl, naphthyl, pyridyl, pyrimidinyl, triazinyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, phenylcarbazolyl, dibenzofuranyl, dibenzothienyl, dibenzosilolyl, dimethyldibenzosilolyl, diphenyldibenzosilolyl, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 )、-P(=O)(Q 31 )(Q 32 ) or any combination thereof, and

[0282] Q 31 to Q 33 may each independently be hydrogen, deuterium, C1-C 20 alkyl, C1-C 20An alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a pyridyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, or a triazinyl group.

[0283] According to an embodiment, in Formula 30, L 51 and R 51 The bond between, L 52 and R 52 The bond between, L 53 and R 53 The bond between, two or more Ls 51 The bond between, two or more Ls 52 The bond between, two or more Ls 53 The bond between, L in Formula 30 51 and X 54 and X 55 The bond between the carbons, L in Formula 30 52 and X 54 and X 56 The bond between the carbons, and L in Formula 30 53 and X 55 and X 56 The bond between the carbons may each be a "carbon-carbon single bond".

[0284] In Formula 30, X 54 May be N or C(R 54 ), X 55 May be N or C(R 55 ), X 56 May be N or C(R 56 ), and X 54 To X 56 At least one of may each be N. R 54 To R 56 May each be the same as described herein. For example, X 54 To X 56 Two or three of may each be N.

[0285] In the specification, R 51 To R 56 , R 71 To R 74 , R 81 To R 85 , R 82a , R 82b , R 83a , R 83b , R 84a and R 84b May each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, unsubstituted or substituted with at least one R 10a Substituted C1-C 60An alkyl group, unsubstituted or substituted by at least one R 10a substituted C2-C 60 An alkenyl group, unsubstituted or substituted by at least one R 10a substituted C2-C 60 An alkynyl group, unsubstituted or substituted by at least one R 10a substituted C1-C 60 An alkoxy group, unsubstituted or substituted by at least one R 10a substituted C3-C 60 A carbocyclic group, unsubstituted or substituted by at least one R 10a substituted C1-C 60 A heterocyclic group, unsubstituted or substituted by at least one R 10a substituted C6-C 60 An aryloxy group, unsubstituted or substituted by at least one R 10a substituted C6-C 60 An arylthio group, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2). Q1 to Q3 may each be the same as described herein.

[0286] For example, R in Formulas 20-1 to 20-5 and Formula 30 51 to R 56 , R 71 to R 74 , R 81 to R 85 , R 82a , R 82b , R 83a , R 83b , R 84a and R 84b may each independently be:

[0287] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C1-C 20 alkyl or C1-C 20 alkoxy;

[0288] Each C1-C 20 alkyl or C1-C 20 alkoxy substituted by: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, C1-C 10 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl or any combination thereof;

[0289] Each unsubstituted or substituted cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C1-C 10 alkyl)phenyl, naphthyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2-benzophenanthryl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzoisothiazolyl, benzoxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azafuranyl, azadibenzosilolyl or a group represented by formula 91: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, C1-C 20 alkyl, C1-C 20 alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C1-C 10 alkyl)phenyl, naphthyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2-benzophenanthryl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzoisothiazolyl, benzoxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidinyl, -O(Q 31 ), -S(Q 31 ), -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -P(Q 31 )(Q32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ), -P(=O)(Q 31 )(Q 32 ), or any combination thereof; or

[0290] -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2), and

[0291] Q1 to Q3 and Q 31 to Q 33 may each independently be:

[0292] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H or -CD2CDH2; or

[0293] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, naphthyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or triazinyl, each unsubstituted or substituted by: deuterium, C1-C 10 alkyl, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof:

[0294] [Formula 91]

[0295]

[0296] In Formula 91,

[0297] ring CY 91 and ring CY 92 may each independently be unsubstituted or C5-C 10a substituted by at least one R 30 carbocyclic group or unsubstituted or C1-C 10a substituted by at least one R 30 heterocyclic group,

[0298] X 91 may be a single bond, O, S, N(R 91 ), B(R 91 ), C(R 91a )(R 91b ) or Si(R 91a)(R 91b ),

[0299] R 91 , R 91a and R 91b can be respectively compared with the R 82 , R 82a and R 82b Same as described,

[0300] R 10a may be the same as described herein, and

[0301] *Indicates the binding site with adjacent atoms.

[0302] For example, in Equation 91,

[0303] Cyclo 91 and CY 92 may be each independently unsubstituted or substituted with at least one R 10a substituted phenyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl or triazinyl, and

[0304] R 91 , R 91a and R 91b Can be independently:

[0305] Hydrogen or C1-C 10 Alkyl; or

[0306] phenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl or triazinyl, each unsubstituted or substituted by: deuterium, C1-C 10 Alkyl, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof.

[0307] According to another embodiment, R in Formulas 20-1 to 20-5 and 30 51 To R 56 , R 71 To R 74 , R 81 To R 85 , R 82a , R 82b , R 83a , R 83b , R 84a and R 84b Can be independently:

[0308] Hydrogen, deuterium, -F, cyano, nitro, -CH3, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, a group represented by any one of Formula 9-1 to Formula 9-39 and Formula 9-44 to Formula 9-67, a group represented by any one of Formula 10-1 to Formula 10-154 and Formula 10-201 to Formula 10-368, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3) or -P(=O)(Q1)(Q2), where Q1 to Q3 may each be the same as described herein:

[0309]

[0310]

[0311]

[0312]

[0313]

[0314]

[0315]

[0316]

[0317]

[0318] In Formula 9-1 to Formula 9-39, Formula 9-44 to Formula 9-67, Formula 10-1 to Formula 10-154 and Formula 10-201 to Formula 10-368, * indicates the binding site to an adjacent atom, Ph may be phenyl, D may be a deuterium atom, TMS may be trimethylsilyl, and TMG may be trimethylgermyl.

[0319] In Formula 20-1 to Formula 20-5, a71 to a74 respectively indicate the number of R 71 to R 74 and may each independently be an integer selected from 0 to 20. When a71 is 2 or greater, two or more R 71 may be the same as or different from each other, when a72 is 2 or greater, two or more R 72 may be the same as or different from each other, when a73 is 2 or greater, two or more R 73 may be the same as or different from each other, and when a74 is 2 or greater, two or more R 74 may be the same as or different from each other. In an embodiment, a71 to a74 may each independently be an integer selected from 0 to 8.

[0320] In an embodiment, in formula 30, the group represented by *-(L 51 ) b51 -R 51 and the group represented by *-(L 52 ) b52 -R 52 may each not be a phenyl group.

[0321] According to an embodiment, in formula 30, the group represented by *-(L 51 ) b51 -R 51 and the group represented by *-(L 52 ) b52 -R 52 may be the same as each other.

[0322] According to another embodiment, in formula 30, the group represented by *-(L 51 ) b51 -R 51 and the group represented by *-(L 52 ) b52 -R 52 may be different from each other.

[0323] According to another embodiment, in formula 30, b51 and b52 may each independently be 1, 2, or 3, and L 51 and L 52 may each independently be a phenyl group, a pyridyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, or a triazinyl group that is unsubstituted or substituted by at least one R 10a .

[0324] In an embodiment, in formula 30, R 51 and R 52 may each independently be an unsubstituted or R 10a -substituted C3-C 60 carbocyclic group, an unsubstituted or R 10a -substituted C1-C 60 heterocyclic group, an unsubstituted or R 10a -substituted C6-C 60 aryloxy group, an unsubstituted or R 10a -substituted C6-C 60 arylthio group, -C(Q1)(Q2)(Q3), or -Si(Q1)(Q2)(Q3), and

[0325] Q1 to Q3 may each independently be an unsubstituted or deuterium-, -F-, cyano-, C1-C 60 alkyl-, C1-C 60C3-C substituted with alkoxy, phenyl, biphenyl or any combination thereof 60 carbocyclic group or C1-C 60 heterocyclic group.

[0326] According to an embodiment, in Formula 30,

[0327] The group represented by *-(L 51 ) b51 -R 51 may be a group represented by one of Formulas CY51-1 to CY51-26, and / or

[0328] The group represented by *-(L 52 ) b52 -R 52 may be a group represented by one of Formulas CY52-1 to CY52-26, and / or

[0329] The group represented by *-(L 53 ) b53 -R 53 may be a group represented by one of Formulas CY53-1 to CY53-27, -C(Q1)(Q2)(Q3) or -Si(Q1)(Q2)(Q3), where Q1 to Q3 may each be the same as described herein:

[0330]

[0331]

[0332]

[0333] In Formulas CY51-1 to CY51-26, Formulas CY52-1 to CY52-26 and Formulas CY53-1 to CY53-27,

[0334] Y 63 may be a single bond, O, S, N(R 63 )), B(R 63 )), C(R 63a )(R 63b ) or Si(R 63a )(R 63b ),

[0335] Y 64 may be a single bond, O, S, N(R 64 )), B(R 64 )), C(R 64a )(R 64b ) or Si(R 64a )(R 64b ),

[0336] Y 67 may be a single bond, O, S, N(R 67 ), B(R 67 ), C(R 67a )(R 67b ), or Si(R 67a )(R 67b ),

[0337] Y 68 may be a single bond, O, S, N(R 68 ), B(R 68 ), C(R 68a )(R 68b ), or Si(R 68a )(R 68b ),

[0338] Y in Formula CY51-16 and Formula CY51-17 63 and Y 64 may not both be single bonds at the same time,

[0339] Y in Formula CY52-16 and Formula CY52-17 67 and Y 68 may not both be single bonds at the same time,

[0340] R 51a to R 51e , R 61 to R 64 , R 63a , R 63b , R 64a and R 64b may each independently be the same as described herein for R 51 , where R 51a to R 51e may each not be hydrogen,

[0341] R 52a to R 52e , R 65 to R 68 , R 67a , R 67b , R 68a and R 68b may each independently be the same as described herein for R 52 , where R 52a to R 52e may each not be hydrogen,

[0342] R 53a to R 53e , R 69a and R 69b may each independently be the same as described herein for R53 is the same as described, where R 53a to R 53e may each be not hydrogen, and

[0343] * indicates the binding site to the adjacent atom.

[0344] In an embodiment, in Formula CY51-1 to Formula CY51-26 and Formula CY52-1 to Formula CY52-26, R 51a to R 51e and R 52a to R 52e may each independently be:

[0345] Each unsubstituted or substituted cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C1-C 10 alkyl)phenyl, naphthyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2-benzophenanthryl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, azafuranyl, azadibenzosilolyl or a group represented by Formula 91: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, C1-C 20 alkyl, C1-C 20 alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C1-C 10alkyl)phenyl, naphthyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, 1,2-benzophenanthryl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuryl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuryl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidinyl or any combination thereof; or

[0346] -C(Q1)(Q2)(Q3) or -Si(Q1)(Q2)(Q3), and

[0347] Q1 to Q3 may each independently be phenyl, naphthyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or triazinyl which is unsubstituted or substituted by the following: deuterium, C1-C 10 alkyl, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl or any combination thereof,

[0348] In Formulae CY51-16 and CY51-17, Y 63 may be O or S, and Y 64 may be Si(R 64a )(R 64b ); or Y 63 may be Si(R 63a )(R 63b ), and Y 64 may be O or S, and

[0349] In Formulae CY52-16 and CY52-17, Y 67 may be O or S, and Y 68 may be Si(R 68a )(R 68b ); or Y 67 may be Si(R 67a )(R 67b ), and Y 68 may be O or S.

[0350] In an embodiment, in Formulae 20-1 to 20-5, L 81 to L 85 may each independently be:

[0351] a single bond;

[0352] *-C(Q4)(Q5)-*' or *-Si(Q4)(Q5)-*'; or

[0353] Each unsubstituted or substituted phenyl, naphthyl, anthracenyl, phenanthryl, triphenylenyl, pyrenyl, 1,2-benzophenanthrenyl, cyclopentadienyl, furyl, thienyl, silolyl, indenyl, fluorenyl, indolyl, carbazolyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, benzosilolyl, dibenzosilolyl, pyridyl, pyrrolyl, benzoxadiazolyl or benzothiadiazolyl: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C1-C 20 alkyl, C1-C 20 alkoxy, phenyl, naphthyl, pyridyl, pyrimidinyl, triazinyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, carbazolyl, phenylcarbazolyl, dibenzofuranyl, dibenzothienyl, dibenzosilolyl, dimethyldibenzosilolyl, diphenyldibenzosilolyl, -O(Q 31 ), -S(Q 31 ), -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -P(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ), -P(=O)(Q 31 )(Q 32 ), or any combination thereof, and

[0354] Q4, Q5 and Q 31 to Q 33 can each independently be hydrogen, deuterium, C1-C 20 alkyl, C1-C 20 alkoxy, phenyl, biphenyl, terphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl or triazinyl.

[0355] In an embodiment, in Formula 402, X 401 can be nitrogen and X 402 can be carbon, or X 401 and X 402 can each be nitrogen.

[0356] In an embodiment, in Formula 401, when xc1 is 2 or greater, two or more of the two rings A 401 in L 401 can optionally be connected via T as a linking group402 are connected to each other, or two rings A 402 may optionally be connected via T as a linking group 403 to each other (see Compounds PD1 to PD4 and Compound PD7). T 402 and T 403 may each independently be the same as those described herein for T 401 described.

[0357] In Formula 401, L 402 may be an organic ligand. For example, L 402 may include a halogen group, a diketone group (e.g., acetylacetonate group), a carboxylic acid group (e.g., picolinate group), -C(=O), an isocyano group, a -CN group, a phosphorus-containing group (e.g., phosphine group, phosphite group, etc.) or any combination thereof.

[0358] [Detailed Examples of the Second to Fourth Compounds]

[0359] According to an embodiment, the second compound may include at least one of Compounds HTH1 to HTH55:

[0360]

[0361]

[0362] According to another embodiment, the third compound may include at least one of Compounds ETH1 to ETH86:

[0363]

[0364]

[0365]

[0366] According to an embodiment, the fourth compound may include at least one of Compounds PD1 to PD41:

[0367]

[0368]

[0369]

[0370] In Compounds HTH1 to HTH55 and Compounds ETH1 to ETH86, Ph may be phenyl, D5 represents being substituted with five deuterium atoms, and D4 represents being substituted with four deuterium atoms.

[0371] According to an embodiment, the light-emitting device may satisfy at least one of Conditions 1 to 4:

[0372] [Condition 1]

[0373] The lowest unoccupied molecular orbital (LUMO) energy level (eV) of the second compound > the LUMO energy level (eV) of the fourth compound

[0374] [Condition 2]

[0375] The LUMO energy level (eV) of the fourth compound > the LUMO energy level (eV) of the third compound

[0376] [Condition 3]

[0377] The highest occupied molecular orbital (HOMO) energy level (eV) of the fourth compound > the HOMO energy level (eV) of the second compound

[0378] [Condition 4]

[0379] The HOMO energy level (eV) of the second compound > the HOMO energy level (eV) of the third compound.

[0380] The HOMO energy level and the LUMO energy level of each of the fourth compound, the second compound, and the third compound can each be negative values and can be measured according to methods of the prior art.

[0381] According to another embodiment, the absolute value of the difference between the LUMO energy level of the fourth compound and the LUMO energy level of the third compound can be in the range of about 0.1 eV to about 1.0 eV, the absolute value of the difference between the LUMO energy level of the fourth compound and the LUMO energy level of the second compound can be in the range of about 0.1 eV to about 1.0 eV, the absolute value of the difference between the HOMO energy level of the fourth compound and the HOMO energy level of the third compound can be less than or equal to about 1.25 eV (for example, in the range of about 0.2 eV to about 1.25 eV), and the absolute value of the difference between the HOMO energy level of the fourth compound and the HOMO energy level of the second compound can be less than or equal to about 1.25 eV (for example, in the range of about 0.2 eV to about 1.25 eV).

[0382] When the relationship between the LUMO energy level and the HOMO energy level satisfies the above conditions, a balance between holes and electrons in the injection emission layer can be achieved.

[0383] The light-emitting device can have the structure of the first embodiment or the second embodiment:

[0384] [Description of the First Embodiment]

[0385] According to the first embodiment, the first compound may be included in the emission layer in the interlayer of the light-emitting device, wherein the emission layer may further include a host, the first compound may be different from the host, and the emission layer may emit phosphorescence or fluorescence from the first compound. For example, according to the first embodiment, the first compound may be a dopant or an emitter. For example, the first compound may be a phosphorescent dopant or a phosphorescent emitter.

[0386] The phosphorescence or fluorescence emitted from the first compound may be blue light.

[0387] The emission layer may further include a co-dopant. The co-dopant may be used as a sensitizer, which improves the luminescence efficiency of the first compound by effectively transferring energy to the first compound that is a dopant or an emitter.

[0388] The co-dopant may be different from the first compound and the host.

[0389] For example, the co-dopant may be a phosphorescent dopant.

[0390] [Description of the second embodiment]

[0391] According to the second embodiment, the first compound may be included in the emission layer in the interlayer of the light-emitting device, wherein the emission layer may further include a host and a dopant, the first compound may be different from the host and the dopant, and the emission layer may emit phosphorescence or fluorescence (e.g., delayed fluorescence) from the dopant.

[0392] For example, the first compound in the second embodiment may be used as a co-dopant that transfers energy to the dopant (or emitter), but may not be used as a dopant.

[0393] As another example, the first compound in the second embodiment may be used as an emitter and may also be used as a co-dopant that transfers energy to the dopant (or emitter).

[0394] For example, the phosphorescence or fluorescence emitted from the dopant (or emitter) in the second embodiment may be blue phosphorescence or blue fluorescence (e.g., blue delayed fluorescence).

[0395] The dopant (or emitter) in the second embodiment may be any phosphorescent dopant material (e.g., the organometallic compound represented by Formula 401 in the specification) or any fluorescent dopant material (e.g., in the specification, the polycyclic compound represented by Formula 1, the compound represented by Formula 501, or any combination thereof).

[0396] In the first embodiment and the second embodiment, the blue light may be blue light having a maximum emission wavelength in the range of about 390 nm to about 500 nm. For example, the blue light may have a maximum emission wavelength in the range of about 410 nm to about 490 nm. For example, the blue light may have a maximum emission wavelength in the range of about 430 nm to about 480 nm. For example, the blue light may have a maximum emission wavelength in the range of about 440 nm to about 475 nm. For example, the blue light may have a maximum emission wavelength in the range of about 455 nm to about 470 nm.

[0397] The co - dopant in the first embodiment may include, for example, a fourth compound represented by Formula 401.

[0398] The host in the first embodiment and the second embodiment may be any host material (e.g., in the specification, a compound represented by Formula 301, a compound represented by Formula 301 - 1, a compound represented by Formula 301 - 2, or any combination thereof).

[0399] In another embodiment, the host in the first embodiment and the second embodiment may be a second compound, a third compound, or any combination thereof.

[0400] On the other hand, an electronic device including a light - emitting device is provided. The electronic device may further include a thin - film transistor. For example, in an embodiment, the electronic device may further include a thin - film transistor including a source electrode and a drain electrode, wherein a first electrode of the light - emitting device may be electrically connected to the source electrode or the drain electrode. In an embodiment, the electronic device may further include a color filter, a color conversion layer, a touch - screen layer, a polarization layer, or any combination thereof. The electronic device may be the same as those described herein.

[0401] Figure 1 description]

[0402] Figure 1 FIG. is a schematic cross - sectional view of a light - emitting device 10 according to an embodiment. The light - emitting device 10 includes a first electrode 110, an interlayer 130, and a second electrode 150.

[0403] Hereinafter, with reference to Figure 1 the structure of the light - emitting device 10 according to an embodiment and a method of manufacturing the light - emitting device 10 will be described.

[0404] [First electrode 110]

[0405] In Figure 1 ​Among them, the substrate may further be disposed under the first electrode 110 or on the second electrode 150. In an embodiment, the substrate may be a glass substrate or a plastic substrate. In an embodiment, the substrate may be a flexible substrate and may include a plastic having excellent heat resistance and durability, such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or any combination thereof.

[0406] The first electrode 110 may be formed by, for example, depositing or sputtering a material for forming the first electrode 110 on the substrate. When the first electrode 110 is an anode, a high work function material that facilitates hole injection may be used as the material for forming the first electrode 110.

[0407] The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. In order to form the first electrode 110 as a transmissive electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof may be used as the material for forming the first electrode 110. The first electrode 110 may be a semi-transmissive electrode or a reflective electrode, and the material for forming the first electrode 110 may include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.

[0408] The first electrode 110 may have a single-layer structure composed of a single layer or a multi-layer structure including multiple layers. For example, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO.

[0409] [Interlayer 130]

[0410] The interlayer 130 may be located on the first electrode 110. The interlayer 130 may include an emission layer.

[0411] The interlayer 130 may further include a hole transport region between the first electrode 110 and the emission layer and an electron transport region between the emission layer and the second electrode 150.

[0412] In addition to various organic materials, the interlayer 130 may further include a metal-containing compound (such as an organometallic compound) or an inorganic material (such as a quantum dot), etc.

[0413] In an embodiment, the interlayer 130 may include two or more emission units stacked between the first electrode 110 and the second electrode 150, and at least one charge generation layer between adjacent units among the two or more emission units. When the interlayer 130 includes two or more emission units and at least one charge generation layer as described above, the light emitting device 10 may be a tandem light emitting device.

[0414] [Hole transport region in interlayer 130]

[0415] The hole transport region may have: a single-layer structure composed of layers (composed of a single material), a single-layer structure composed of layers including different materials, or a multi-layer structure including multiple layers (including different materials).

[0416] The hole transport region may include a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, or any combination thereof.

[0417] In an embodiment, the hole transport region may have a multi-layer structure including a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission assisting layer structure, a hole injection layer / emission assisting layer structure, a hole transport layer / emission assisting layer structure, or a hole injection layer / hole transport layer / electron blocking layer structure. The layers of each structure may be stacked from the first electrode 110 in their respective specified order, but the structure of the hole transport region is not limited thereto.

[0418] The hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:

[0419] [Formula 201]

[0420]

[0421] [Formula 202]

[0422]

[0423] In Formula 201 and Formula 202,

[0424] L 201 to L 204 may each independently be an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group,

[0425] L 205 may be *-O-*', *-S-*', *-N(Q 201 )-*', an unsubstituted or at least one R 10a substituted C1-C 20 alkylene group, an unsubstituted or at least one R 10a substituted C2-C 20 alkenylene group, an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R10a Substituted C1-C 60 heterocyclic group,

[0426] xa1 to xa4 can each independently be an integer selected from 0 to 5,

[0427] xa5 can be an integer selected from 1 to 10,

[0428] R 201 to R 204 and Q 201 can each independently be an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group,

[0429] R 201 and R 202 can optionally be linked to each other via a single bond, an unsubstituted or at least one R 10a substituted C1-C5 alkylene or an unsubstituted or at least one R 10a substituted C2-C5 alkenylene to form an unsubstituted or at least one R 10a substituted C8-C 60 polycyclic group (e.g., carbazolyl, etc.) (e.g., see compound HT16, etc.),

[0430] R 203 and R 204 can optionally be linked to each other via a single bond, an unsubstituted or at least one R 10a substituted C1-C5 alkylene or an unsubstituted or at least one R 10a substituted C2-C5 alkenylene to form an unsubstituted or at least one R 10a substituted C8-C 60 polycyclic group, and

[0431] na1 can be an integer selected from 1 to 4.

[0432] In an embodiment, the compound represented by formula 201 and the compound represented by formula 202 can each independently include at least one of the groups represented by formula CY201 to formula CY217:

[0433]

[0434] In formula CY201 to formula CY217, R 10b and R 10c can each independently be the same as described herein for R 10a and the ring CY 201 to the ring CY204 may each independently be a C3-C 20 carbocyclic group or a C1-C 20 heterocyclic group, and at least one hydrogen in Formulae CY201 to CY217 may be unsubstituted or substituted by R as described herein 10a .

[0435] According to an embodiment, in Formulae CY201 to CY217, ring CY 201 to ring CY 204 may each independently be a phenyl group, a naphthyl group, a phenanthryl group or an anthryl group.

[0436] According to another embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may include at least one of the groups represented by Formulae CY201 to CY203.

[0437] According to another embodiment, the compound represented by Formula 201 may include at least one of the groups represented by Formulae CY201 to CY203 and at least one of the groups represented by Formulae CY204 to CY217.

[0438] According to another embodiment, in Formula 201, xa1 may be 1, R 201 may be a group represented by one of Formulae CY201 to CY203, xa2 may be 0, and R 202 may be a group represented by one of Formulae CY204 to CY207.

[0439] According to another embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each not include a group represented by one of Formulae CY201 to CY203.

[0440] According to another embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each not include a group represented by one of Formulae CY201 to CY203, and may each independently include at least one of the groups represented by Formulae CY204 to CY217.

[0441] In another embodiment, the compound represented by Formula 201 and the compound represented by Formula 202 may each not include a group represented by one of Formulae CY201 to CY217.

[0442] In an embodiment, the hole transport region may include one of Compounds HT1 to HT46, m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), or any combination thereof:

[0443]

[0444]

[0445]

[0446]

[0447]

[0448] The thickness of the hole transport region may be in the range of about to about For example, the thickness of the hole transport region may be in the range of about to about When the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, the thickness of the hole injection layer may be in the range of about to about and the thickness of the hole transport layer may be in the range of about to about For example, the thickness of the hole injection layer may be in the range of about to about For example, the thickness of the hole transport layer may be in the range of about to about When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within any of these ranges, satisfactory hole transport characteristics can be obtained without significantly increasing the driving voltage.

[0449] The emission assisting layer may increase the light emission efficiency by compensating for the optical resonance distance according to the wavelength of the light emitted from the emission layer, and the electron blocking layer may block the leakage of electrons from the emission layer to the hole transport region. Materials that may be included in the hole transport region may be included in the emission assisting layer and the electron blocking layer.

[0450] [p-dopant]

[0451] In addition to these materials, the hole transport region may further include a charge generation material for improving the conductive properties. The charge generation material may be uniformly or non-uniformly dispersed in the hole transport region (e.g., in the form of a single layer composed of the charge generation material).

[0452] The charge generation material may be, for example, a p-dopant.

[0453] For example, the lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant may be less than or equal to about -3.5 eV.

[0454] According to an embodiment, the p-dopant may include a quinone derivative, a cyanide compound, a compound including element EL1 and element EL2, or any combination thereof.

[0455] Examples of the quinone derivative may include TCNQ, F4-TCNQ, etc.

[0456] Examples of the cyanide compound may include HAT-CN, a compound represented by Formula 221, etc.:

[0457]

[0458] [Formula 221]

[0459]

[0460] In Formula 221,

[0461] R 221 to R 223 may each independently be an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group, and

[0462] R 221 to R 223 at least one of which may each independently be a C3-C 60 carbocyclic group or a C1-C 60 heterocyclic group each substituted with: a cyano group; -F; -Cl; -Br; -I; a C1-C 20 alkyl group substituted with a cyano group, -F, -Cl, -Br, -I, or any combination thereof; or any combination thereof.

[0463] In the compound including element EL1 and element EL2, element EL1 may be a metal, a metalloid, or any combination thereof, and element EL2 may be a non-metal, a metalloid, or any combination thereof.

[0464] Examples of metals may include: alkali metals (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); alkaline earth metals (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), etc.); transition metals (e.g., titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Co), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au), etc.); post-transition metals (e.g., zinc (Zn), indium (In), tin (Sn), etc.); lanthanide metals (e.g., lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), etc.), etc.

[0465] Examples of metalloids may include silicon (Si), antimony (Sb), tellurium (Te), etc.

[0466] Examples of non-metals may include oxygen (O), halogens (e.g., F, Cl, Br, I, etc.), etc.

[0467] For example, a compound including element EL1 and element EL2 may include metal oxides, metal halides (e.g., metal fluorides, metal chlorides, metal bromides, metal iodides, etc.), metalloid halides (e.g., metalloid fluorides, metalloid chlorides, metalloid bromides, metalloid iodides, etc.), metal tellurides, or any combination thereof.

[0468] Examples of metal oxides may include tungsten oxides (e.g., WO, W2O3, WO2, WO3, W2O5, etc.), vanadium oxides (e.g., VO, V2O3, VO2, V2O5, etc.), molybdenum oxides (MoO, Mo2O3, MoO2, MoO3, Mo2O5, etc.), rhenium oxides (e.g., ReO3, etc.), etc.

[0469] Examples of metal halides may include alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, lanthanide metal halides, etc.

[0470] Examples of alkali metal halides may include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, CsI, etc.

[0471] Examples of alkaline earth metal halides may include BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2, SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, BeI2, MgI2, CaI2, SrI2, BaI2, etc.

[0472] Examples of transition metal halides may include titanium halides (e.g., TiF4, TiCl4, TiBr4, TiI4, etc.), zirconium halides (e.g., ZrF4, ZrCl4, ZrBr4, ZrI4, etc.), hafnium halides (e.g., HfF4, HfCl4, HfBr4, HfI4, etc.), vanadium halides (e.g., VF3, VCl3, VBr3, VI3, etc.), niobium halides (e.g., NbF3, NbCl3, NbBr3, NbI3, etc.), tantalum halides (e.g., TaF3, TaCl3, TaBr3, TaI3, etc.), chromium halides (e.g., CrF3, CrCl3, CrBr3, CrI3, etc.), molybdenum halides (e.g., MoF3, MoCl3, MoBr3, MoI3, etc.), tungsten halides (e.g., WF3, WCl3, WBr3, WI3, etc.), manganese halides (e.g., MnF2, MnCl2, MnBr2, MnI2, etc.), technetium halides (e.g., TcF2, TcCl2, TcBr2, TcI2, etc.), rhenium halides (e.g., ReF2, ReCl2, ReBr2, ReI2, etc.), ferrous halides (e.g., FeF2, FeCl2, FeBr2, FeI2, etc.), ruthenium halides (e.g., RuF2, RuCl2, RuBr2, RuI2, etc.), osmium halides (e.g., OsF2, OsCl2, OsBr2, OsI2, etc.), cobalt halides (e.g., CoF2, CoCl2, CoBr2, CoI2, etc.), rhodium halides (e.g., RhF2, RhCl2, RhBr2, RhI2, etc.), iridium halides (e.g., IrF2, IrCl2, IrBr2, IrI2, etc.), nickel halides (e.g., NiF2, NiCl2, NiBr2, NiI2, etc.), palladium halides (e.g., PdF2, PdCl2, PdBr2, PdI2, etc.), platinum halides (e.g., PtF2, PtCl2, PtBr2, PtI2, etc.), cuprous halides (e.g., CuF, CuCl, CuBr, CuI, etc.), silver halides (e.g., AgF, AgCl, AgBr, AgI, etc.), gold halides (e.g., AuF, AuCl, AuBr, AuI, etc.), etc.

[0473] Examples of post-transition metal halides may include zinc halides (e.g., ZnF2, ZnCl2, ZnBr2, ZnI2, etc.), indium halides (e.g., InI3, etc.), tin halides (e.g., SnI2, etc.), etc.

[0474] Examples of lanthanide metal halides may include YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3, SmCl3, YbBr, YbBr2, YbBr3, SmBr3, YbI, YbI2, YbI3, SmI3, etc.

[0475] Examples of metalloid halides may include antimony halides (e.g., SbCl5, etc.), etc.

[0476] Examples of metal tellurides may include alkali metal tellurides (e.g., Li2Te, Na2Te, K2Te, Rb2Te, Cs2Te, etc.), alkaline earth metal tellurides (e.g., BeTe, MgTe, CaTe, SrTe, BaTe, etc.), transition metal tellurides (e.g., TiTe2, ZrTe2, HfTe2, V2Te3, Nb2Te3, Ta2Te3, Cr2Te3, Mo2Te3, W2Te3, MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu2Te, CuTe, Ag2Te, AgTe, Au2Te, etc.), post-transition metal tellurides (e.g., ZnTe, etc.), and lanthanide metal tellurides (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.).

[0477] [Emission layer in the interlayer 130]

[0478] When the light-emitting device 10 is a full-color light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and / or a blue emission layer according to sub-pixels. In an embodiment, the emission layer may have a stacked structure of two or more layers among a red emission layer, a green emission layer, and a blue emission layer, where the two or more layers may be in contact with each other or may be separated from each other to emit white light, or may be a structure in which two or more of a red light-emitting material, a green light-emitting material, and a blue light-emitting material are mixed with each other in a single layer to emit white light. For example, the emission layer may emit blue light.

[0479] According to an embodiment, the emission layer may include a condensed-ring compound represented by Formula 1 as described herein.

[0480] In an embodiment, the emission layer may include a host and a dopant.

[0481] According to an embodiment, the dopant may include a polycyclic compound represented by Formula 1 as described herein. In an embodiment, in addition to the polycyclic compound represented by Formula 1, the dopant may further include a phosphorescent dopant, a fluorescent dopant, or any combination thereof. In addition to the polycyclic compound represented by Formula 1, the emission layer may further include a phosphorescent dopant or a fluorescent dopant, etc. The phosphorescent dopant and the fluorescent dopant will be described later.

[0482] Based on 100 parts by weight of the host, the amount of the dopant in the emission layer may be in the range of about 0.01 part by weight to about 15 parts by weight.

[0483] In an embodiment, the emission layer may include quantum dots.

[0484] As used herein, the term “quantum dot” may be a crystal of a semiconductor compound and may include any material capable of emitting light of various emission wavelengths according to the size of the crystal.

[0485] In an embodiment, the emission layer may include a delayed fluorescence material. The delayed fluorescence material may be used as a host or a dopant in the emission layer.

[0486] The thickness of the emission layer may be in the range of about to about . For example, the thickness of the emission layer may be in the range of about to about . When the thickness of the emission layer is within any of these ranges, excellent light-emitting characteristics may be obtained without significantly increasing the driving voltage.

[0487] [Host]

[0488] The host in the emission layer may include the second compound or the third compound described in the specification, or any combination thereof.

[0489] In an embodiment, the host may include a compound represented by Formula 301:

[0490] [Formula 301]

[0491] [Ar 301 xb11 -[(L 301 ) xb1 -R 301 xb21 .

[0492] In Formula 301,

[0493] Ar 301 and L 301 may each independently be an unsubstituted or at least one R 10a substituted C3-C 60 ​​A carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group,

[0494] xb11 can be 1, 2 or 3,

[0495] xb1 can be an integer selected from 0 to 5,

[0496] R 301 can be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or at least one R 10a substituted C1-C 60 alkyl, unsubstituted or at least one R 10a substituted C2-C 60 alkenyl, unsubstituted or at least one R 10a substituted C2-C 60 alkynyl, unsubstituted or at least one R 10a substituted C1-C 60 alkoxy, unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group, unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group, -Si(Q 301 )(Q 302 )(Q 303 )、-N(Q 301 )(Q 302 )、-B(Q 301 )(Q 302 )、-C(=O)(Q 301 )、-S(=O)2(Q 301 ) or -P(=O)(Q 301 )(Q 302 ),

[0497] xb21 can be an integer selected from 1 to 5, and

[0498] Q 301 to Q 303 can each independently be the same as described herein for Q1.

[0499] In an embodiment, in Formula 301, when xb11 is 2 or greater, two or more Ar 301 can be connected to each other via a single bond.

[0500] In an embodiment, the host can include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:

[0501] [Formula 301-1]

[0502]

[0503] [Formula 301-2]

[0504]

[0505] In Formula 301-1 and Formula 301-2,

[0506] Ring A 301 to Ring A 304 may each independently be an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group,

[0507] X 301 may be O, S, N[(L 304 ) xb4 -R 304 ) 304 )(R 305 ) or Si(R 304 )(R 305 ),

[0508] xb22 and xb23 may each independently be 0, 1 or 2,

[0509] L 301 , xb1 and R 301 may each be the same as described herein,

[0510] L 302 to L 304 may each independently be the same as described herein for L 301 ,

[0511] xb2 to xb4 may each independently be the same as described herein for xb1, and

[0512] R 302 to R 305 and R 311 to R 314 may each independently be the same as described herein for R 301 .

[0513] In an embodiment, the host may comprise an alkaline earth metal complex, a late transition metal complex, or any combination thereof. For example, the host may comprise a Be complex (e.g., compound H55), a Mg complex, a Zn complex, or any combination thereof.

[0514] In another embodiment, the host may include one of compounds H1 to H124, 9,10-bis(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN), 9,10-bis(2-naphthyl)-2-tert-butyl-anthracene (TBADN), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 1,3-bis(9-carbazolyl)benzene (mCP), 1,3,5-tris(carbazol-9-yl)benzene (TCP), or any combination thereof:

[0515]

[0516]

[0517]

[0518]

[0519]

[0520]

[0521]

[0522] [Phosphorescent dopant]

[0523] In an embodiment, the phosphorescent dopant may include at least one transition metal as a central metal.

[0524] The phosphorescent dopant may include monodentate ligands, bidentate ligands, tridentate ligands, tetradentate ligands, pentadentate ligands, hexadentate ligands, or any combination thereof.

[0525] The phosphorescent dopant may be electrically neutral.

[0526] In an embodiment, the phosphorescent dopant may include an organometallic compound represented by Formula 401:

[0527] [Formula 401]

[0528] M(L 401 ) xc1 (L 402 ) xc2

[0529] [Formula 402]

[0530]

[0531] Formula 401 and Formula 402 may be the same as those described herein.

[0532] The phosphorescent dopant may include, for example, one of compounds PD1 to PD41 or any combination thereof.

[0533] [Fluorescent dopant]

[0534] The fluorescent dopant may include an amine group-containing compound, a styryl group-containing compound, or any combination thereof.

[0535] In an embodiment, the fluorescent dopant may include a compound represented by Formula 501:

[0536] [Formula 501]

[0537]

[0538] In Formula 501,

[0539] Ar 501 , L 501 to L 503 , R 501 and R 502 may each independently be an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group,

[0540] xd1 to xd3 may each independently be 0, 1, 2, or 3, and

[0541] xd4 may be 1, 2, 3, 4, 5, or 6.

[0542] In an embodiment, in Formula 501, Ar 501 may be a fused ring group in which three or more monocyclic groups are fused together (e.g., anthryl, 1,2-benzophenanthryl, pyrenyl, etc.).

[0543] In an embodiment, in Formula 501, xd4 may be 2.

[0544] In an embodiment, the fluorescent dopant may include one of compounds FD1 to FD36, DPVBi, DPAVBi, or any combination thereof:

[0545]

[0546]

[0547]

[0548] [Electron transport region in interlayer 130]

[0549] The electron transport region may have: a single-layer structure composed of layers (composed of a single material), a single-layer structure composed of layers including different materials, or a multi-layer structure including multiple layers (including different materials).

[0550] The electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0551] In an embodiment, the electron transport region may have an electron transport layer / electron injection layer structure, a hole blocking layer / electron transport layer / electron injection layer structure, an electron control layer / electron transport layer / electron injection layer structure, a buffer layer / electron transport layer / electron injection layer structure, etc., where the layers of each structure may be stacked from the emission layer in their respective specified order, but the structure of the electron transport region is not limited thereto.

[0552] In an embodiment, the electron transport region (e.g., the buffer layer, hole blocking layer, electron control layer, or electron transport layer in the electron transport region) may include a metal-free compound, the metal-free compound including at least one nitrogen-containing C1-C lacking π electrons 60 cyclic group.

[0553] In an embodiment, the electron transport region may include a compound represented by Formula 601:

[0554] [Formula 601]

[0555] [Ar 601 xe11 -[(L 601 ) xe1 -R 601 xe21 .

[0556] In Formula 601,

[0557] Ar 601 and L 601 may each independently be an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group or an unsubstituted or at least one R 10a substituted C1-C 60 heterocyclic group,

[0558] xe11 may be 1, 2, or 3,

[0559] xe1 may be 0, 1, 2, 3, 4, or 5,

[0560] R 601 may be an unsubstituted or at least one R 10a substituted C3-C 60 carbocyclic group, an unsubstituted or at least one R 10a ​​Substituted C1-C 60 heterocyclic group, -Si(Q 601 )(Q 602 )(Q 603 ), -C(=O)(Q 601 ), -S(=O)2(Q 601 ), or -P(=O)(Q 601 )(Q 602 ),

[0561] Q 601 to Q 603 may each independently be the same as described herein for Q1,

[0562] xe21 may be 1, 2, 3, 4, or 5, and

[0563] Ar 601 , L 601 and R 601 in at least one of which may each independently be an unsubstituted or R 10a -substituted π-deficient nitrogen-containing C1-C 60 cyclic group.

[0564] In an embodiment, in Formula 601, when xe11 is 2 or greater, two or more Ar 601 may be connected to each other via a single bond.

[0565] In an embodiment, in Formula 601, Ar 601 may be an unsubstituted or R 10a -substituted anthryl group.

[0566] In an embodiment, the electron transport region may include a compound represented by Formula 601-1:

[0567] [Formula 601-1]

[0568]

[0569] In Formula 601-1,

[0570] X 614 may be N or C(R 614 ), X 615 may be N or C(R 615 ), X 616 may be N or C(R 616 ), and at least one of X 614 to X 616 may each be N,

[0571] L 611 to L 613 may each independently be the same as described herein for L601 Same as described,

[0572] Xe611 to Xe613 can each independently be the same as that described for Xe1 herein,

[0573] R 611 to R 613 can each independently be the same as that described for R 601 herein, and

[0574] R 614 to R 616 can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C1-C 20 alkyl, C1-C 20 alkoxy, unsubstituted or substituted by at least one R 10a substituted C3-C 60 carbocyclic group or unsubstituted or substituted by at least one R 10a substituted C1-C 60 heterocyclic group.

[0575] In an embodiment, in Formula 601 and Formula 601-1, Xe1 and Xe611 to Xe613 can each independently be 0, 1, or 2.

[0576] In an embodiment, the electron transport region can include one of Compounds ET1 to ET45, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, TAZ, NTAZ, or any combination thereof:

[0577]

[0578]

[0579]

[0580]

[0581] The thickness of the electron transport region can be in the range of about to about For example, the thickness of the electron transport region can be in the range of about to about When the electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, the thickness of the buffer layer, the hole blocking layer, or the electron control layer can each independently be in the range of about to about within a range. For example, the thicknesses of the buffer layer, hole blocking layer, or electron control layer can each independently be in the range of about to about The thickness of the electron transport layer can be in the range of about to about For example, the thickness of the electron transport layer can be in the range of about to about When the thicknesses of the buffer layer, hole blocking layer, electron control layer, electron transport layer, and / or electron transport region are within any of these ranges, satisfactory electron transport characteristics can be obtained without significantly increasing the driving voltage.

[0582] In addition to the above materials, the electron transport region (e.g., the electron transport layer in the electron transport region) can further include a metal-containing material.

[0583] The metal-containing material can include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The metal ions of the alkali metal complex can be Li ions, Na ions, K ions, Rb ions, or Cs ions, and the metal ions of the alkaline earth metal complex can be Be ions, Mg ions, Ca ions, Sr ions, or Ba ions.

[0584] The ligands coordinated with the metal ions of the alkali metal complex or alkaline earth metal complex can include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxyphenyl oxadiazole, hydroxyphenyl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzimidazole, hydroxyphenyl benzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.

[0585] For example, the metal-containing material can include a Li complex. The Li complex can include, for example, compound ET-D1(Liq) or compound ET-D2:

[0586]

[0587] The electron transport region can include an electron injection layer that facilitates the injection of electrons from the second electrode 150. The electron injection layer can contact (e.g., directly contact) the second electrode 150.

[0588] The electron injection layer can have: a single-layer structure composed of a layer (composed of a single material), a single-layer structure composed of layers including different materials, or a multilayer structure including multiple layers (including different materials).

[0589] The electron injection layer can include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.

[0590] The alkali metals may include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metals may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metals may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.

[0591] The alkali metal compound, alkaline earth metal compound, and rare earth metal compound may include oxides, halides (e.g., fluorides, chlorides, bromides, iodides, etc.), or tellurides of alkali metals, alkaline earth metals, and rare earth metals, or any combination thereof.

[0592] The alkali metal compound may include alkali metal oxides such as Li2O, Cs2O, K2O, etc., alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI, etc., or any combination thereof. The alkaline earth metal compound may include alkaline earth metal oxides such as BaO, SrO, CaO, Ba x Sr 1-x O (where x is a real number satisfying the condition 0 < x < 1), Ba x Ca 1-x O (where x is a real number satisfying the condition 0 < x < 1), etc. The rare earth metal compound may include YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, ScI3, TbI3, or any combination thereof. The rare earth metal compound may include lanthanide metal tellurides. Examples of lanthanide metal tellurides may include LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La2Te3, Ce2Te3, Pr2Te3, Nd2Te3, Pm2Te3, Sm2Te3, Eu2Te3, Gd2Te3, Tb2Te3, Dy2Te3, Ho2Te3, Er2Te3, Tm2Te3, Yb2Te3, and Lu2Te3, etc.

[0593] The alkali metal complex, alkaline earth metal complex, and rare earth metal complex may include alkali metal ions, alkaline earth metal ions, or rare earth metal ions and ligands bonded to the metal ions (e.g., hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxyphenyl oxadiazole, hydroxyphenyl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzimidazole, hydroxyphenyl benzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof).

[0594] The electron injection layer may consist only 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, or the electron injection layer may further include an organic material (e.g., a compound represented by Formula 601).

[0595] According to an embodiment, the electron injection layer may be composed of an alkali metal compound (e.g., an alkali metal halide); or the electron injection layer may be composed of an alkali metal compound (e.g., an alkali metal halide) and an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof. For example, the electron injection layer may be a KI:Yb co-deposited layer, a RbI:Yb co-deposited layer, etc.

[0596] 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.

[0597] The thickness of the electron injection layer may be in the range of about to about . For example, the thickness of the electron injection layer may be in the range of about to about . When the thickness of the electron injection layer is within any of these ranges, satisfactory electron injection characteristics can be obtained without significantly increasing the driving voltage.

[0598] [Second Electrode 150]

[0599] The second electrode 150 may be located on the interlayer 130 as described above. The second electrode 150 may be a cathode serving as an electron injection electrode. When the second electrode 150 is a cathode, the material used to form the second electrode 150 may include a material having a low work function, such as a metal, an alloy, a conductive compound, or any combination thereof.

[0600] The second electrode 150 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ytterbium (Yb), silver-ytterbium (Ag-Yb), ITO, IZO, or any combination thereof. The second electrode 150 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.

[0601] The second electrode 150 may have: a single-layer structure having a single layer or a multilayer structure.

[0602] [Capping Layer]

[0603] The light-emitting device 10 may include a first capping layer outside the first electrode 110 and / or a second capping layer outside the second electrode 150. For example, the light-emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the interlayer 130, and the second electrode 150 are stacked in this specified order, a structure in which the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are stacked in this specified order, or a structure in which the first capping layer, the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are stacked in this specified order.

[0604] The light generated in the emission layer of the interlayer 130 of the light-emitting device 10 may be extracted to the outside through the first electrode 110 that can serve as a semi-transmissive electrode or a transmissive electrode and through the first capping layer. The light generated in the emission layer of the interlayer 130 of the light-emitting device 10 may be extracted to the outside through the second electrode 150 that can serve as a semi-transmissive electrode or a transmissive electrode and through the second capping layer.

[0605] The first capping layer and the second capping layer may each increase the external light-emitting efficiency according to the principle of constructive interference. Accordingly, the light extraction efficiency of the light-emitting device 10 is increased, thereby improving the light-emitting efficiency of the light-emitting device 10.

[0606] The first capping layer and the second capping layer may each include a material having a refractive index greater than or equal to about 1.6 (relative to a wavelength of about 589 nm).

[0607] The first capping layer and the second capping layer may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or an organic-inorganic composite capping layer including an organic material and an inorganic material.

[0608] At least one of the first capping layer and the second capping layer may each independently include a carbocyclic compound, a heterocyclic compound, an amino group-containing compound, a porphyrin derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compound, the heterocyclic compound, and the amino group-containing compound may optionally be substituted with substituents including O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof.

[0609] According to an embodiment, at least one of the first capping layer and the second capping layer may each independently include an amino group-containing compound.

[0610] In an embodiment, at least one of the first capping layer and the second capping layer may each independently include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof.

[0611] According to another embodiment, at least one of the first capping layer and the second capping layer may each independently include one of compounds HT28 to HT33, one of compounds CP1 to CP6, β-NPB, or any combination thereof:

[0612]

[0613] [Film]

[0614] The polycyclic compound represented by Formula 1 may be included in various films. Accordingly, an embodiment provides a film including the polycyclic compound represented by Formula 1. The film may be, for example, an optical member (or a light control device) (e.g., a color filter, a color conversion member, a capping layer, a light extraction efficiency enhancement layer, a selective light absorption layer, a polarization layer, a layer containing quantum dots, etc.), a light-blocking member (e.g., a light reflection layer, a light absorption layer, etc.), a protection member (e.g., an insulating layer, a dielectric layer, etc.), etc.

[0615] [Electronic device]

[0616] The light-emitting device may be included in various electronic devices. For example, the electronic device including the light-emitting device may be a light-emitting device or an authentication device, etc.

[0617] In addition to the light-emitting device, the electronic device (e.g., a light-emitting device) may further include a color filter, a color conversion layer, or a color filter and a color conversion layer. The color filter and / or the color conversion layer may be located in at least one direction in which the light emitted from the light-emitting device travels. For example, the light emitted from the light-emitting device may be blue light or white light. The light-emitting device may be the light-emitting device described herein. According to an embodiment, the color conversion layer may include quantum dots. The quantum dots may be, for example, the quantum dots described herein.

[0618] The electronic device may include a first substrate. The first substrate may include a plurality of sub-pixels, the color filter may include a plurality of color filter regions respectively corresponding to the plurality of sub-pixels, and the color conversion layer may include a plurality of color conversion regions respectively corresponding to the plurality of sub-pixels.

[0619] The pixel defining layer may be located between the plurality of sub-pixels to define each sub-pixel.

[0620] The color filter may further include a plurality of color filter regions and a light-blocking pattern located between the plurality of color filter regions, and the color conversion layer may further include a plurality of color conversion regions and a light-blocking pattern located between the plurality of color conversion regions.

[0621] The color filter region (or color conversion region) may include a first region emitting first color light, a second region emitting second color light, and / or a third region emitting third color light, where the first color light, the second color light, and / or the third color light may have different maximum emission wavelengths from each other. For example, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. In an embodiment, the color filter region (or color conversion region) may include quantum dots. In an embodiment, the first region may include red quantum dots, the second region may include green quantum dots, and the third region may not include quantum dots. The quantum dots may be the quantum dots described herein. The first region, the second region, and / or the third region may each include a scatterer.

[0622] In an embodiment, the light-emitting device may emit first light, the first region may absorb the first light to emit first-first color light, the second region may absorb the first light to emit second-first color light, and the third region may absorb the first light to emit third-first color light. The first-first color light, the second-first color light, and the third-first color light may have different maximum emission wavelengths from each other. In an embodiment, the first light may be blue light, the first-first color light may be red light, the second-first color light may be green light, and the third-first color light may be blue light.

[0623] In addition to the light-emitting device as described above, the electronic device may further include a thin film transistor. The thin film transistor may include a source electrode, a drain electrode, and an active layer, where any one of the source electrode and the drain electrode may be electrically connected to any one of the first electrode and the second electrode of the light-emitting device.

[0624] The thin film transistor may further include a gate electrode or a gate insulating film, etc.

[0625] The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, etc.

[0626] The electronic device may further include a sealing portion for sealing the light-emitting device. The sealing portion may be located between the color filter and / or the color conversion layer and the light-emitting device. The sealing portion may allow the light from the light-emitting device to be extracted to the outside, and may prevent environmental air and / or moisture from penetrating into the light-emitting device. The sealing portion may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing portion may be a thin film encapsulation layer including one or more organic layers and / or inorganic layers. When the sealing portion is a thin film encapsulation layer, the electronic device may be flexible.

[0627] In addition to a color filter and / or a color conversion layer, various functional layers may be further included on the sealing portion according to the use of the electronic device. Examples of the functional layer are a touch screen layer, a polarization layer, etc. The touch screen layer may be a pressure-sensitive touch screen layer, a capacitive touch screen layer, or an infrared touch screen layer. The authentication device may be, for example, a biometric authentication device that authenticates an individual by using biometric information of a living body (e.g., a fingertip, a pupil, etc.).

[0628] In addition to the light-emitting device as described above, the authentication device may further include a biometric information collector.

[0629] The electronic device may be applied to various displays, light sources, lighting devices, personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic notebooks, electronic dictionaries, electronic game machines, medical tools (e.g., electronic thermometers, sphygmomanometers, glucometers, pulse measuring devices, pulse wave measuring devices, electrocardiogram monitors, ultrasonic diagnostic devices, or endoscope monitors), fish finders, various measuring tools, meters (e.g., meters for vehicles, aircraft, and ships), and projectors, etc.

[0630] Figure 2 and Figure 3 description of]

[0631] Figure 2 is a schematic cross-sectional view of an electronic device according to an embodiment.

[0632] Figure 2 The electronic device may include a substrate 100, a thin film transistor (TFT), a light-emitting device, and a sealing portion 300 that seals the light-emitting device.

[0633] The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. A buffer layer 210 may be located on the substrate 100. The buffer layer 210 may prevent the penetration of impurities through the substrate 100 and may provide a flat surface on the substrate 100.

[0634] The TFT may be located on the buffer layer 210. The TFT may include an active layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.

[0635] The active layer 220 may include an inorganic semiconductor such as silicon or polysilicon, an organic semiconductor, or an oxide semiconductor, and may include a source region, a drain region, and a channel region.

[0636] A gate insulating film 230 for insulating the active layer 220 from the gate electrode 240 may be located on the active layer 220, and the gate electrode 240 may be located on the gate insulating film 230.

[0637] ​The interlayer insulating film 250 may be located on the gate electrode 240. The interlayer insulating film 250 may be located between the gate electrode 240 and the source electrode 260 to insulate the gate electrode 240 from the source electrode 260, and between the gate electrode 240 and the drain electrode 270 to insulate the gate electrode 240 from the drain electrode 270.

[0638] The source electrode 260 and the drain electrode 270 may be located on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose the source region and the drain region of the active layer 220, and the source electrode 260 and the drain electrode 270 may respectively contact the exposed portions of the source region and the drain region of the active layer 220.

[0639] The TFT may be electrically connected to the light-emitting device to drive the light-emitting device, and may be covered and protected by the passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or any combination thereof. The light-emitting device may be provided on the passivation layer 280. The light-emitting device may include a first electrode 110, an interlayer 130, and a second electrode 150.

[0640] The first electrode 110 may be located on the passivation layer 280. The passivation layer 280 may not completely cover the drain electrode 270 and may expose a part of the drain electrode 270. The first electrode 110 may be electrically connected to the exposed portion of the drain electrode 270.

[0641] The pixel defining layer 290 including an insulating material may be located on the first electrode 110. The pixel defining layer 290 may expose the region of the first electrode 110, and the interlayer 130 may be formed on the exposed region of the first electrode 110. The pixel defining layer 290 may be a polyimide or polyacrylic acid organic film. Although not shown in Figure 2 , at least some layers of the interlayer 130 may extend beyond the upper portion of the pixel defining layer 290 and be provided in the form of a common layer.

[0642] The second electrode 150 may be located on the interlayer 130, and a capping layer 170 may be further included on the second electrode 150. The capping layer 170 may be formed to cover the second electrode 150.

[0643] The sealing portion 300 may be located on the capping layer 170. The sealing portion 300 may be located on the light-emitting device to protect the light-emitting device from moisture and / or oxygen. The sealing portion 300 may include: an inorganic film including silicon nitride (SiN x ) and silicon oxide (SiO x) indium tin oxide, indium zinc oxide, or any combination thereof; an organic film including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyvinyl sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, acrylic resins (e.g., polymethyl methacrylate, polyacrylic acid, etc.), epoxy resins (e.g., aliphatic glycidyl ether (AGE), etc.), or any combination thereof; or any combination of an inorganic film and an organic film.

[0644] Figure 3 is a schematic cross-sectional view of an electronic device according to another embodiment.

[0645] Figure 3 The electronic device of Figure 2 may differ from the electronic device of Figure 3 at least in that the light-blocking pattern 500 and the functional region 400 are further included on the sealing portion 300. The functional region 400 may be a color filter region, a color conversion region, or a combination of a color filter region and a color conversion region. According to an embodiment,

[0646] Figure 4 description of

[0647] Figure 4 is a schematic perspective view of an electronic device 1 including a light-emitting device according to an embodiment.

[0648] The electronic device 1 may be a device for displaying moving images or still images, and may be not only a portable electronic device such as a mobile phone, a smartphone, a tablet personal computer (PC), a mobile communication terminal, an electronic notebook computer, an e-book, a portable multimedia player (PMP), a navigation device, or a ultra-mobile PC (UMPC), but also various products such as a television, a laptop computer, a monitor, or a billboard, or an Internet of Things (IoT) device, etc., or a part thereof. In an embodiment, the electronic device 1 may be a wearable device such as a smartwatch, a watch phone, a glasses-type display, or a head-mounted display (HMD), or a part of a wearable device. However, the embodiment is not limited thereto.

[0649] Examples of the electronic device 1 may include a vehicle dashboard, a vehicle center console, a center information display disposed on the vehicle dashboard, an in-vehicle rearview mirror display replacing the vehicle side mirror, an entertainment display for the vehicle rear seat or disposed on the front seat backrest, a head-up display (HUD) mounted in front of the vehicle or projected on the front window glass, or a computer-generated holographic augmented reality head-up display (CGH AR HUD). For ease of explanation, Figure 4 the case where the electronic device 1 is a smartphone is illustrated.

[0650] ​The electronic device 1 may include a display area DA and a non-display area NDA outside the display area DA. The display device may implement an image through a two-dimensional array of pixels arranged in the display area DA.

[0651] The non-display area NDA may be an area that does not display an image and may surround the display area DA. A driver or the like for supplying an electrical signal or power to a display element arranged in the display area DA may be arranged in the non-display area NDA. A pad, which may be electrically connected to an electronic component or a printed circuit board or the like, may be arranged in the non-display area NDA.

[0652] In the electronic device 1, the length in the x-axis direction and the length in the y-axis direction may be different from each other. For example, as Figure 4 shown, the length in the x-axis direction may be shorter than the length in the y-axis direction. As another example, the length in the x-axis direction may be the same as the length in the y-axis direction. As another example, the length in the x-axis direction may be longer than the length in the y-axis direction.

[0653] Figure 5 and Figures 6A to 6C description]

[0654] Figure 5 FIG. 19 is a schematic perspective view of the exterior of a vehicle 1000 as an electronic device including a light-emitting device according to an embodiment. Figures 6A to 6C FIGS. 20 and 21 are schematic views of the interior of the vehicle 1000 according to an embodiment.

[0655] Refer to Figure 5 、 Figure 6A 、 Figure 6B and Figure 6C As shown in FIGS. 32 to 35, the vehicle 1000 may include various devices for moving an object to be transported (such as a person, an object, or an animal, etc.) from a starting point to a destination. The vehicle 1000 may include a vehicle traveling on a road or a track, a ship moving on an ocean or a river, an airplane flying in the air by the action of air, and the like.

[0656] The vehicle 1000 may travel on a road or a track. The vehicle 1000 may move in a selectable direction according to the rotation of at least one wheel. Examples of the vehicle 1000 may include a three-wheeled or four-wheeled vehicle, construction machinery, a two-wheeled vehicle, a prime mover, a bicycle, and a train traveling on a track.

[0657] ​Vehicle 1000 may include a body having an interior and an exterior, and a chassis, which is a part other than the body where mechanical equipment for driving is installed as other components. The exterior of the body may include a front panel, a hood, a roof panel, a rear panel, a trunk, and pillars provided at the boundaries between the doors, etc. The chassis of vehicle 1000 may include a power generation device, a power transmission device, a driving device, a steering device, a braking device, a suspension device, a transmission device, a fuel device, front wheels and rear wheels, and left and right wheels, etc.

[0658] Vehicle 1000 may include side window glass 1100, front window glass 1200, side mirrors 1300, an instrument cluster 1400, a center console 1500, a passenger seat dashboard 1600, and a display device 2.

[0659] Side window glass 1100 and front window glass 1200 may be separated by a pillar disposed between side window glass 1100 and front window glass 1200.

[0660] Side window glass 1100 may be installed on the side of vehicle 1000. In an embodiment, side window glass 1100 may be installed on the door of vehicle 1000. A plurality of side window glass 1100 may be provided and may face each other. In an embodiment, side window glass 1100 may include a first side window glass 1110 and a second side window glass 1120. In an embodiment, the first side window glass 1110 may be arranged adjacent to the instrument cluster 1400, and the second side window glass 1120 may be arranged adjacent to the passenger seat dashboard 1600.

[0661] In an embodiment, side window glass 1100 may be spaced apart from each other in the x-axis direction or the -x-axis direction (a direction opposite to the x-axis direction). For example, the first side window glass 1110 and the second side window glass 1120 may be spaced apart from each other in the x-axis direction or the -x-axis direction. For example, a virtual straight line L connecting side window glass 1100 may extend in the x-axis direction or the -x-axis direction. For example, a virtual straight line L connecting the first side window glass 1110 and the second side window glass 1120 to each other may extend in the x-axis direction or the -x-axis direction.

[0662] Front window glass 1200 may be installed in the front of vehicle 1000. Front window glass 1200 may be disposed between side window glass 1100 that face each other.

[0663] Side mirrors 1300 may provide a rear view of vehicle 1000. Side mirrors 1300 may be installed on the exterior of the body of vehicle 1000. In an embodiment, a plurality of side mirrors 1300 may be provided. Any one of the plurality of side mirrors 1300 may be disposed outside the first side window glass 1110, and another one of the plurality of side mirrors 1300 may be disposed outside the second side window glass 1120.

[0664] The instrument cluster 1400 may be arranged in front of the steering wheel. The instrument cluster 1400 may include a tachometer, a speedometer, a coolant thermometer, a fuel gauge, turn indicators, high beam indicators, warning lights, seat belt warning lights, an odometer, a trip meter, an automatic gearshift indicator light, door open warning lights, an engine oil warning light, and / or a low fuel warning light.

[0665] The center console 1500 may include a control panel on which buttons for adjusting an audio device, an air conditioning device, and a seat heater are arranged. The center console 1500 may be arranged on one side of the instrument cluster 1400.

[0666] The passenger seat dashboard 1600 may be spaced apart from the instrument cluster 1400, and the center console 1500 is arranged between the passenger seat dashboard 1600 and the instrument cluster 1400. In an embodiment, the instrument cluster 1400 may be arranged corresponding to the driver's seat (not shown), and the passenger seat dashboard 1600 may be provided corresponding to the passenger seat (not shown). In an embodiment, the instrument cluster 1400 may be adjacent to the first side window glass 1110, and the passenger seat dashboard 1600 may be adjacent to the second side window glass 1120.

[0667] In an embodiment, the display device 2 may include a display panel 3, and the display panel 3 may display an image. The display device 2 may be arranged inside the vehicle 1000. In an embodiment, the display device 2 may be arranged between the side window glasses 1100 facing each other. The display device 2 may be arranged on at least one of the instrument cluster 1400, the center console 1500, and the passenger seat dashboard 1600.

[0668] The display device 2 may include an organic light emitting display device, an inorganic electroluminescent (EL) display device, a quantum dot display device, etc. Hereinafter, as the display device 2 according to an embodiment, an organic light emitting display device including a light emitting device according to the present disclosure will be described as an example. However, various types of display devices as described above may be used in the embodiment.

[0669] See Figure 6A , the display device 2 may be arranged on the center console 1500. In an embodiment, the display device 2 may display navigation information. In an embodiment, the display device 2 may display information about audio settings, video settings, or vehicle settings.

[0670] See Figure 6B, the display device 2 may be arranged on the instrument cluster 1400. When the display device 2 is arranged on the instrument cluster 1400, the instrument cluster 1400 may display driving information and the like through the display device 2. For example, the instrument cluster 1400 may digitally implement driving information. The instrument cluster 1400 may digitally display vehicle information and driving information as images. For example, the pointer and instrument of the tachometer and various warning light icons may be displayed through digital signals.

[0671] See also Figure 6C , the display device 2 may be arranged on the passenger seat instrument panel 1600. The display device 2 may be embedded in the passenger seat instrument panel 1600 or arranged on the passenger seat instrument panel 1600. In an embodiment, the display device 2 arranged on the passenger seat instrument panel 1600 may display an image related to the information displayed on the instrument cluster 1400 and / or the information displayed on the center console 1500. In another embodiment, the display device 2 arranged on the passenger seat instrument panel 1600 may display information different from the information displayed on the instrument cluster 1400 and / or the information displayed on the center console 1500.

[0672] [Manufacturing method]

[0673] The various layers included in the hole transport region, the emission layer, and the various layers included in the electron transport region can be formed in a selected region by using various methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, laser induced thermal imaging (LITI), etc.

[0674] When the various layers included in the hole transport region, the emission layer, and the various layers included in the electron transport region are formed by vacuum deposition, the deposition temperature may be within a range of about 100° C. to about 500° C., about 10 -8 To about 10 -3 Torr in the range of vacuum and about / second to about The deposition was performed at a deposition rate in the range of 100 Å / s.

[0675] [Definition of terms]

[0676] As used herein, the term "C3-C 60 The "carbocyclic group" may be a cyclic group consisting of only carbon atoms as ring atoms and having 3 to 60 carbon atoms, for example, C3-C 50 Carbocyclic group, C3-C 40 Carbocyclic group, C3-C 30 Carbocyclic group, C3-C 20 Carbocyclic or C3-C 10 Carbocyclic groups, and as used herein, the term "C1-C60 The "heterocyclic group" may be a cyclic group having 1 to 60 carbon atoms and further including heteroatoms as ring-forming atoms in addition to carbon, for example, C1-C 50 Heterocyclic group, C1-C 40 Heterocyclic group, C1-C 30 Heterocyclic group, C1-C 20 Heterocyclic or C1-C 10 Heterocyclic group. C3-C 60 Carbocyclic and C1-C 60 The heterocyclic groups may each be a monocyclic group consisting of one ring or a polycyclic group in which two or more rings are fused to each other. 60 The heterocyclic group can have 3 to 61 ring-forming atoms.

[0677] As used herein, the term "cyclic group" may be C3-C 60 Carbocyclic or C1-C 60 Heterocyclic group.

[0678] As used herein, the term "π-electron-rich C3-C 60 The "cyclic group" may be a cyclic group having 3 to 60 carbon atoms and may not include *-N=*' as a ring-forming part, and the term "π-electron-deficient nitrogen-containing C1-C 60 The "cyclic group" may be a heterocyclic group having 1 to 60 carbon atoms and may include *-N=*' as a ring-forming portion.

[0679] In an embodiment,

[0680] C3-C 60 The carbocyclic group may be a T1 group, or a group in which two or more T1 groups are fused to each other (e.g., a cyclopentadienyl group, an adamantyl group, a norbornyl group, a phenyl group, a pentalenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylene group, a pyrenyl group, a 1,2-triphenylene group, a peryl group, a pentaphenanthrenyl group, a heptalenyl group, a tetracenyl group, a phenanthrenyl group, a hexacenyl group, a pentacenyl group, a rubidenyl group, a coronenyl group, an ovalenyl group, an indenyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, an indenophenanthrenyl group, or an indenoanthryl group),

[0681] C1-C 60The heterocyclic group may be a T2 group, a group in which two or more T2 groups are fused to each other, or a group in which one or more T2 groups and one or more T1 groups are fused to each other (e.g., a pyrrolyl group, a thienyl group, a furyl group, an indolyl group, a benzindolyl group, a naphthoindolyl group, an isoindolyl group, a benzisoindolyl group, a naphthoisoindolyl group, a benzothiorolyl group, a benzothiophenyl group, a benzofuranyl group, a carbazolyl group, a dibenzothiorolyl group, a dibenzothiophenyl group, a dibenzofuranyl group, an indenocarbazolyl group, an indolcarbazolyl group, a benzofuranocarbazolyl group, a benzothiophenylcarbazolyl group, a benzothiorolocarbazolyl group, a benzoindolcarbazolyl group, a benzocarbazolyl group, a benzonaphthofuranoyl group, a benzonaphthothiophenyl group, a benzonaphthothiorolyl group, a benzofuranodi ... thienyl, benzothienodibenzothienyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl quinolinyl, benzoisoquinolinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinyl, cinnolinyl, phthalazinyl, naphthyridinyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazine, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafluorenyl, azadibenzothiazolyl, azadibenzothiopheneyl, azadibenzofuranyl, etc.),

[0682] Pi-electron-rich C3-C 60 The cyclic group may be a T1 group, a group in which two or more T1 groups are fused to each other, a T3 group, a group in which two or more T3 groups are fused to each other, or a group in which one or more T3 groups and one or more T1 groups are fused to each other (e.g., C3-C 60 carbocyclic group, 1H-pyrrolyl, thiolyl, borocyclopentyl, 2H-pyrrolyl, 3H-pyrrolyl, thienyl, furyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzothiolyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzothiolyl, dibenzothiophenyl, dibenzofuranyl, indenocarbazolyl, indolcarbazolyl, benzofuranocarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzothiophenylcarbazolyl, benzoindolcarbazolyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothienyl, benzonaphthothiolyl, benzofuranodibenzofuranyl, benzofuranodibenzothiophenyl, benzothiophenyldibenzothiophenyl, etc.),

[0683] π-electron-deficient nitrogen-containing C1-C 60The cyclic group may be a T4 group, a group in which two or more T4 groups are fused to each other, a group in which one or more T4 groups and one or more T1 groups are fused to each other, a group in which one or more T4 groups and one or more T3 groups are fused to each other, or a group in which one or more T4 groups, one or more T1 groups, and one or more T3 groups are fused to each other (e.g., pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, benzisoquinolyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinyl, cinnolinyl, phthalazinyl, naphthyridinyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafluorenyl, azadibenzothiazolyl, azadibenzothiophenyl, azadibenzofuranyl, etc.),

[0684] wherein the T1 group can be cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclobutenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cyclohexadienyl, cycloheptenyl, adamantyl, norbornane (or bicyclo[2.2.1]heptane) group, norbornyl, bicyclo[1.1.1]pentane, bicyclo[2.1.1]hexane, bicyclo[2.2.2]octane or phenyl,

[0685] The T2 group can be furanyl, thienyl, 1H-pyrrolyl, thiolyl, borocyclopentyl, 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azathiarolyl, azaborolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, tetraazinyl, pyrrolidinyl, imidazolidinyl, dihydropyrrolyl, piperidinyl, tetrahydropyridinyl, dihydropyridinyl, hexahydropyrimidinyl, tetrahydropyrimidinyl, dihydropyrimidinyl, piperazinyl, tetrahydropyrazinyl, dihydropyrazinyl, tetrahydropyridazinyl or dihydropyridazinyl,

[0686] The T3 group may be furanyl, thienyl, 1H-pyrrolyl, thiolsyl or borocyclopentadienyl, and

[0687] The T4 group can be 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azathioyl, azaborolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl or tetrazinyl.

[0688] As used herein, the terms "cyclic group", "C3-C 60 Carbocyclic group", "C1-C 60 Heterocyclic group", "π-electron-rich C3-C 60 Cyclic group" or "π-electron-deficient nitrogen-containing C1-C 60 The "cyclic group" may each be a monovalent group or a polyvalent group (e.g., a divalent group, a trivalent group, a tetravalent group, etc.) condensed with any cyclic group according to the structure of the formula using the corresponding term. For example, "phenyl" may be benzo, phenyl, phenylene, etc., and those skilled in the art may easily understand these groups based on the structure of the formula including "phenyl".

[0689] Unit price C3-C 60 Carbocyclic or monovalent C1-C 60 Examples of heterocyclic groups may include C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C1-C 60 heteroaryl, monovalent non-aromatic fused polycyclic group and monovalent non-aromatic fused heteropolycyclic group. 60 Carbocyclic or divalent C1-C 60 Examples of heterocyclic groups may include C3-C 10 Cycloalkylene, C1-C 10 Heterocycloalkylene, C3-C 10 Cycloalkenylene, C1-C 10 Heterocycloalkenylene, C6-C 60 Arylene, C1-C 60 a heteroarylene group, a divalent non-aromatic fused polycyclic group, and a divalent non-aromatic fused heteropolycyclic group.

[0690] As used herein, the term "C1-C 60 The "alkyl" may be a straight or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, for example, C1-C 50 Alkyl, C1-C 30 Alkyl, C1-C 20 Alkyl or C1-C 10The term "C1-C1-alkyl" may be used herein, and examples thereof 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, 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, and the like. As used herein, the term "C1-C1-alkyl" may be used herein. 60 The "alkylene" may be a C1-C 60 The alkyl group has substantially the same structure as a divalent group.

[0691] As used herein, the term "C2-C 60 The "alkenyl" may be a C2-C 60 A monovalent hydrocarbon group having one or more carbon-carbon double bonds in the middle or at the end of the alkyl group, for example, C2-C 30 Alkenyl, C2-C 20 Alkenyl or C2-C 10 The term "C2-C4-alkenyl" as used herein may include vinyl, propenyl, butenyl, etc. 60 "Alkenylene" can be C2-C 60 The alkenyl group has a divalent group having substantially the same structure.

[0692] As used herein, the term "C2-C 60 "Alkynyl" may be a C2-C 60 A monovalent hydrocarbon group having one or more carbon-carbon triple bonds in the middle or at the end of the alkyl group, for example, C2-C 30 Alkynyl, C2-C 20 Alkynyl or C2-C 10 The term "C2-C 2-alkynyl" as used herein may include ethynyl, propynyl, and the like. 60 "Alkyne" can be C2-C 60 Alkynyl groups have substantially the same structure as a divalent group.

[0693] As used herein, the term "C1-C 60 "Alkoxy" may be -O(A 101 )(where A 101 Can be C1-C 60 A monovalent group represented by an alkyl group, for example, C1-C 30 Alkoxy, C1-C 20 Alkoxy or C1-C 10 Alkoxy group, and examples thereof may include methoxy group, ethoxy group, isopropoxy group, and the like.

[0694] As used herein, the term "C3-C 10The "cycloalkyl" may be a monovalent saturated hydrocarbon ring group having 3 to 10 carbon atoms, and examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl (or bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, and the like. As used herein, the term "C3-C 10 The cycloalkylene group may be C3-C 10 The cycloalkyl group has a divalent group having substantially the same structure.

[0695] As used herein, the term "C1-C 10 The term "heterocycloalkyl" as used herein may be a monovalent cyclic group of 1 to 10 carbon atoms further including at least one heteroatom as a ring-forming atom in addition to carbon atoms, and examples thereof may include 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl, tetrahydrothienyl, and the like. 10 The "heterocycloalkylene" may be a C1-C 10 The heterocycloalkyl group has substantially the same structure as a divalent group.

[0696] As used herein, the term "C3-C 10 The term "C3-C4-cycloalkenyl" as used herein may be a monovalent cyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and having no aromaticity, and examples thereof may include cyclopentenyl, cyclohexenyl, cycloheptenyl, and the like. 10 The cycloalkenylene group may be 10 The cycloalkenyl group has a divalent group having substantially the same structure.

[0697] As used herein, the term "C1-C 10 The "heterocycloalkenyl group" may be a monovalent cyclic group of 1 to 10 carbon atoms which further includes at least one heteroatom as a ring-forming atom in addition to carbon atoms in its cyclic structure and has at least one double bond. 10 Examples of heterocycloalkenyl groups may include 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl, 2,3-dihydrothienyl, and the like. As used herein, the term “C1-C 10 The "heterocycloalkenylene" may be a C1-C 10 The heterocycloalkenyl group has a divalent group having substantially the same structure.

[0698] As used herein, the term "C6-C 60 The "aryl group" may be a monovalent group of a carbocyclic aromatic system having 6 to 60 carbon atoms, for example, C6-C 50 Aryl, C6-C 40 Aryl, C6-C 30Aryl, C6-C 20 Aryl or C6-C 15 Aryl, and as used herein the term "C6-C 60 The "arylene group" may be a divalent group of a carbocyclic aromatic system having 6 to 60 carbon atoms. 60 Examples of aryl groups may include phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenanthrenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylene, pyrenyl, 1,2-triphenylenyl, peryl, pentaphenanthrenyl, heptalenyl, tetracenyl, pyrenyl, hexenyl, pentacene, rubenyl, coronenyl, ovalenyl, and the like. 60 Aryl and C6-C 60 When the arylene groups each include two or more rings, the respective rings may be fused to each other.

[0699] As used herein, the term "C1-C 60 The "heteroaryl group" may be a monovalent group of a heterocyclic aromatic system having 1 to 60 carbon atoms, further including at least one heteroatom as a ring-forming atom in addition to carbon atoms, for example, C1-C 50 Heteroaryl, C1-C 40 Heteroaryl, C1-C 30 Heteroaryl, C1-C 20 Heteroaryl or C1-C 10 As used herein, the term "C1-C 60 The "heteroarylene group" may be a divalent group of a heterocyclic aromatic system having 1 to 60 carbon atoms, further including at least one heteroatom as a ring-forming atom in addition to carbon atoms. 60 Examples of heteroaryl groups may include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolyl, benzoquinolyl, isoquinolyl, benzoisoquinolyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthrolinyl, phthalazinyl, naphthyridinyl, and the like. 60 Heteroaryl and C1-C 60 When the heteroarylene groups each include two or more rings, the respective rings may be fused to each other.

[0700] The term "monovalent non-aromatic fused polycyclic group" as used herein may be a monovalent group (e.g., having 8 to 60 carbon atoms) having two or more rings fused to each other, only carbon atoms as ring-forming atoms, and no aromaticity in its entire molecular structure, for example, C8-C 60 Monovalent non-aromatic fused polycyclic group, C8-C 50 Monovalent non-aromatic fused polycyclic group, C8-C 40 Monovalent non-aromatic fused polycyclic group, C8-C 30 Monovalent non-aromatic fused polycyclic group or C8-C20 Monovalent non-aromatic condensed polycyclic group. Examples of the monovalent non-aromatic condensed polycyclic group may include indenyl, fluorenyl, spirobifluorenyl, benzofluorenyl, indenophenanthryl, indenoanthryl, etc. The term "divalent non-aromatic condensed polycyclic group" as used herein may be a divalent group having substantially the same structure as the monovalent non-aromatic condensed polycyclic group.

[0701] The term "monovalent non-aromatic fused heteropolycyclic group" as used herein may be a monovalent group (for example, having 1 to 60 carbon atoms) having two or more rings fused to each other, further including at least one heteroatom as a ring-forming atom in addition to carbon atoms, and having no aromaticity in its entire molecular structure, for example, C1-C 60 Monovalent non-aromatic fused heteropolycyclic group, C1-C 50 Monovalent non-aromatic fused heteropolycyclic group, C1-C 40 Monovalent non-aromatic fused heteropolycyclic group, C1-C 30 Monovalent non-aromatic fused heteropolycyclic group or C1-C 20 Monovalent non-aromatic condensed heteropolycyclic group. Examples of the monovalent non-aromatic condensed heteropolycyclic group may include pyrrolyl, thienyl, furanyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzothioyl, benzothiophenyl, benzofuranyl, carbazolyl, dibenzothioyl, dibenzothiophenyl, dibenzofuranyl, azacarbazolyl, azafluorenyl, azadibenzothioyl, azadibenzothiophenyl, azadibenzofuranyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl The term "divalent non-aromatic condensed heteropolycyclic group" as used herein may be a divalent group having substantially the same structure as the monovalent non-aromatic condensed heteropolycyclic group.

[0702] As used herein, the term "C6-C 60 The "aryloxy" may be -O(A 102 )(where A 102 Can be C6-C 60 Aryl) group, for example, C6-C 50 Aryloxy, C6-C 40Aryloxy, C6-C 30 Aryloxy, C6-C 20 Aryloxy or C6-C 15 Aryloxy, and as used herein the term "C6-C 60 The "arylthio" group may be -S(A 103 )(where A 103 Can be C6-C 60 Aryl) group, for example, C6-C 50 Arylthio, C6-C 40 Arylthio, C6-C 30 Arylthio, C6-C 20 Arylthio or C6-C 15 Arylthio.

[0703] The term "C7-C 60 The "aralkyl" may be -(A 104 )(A 105 )(where A 104 Can be C1-C 54 Alkylene, and A 105 Can be C6-C 59 A group represented by an aryl group, for example, a C7-C 50 Aralkyl, C7-C 40 Aralkyl, C7-C 30 Aralkyl, C7-C 20 Arylalkyl or C7-C 15 Aralkyl, and the term "C2-C 60 The heteroarylalkyl group may be -(A 106 )(A 107 )(where A 106 Can be C1-C 59 Alkylene, and A 107 Can be C1-C 59 heteroaryl) group, for example, C2-C 50 Heteroarylalkyl, C2-C 40 Heteroarylalkyl, C2-C 30 Heteroarylalkyl, C2-C 20 Heteroarylalkyl or C2-C 15 Heteroaralkyl.

[0704] In the specification, the group "R 10a ” and “R 10b " can be:

[0705] deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazine or hydrazone;

[0706] Each unsubstituted or substituted C1-C60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy or C1-C 60 Alkylthio: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C2-C 60 Heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O)2(Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof;

[0707] Each unsubstituted or substituted C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Arylalkyl or C2-C 60 Heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C2-C 60 Heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22)、-C(=O)(Q 21 )、-S(=O)2(Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof; or

[0708] -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-Ge(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ).

[0709] In the specification, as used herein, the groups Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; or each unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 C1-C12-substituted alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, or any combination thereof 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Arylalkyl or C2-C 60 Heteroaralkyl.

[0710] As used herein, the term "heteroatom" can be any atom other than carbon and hydrogen atoms. Examples of heteroatoms can include B, O, S, N, P, Si, B, Ge, Se, or any combination thereof.

[0711] As used herein, the term "transition metal" can include hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), gold (Au), etc.

[0712] In the specification, the term "Ph" refers to phenyl, the term "Me" refers to methyl, the term "Et" refers to ethyl, the term "tert-Bu" or "Bu t ” each refers to tert-butyl, and the term "OMe" refers to methoxy.

[0713] As used herein, the term "biphenyl" can be "phenyl substituted with phenyl". For example, "biphenyl" can be a substituted phenyl having a C6-C 60 aryl as a substituent.

[0714] As used herein, the term "terphenyl" can be "phenyl substituted with biphenyl". For example, "terphenyl" can be a substituted phenyl having a C6-C 60 aryl substituted with a C6-C 60 aryl as a substituent.

[0715] Unless otherwise defined, the symbols *, *', and *" as used herein each refer to the binding site to an adjacent atom in the corresponding formula or moiety.

[0716] Hereinafter, the compounds according to the embodiments and the light-emitting devices according to the embodiments will be described in detail with reference to the following synthesis examples and examples. The phrase "using B instead of A" used in the description of the synthesis examples means using the same molar equivalent of B instead of A.

[0717] [Synthesis Examples and Examples]

[0718] Synthesis Example 1: Synthesis of Compound 1

[0719]

[0720] Synthesis of Intermediate 1-1

[0721] 1,3-Dibromo-5-chlorobenzene (1 eq), [1,1':3',1"-terphenyl]-2'-amine (2 eq), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq), tri-tert-butylphosphine (0.1 eq) and sodium tert-butoxide (3 eq) were dissolved in toluene and stirred at 110°C for 12 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried over MgSO4 under reduced pressure. The obtained product was purified by column chromatography with MC and n-hexane to obtain intermediate 1-1. (Yield: 82%)

[0722] Synthesis of intermediate 1-2

[0723] Intermediate 1-1 (1 eq), 4-iodo-1,1'-biphenyl (2 eq), tri(dibenzylideneacetone)dipalladium (0) (0.25 eq), tri-tert-butylphosphine (0.5 eq) and sodium tert-butoxide (3 eq) were dissolved in o-xylene and stirred at 150°C for 60 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried with MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain intermediate 1-2. (Yield: 31%)

[0724] Synthesis of intermediate 1-3

[0725] Intermediate 1-2 (1 eq) was dissolved in o-dichlorobenzene and cooled to 0°C, and BBr3 (3 eq) was slowly injected thereinto in a nitrogen atmosphere. After the addition was completed, the temperature was raised to 180°C, followed by stirring for 24 hours. After cooling, triethylamine was slowly added dropwise to the flask containing the reactants to terminate the reaction, and ethanol was added to the reactants to cause precipitation, thereby obtaining a reaction product. The obtained solid was purified by column chromatography with MC and n-hexane, and recrystallized using toluene and acetone to obtain intermediate 1-3. (Yield: 3%)

[0726] Synthesis of compound 1

[0727] Intermediate 1-3 (1 eq), carbazole (1.5 eq), tris(dibenzylideneacetone)dipalladium (0) (0.05 eq), tri-tert-butylphosphine (0.1 eq) and sodium tert-butoxide (3 eq) were dissolved in o-xylene and stirred at 150° C. for 36 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried with MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain compound 1. (Yield: 62%)

[0728] Synthesis Example 2: Synthesis of Compound 2

[0729]

[0730] Synthesis of intermediate 2-1

[0731] 1,3-Dibromo-5-(tert-butyl)benzene (1 eq), 5'-(tert-butyl)-[1,1':3',1"-terphenyl]-2'-amine (2 eq), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq), tri-tert-butylphosphine (0.1 eq) and sodium tert-butoxide (3 eq) were dissolved in toluene and stirred at 110°C for 12 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried over MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain intermediate 2-1. (Yield: 71%)

[0732] Synthesis of intermediate 2-2

[0733] Intermediate 2-1 (1 eq), 4-iodo-1,1'-biphenyl (4 eq), tris(dibenzylideneacetone)dipalladium (0) (0.15 eq), tri-tert-butylphosphine (0.3 eq) and sodium tert-butoxide (4 eq) were dissolved in o-xylene and stirred at 150°C for 48 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried with MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain intermediate 2-2. (Yield: 33%)

[0734] Synthesis of compound 2

[0735] Intermediate 2-2 (1 eq) was dissolved in o-dichlorobenzene and cooled to 0°C, and BBr3 (5 eq) was slowly injected thereinto in a nitrogen atmosphere. After the addition was completed, the temperature was raised to 180°C, followed by stirring for 24 hours. After cooling, triethylamine was slowly added dropwise to the flask containing the reactants to terminate the reaction, and ethanol was added to the reactants to cause precipitation, thereby obtaining a reaction product. The obtained solid was purified by column chromatography with MC and n-hexane, and recrystallized using toluene and acetone to obtain compound 2. (Yield: 4%)

[0736] Synthesis Example 3: Synthesis of Compound 3

[0737]

[0738] Synthesis of intermediate 3-1

[0739] 1,3-Dibromo-5-(tert-butyl)benzene (1 eq), [1,1':3',1"-terphenyl]-2'-amine (2 eq), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq), tri-tert-butylphosphine (0.1 eq) and sodium tert-butoxide (3 eq) were dissolved in toluene and stirred at 110°C for 12 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried over MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain intermediate 3-1. (Yield: 68%)

[0740] Synthesis of intermediate 3-2

[0741] Intermediate 3-1 (1 eq), 1-(4-bromophenyl)dibenzo[b,d]furan (4 eq), tri(dibenzylideneacetone)dipalladium(0) (0.15 eq), tri-tert-butylphosphine (0.3 eq) and sodium tert-butoxide (4 eq) were dissolved in o-xylene and stirred at 150° C. for 48 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried with MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain intermediate 3-2. (Yield: 27%)

[0742] Synthesis of compound 3

[0743] Intermediate 3-2 (1 eq) was dissolved in o-dichlorobenzene and cooled to 0 ° C, and BBr3 (5 eq) was slowly injected thereinto in a nitrogen atmosphere. After the addition was completed, the temperature was raised to 180 ° C, followed by stirring for 24 hours. After cooling, triethylamine was slowly added dropwise to the flask containing the reactants to terminate the reaction, and ethanol was added to the reactants to cause precipitation, thereby obtaining a reaction product. The obtained solid was purified by column chromatography with MC and n-hexane, and recrystallized using toluene and acetone to obtain compound 3. (Yield: 3%)

[0744] Synthesis Example 4: Synthesis of Compound 4

[0745]

[0746] Synthesis of intermediate 4-1

[0747] Intermediate 3-1 (1 eq), 4-iodo-1,1'-biphenyl (1 eq), tris(dibenzylideneacetone)dipalladium (0) (0.15 eq), tri-tert-butylphosphine (0.3 eq) and sodium tert-butoxide (4 eq) were dissolved in o-xylene and stirred at 150°C for 48 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried with MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain intermediate 4-1. (Yield: 30%)

[0748] Synthesis of intermediate 4-2

[0749] Intermediate 4-1 (1 eq), 9-(3-bromophenyl)-9H-carbazole (2 eq), tris(dibenzylideneacetone)dipalladium(0) (0.15 eq), tri-tert-butylphosphine (0.3 eq) and sodium tert-butoxide (4 eq) were dissolved in o-xylene and stirred at 150° C. for 48 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried with MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain intermediate 4-2. (Yield: 44%)

[0750] Synthesis of compound 4

[0751] Intermediate 4-2 (1 eq) was dissolved in o-dichlorobenzene and cooled to 0 ° C, and BBr3 (5 eq) was slowly injected thereinto in a nitrogen atmosphere. After the addition was completed, the temperature was raised to 180 ° C, followed by stirring for 24 hours. After cooling, triethylamine was slowly added dropwise to the flask containing the reactants to terminate the reaction, and ethanol was added to the reactants to cause precipitation, thereby obtaining a reaction product. The obtained solid was purified by column chromatography with MC and n-hexane, and recrystallized using toluene and acetone to obtain compound 4. (Yield: 3%)

[0752] Synthesis Example 5: Synthesis of Compound 5

[0753]

[0754] Synthesis of intermediate 5-1

[0755] Intermediate 3-1 (1 eq), 9-(3-bromophenyl)-3,6-di-tert-butyl-9H-carbazole (4 eq), tris(dibenzylideneacetone)dipalladium(0) (0.15 eq), tri-tert-butylphosphine (0.3 eq) and sodium tert-butoxide (4 eq) were dissolved in o-xylene and stirred at 150° C. for 48 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried with MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain intermediate 5-1. (Yield: 43%)

[0756] Synthesis of compound 5

[0757] Intermediate 5-1 (1 eq) was dissolved in o-dichlorobenzene and cooled to 0°C, and BBr3 (5 eq) was slowly injected thereinto in a nitrogen atmosphere. After the addition was completed, the temperature was raised to 180°C, followed by stirring for 24 hours. After cooling, triethylamine was slowly added dropwise to the flask containing the reactants to terminate the reaction, and ethanol was added to the reactants to cause precipitation, thereby obtaining a reaction product. The obtained solid was purified by column chromatography with MC and n-hexane, and recrystallized using toluene and acetone to obtain compound 5. (Yield: 6%)

[0758] Synthesis Example 6: Synthesis of Compound 6

[0759]

[0760] Synthesis of intermediate 6-1

[0761] 2-(3,5-dichlorophenyl)dibenzo[b,d]furan (1 eq), [1,1':3',1"-terphenyl]-2'-amine (2 eq), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq), tri-tert-butylphosphine (0.1 eq) and sodium tert-butoxide (3 eq) were dissolved in o-xylene and stirred at 140°C for 12 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried over MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain Intermediate 6-1. (Yield: 80%)

[0762] Synthesis of intermediate 6-2

[0763] Intermediate 6-1 (1 eq), 9-(3-bromophenyl)-9H-carbazole (4 eq), tris(dibenzylideneacetone)dipalladium(0) (0.15 eq), tri-tert-butylphosphine (0.3 eq) and sodium tert-butoxide (4 eq) were dissolved in o-xylene and stirred at 150° C. for 48 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried with MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain intermediate 6-2. (Yield: 37%)

[0764] Synthesis of compound 6

[0765] Intermediate 6-2 (1 eq) was dissolved in o-dichlorobenzene and cooled to 0°C, and BBr3 (5 eq) was slowly injected thereinto in a nitrogen atmosphere. After the addition was completed, the temperature was raised to 180°C, followed by stirring for 24 hours. After cooling, triethylamine was slowly added dropwise to the flask containing the reactants to terminate the reaction, and ethanol was added to the reactants to cause precipitation, thereby obtaining a reaction product. The obtained solid was purified by column chromatography with MC and n-hexane, and recrystallized using toluene and acetone to obtain compound 6. (Yield: 5%)

[0766] Synthesis Example 7: Synthesis of Compound 7

[0767]

[0768] Synthesis of intermediate 7-1

[0769] 3,5-dichloro-1,1'-biphenyl (1eq), 3',5'-di-tert-butyl-[1,1'-biphenyl]-2-amine (2.2eq), tris(dibenzylideneacetone)dipalladium (0) (0.05eq), tri-tert-butylphosphine (0.1eq) and sodium tert-butoxide (3eq) were dissolved in toluene and stirred at 100°C for 12 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried with MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain intermediate 7-1. (Yield: 84%)

[0770] Synthesis of intermediate 7-2

[0771] Intermediate 7-1 (1 eq), 9-(3-bromophenyl)-9H-carbazole (2.2 eq), tris(dibenzylideneacetone)dipalladium (0) (0.05 eq), tri-tert-butylphosphine (0.1 eq) and sodium tert-butoxide (3 eq) were dissolved in toluene and stirred at 110° C. for 24 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried with MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain intermediate 7-2. (Yield: 64%)

[0772] Synthesis of compound 7

[0773] Intermediate 7-2 (1 eq) was dissolved in o-dichlorobenzene and cooled to 0 ° C, and BBr3 (5 eq) was slowly injected thereinto in a nitrogen atmosphere. After the addition was completed, the temperature was raised to 180 ° C, followed by stirring for 24 hours. After cooling, triethylamine was slowly added dropwise to the flask containing the reactants to terminate the reaction, and ethanol was added to the reactants to cause precipitation, thereby obtaining a reaction product. The obtained solid was purified by column chromatography with MC and n-hexane, and recrystallized using toluene and acetone to obtain compound 7. (Yield: 6%)

[0774] Synthesis Example 8: Synthesis of Compound 8

[0775]

[0776] Synthesis of intermediate 8-1

[0777] 1,3-Dibromo-5-(tert-butyl)benzene (1 eq), [1,1':3',1":3",1"'-tetraphenyl]-2'-amine (2 eq), tris(dibenzylideneacetone)dipalladium(0) (0.1 eq), tri-tert-butylphosphine (0.2 eq) and sodium tert-butoxide (3 eq) were dissolved in toluene and stirred at 110° C. for 24 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried over MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain intermediate 8-1. (Yield: 69%)

[0778] Synthesis of intermediate 8-2

[0779] Intermediate 8-1 (1 eq), 9-(3-bromophenyl)-9H-carbazole (4 eq), tris(dibenzylideneacetone)dipalladium(0) (0.15 eq), tri-tert-butylphosphine (0.3 eq) and sodium tert-butoxide (4 eq) were dissolved in o-xylene and stirred at 150° C. for 48 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried with MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain intermediate 8-2. (Yield: 35%)

[0780] Synthesis of compound 8

[0781] Intermediate 8-2 (1 eq) was dissolved in o-dichlorobenzene and cooled to 0 ° C, and BBr3 (5 eq) was slowly injected thereinto in a nitrogen atmosphere. After the addition was completed, the temperature was raised to 180 ° C, followed by stirring for 24 hours. After cooling, triethylamine was slowly added dropwise to the flask containing the reactants to terminate the reaction, and ethanol was added to the reactants to cause precipitation, thereby obtaining a reaction product. The obtained solid was purified by column chromatography with MC and n-hexane, and recrystallized using toluene and acetone to obtain compound 8. (Yield: 4%)

[0782] Synthesis Example 9: Synthesis of Compound 9

[0783]

[0784] Synthesis of intermediate 9-1

[0785] Intermediate 2-1 (1 eq), 9-(3-bromophenyl)-3,6-di-tert-butyl-9H-carbazole (1 eq), tris(dibenzylideneacetone)dipalladium (0) (0.15 eq), tri-tert-butylphosphine (0.3 eq) and sodium tert-butoxide (4 eq) were dissolved in toluene and stirred at 150° C. for 48 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried with MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain intermediate 9-1. (Yield: 31%)

[0786] Synthesis of compound 9

[0787] Intermediate 9-1 (1 eq) was dissolved in o-dichlorobenzene and cooled to 0°C, and BBr3 (5 eq) was slowly injected thereinto in a nitrogen atmosphere. After the addition was completed, the temperature was raised to 180°C, followed by stirring for 24 hours. After cooling, triethylamine was slowly added dropwise to the flask containing the reactants to terminate the reaction, and ethanol was added to the reactants to cause precipitation, thereby obtaining a reaction product. The obtained solid was purified by column chromatography with MC and n-hexane, and recrystallized using toluene and acetone to obtain compound 9. (Yield: 4%)

[0788] Synthesis Example 10: Synthesis of Compound 10

[0789]

[0790] Synthesis of Intermediate 10-1

[0791] Intermediate 3-1 (1 eq), 9-(3-bromophenyl)-9H-carbazole (4 eq), tris(dibenzylideneacetone)dipalladium(0) (0.15 eq), tri-tert-butylphosphine (0.3 eq) and sodium tert-butoxide (4 eq) were dissolved in o-xylene and stirred at 150° C. for 48 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried with MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain intermediate 10-1. (Yield: 32%)

[0792] Synthesis of compound 10

[0793] Intermediate 10-1 (1 eq) was dissolved in o-dichlorobenzene and cooled to 0 ° C, and BBr3 (5 eq) was slowly injected thereinto in a nitrogen atmosphere. After the addition was completed, the temperature was raised to 180 ° C, followed by stirring for 24 hours. After cooling, triethylamine was slowly added dropwise to the flask containing the reactants to terminate the reaction, and ethanol was added to the reactants to cause precipitation, thereby obtaining a reaction product. The obtained solid was purified by column chromatography with MC and n-hexane, and recrystallized using toluene and acetone to obtain compound 10. (yield: 5%)

[0794] Synthesis Example 11: Synthesis of Compound 11

[0795]

[0796] Synthesis of Intermediate 11-1

[0797] Intermediate 2-1 (1 eq), 9-(3-bromophenyl)-9H-carbazole (4 eq), tris(dibenzylideneacetone)dipalladium(0) (0.15 eq), tri-tert-butylphosphine (0.3 eq) and sodium tert-butoxide (4 eq) were dissolved in o-xylene and stirred at 150° C. for 48 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried with MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain intermediate 11-1. (Yield: 27%)

[0798] Synthesis of compound 11

[0799] Intermediate 11-1 (1 eq) was dissolved in o-dichlorobenzene and cooled to 0 ° C, and BBr3 (5 eq) was slowly injected thereinto in a nitrogen atmosphere. After the addition was completed, the temperature was raised to 180 ° C, followed by stirring for 24 hours. After cooling, triethylamine was slowly added dropwise to the flask containing the reactants to terminate the reaction, and ethanol was added to the reactants to cause precipitation, thereby obtaining a reaction product. The obtained solid was purified by column chromatography with MC and n-hexane, and recrystallized using toluene and acetone to obtain compound 11. (Yield: 7%)

[0800] Synthesis Example 12: Synthesis of Compound 12

[0801]

[0802] Synthesis of intermediate 12-1

[0803] 3,5-Dichloro-1,1'-biphenyl (1 eq), [1,1':3',1"-terphenyl]-2'-amine (2 eq), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq), tri-tert-butylphosphine (0.1 eq) and sodium tert-butoxide (3 eq) were dissolved in o-xylene and stirred at 140°C for 12 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried over MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain Intermediate 12-1. (Yield: 62%)

[0804] Synthesis of intermediate 12-2

[0805] Intermediate 12-1 (1 eq), 9-(3-bromophenyl)-3,6-di-tert-butyl-9H-carbazole (4 eq), tris(dibenzylideneacetone)dipalladium(0) (0.15 eq), tri-tert-butylphosphine (0.3 eq) and sodium tert-butoxide (4 eq) were dissolved in o-xylene and stirred at 150° C. for 48 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried with MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain intermediate 12-2. (Yield: 41%)

[0806] Synthesis of Compound 12

[0807] Dissolve Intermediate 12-2 (1 eq) in o-dichlorobenzene and cool to 0 °C, and slowly inject BBr3 (5 eq) into it under a nitrogen atmosphere. After the addition is complete, raise the temperature to 180 °C and then stir for 24 hours. After cooling, slowly add triethylamine dropwise to the flask containing the reactants to terminate the reaction, and add ethanol to the reactants to cause precipitation, thereby obtaining the reaction product. The obtained solid is purified by column chromatography using MC and n-hexane, and recrystallized using toluene and acetone to obtain Compound 12. (Yield: 4%)

[0808] Synthesis Example 13: Synthesis of Compound 13

[0809]

[0810] Synthesis of Intermediate 13-1

[0811] Dissolve 1,3-dibromo-5-(tert-butyl)benzene (1 eq), 3,5,5'-tritert-butyl-[1,1':3',1”-terphenyl]-2'-amine (2 eq), tris(dibenzylideneacetone)dipalladium(0) (0.15 eq), tert-butylphosphine (0.3 eq) and sodium tert-butoxide (3 eq) in o-xylene and stir at 140 °C for 12 hours. After cooling and washing three times with ethyl acetate and water, separate the organic layer and dry it with MgSO4 under reduced pressure. The obtained product is purified by column chromatography using MC and n-hexane to obtain Intermediate 13-1.

[0812] (Yield: 53%)

[0813] Synthesis of Intermediate 13-2

[0814] Dissolve Intermediate 13-1 (1 eq), 9-(3-bromophenyl)-9H-carbazole (4 eq), tris(dibenzylideneacetone)dipalladium(0) (0.15 eq), tert-butylphosphine (0.3 eq) and sodium tert-butoxide (4 eq) in o-xylene and stir at 150 °C for 48 hours. After cooling and washing three times with ethyl acetate and water, separate the organic layer and dry it with MgSO4 under reduced pressure. The obtained product is purified by column chromatography using MC and n-hexane to obtain Intermediate 13-2. (Yield: 35%)

[0815] Synthesis of Compound 13

[0816] Intermediate 13-2 (1 eq) was dissolved in o-dichlorobenzene and cooled to 0 °C, and BBr3 (5 eq) was slowly injected into it under a nitrogen atmosphere. After the dropping was completed, the temperature was raised to 180 °C, and then stirred for 24 hours. After cooling, triethylamine was slowly added dropwise to the flask containing the reactants to terminate the reaction, and ethanol was added to the reactants to cause precipitation, thereby obtaining the reaction product. The obtained solid was purified by column chromatography using MC and n-hexane, and recrystallized using toluene and acetone to obtain Compound 13. (Yield: 2%)

[0817] Synthesis Example 14: Synthesis of Compound 14

[0818]

[0819] Synthesis of Intermediate 14-1

[0820] 1,3-Dibromo-5-(tert-butyl)benzene (1 eq), 3,3”,5'-tritert-butyl-[1,1':3',1”-terphenyl]-2'-amine (2 eq), tris(dibenzylideneacetone)dipalladium(0) (0.15 eq), tert-butylphosphine (0.3 eq) and sodium tert-butoxide (5 eq) were dissolved in o-xylene and stirred at 140 °C for 12 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried over MgSO4 under reduced pressure. The obtained product was purified by column chromatography using MC and n-hexane to obtain Intermediate 14-1.

[0821] (Yield: 48%)

[0822] Synthesis of Intermediate 14-2

[0823] Intermediate 14-1 (1 eq), 9-(3-bromophenyl)-9H-carbazole-D8 (4 eq), tris(dibenzylideneacetone)dipalladium(0) (0.15 eq), tert-butylphosphine (0.3 eq) and sodium tert-butoxide (4 eq) were dissolved in o-xylene and stirred at 150 °C for 48 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried over MgSO4 under reduced pressure. The obtained product was purified by column chromatography using MC and n-hexane to obtain Intermediate 14-2. (Yield: 27%)

[0824] Synthesis of Compound 14

[0825] Intermediate 14-2 (1 eq) was dissolved in o-dichlorobenzene and cooled to 0 °C, and BBr3 (5 eq) was slowly injected into it under a nitrogen atmosphere. After the dropping was completed, the temperature was raised to 180 °C, and then stirred for 24 hours. After cooling, triethylamine was slowly added dropwise to the flask containing the reactants to terminate the reaction, and ethanol was added to the reactants to cause precipitation, thereby obtaining the reaction product. The obtained solid was purified by column chromatography using MC and n-hexane, and recrystallized using toluene and acetone to obtain Compound 14. (Yield: 2%)

[0826] Synthesis Example 15: Synthesis of Compound 15

[0827]

[0828] Synthesis of Intermediate 15-1

[0829] 1,3-Dibromo-5-(tert-butyl)benzene (1 eq), 4,4”,5'-tritert-butyl-[1,1':3',1”-terphenyl]-2'-amine (2 eq), tris(dibenzylideneacetone)dipalladium(0) (0.15 eq), tert-butylphosphine (0.3 eq) and sodium tert-butoxide (5 eq) were dissolved in o-xylene and stirred at 140 °C for 12 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried over MgSO4 under reduced pressure. The obtained product was purified by column chromatography using MC and n-hexane to obtain Intermediate 15-1.

[0830] (Yield: 42%)

[0831] Synthesis of Intermediate 15-2

[0832] Intermediate 15-1 (1 eq), 9-(3-bromophenyl)-9H-carbazole-D8 (4 eq), tris(dibenzylideneacetone)dipalladium(0) (0.15 eq), tert-butylphosphine (0.3 eq) and sodium tert-butoxide (4 eq) were dissolved in o-xylene and stirred at 150 °C for 48 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried over MgSO4 under reduced pressure. The obtained product was purified by column chromatography using MC and n-hexane to obtain Intermediate 15-2. (Yield: 31%)

[0833] Synthesis of Compound 15

[0834] Intermediate 15-2 (1 eq) was dissolved in o-dichlorobenzene and cooled to 0 ° C, and BBr3 (5 eq) was slowly injected thereinto in a nitrogen atmosphere. After the addition was completed, the temperature was raised to 180 ° C, followed by stirring for 24 hours. After cooling, triethylamine was slowly added dropwise to the flask containing the reactants to terminate the reaction, and ethanol was added to the reactants to cause precipitation, thereby obtaining a reaction product. The obtained solid was purified by column chromatography with MC and n-hexane, and recrystallized using toluene and acetone to obtain compound 15. (yield: 2%)

[0835] Synthesis Example 16: Synthesis of Compound 16

[0836]

[0837] Synthesis of intermediate 16-1

[0838] Intermediate 3-1 (1 eq), 2-(3-bromophenyl)dibenzo[b,d]furan (4 eq), tri(dibenzylideneacetone)dipalladium(0) (0.15 eq), tri-tert-butylphosphine (0.3 eq) and sodium tert-butoxide (5 eq) were dissolved in o-xylene and stirred at 150° C. for 24 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried with MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain intermediate 16-1. (Yield: 41%)

[0839] Synthesis of compound 16

[0840] Intermediate 16-1 (1 eq) was dissolved in o-dichlorobenzene and cooled to 0°C, and BBr3 (3 eq) was slowly injected thereinto in a nitrogen atmosphere. After the addition was completed, the temperature was raised to 180°C, followed by stirring for 24 hours. After cooling, triethylamine was slowly added dropwise to the flask containing the reactants to terminate the reaction, and ethanol was added to the reactants to cause precipitation, thereby obtaining a reaction product. The obtained solid was purified by column chromatography with MC and n-hexane, and recrystallized using toluene and acetone to obtain compound 16. (Yield: 13%)

[0841] Synthesis Example 17: Synthesis of Compound 17

[0842]

[0843] Synthesis of Intermediate 17-1

[0844] 1,3-Dibromo-5-(tert-butyl)benzene (1 eq), N-(3-(9H-carbazole-9-yl)phenyl)-8-phenyldibenzo[b,d]furan-1-amine (2.2 eq), tri(dibenzylideneacetone)dipalladium(0) (0.05 eq), tri-tert-butylphosphine (0.1 eq) and sodium tert-butoxide (3 eq) were dissolved in toluene and stirred at 100° C. for 12 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried over MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain Intermediate 17-1. (Yield: 75%)

[0845] Synthesis of compound 17

[0846] Intermediate 17-1 (1 eq) was dissolved in o-dichlorobenzene and cooled to 0°C, and BBr3 (3 eq) was slowly injected thereinto in a nitrogen atmosphere. After the addition was completed, the temperature was raised to 180°C, followed by stirring for 24 hours. After cooling, triethylamine was slowly added dropwise to the flask containing the reactants to terminate the reaction, and ethanol was added to the reactants to cause precipitation, thereby obtaining a reaction product. The obtained solid was purified by column chromatography with MC and n-hexane, and recrystallized using toluene and acetone to obtain compound 17. (Yield: 21%)

[0847] Synthesis Example 18: Synthesis of Compound 18

[0848]

[0849] Synthesis of intermediate 18-1

[0850] 1,3-dibromo-5-(tert-butyl)benzene (1 eq), 3',5'-di-tert-butyl-N-(3-(3,6-di-tert-butyl-9H-carbazole-9-yl)phenyl)-[1,1'-biphenyl]-2-amine (2.2 eq), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq), tri-tert-butylphosphine (0.1 eq) and sodium tert-butoxide (3 eq) were dissolved in toluene and stirred at 100° C. for 12 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried over MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain intermediate 18-1. (Yield: 66%)

[0851] Synthesis of compound 18

[0852] Intermediate 18-1 (1 eq) was dissolved in o-dichlorobenzene and cooled to 0°C, and BBr3 (3 eq) was slowly injected thereinto in a nitrogen atmosphere. After the addition was completed, the temperature was raised to 180°C, followed by stirring for 24 hours. After cooling, triethylamine was slowly added dropwise to a flask containing the reactants to terminate the reaction, and ethanol was added to the reactants to cause precipitation, thereby obtaining a reaction product. The obtained solid was purified by column chromatography with MC and n-hexane, and recrystallized using toluene and acetone to obtain compound 18. (Yield: 17%)

[0853] Synthesis Example 19: Synthesis of Compound 19

[0854]

[0855] Synthesis of intermediate 19-1

[0856] 3,5-di-tert-butyl-3',5'-dichloro-1,1'-biphenyl (1 eq), [1,1':3',1"-terphenyl]-2'-amine (2 eq), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq), tri-tert-butylphosphine (0.1 eq) and sodium tert-butoxide (3 eq) were dissolved in toluene and stirred at 110°C for 12 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried over MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain Intermediate 19-1. (Yield: 81%)

[0857] Synthesis of intermediate 19-2

[0858] Intermediate 19-1 (1 eq), 3-bromo-6'-phenyl-1,1':2',1"-terphenyl (4 eq), tris(dibenzylideneacetone)dipalladium(0) (0.15 eq), tri-tert-butylphosphine (0.3 eq) and sodium tert-butoxide (5 eq) were dissolved in o-xylene and stirred at 150°C for 24 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried over MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain Intermediate 19-2. (Yield: 32%)

[0859] Synthesis of compound 19

[0860] Intermediate 19-2 (1 eq) was dissolved in o-dichlorobenzene and cooled to 0 ° C, and BBr3 (3 eq) was slowly injected thereinto in a nitrogen atmosphere. After the addition was completed, the temperature was raised to 180 ° C, followed by stirring for 24 hours. After cooling, triethylamine was slowly added dropwise to the flask containing the reactants to terminate the reaction, and ethanol was added to the reactants to cause precipitation, thereby obtaining a reaction product. The obtained solid was purified by column chromatography with MC and n-hexane, and recrystallized using toluene and acetone to obtain compound 19. (yield: 13%)

[0861] Synthesis Example 20: Synthesis of Compound 20

[0862]

[0863] Synthesis of Intermediate 20-1

[0864] 1,3-Dibromo-5-(tert-butyl)benzene (1 eq), 4-(tert-butyl)-N-(3-(dibenzo[b,d]furan-2-yl)phenyl)-2-(triphenylene-2-yl)aniline (2.2 eq), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq), tri-tert-butylphosphine (0.1 eq) and sodium tert-butoxide (3 eq) were dissolved in toluene and stirred at 100° C. for 12 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried over MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain Intermediate 20-1. (Yield: 59%)

[0865] Synthesis of compound 20

[0866] Intermediate 20-1 (1 eq) was dissolved in o-dichlorobenzene and cooled to 0°C, and BBr3 (3 eq) was slowly injected thereinto in a nitrogen atmosphere. After the addition was completed, the temperature was raised to 180°C, followed by stirring for 24 hours. After cooling, triethylamine was slowly added dropwise to a flask containing the reactants to terminate the reaction, and ethanol was added to the reactants to cause precipitation, thereby obtaining a reaction product. The obtained solid was purified by column chromatography with MC and n-hexane, and recrystallized using toluene and acetone to obtain compound 20. (yield: 12%)

[0867] Synthesis Example 21: Synthesis of Compound 21

[0868]

[0869] Synthesis of Intermediate 21-1

[0870] 1,3-Dibromo-5-chlorobenzene (1 eq), N-(2-(3,6-di-tert-butyl-9H-carbazole-9-yl)phenyl)-[1,1'-biphenyl]-4-amine (2 eq), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq), BINAP (0.1 eq) and sodium tert-butoxide (3 eq) were dissolved in toluene and stirred at 85°C for 8 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried over MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain intermediate 21-1. (Yield: 56%)

[0871] Synthesis of Intermediate 21-2

[0872] Intermediate 21-1 (1 eq) was dissolved in o-dichlorobenzene and cooled to 0°C, and BBr3 (3 eq) was slowly injected thereinto in a nitrogen atmosphere. After the addition was completed, the temperature was raised to 180°C, followed by stirring for 24 hours. After cooling, triethylamine was slowly added dropwise to the flask containing the reactants to terminate the reaction, and ethanol was added to the reactants to cause precipitation, thereby obtaining a reaction product. The obtained solid was purified by column chromatography with MC and n-hexane, and recrystallized using toluene and acetone to obtain intermediate 21-2. (Yield: 28%)

[0873] Synthesis of compound 21

[0874] Intermediate 21-2 (1 eq), 3,6-di-tert-butyl-9H-carbazole (1.5 eq), tris(dibenzylideneacetone)dipalladium (0) (0.05 eq), tri-tert-butylphosphine (0.1 eq) and sodium tert-butoxide (3 eq) were dissolved in toluene and stirred at 110° C. for 12 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried with MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain compound 21. (Yield: 77%)

[0875] Synthesis Example 22: Synthesis of Compound 22

[0876]

[0877] Synthesis of Intermediate 22-1

[0878] 1,3-Dibromo-5-chlorobenzene (1 eq), N-(2-(9H-carbazole-9-yl)phenyl)-9-phenyl-9H-carbazole-2-amine (2 eq), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq), BINAP (0.1 eq) and sodium tert-butoxide (3 eq) were dissolved in toluene and stirred at 85°C for 8 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried over MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain Intermediate 22-1. (Yield: 57%)

[0879] Synthesis of intermediate 22-2

[0880] Intermediate 22-1 (1 eq) was dissolved in o-dichlorobenzene and cooled to 0°C, and BBr3 (3 eq) was slowly injected thereinto in a nitrogen atmosphere. After the addition was completed, the temperature was raised to 180°C, followed by stirring for 24 hours. After cooling, triethylamine was slowly added dropwise to the flask containing the reactants to terminate the reaction, and ethanol was added to the reactants to cause precipitation, thereby obtaining a reaction product. The obtained solid was purified by column chromatography with MC and n-hexane, and recrystallized using toluene and acetone to obtain intermediate 22-2. (Yield: 23%)

[0881] Synthesis of compound 22

[0882] Intermediate 22-2 (1 eq), 2,7-di-tert-butyl-9H-carbazole (1.5 eq), tris(dibenzylideneacetone)dipalladium (0) (0.05 eq), tri-tert-butylphosphine (0.1 eq) and sodium tert-butoxide (3 eq) were dissolved in toluene and stirred at 110° C. for 12 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried with MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain compound 22. (Yield: 73%)

[0883] Synthesis Example 23: Synthesis of Compound 23

[0884]

[0885] Synthesis of Intermediate 23-1

[0886] 1,3-dibromo-5-(tert-butyl)benzene (1 eq), N-(3',5'-di-tert-butyl-[1,1'-biphenyl]-3-yl)-9,9'-spirobi[fluorene]-1-amine (2.2 eq), tri(dibenzylideneacetone)dipalladium(0) (0.05 eq), tri-tert-butylphosphine (0.1 eq) and sodium tert-butoxide (3 eq) were dissolved in toluene and stirred at 100° C. for 12 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried over MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain intermediate 23-1. (Yield: 68%)

[0887] Synthesis of compound 23

[0888] Intermediate 23-1 (1 eq) was dissolved in o-dichlorobenzene and cooled to 0 ° C, and BBr3 (3 eq) was slowly injected thereinto in a nitrogen atmosphere. After the addition was completed, the temperature was raised to 180 ° C, followed by stirring for 24 hours. After cooling, triethylamine was slowly added dropwise to the flask containing the reactants to terminate the reaction, and ethanol was added to the reactants to cause precipitation, thereby obtaining a reaction product. The obtained solid was purified by column chromatography with MC and n-hexane, and recrystallized using toluene and acetone to obtain compound 23. (Yield: 8%)

[0889] Synthesis Example 24: Synthesis of Compound 24

[0890]

[0891] Synthesis of Intermediate 24-1

[0892] 1,3-Dibromo-5-chlorobenzene (1 eq), N-([1,1'-biphenyl]-4-yl)-[1,1':3',1"-terphenyl]-2'-amine (0.9 eq), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq), BINAP (0.1 eq) and sodium tert-butoxide (3 eq) were dissolved in toluene and stirred at 85°C for 8 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried over MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain Intermediate 24-1. (Yield: 48%)

[0893] Synthesis of intermediate 24-2

[0894] Intermediate 24-1 (1 eq), N-([1,1'-biphenyl]-2-yl)-9,9'-spirobi[fluorene]-3-amine (0.9 eq), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq), BINAP (0.1 eq) and sodium tert-butoxide (3 eq) were dissolved in toluene and stirred at 85°C for 8 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried with MgSO4 under reduced pressure. The organic layer was purified by column chromatography with MC and n-hexane to obtain intermediate 24-2. (Yield: 56%)

[0895] Synthesis of intermediate 24-3

[0896] Intermediate 24-2 (1 eq) was dissolved in o-dichlorobenzene and cooled to 0°C, and BBr3 (3 eq) was slowly injected thereinto in a nitrogen atmosphere. After the addition was completed, the temperature was raised to 180°C, followed by stirring for 24 hours. After cooling, triethylamine was slowly added dropwise to the flask containing the reactants to terminate the reaction, and ethanol was added to the reactants to cause precipitation, thereby obtaining a reaction product. The obtained solid was purified by column chromatography with MC and n-hexane, and recrystallized using toluene and acetone to obtain intermediate 24-2. (Yield: 18%)

[0897] Synthesis of compound 24

[0898] Intermediate 24-3 (1 eq), carbazole (1.5 eq), tris(dibenzylideneacetone)dipalladium (0) (0.05 eq), tri-tert-butylphosphine (0.1 eq) and sodium tert-butoxide (3 eq) were dissolved in toluene and stirred at 110° C. for 12 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried with MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain compound 24. (Yield: 80%)

[0899] Synthesis Example 25: Synthesis of Compound 25

[0900]

[0901] Synthesis of Intermediate 25-1

[0902] Intermediate 2-1 (1 eq), 4-bromo-2-(tert-butyl)-1,1'-biphenyl (3.5 eq), tri(dibenzylideneacetone)dipalladium (0) (0.15 eq), tri-tert-butylphosphine (0.3 eq) and sodium tert-butoxide (5 eq) were dissolved in o-xylene and stirred at 150°C for 48 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried with MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain intermediate 25-1. (Yield: 42%)

[0903] Synthesis of compound 25

[0904] Intermediate 25-1 (1 eq) was dissolved in o-dichlorobenzene and cooled to 0°C, and BBr3 (3 eq) was slowly injected thereinto in a nitrogen atmosphere. After the addition was completed, the temperature was raised to 180°C, followed by stirring for 24 hours. After cooling, triethylamine was slowly added dropwise to the flask containing the reactants to terminate the reaction, and ethanol was added to the reactants to cause precipitation, thereby obtaining a reaction product. The obtained solid was purified by column chromatography with MC and n-hexane, and recrystallized using toluene and acetone to obtain compound 25. (Yield: 19%)

[0905] Synthesis Example 26: Synthesis of Compound 26

[0906]

[0907] Synthesis of Intermediate 26-1

[0908] 5-(tert-butyl)-N1,N3-bis(5"-(tert-butyl)-[1,1':3',1":3",1"':3"',1""-pentaphenyl]-2"-yl)benzene-1,3-diamine (1eq), 9-(3-bromophenyl)-9H-carbazole (4eq), tris(dibenzylideneacetone)dipalladium(0) (0.15eq), tri-tert-butylphosphine (0.3eq) and sodium tert-butoxide (5eq) were dissolved in toluene and stirred at 150°C for 60 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried over MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain intermediate 26-1. (Yield: 33%)

[0909] Synthesis of compound 26

[0910] Intermediate 26-1 (1 eq) was dissolved in o-dichlorobenzene and cooled to 0°C, and BBr3 (3 eq) was slowly injected thereinto in a nitrogen atmosphere. After the addition was completed, the temperature was raised to 180°C, followed by stirring for 24 hours. After cooling, triethylamine was slowly added dropwise to the flask containing the reactants to terminate the reaction, and ethanol was added to the reactants to cause precipitation, thereby obtaining a reaction product. The obtained solid was purified by column chromatography with MC and n-hexane, and recrystallized using toluene and acetone to obtain compound 26. (Yield: 14%)

[0911] Synthesis Example 27: Synthesis of Compound 27

[0912]

[0913] Synthesis of Intermediate 27-1

[0914] N-(3-bromo-5-(tert-butyl)phenyl)-5"-(tert-butyl)-[1,1':3',1":3",1"':3"',1""-pentaphenyl]-2"-amine (1 eq), [1,1':3',1"-terphenyl]-2'-amine (1 eq), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq), tri-tert-butylphosphine (0.1 eq) and sodium tert-butoxide (3 eq) were dissolved in toluene and stirred at 100°C for 12 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried over MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain intermediate 27-1. (Yield: 84%)

[0915] Synthesis of Intermediate 27-2

[0916] Intermediate 27-1 (1 eq), 9-(3-bromophenyl)-9H-carbazole (4 eq), tris(dibenzylideneacetone)dipalladium(0) (0.15 eq), tri-tert-butylphosphine (0.3 eq) and sodium tert-butoxide (5 eq) were dissolved in toluene and stirred at 150° C. for 60 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried with MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain intermediate 27-2. (Yield: 33%)

[0917] Synthesis of compound 27

[0918] Intermediate 27-2 (1 eq) was dissolved in o-dichlorobenzene and cooled to 0 ° C, and BBr3 (3 eq) was slowly injected thereinto in a nitrogen atmosphere. After the addition was completed, the temperature was raised to 180 ° C, followed by stirring for 24 hours. After cooling, triethylamine was slowly added dropwise to the flask containing the reactants to terminate the reaction, and ethanol was added to the reactants to cause precipitation, thereby obtaining a reaction product. The obtained solid was purified by column chromatography with MC and n-hexane, and recrystallized using toluene and acetone to obtain compound 27. (Yield: 13%)

[0919] Synthesis Example 28: Synthesis of Compound 28

[0920]

[0921] Synthesis of Intermediate 28-1

[0922] 1,3-Dibromo-5-(tert-butyl)benzene (1 eq), N-(3-(9H-carbazole-9-yl)phenyl)-3-phenyldibenzo[b,d]furan-4-amine (2.2 eq), tri(dibenzylideneacetone)dipalladium(0) (0.05 eq), tri-tert-butylphosphine (0.1 eq) and sodium tert-butoxide (3 eq) were dissolved in toluene and stirred at 110° C. for 12 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried over MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain Intermediate 28-1. (Yield: 70%)

[0923] Synthesis of compound 28

[0924] Intermediate 28-1 (1 eq) was dissolved in o-dichlorobenzene and cooled to 0°C, and BBr3 (3 eq) was slowly injected thereinto in a nitrogen atmosphere. After the addition was completed, the temperature was raised to 180°C, followed by stirring for 24 hours. After cooling, triethylamine was slowly added dropwise to a flask containing the reactants to terminate the reaction, and ethanol was added to the reactants to cause precipitation, thereby obtaining a reaction product. The obtained solid was purified by column chromatography with MC and n-hexane, and recrystallized using toluene and acetone to obtain compound 28. (Yield: 15%)

[0925] Synthesis Example 29: Synthesis of Compound 29

[0926]

[0927] Synthesis of Intermediate 29-1

[0928] N-(3-bromo-5-(tert-butyl)phenyl)-[1,1'-biphenyl]-2-amine (1eq), 3-(3-bromo-5-iodophenoxy)-1,1'-biphenyl (131eq), tris(dibenzylideneacetone)dipalladium(0) (0.05eq), tri-tert-butylphosphine (0.1eq) and sodium tert-butoxide (3eq) were dissolved in toluene and stirred at 800°C for 12 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried with MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain Intermediate 29-1 (yield: 54%)

[0929] Synthesis of intermediate 29-2

[0930] Intermediate 29-1 (1 eq), N-(3-(9H-carbazole-9-yl)phenyl)-[1,1':3',1"-terphenyl]-2'-amine (3 eq), tris(dibenzylideneacetone)dipalladium(0) (0.15 eq), tri-tert-butylphosphine (0.3 eq) and sodium tert-butoxide (5 eq) were dissolved in toluene and stirred at 150° C. for 48 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried over MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain Intermediate 29-2. (Yield: 31%)

[0931] Synthesis of compound 29

[0932] Intermediate 29-2 (1 eq) was dissolved in o-dichlorobenzene and cooled to 0 ° C, and BBr3 (5 eq) was slowly injected thereinto in a nitrogen atmosphere. After the addition was completed, the temperature was raised to 180 ° C, followed by stirring for 24 hours. After cooling, triethylamine was slowly added dropwise to the flask containing the reactants to terminate the reaction, and ethanol was added to the reactants to cause precipitation, thereby obtaining a reaction product. The obtained solid was purified by column chromatography with MC and n-hexane, and recrystallized using toluene and acetone to obtain compound 29. (Yield: 25%)

[0933] Synthesis Example 30: Synthesis of Compound 30

[0934]

[0935] Synthesis of Intermediate 30-1

[0936] N1-([1,1'-biphenyl]-2-yl)-N3-([1,1'-biphenyl]-3-yl)-N3-([1,1':3',1"-terphenyl]-2'-yl)-5-(tert-butyl)benzene-1,3-diamine (1 eq), N-(3-bromo-5-(3-chlorophenoxy)phenyl)-N-(3-chlorophenyl)-[1,1':3',1"-terphenyl]-2'-amine (1.1 eq), tris(dibenzylideneacetone)dipalladium(0) (0.05 eq), BINAP (0.1 eq) and sodium tert-butoxide (3 eq) were dissolved in toluene and stirred at 90° C. for 12 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried over MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain Intermediate 30-1. (Yield: 29%)

[0937] Synthesis of Intermediate 30-2

[0938] Intermediate 30-1 (1 eq), carbazole (2.2 eq), tris(dibenzylideneacetone)dipalladium (0) (0.05 eq), tri-tert-butylphosphine (0.1 eq) and sodium tert-butoxide (3 eq) were dissolved in toluene and stirred at 100° C. for 12 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried with MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain intermediate 30-2. (Yield: 80%)

[0939] Synthesis of compound 30

[0940] Intermediate 30-2 (1 eq) was dissolved in o-dichlorobenzene and cooled to 0 ° C, and BBr3 (5 eq) was slowly injected thereinto in a nitrogen atmosphere. After the addition was completed, the temperature was raised to 180 ° C, followed by stirring for 24 hours. After cooling, triethylamine was slowly added dropwise to the flask containing the reactants to terminate the reaction, and ethanol was added to the reactants to cause precipitation, thereby obtaining a reaction product. The obtained solid was purified by column chromatography with MC and n-hexane, and recrystallized using toluene and acetone to obtain compound 30. (yield: 15%)

[0941] Synthesis Example 31: Synthesis of Compound 31

[0942]

[0943] Synthesis of Intermediate 31-1

[0944] N1-([1,1'-biphenyl]-3-yl)-N1,N3-bis([1,1':3',1"-terphenyl]-2'-yl)-5-(tert-butyl)benzene-1,3-diamine (1eq), 4,4"-((5-bromo-1,3-phenylene)bis(oxy))bis-1,1'-biphenyl (1.5eq), tris(dibenzylideneacetone)dipalladium(0) (0.15eq), tri-tert-butylphosphine (0.3eq) and sodium tert-butoxide (5eq) were dissolved in o-xylene and stirred at 150°C for 48 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried over MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain intermediate 31-1. (Yield: 38%)

[0945] Synthesis of compound 31

[0946] Intermediate 31-1 (1 eq) was dissolved in o-dichlorobenzene and cooled to 0 ° C, and BBr3 (5 eq) was slowly injected thereinto in a nitrogen atmosphere. After the addition was completed, the temperature was raised to 180 ° C, followed by stirring for 24 hours. After cooling, triethylamine was slowly added dropwise to the flask containing the reactants to terminate the reaction, and ethanol was added to the reactants to cause precipitation, thereby obtaining a reaction product. The obtained solid was purified by column chromatography with MC and n-hexane, and recrystallized using toluene and acetone to obtain compound 31. (Yield: 29%)

[0947] Synthesis Example 32: Synthesis of Compound 32

[0948]

[0949] Synthesis of Intermediate 32-1

[0950] N1-(3-(9H-carbazole-9-yl)phenyl)-N3-(3-bromophenyl)-5-(tert-butyl)-N1,N3-bis(dibenzo[b,d]furan-1-yl)benzene-1,3-diamine (1 eq), N-(3-(tert-butyl)-5-(dibenzo[b,d]furan-1-oxy)phenyl)dibenzo[b,d]furan-1-amine (1 eq), tri(dibenzylideneacetone)dipalladium(0) (0.15 eq), tri-tert-butylphosphine (0.2 eq) and sodium tert-butoxide (5 eq) were dissolved in o-xylene and stirred at 150° C. for 36 hours. After cooling and washing three times with ethyl acetate and water, the organic layer was separated therefrom and dried over MgSO4 under reduced pressure. The resulting product was purified by column chromatography with MC and n-hexane to obtain Intermediate 32-1. (Yield: 48%)

[0951] Synthesis of compound 32

[0952] Intermediate 32-1 (1 eq) was dissolved in o-dichlorobenzene and cooled to 0 ° C, and BBr3 (5 eq) was slowly injected thereinto in a nitrogen atmosphere. After the addition was completed, the temperature was raised to 180 ° C, followed by stirring for 24 hours. After cooling, triethylamine was slowly added dropwise to the flask containing the reactants to terminate the reaction, and ethanol was added to the reactants to cause precipitation, thereby obtaining a reaction product. The obtained solid was purified by column chromatography with MC and n-hexane, and recrystallized using toluene and acetone to obtain compound 32. (Yield: 6%)

[0953] Evaluation Example 1: Surface area to volume ratio value and molecular weight measurement

[0954] The surface area and volume values ​​of the above compounds and comparative example compounds were measured, and the results of the surface area divided by the volume are shown in Tables 1 and 2, as well as the molecular weight measurements.

[0955] [Table 1]

[0956]

[0957]

[0958] [Table 2]

[0959]

[0960]

[0961] Evaluation Example 2: Sublimation Temperature

[0962] Place 1 g of the compound powder at one end of a sublimation purification tube, and connect the extended tube thereto. Place the sublimation purification tube in a sublimation purifier, set to high vacuum and high temperature. Set the part where the compound is located to the highest temperature, and set the temperature in each part to decrease with increasing distance, such that the sublimated substance re-forms into a liquid or solid at different positions depending on the molecular weight. Measure the sublimation temperature. The results are shown in Table 3.

[0963] [Table 3]

[0964] Compound number Sublimation temperature (°C) Compound number Sublimation temperature (°C) 1 325 DABNA-1 230 2 310 DABNA-2 280 3 285 t-DABNA 260 4 310 CzB 280 5 350 a 260 6 355 b 390 7 360 c 370 8 330 d 300 9 330 e 290 10 355 g 280 11 320 h 380 12 360 i 300 13 330 j 260 14 325 k 340 15 325 v-DABNA 435 16 320 l 320 17 340 m 320 18 340 n 280 19 320 o 330 20 360 p 310 21 355 q 330 22 355 23 345 24 335 25 285 26 330 27 325 28 320 29 365 30 365 31 330 32 355

[0965] Example 1

[0966] As the anode, a substrate with ITO deposited thereon is cut into a size of 50 mm × 50 mm × 0.5 mm, ultrasonically treated with isopropyl alcohol and pure water for 5 minutes each, cleaned by ultraviolet irradiation and exposure to ozone for 30 minutes, and the ITO substrate is mounted on a vacuum deposition device.

[0967] Deposit the compound HT3 doped with HAT-CN on the ITO substrate to form a hole injection layer with a thickness of and deposit the compound HT3 by vacuum deposition on the hole injection layer to form a hole transport layer with a thickness of Form an electron blocking layer with a thickness of on the hole transport layer by using the compound HTH29.

[0968] Co-deposit the compound HTH29 (second compound), compound ETH66 (third compound), compound PD38 (fourth compound), and compound 1 (first compound) on the electron blocking layer at their respective weight ratios of 56.3 wt%: 30.3 wt%: 13 wt%: 0.4 wt% to form an emission layer with a thickness of

[0969] Deposit the compound ETH2 on the emission layer to form a layer with a thickness of​ A hole blocking layer with a thickness of... The compound ETH2:Liq is deposited on the hole blocking layer at a weight ratio of 5:5 to form a... An electron transport layer with a thickness of...

[0970] On the electron transport layer, LiF with a thickness of... is formed, and Al is deposited thereon to form a cathode with a thickness of... thereby completing the fabrication of the light-emitting device.

[0971]

[0972] Examples and Comparative Examples

[0973] A light-emitting device is fabricated using substantially the same method as in Example 1, except that when forming the emission layer, the first to fourth compounds are changed as shown in Table 4.

[0974] Evaluation Example 3

[0975] The driving voltage (V), luminous efficiency (cd / A), maximum emission wavelength (nm), and lifetime (T 2 ) of the light-emitting devices fabricated in the examples and comparative examples are measured using a Keithley SMU 236 and a luminance meter PR650 at a luminance of 1,000 cd / m 95 respectively, and the results are shown in Table 4. In Table 4, the lifetime (T 95 ) is a measure of the time (hr) it takes for the luminance to decrease to 95% of the initial luminance. The lifetime values are expressed based on Comparative Example 3.

[0976] [Table 4]

[0977]

[0978]

[0979]

[0980] As can be seen from Table 4, the light-emitting devices according to Examples 1 to 32 have excellent driving voltage, luminous efficiency, and lifetime characteristics.

[0981] As can be seen from Table 4, compared with the light-emitting devices of Comparative Examples 1 to 15, the light-emitting devices according to Examples 1 to 32 have improved driving voltage, luminous efficiency, and lifetime characteristics.

[0982] According to an embodiment, by including a polycyclic compound represented by Formula 1, the light-emitting device can have excellent driving voltage, luminous efficiency, and lifetime characteristics, and high-quality electronic devices can be fabricated using the light-emitting device.​

[0983] Embodiments have been disclosed herein, and although terms are employed, they are used and interpreted only in a general and descriptive sense and not for purposes of limitation. In some instances, as will be apparent to those of ordinary skill in the art, features, characteristics, and / or elements described in connection with an embodiment may be used singly or in combination with features, characteristics, and / or elements described in connection with other embodiments, unless specifically indicated otherwise. Accordingly, those of ordinary skill in the art will understand that various changes in form and detail may be made without departing from the spirit and scope of the present disclosure.

Claims

1. A light emitting device, comprising: a first electrode; a second electrode facing the first electrode; as well as an interlayer between the first electrode and the second electrode and including an emitting layer, wherein The interlayer includes a condensed ring compound, The fused ring compound includes a boron atom, The surface area to volume ratio of the fused ring compound is less than or equal to , and The condensed ring compound has a molecular weight greater than or equal to 1,000 g / mol.

2. The light emitting device according to claim 1, wherein The first electrode is an anode, The second electrode is a cathode, The interlayer further comprises: a hole transport region between the first electrode and the emissive layer; as well as an electron transport region between the emission layer and the second electrode, The hole transport region includes a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer or any combination thereof, and The electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer or any combination thereof. The light-emitting device according to claim 1 , wherein the emission layer comprises the condensed-cyclic compound.

4. The light emitting device according to claim 3, wherein The condensed ring compound in the emission layer is a thermally activated delayed fluorescence emitter, and The emission layer emits delayed fluorescence.

5. The light emitting device according to claim 1, comprising: a first compound including the fused ring compound; as well as A second compound including a group represented by Formula 20, including at least one π-electron-deficient nitrogen-containing C1-C 60 a third compound of a cyclic group, a fourth compound comprising a transition metal, or any combination thereof, wherein The first compound, the second compound, the third compound and the fourth compound are different from each other: Formula 20 In formula 20, Cyclo 71 and CY 72 Each is independently a π-electron-rich C3-C 60 Cyclic group or pyridyl group, X 71 is: a single bond; or a linking group comprising O, S, N, B, C, Si or any combination thereof, * is the binding site with the adjacent atom, and Excluding CBP and mCBP from the second compound:

6. The light emitting device according to claim 5, wherein The transmitting layer comprises: the first compound including the condensed ring compound; as well as at least one of the second compound and the third compound, and The emissive layer optionally further comprises the fourth compound. 7 . The light-emitting device according to claim 5 , wherein the third compound comprises a pyridyl group, a pyrimidyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group or any combination thereof.

8. An electronic device comprising the light emitting device according to any one of claims 1 to 7.

9. The electronic device according to claim 8, further comprising: Thin film transistors, where The thin film transistor includes a source electrode and a drain electrode, and The first electrode of the light emitting device is electrically connected to the source electrode or the drain electrode.

10. A condensed ring compound comprising: A core comprising at least one cyclic group comprising a boron atom and a nitrogen atom as ring atoms, wherein The surface area to volume ratio of the fused ring compound is less than or equal to , and The condensed ring compound has a molecular weight greater than or equal to 1,000 g / mol. The condensed ring compound according to claim 10 , wherein the sublimation temperature of the condensed ring compound is less than or equal to 370° C. . 12 . The condensed ring compound according to claim 10 , wherein at least one hydrogen atom of the core of the condensed ring compound is substituted with a substituent having a molecular weight greater than or equal to 153 g / mol.

13. The fused ring compound according to claim 12, wherein The core includes at least two nitrogen atoms, and At least one of the at least two nitrogen atoms is linked to a substituent having a molecular weight greater than or equal to 153 g / mol.

14. The fused ring compound according to claim 12, wherein the substituent having a molecular weight greater than or equal to 153 g / mol comprises a group represented by formula A: Formula A Wherein in formula A, Ar 11 and Ar 12 Each independently is C3-C 60 Carbocyclic or C1-C 60 Heterocyclic group, Z1 and Z2 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkylthio, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 arylthio, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2), Two or more adjacent groups in the number b1 of Z1 are optionally bonded to each other to form an unsubstituted or substituted group. 10b Substituted C5-C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10b Substituted C1-C 30 Heterocyclic group, Two or more adjacent groups in the number b2 of Z2 are optionally bonded to each other to form an unsubstituted or substituted group. 10b Substituted C5-C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10b Substituted C1-C 30 Heterocyclic group, Two or more adjacent groups in the number b1 of Z1 and the number b2 of Z2 are optionally bonded to each other to form an unsubstituted or substituted group. 10b Substituted C5-C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10b Substituted C1-C 30 Heterocyclic group, b1 and b2 are each independently an integer selected from 0 to 10, * indicates the binding site with adjacent atoms, R 10a and R 10b Each independently is: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazine or hydrazone; Each unsubstituted or substituted 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, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C2-C 60 Heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O)2(Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof; Each unsubstituted or substituted C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Arylalkyl or C2-C 60 Heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C2-C 60 Heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof; or -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-Ge(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) or -P(=O)(Q 31 )(Q 32 ) and Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 are independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; or each is unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 C1-C12-substituted alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, or any combination thereof 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Arylalkyl or C2-C 60 Heteroaralkyl.

15. The condensed ring compound according to claim 10, wherein the condensed ring compound is represented by Formula 1: Formula 1 In formula 1, Ring CY1 to Ring CY3, Ar 11 and Ar 12 Each independently is C3-C 60 Carbocyclic or C1-C 60 Heterocyclic group, Ar2 is unsubstituted or substituted with at least one R 10a Substituted C3-C 60 The carbocyclic group is either unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, R1 to R3, Z1 and Z2 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted by at least one R 10a Substituted C1-C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkylthio, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Arylthio, unsubstituted or substituted with at least one R 10a Substituted C7-C 60 Aralkyl, -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2), Two or more adjacent groups in the number a1 of R1 are optionally bonded to each other to form an unsubstituted or substituted group. 10b Substituted C5-C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10b Substituted C1-C 30 Heterocyclic group, Two or more adjacent groups in the number a2 of R2 are optionally bonded to each other to form an unsubstituted or substituted group. 10b Substituted C5-C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10b Substituted C1-C 30 Heterocyclic group, Two or more adjacent groups in the number a3 of R3 are optionally bonded to each other to form an unsubstituted or substituted group. 10b Substituted C5-C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10b Substituted C1-C 30 Heterocyclic group, Two or more adjacent groups in the number b1 of Z1 are optionally bonded to each other to form an unsubstituted or substituted group. 10b Substituted C5-C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10b Substituted C1-C 30 Heterocyclic group, Two or more adjacent groups in the number b2 of Z2 are optionally bonded to each other to form an unsubstituted or substituted group. 10b Substituted C5-C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10b Substituted C1-C 30 Heterocyclic group, Two or more adjacent groups in the number b1 of Z1 and the number b2 of Z2 are optionally bonded to each other to form an unsubstituted or substituted group. 10b Substituted C5-C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10b Substituted C1-C 30 Heterocyclic group, a1 to a3, b1 and b2 are each independently an integer selected from 0 to 10, R 10a and R 10b Each independently is: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazine or hydrazone; Each unsubstituted or substituted 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, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C2-C 60 Heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O)2(Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof; Each unsubstituted or substituted C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Arylalkyl or C2-C 60 Heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C2-C 60 Heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof; or -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-Ge(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 )或-P(=O)(Q 31 )(Q 32 ), and Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 are independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; or each is unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 C1-C12-substituted alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, or any combination thereof 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Arylalkyl or C2-C 60 Heteroaralkyl.

16. The fused ring compound according to claim 15, wherein Ar2 is a group represented by formula B: Formula B In formula B, Ar 13 and Ar 14 Each independently is C3-C 60 Carbocyclic or C1-C 60 Heterocyclic group, Z3 and Z4 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkenyl, unsubstituted or substituted with at least one R 10a Substituted C2-C 60 Alkynyl, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkoxy, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Alkylthio, unsubstituted or substituted with at least one R 10a Substituted C3-C 60 Carbocyclic group, unsubstituted or substituted with at least one R 10a Substituted C1-C 60 Heterocyclic group, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 Aryloxy, unsubstituted or substituted with at least one R 10a Substituted C6-C 60 arylthio, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2), Two or more adjacent groups in the number b3 of Z3 are optionally bonded to each other to form an unsubstituted or substituted group. 10b Substituted C5-C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10b Substituted C1-C 30 Heterocyclic group, Two or more adjacent groups in the number b4 of Z4 are optionally bonded to each other to form an unsubstituted or substituted group. 10b Substituted C5-C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10b Substituted C1-C 30 Heterocyclic group, Two or more adjacent groups in the number b3 of Z3 and the number b4 of Z4 are optionally bonded to each other to form an unsubstituted or substituted group. 10b Substituted C5-C 30 The carbocyclic group is either unsubstituted or substituted with at least one R 10b Substituted C1-C 30 Heterocyclic group, b3 and b4 are each independently an integer selected from 0 to 10, * indicates the binding site with adjacent atoms, R 10a and R 10b Each independently is: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amidino, hydrazine or hydrazone; Each unsubstituted or substituted 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, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C2-C 60 Heteroaralkyl, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O)2(Q 11 )、-P(=O)(Q 11 )(Q 12 ) or any combination thereof; Each unsubstituted or substituted C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Arylalkyl or C2-C 60 Heteroaralkyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Aralkyl, C2-C 60 Heteroaralkyl, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 )、-P(=O)(Q 21 )(Q 22 ) or any combination thereof; or -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-Ge(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 )或-P(=O)(Q 31 )(Q 32 ), and Q1 to Q3, Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 are independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; or each is unsubstituted or substituted with deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 C1-C12-substituted alkyl, phenyl, biphenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, or any combination thereof 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy, C6-C 60 Arylthio, C7-C 60 Arylalkyl or C2-C 60 Heteroaralkyl.

17. The fused ring compound according to claim 15, wherein Ar 11 and Ar 12 Each independently is C6-C 60 Aryl, C1-C 60 a heteroaryl group, a non-aromatic fused polycyclic group or a non-aromatic fused heteropolycyclic group.

18. The fused ring compound according to claim 15, wherein a1 to a3 are each independently an integer selected from 1 to 10, At least one of the a1 number of R1 is not hydrogen, At least one of the a2 number of R2 is not hydrogen, and At least one of the a3 number of R3 is not hydrogen.

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