Light-emitting device and electronic device comprising a heterocyclic compound

Abstract

A light-emitting device includes a first electrode; a second electrode facing the first electrode; and an intermediate layer between the first electrode and the second electrode and including an emissive layer, wherein the intermediate layer includes a heterocyclic compound of Formula 1: Formula 1 wherein, in Formula 1, the variables are described herein.

Description

[0001] Cross-references to related applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2021-0034236, filed with the Korean Intellectual Property Office on March 16, 2021, which is incorporated herein by reference for all purposes as if fully set forth herein. Technical Field

[0003] Embodiments of the present invention generally relate to display devices, and more specifically, to heterocyclic compounds and to light-emitting devices and electronic devices comprising said heterocyclic compounds. Background Technology

[0004] Organic light-emitting devices (OLEDs) are self-emitting devices that offer advantages over other devices in the field, including wide viewing angles, high contrast, short response times, and superior performance in terms of brightness, driving voltage, and response speed.

[0005] An organic light-emitting device may include a first electrode located on a substrate, and a hole transport region, an emitter layer, an electron transport region, and a second electrode sequentially stacked on the first electrode. Holes supplied by the first electrode can move towards the emitter layer through the hole transport region, and electrons supplied by the second electrode can move towards the emitter layer through the electron transport region. Charge carriers such as holes and electrons recombine in the emitter layer to generate excitons. These excitons transition from an excited state to the ground state, thereby generating light.

[0006] The information disclosed in this background section is only for understanding the background of the inventive concept, and therefore may contain information that does not constitute prior art. Summary of the Invention

[0007] When a light-emitting device and electronic device constructed according to the principles and exemplary embodiments of the present invention comprises a heterocyclic compound represented by one or more of the formulas disclosed herein, the light-emitting device may have a low driving voltage, high emission efficiency and high external quantum efficiency, and can be used to manufacture high-quality electronic devices.

[0008] Other features of the inventive concept will be set forth in the following description and will be apparent to some extent from the description, or may be learned by practice of the inventive concept.

[0009] According to one aspect of the invention, a light-emitting device includes: a first electrode; a second electrode facing the first electrode; and an intermediate layer between the first electrode and the second electrode, comprising an emitting layer, wherein the intermediate layer comprises a heterocyclic compound of formula 1:

[0010] Formula 1

[0011]

[0012] Formula 1-1

[0013]

[0014] Formula 1-2

[0015]

[0016] In Equations 1, 1-1, and 1-2, the variables are defined in this paper.

[0017] The heterocyclic compound of Formula 1 can be included in the emission layer.

[0018] The organometallic compound of formula 401 may be further included in the emitter layer.

[0019] Formula 401

[0020] M(L 401 ) xc1 (L 402 ) xc2

[0021] Formula 402

[0022]

[0023] In Equations 401 and 402, the variables are defined in this paper.

[0024] The emitting layer can be configured to emit blue light.

[0025] The emitter layer may further include a host, and the amount of the host may be greater than the amount of the heterocyclic compound of Formula 1.

[0026] The host may include two different host compounds.

[0027] The host may include hole transport host compounds and electron transport host compounds.

[0028] The intermediate layer may further include a hole transport region between the first electrode and the emitter layer and an electron transport region between the emitter layer and the second electrode. The hole transport region may include a hole injection layer, a hole transport layer, an emitter assist 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.

[0029] The emitter layer may contain a heterocyclic compound of Formula 1, and the hole transport region may contain a compound of Formula 201, a compound of Formula 202, or any combination thereof:

[0030] Formula 201

[0031]

[0032] Formula 202

[0033]

[0034] In Equations 201 and 202, the variables are defined in this paper.

[0035] Each of Formulas 201 and 202 may contain at least one group from Formulas CY201 to CY217, as defined herein.

[0036] The emitter layer may comprise a heterocyclic compound of Formula 1, and the electron transport region comprises a compound of Formula 601.

[0037] Formula 601

[0038] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21

[0039] In Equation 601, the variables are defined in this paper.

[0040] The electron transport layer in the electron transport region may comprise a compound of formula 601, and the electron transport layer may further comprise a metal-containing material.

[0041] The metal-containing material may include post-transition metal complexes, alkali metal complexes, alkaline earth metal complexes, or any combination thereof.

[0042] Variables Y1 and Y2 can each be boron.

[0043] Equation 1-2 can be either Equation 1-2-1 or Equation 1-2-2:

[0044]

[0045] In Equations 1-2-1 and 1-2-2, the variables are defined in this paper.

[0046] Equation 1-2 can be one of Equations 2-1 to 2-57, and the variables are defined in this document.

[0047] Equation 1-1 can have Equation 1-1-1:

[0048] Formula 1-1-1

[0049]

[0050] In Equation 1-1-1, the variables are defined in this paper.

[0051] The light-emitting device may further include a covering layer outside the first electrode or the second electrode, and the covering layer may contain one or more carbocyclic compounds, heterocyclic compounds, amine-based compounds, porphyrin derivatives, phthalocyanine derivatives, naphthalene phthalocyanine derivatives, alkali metal complexes, alkaline earth metal complexes, or any combination thereof.

[0052] Electronic devices may include light-emitting devices as described above.

[0053] 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 at least one of the source electrode and the drain electrode of the thin-film transistor.

[0054] It should be understood that both the foregoing general description and the following detailed description are exemplary and explanatory, and are intended to provide further explanation of the claimed invention. Attached Figure Description

[0055] The accompanying drawings are included to provide a further understanding of the invention and are incorporated in and form a part of this specification. The drawings illustrate exemplary embodiments of the invention and, together with the description, serve to explain the inventive concept.

[0056] Figure 1 This is a schematic cross-sectional view of an embodiment of a light-emitting device constructed according to the principles of the present invention.

[0057] Figure 2 This is a schematic cross-sectional view of an embodiment of a light-emitting device including a light-emitting device constructed according to the principles of the present invention.

[0058] Figure 3 This is a schematic cross-sectional view of another embodiment of a light-emitting device including a light-emitting device constructed according to the principles of the present invention. Detailed Implementation

[0059] In the following description, numerous specific details are set forth for purposes of explanation in order to provide a thorough understanding of various embodiments or implementations of the invention. As used herein, "implementation" and "implementation" are interchangeable terms and are non-limiting examples of one or more apparatuses or methods employing the inventive concept disclosed herein. However, it will be apparent, however, that various embodiments may be practiced without these specific details, or may be practiced with one or more equivalent arrangements. In other instances, well-known structures and apparatuses are shown in block diagram form to avoid unnecessarily obscuring the various embodiments. Furthermore, the various embodiments may be different, but are not necessarily exclusive. For example, the specific shape, configuration, and characteristics of an embodiment may be used or implemented in another embodiment without departing from the inventive concept.

[0060] Unless otherwise specified, the illustrated embodiments should be understood as exemplary features providing different details of some ways in which the inventive concept can be implemented in practice. Therefore, unless otherwise specified, features, components, modules, layers, films, panels, areas and / or aspects (hereinafter individually or collectively referred to as “elements”) of various embodiments may be combined, separated, interchanged and / or rearranged in other ways without departing from the inventive concept.

[0061] Crosshairs and / or shading are typically used in accompanying drawings to clarify boundaries between adjacent elements. Thus, the presence or absence of crosshairs or shading does not express or indicate any preference or need for particular materials, material properties, dimensions, scales, commonalities between illustrated elements, and / or any other characteristics, properties, or characteristics of the elements, unless otherwise specified. Furthermore, in the accompanying drawings, the dimensions and relative dimensions of elements may be enlarged for clarity and / or descriptive purposes. When embodiments can be implemented differently, the specific process sequence may differ from the order of description. For example, two consecutively described processes may be performed substantially simultaneously or in the reverse order of description. Moreover, the same reference numerals denote the same elements, and repeated explanations are omitted to avoid redundancy.

[0062] When a component or layer is referred to as being "on," "connected to," or "attached to" another component or layer, it can be directly on, directly connected to, or directly attached to another component or layer, or there can be an intermediate component or layer. However, when a component or layer is referred to as being "directly on," "directly connected to," or "directly attached to" another component or layer, there is no intermediate component or layer. Therefore, the term "connected" can refer to a physical connection, an electrical connection, and / or a fluid connection, with or without an intermediate component. Furthermore, the D1-axis, D2-axis, and D3-axis are not limited to the three axes of a Cartesian coordinate system, such as the x-axis, y-axis, and z-axis, and can be interpreted in a broader sense. For example, the D1-axis, D2-axis, and D3-axis can be perpendicular to each other, or can represent different directions that are not perpendicular to each other. For the purposes of this disclosure, "at least one of X, Y, and Z" and "at least one selected from the group consisting of X, Y, and Z" can be interpreted as only X, only Y, only Z, or any combination of two or more of X, Y, and Z, for example, XYZ, XYY, YZ, and ZZ. As used herein, the term "and / or" includes any combination and all combinations of one or more of the relevant listed items.

[0063] Although the terms “first,” “second,” etc., may be used herein to describe various types of elements, these elements should not be limited by these terms. These terms are used to distinguish one element from another. Therefore, without departing from the teachings of this disclosure, the first element discussed below may be referred to as the second element.

[0064] Spatial relative terms such as “below,” “under,” “lower,” “lower,” “above,” “above,” “higher,” and “side” (e.g., as in “sidewall”) may be used herein for descriptive purposes and thereby to describe the relationship between one element and another as illustrated in the accompanying drawings. Spatial relative terms are intended to cover different orientations of the equipment in use, operation, and / or manufacture other than those described in the accompanying drawings. For example, if the equipment in the accompanying drawings is flipped, an element described as “below” or “under” other elements or features would be oriented “above” other elements or features. Thus, the term “below” can encompass both the above and below orientations. Furthermore, the equipment may be oriented in other ways (e.g., rotated 90 degrees or in other orientations), and in such cases, the spatial relative descriptors used herein are interpreted accordingly.

[0065] The terminology used herein is for the purpose of describing particular embodiments and is not intended to be limiting. As used herein, the singular forms “a,” “an,” and “the” are intended to also include the plural forms unless the context clearly indicates otherwise. Furthermore, the terms “comprises,” “comprising,” “includes,” and / or “including”, when used in this specification, specify the presence of a defined feature, integer, step, operation, element, component, and / or group thereof, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, and / or groups thereof. It should also be noted that, as used herein, the terms “substantially,” “about,” and other similar terms are used as approximations rather than terms of degree, and thus to explain inherent deviations in measured, calculated, and / or provided values ​​that would be recognized by one of ordinary skill in the art.

[0066] The cross-sectional and / or exploded views described herein are schematic illustrations of idealized embodiments and / or intermediate structures. Thus, variations in the shapes of the illustrations should be expected due to, for example, manufacturing techniques and / or tolerances. Therefore, the embodiments disclosed herein should not necessarily be interpreted as limited to the specific illustrative shapes of the areas, but should include deviations in shape resulting from, for example, manufacturing processes. In this way, the areas illustrated in the figures can be schematic in nature, and the shapes of these areas may not reflect the actual shapes of the areas of the device, and are not necessarily intended to be limiting.

[0067] Unless otherwise defined, all terms used herein (including technical and scientific terms) shall have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure is a part. Terms (such as those defined in common dictionaries) shall be interpreted as having a meaning consistent with their meaning in the context of the relevant field and shall not be interpreted in an idealized or overly formal sense unless expressly defined herein.

[0068] The light-emitting device (e.g., an organic light-emitting device) may include a first electrode; a second electrode facing the first electrode; an intermediate layer between the first electrode and the second electrode and including an emitting layer; and a heterocyclic compound represented by Formula 1.

[0069] First, heterocyclic compounds can be represented by Formula 1:

[0070] Formula 1

[0071]

[0072] In Equation 1,

[0073] A1 can be a group represented by formula 1-1.

[0074] B1 can be a group represented by formula 1-2, and

[0075] n1 can be an integer from 1 to 10.

[0076] Formula 1-1

[0077]

[0078] Formula 1-2

[0079]

[0080] In Equation 1-2, * indicates the binding site with A1 in Equation 1.

[0081] While not wishing to be bound by theory, because the heterocyclic compounds represented by Formula 1 contain groups represented by Formulas 1-2 as substituents of Formula 1-1, light-emitting devices containing such heterocyclic compounds can exhibit excellent driving voltage, emission efficiency, color purity, and lifespan characteristics. Furthermore, CY1 to CY4 in Formula 1-1 can each independently be C5-C. 30 Carbocyclic groups or C1-C 30 Heterocyclic groups. For example, CY1 to CY4 can each be independently a phenyl group, a naphthyl group, an anthracene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group, or a dibenzothiophene group.

[0082] In one or more embodiments, CY1 and CY2 can be identical to each other. For example, CY1 and CY2 can be phenyl groups. In one or more embodiments, CY3 and CY4 can be identical to each other. For example, CY3 and CY4 can each be a phenyl group. In one or more embodiments, CY1 to CY4 can be identical to each other. For example, CY1 to CY4 can each be a phenyl group. The variables Y1 and Y2 in Formula 1-1 can each be independently B, P (=O), or P (=S). In one embodiment, Y1 and Y2 can be identical to each other. For example, Y1 and Y2 can each be B.

[0083] In Equation 1-1, the variable X1 can be O, S, Se, Te, N(Ar1), Al(Ar1) or P(Ar1), X2 can be O, S, Se, Te, N(Ar2), Al(Ar2) or P(Ar2), X3 can be O, S, Se, Te, N(Ar3), Al(Ar3) or P(Ar3), and X4 can be O, S, Se, Te, N(Ar4), Al(Ar4) or P(Ar4). In the implementation scheme, in Equation 1, X1 can be N(Ar1), X2 can be N(Ar2), X3 can be N(Ar3), and X4 can be N(Ar4); X1 can be N(Ar1), X2 can be N(Ar2), X3 can be N(Ar3), and X4 can be O, S, Se, or Te; X1 can be N(Ar1), X2 can be N(Ar2), X3 can be O, S, Se, or Te, and X4 can be N(Ar4); X1 can be N(Ar1), X2 can be O, S, Se, or Te, X3 can be N(Ar3), and X4 can be N(Ar4); or X1 can be O, S, Se, or Te, X2 can be N(Ar2), X3 can be N(Ar3), and X4 can be N(Ar4);

[0084] Variable X1 can be N(Ar1), X2 can be N(Ar2), X3 can be O, S, Se, or Te, and X4 can be O, S, Se, or Te; X1 can be N(Ar1), X2 can be O, S, Se, or Te, X3 can be N(Ar3), and X4 can be O, S, Se, or Te; X1 can be N(Ar1), X2 can be O, S, Se, or Te, X3 can be O, S, Se, or Te, and X4 can be N(Ar4); X1 can be O, S, Se, or Te, X2 can be N(Ar2), X3 can be N(Ar3), and X4 can be O, S, Se, or Te; or X1 can be O, S, Se, or Te, X2 can be O, S, Se, or Te, and X3 can be N... (Ar3), and X4 can be N(Ar4); X1 can be N(Ar1), X2 can be O, S, Se or Te, X3 can be O, S, Se or Te, and X4 can be O, S, Se or Te; X1 can be O, S, Se or Te, X2 can be N(Ar2), X3 can be O, S, Se or Te, and X4 can be O, S, Se or Te; or X1 can be O, S, Se or Te, X2 can be O, S, Se or Te, X3 can be O, S, Se or Te, and X4 can be N(Ar4); or X1 can be O, S, Se or Te, X2 can be O, S, Se or Te, X3 can be O, S, Se or Te, and X4 can be O, S, Se or Te.

[0085] The groups Ar1 to Ar in Formula 1-1 10 Each of the following can be independently a binding site with B1 in Formula 1, a hydrogen group, a deuterium group, a -F group, a -Cl group, a -Br group, an -I group, a hydroxyl group, a cyano group, a nitro group, an unsubstituted group, or a group with at least one R group. 10a Replacement C1-C 60 alkyl groups, unsubstituted or with at least one R 10a Replacement C2-C 60 alkenyl groups, unsubstituted or with at least one R 10a Replacement C2-C 60 The alkynyl group, unsubstituted or with at least one R 10a Replacement C1-C 60 alkoxy group, unsubstituted or with at least one R 10a Replacement C3-C 60 Carbocyclic groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, unsubstituted or with at least one R 10a Replacement C6-C 60 aryloxy group, unsubstituted or with at least one R 10a Replacement C6-C 60 Aryl thioyl groups, -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 Ar1 to Ar 10 At least one of them can be a binding site with B1 in Formula 1.

[0086] In the implementation plan, Ar1 to Ar 10 These can each be an independent binding site to B1 in Formula 1; hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, C1-C 20 alkyl groups or C1-C 20 Alkoxy group; C1-C substituted with deuterium, -CD3, -CD2H, -CDH2, -F, -CF3, -CF2H, -CFH2, -Cl, -CCl3, -CCl2H, -CClH2, -Br, -CBr3, -CBr2H, -CBrH2, -I, -CI3, -CI2H, -CIH2, cyano group or any combination thereof. 20 alkyl groups or C1-C 20Alkoxy groups; each unsubstituted or deuterated, -CD3, -CD2H, -CDH2, -F, -CF3, -CF2H, -CFH2, -Cl, -CCl3, -CCl2H, -CClH2, -Br, -CBr3, -CBr2H, -CBrH2, -I, -CI3, -CI2H, -CIH2, cyano groups, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, terphenyl group, C1-C 20 Alkylphenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracene group, thiophene group, furanyl group, indole group, isoindole group, indole group, carbazole group, benzofuranyl group, benzothiophene group, benzothiophene group, dibenzofuranyl group, dibenzothiophene group, dibenzothiophene group, benzofluorenyl group, benzocarbazole group, naphthobenzofuranyl group, naphthobenzothiophene group, naphthobenzofuranyl group Thiolyl group, dibenzofluorenyl group, dibenzocarbazoyl group, dinaphthofuranyl group, dinaphthothienyl group, dinaphthothiolyl group, indolecarbazoyl group, indolecarbazoyl group, benzofuranocarbazoyl group, benzothiophenocarbazoyl group, benzothiolocarbazoyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, indazoleyl group, purine group, quinolinyl group, isoquinolinyl group, benzoquinoline Benzyl group, benzoisoquinolinyl group, phthalazinyl group, naphthidyl group, quinoxalinyl group, benzoquinoxalinyl group, quinazolinyl group, benzoquinoxalinyl group, phenazinyl group, acridineyl group, phenanthrololinyl group, phenazinyl group, phenoxazinyl group, phenthiazinyl group, phenoxthiazinyl group, benzimidazole group, benzothiazolyl group, benziisothiazolyl group, benzoxazolyl group, benziisoxazolyl group, triazole Benzyl group, tetrazolyl group, thiadiazolyl group, oxadiazolyl group, triazine group, imidazopyridyl group, imidazopyrimidinyl group, oxazolylpyridyl group, thiazopyridyl group, benzonaphthyl group, azafluorenyl group, azaspiro-difluorenyl group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group, azadibenzothiophenyl group, indolepyrroleyl group, indolepyrroleyl group, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32-C(=O)(Q) 31 -S(=O)2(Q) 31 -P(=O)(Q) 31 (Q) 32 ) or any combination thereof, substituted with cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, terphenyl group, C1-C 20 Alkylphenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracene group, thiophene group, furanyl group, indene group, isoindolyl group, indolyl group, carbazole group, benzofuranyl group, benzothiophene group, benzothiopyrrolyl group, dibenzofuranyl group, dibenzothiophene group, dibenzothiopyrrolyl group, benzofluorenyl group, benzocarbazole group, naphthobenzofuranyl group, naphthobenzothiophene group, naphthobenzothiopyrrolyl group, dibenzofluorenyl group, dibenzocarbazole group Dinaphthiofuranyl group, dinaphthiopheneyl group, dinaphthiopheneyl group, indenecarbazolyl group, indolecarbazolyl group, benzofuranocarbazolyl group, benzothiophenecarbazolyl group, benzothiophenecarbazolyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, indazole group, purine group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, benzoisoquinolinyl group, phthalazinyl group, naphthidyl group, quinoxalinyl group, benzoquinoxalinyl group, quinazolinyl Benzyl group, benzoquinazolinyl group, cenolinyl group, phenanthridine group, acridine group, phenanthroline group, phenazinyl group, phenoxazinyl group, phenthiazinyl group, phenoxthiazinyl group, benzimidazole group, benzothiazolyl group, benzisisothiazolyl group, benzooxazolyl group, benzisisooxazolyl group, triazolyl group, tetrazolyl group, thiadiazolyl group, oxiadiazolyl group, triazinyl group, imidazopyridyl group, imidazopyrimidine group, oxazolopyridyl group, thiazopyridyl group, Benzonaphthidyl group, azirmonyl group, azispiro-difluorenyl group, azircarbazoyl group, azirdibenzofuranyl group, azirdibenzothiophenyl group, azirdibenzothiopyrroleyl group, indolepyrroleyl group or indolepyrroleyl group; or -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). For example, Ar1 to Ar 10Each of these can be independently: the binding site with B1 in Formula 1; the unsubstituted or substituted group of hydrogen, deuterium, -CD3, -CD2H, -CDH2, -F, -CF3, -CF2H, -CFH2, -Cl, -CCl3, -CCl2H, -CClH2, -Br, -CBr3, -CBr2H, -CBrH2, -I, -CI3, -CI2H, -CIH2, cyano group, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, terphenyl group, C1-C 20 Alkylphenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracene group, thiophene group, furanyl group, indene group, isoindole group, indole group, carbazole group, benzofuranyl group, benzothiophene group, benzothiopyrrolyl group, dibenzofuranyl group, dibenzothiophene group, dibenzothiopyrrolyl group, benzofluorenyl group, benzocarbazole group, naphthobenzofuranyl group, naphthobenzothiophene group, naphthobenzothiopyrrolyl group, dibenzofluorenyl group, dibenzocarbazole group, dinaphthofuranyl group, dinaphthothiophene group, dinaphthothiopyrrolyl group, indolecarbazole group, benzofuranocarbazole group, benzothiophenecarbazole group, benzothiopyrrolocarbazole group, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 -P(=O)(Q) 31 (Q) 32 ) or any combination thereof, substituted with cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, terphenyl group, C1-C 20Alkylphenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracene group, thiophene group, furanyl group, indene group, isoindolyl group, indolyl group, carbazole group, benzofuranyl group, benzothiophene group, benzothiopyrrolyl group, dibenzofuranyl group, dibenzothiophene group, dibenzothiopyrrolyl group, benzofluorenyl group, benzocarbazole group, naphthobenzofuranyl group, naphthobenzothiophene group, naphthobenzothiopyrrolyl group, dibenzofluorenyl group, dibenzocarbazole group Group, dinaphthofuranyl group, dinaphthothiophenyl group, dinaphthothiophenyl group, indolecarbazoyl group, indolocarbazoyl group, benzofuranocarbazoyl group, benzothiophenocarbazoyl group or benzothiophenocarbazoyl group; or -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).

[0087] In the implementation plan, Ar 10 It can be hydrogen. In the implementation, when Ar9 represents the binding site with B1 in Formula 1, X2 and X4 can each be independently O, S, Se, or Te. The variable T in Formulas 1-2... 11 It can be unsubstituted or replaced by at least one R 10a Replacement C3-C 60 Carbocyclic group, or unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic groups.

[0088] In the implementation plan, T 11 They can be either unsubstituted or replaced by at least one R 10a The substitutions are i) group T1, ii) fused cyclic group in which two or more groups T1 are fused together, iii) group T2, iv) fused cyclic group in which two or more groups T2 are fused together, or v) fused cyclic group in which one or more groups T2 and one or more groups T1 are fused together.

[0089] Group T1 can be a cyclopropane group, cyclobutane group, cyclopentane group, cyclohexane group, cycloheptane group, cyclooctane group, cyclobutene group, cyclopentene group, cyclopentadiene group, cyclohexene group, cyclohexadiene group, cycloheptene group, adamantane group, norbornane (or bicyclo[2.2.1]heptane) group, norbornene group, bicyclo[1.1.1]pentane group, bicyclo[2.1.1]hexane group, bicyclo[2.2.2]octane group or phenyl group.

[0090] Group T2 can be a furan group, thiophene group, 1H-pyrrole group, thiorrole group, borocyclopentadiene group, 2H-pyrrole group, 3H-pyrrole group, imidazole group, pyrazole group, triazole group, tetraazole group, oxazole group, isoxazole group, oxadiazole group, thiazole group, isothiazole group, thiadiazole group, azathirrole group, azaborhexadiene group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, tetraazine group, pyrrolidinyl group, imidazolidinyl group, dihydropyrrole group, piperidine group, tetrahydropyridine group, dihydropyridine group, hexahydropyrimidine group, tetrahydropyrimidine group, dihydropyrimidine group, piperazine group, tetrahydropyrazine group, dihydropyrazine group, tetrahydropyridazine group, or dihydropyridazine group.

[0091] In Equation 1-2, X 11 It can be N or C(R) 11 ), X 12 It can be N or C(R) 12 ), X 13 It can be N or C(R) 13 ), and X 14 It can be N or C(R) 14 In the implementation plan, X 11 To X 14 They can be the same as each other. For example, X 11 It can be C(R) 11 ), X 12 It can be C(R) 12 ), X 13 It can be C(R) 13 ), and X 14 It can be C(R) 14 ).

[0092] The variables R1 to R4 and R in Equations 1-1 and 1-2 11 To R 14 Each of these groups can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 60 alkyl groups, unsubstituted or with at least one R 10a Replacement C2-C 60 alkenyl groups, unsubstituted or with at least one R 10a Replacement C2-C 60 The alkynyl group, unsubstituted or with at least one R 10a Replacement C1-C 60 alkoxy group, unsubstituted or with at least one R 10a Replacement C3-C 60 Carbocyclic groups, unsubstituted or with at least one R10a Replacement C1-C 60 Heterocyclic groups, unsubstituted or with at least one R 10a Replacement C6-C 60 aryloxy group, unsubstituted or with at least one R 10a Replacement C6-C 60 Aryl thioyl groups, -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).

[0093] In the implementation plan, R1 to R4 and R 11 To R 14 These can be, independently: hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, C1-C 20 alkyl groups or C1-C 20 Alkoxy group; C1-C substituted with deuterium, -CD3, -CD2H, -CDH2, -F, -CF3, -CF2H, -CFH2, -Cl, -CCl3, -CCl2H, -CClH2, -Br, -CBr3, -CBr2H, -CBrH2, -I, -CI3, -CI2H, -CIH2, cyano group or any combination thereof. 20 alkyl groups or C1-C 20 Alkoxy groups; each unsubstituted or deuterated, -CD3, -CD2H, -CDH2, -F, -CF3, -CF2H, -CFH2, -Cl, -CCl3, -CCl2H, -CClH2, -Br, -CBr3, -CBr2H, -CBrH2, -I, -CI3, -CI2H, -CIH2, cyano groups, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, terphenyl group, C1-C 20Alkylphenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracene group, thiophene group, furanyl group, indole group, isoindole group, indole group, carbazole group, benzofuranyl group, benzothiophene group, benzothiophene group, dibenzofuranyl group, dibenzothiophene group, dibenzothiophene group, benzofluorenyl group, benzocarbazole group, naphthobenzofuranyl group, naphthobenzothiophene group, naphthobenzofuranyl group Thiolyl group, dibenzofluorenyl group, dibenzocarbazoyl group, dinaphthofuranyl group, dinaphthothienyl group, dinaphthothiolyl group, indolecarbazoyl group, indolecarbazoyl group, benzofuranocarbazoyl group, benzothiophenocarbazoyl group, benzothiolocarbazoyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, indazoleyl group, purine group, quinolinyl group, isoquinolinyl group, benzoquinoline Benzyl group, benzoisoquinolinyl group, phthalazinyl group, naphthidyl group, quinoxalinyl group, benzoquinoxalinyl group, quinazolinyl group, benzoquinoxalinyl group, phenazinyl group, acridineyl group, phenanthrololinyl group, phenazinyl group, phenoxazinyl group, phenthiazinyl group, phenoxthiazinyl group, benzimidazole group, benzothiazolyl group, benziisothiazolyl group, benzoxazolyl group, benziisoxazolyl group, triazole Benzyl group, tetrazolyl group, thiadiazolyl group, oxadiazolyl group, triazine group, imidazopyridyl group, imidazopyrimidinyl group, oxazolylpyridyl group, thiazopyridyl group, benzonaphthyl group, azafluorenyl group, azaspiro-difluorenyl group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group, azadibenzothiophenyl group, indolepyrroleyl group, indolepyrroleyl group, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 -P(=O)(Q) 31 (Q) 32 ) or any combination thereof, substituted with cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, terphenyl group, C1-C 20Alkylphenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracene group, thiophene group, furanyl group, indene group, isoindolyl group, indolyl group, carbazole group, benzofuranyl group, benzothiophene group, benzothiopyrrolyl group, dibenzofuranyl group, dibenzothiophene group, dibenzothiopyrrolyl group, benzofluorenyl group, benzocarbazole group, naphthobenzofuranyl group, naphthobenzothiophene group, naphthobenzothiopyrrolyl group, dibenzofluorenyl group, dibenzocarbazole group Dinaphthiofuranyl group, dinaphthiopheneyl group, dinaphthiopheneyl group, indenecarbazolyl group, indolecarbazolyl group, benzofuranocarbazolyl group, benzothiophenecarbazolyl group, benzothiophenecarbazolyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, indazole group, purine group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, benzoisoquinolinyl group, phthalazinyl group, naphthidyl group, quinoxalinyl group, benzoquinoxalinyl group, quinazolinyl Benzyl group, benzoquinazolinyl group, cenolinyl group, phenanthridine group, acridine group, phenanthroline group, phenazinyl group, phenoxazinyl group, phenthiazinyl group, phenoxthiazinyl group, benzimidazole group, benzothiazolyl group, benzisisothiazolyl group, benzooxazolyl group, benzisisooxazolyl group, triazolyl group, tetrazolyl group, thiadiazolyl group, oxiadiazolyl group, triazinyl group, imidazopyridyl group, imidazopyrimidine group, oxazolopyridyl group, thiazopyridyl group, Benzonaphthidyl group, azirfluorenyl group, azispiro-difluorenyl group, azircarbazolyl group, azirdibenzofuranyl group, azirdibenzothiophenyl group, azirdibenzothiopyrryl group, indolepyrryl group or indolepyrryl group; or -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).

[0094] In Equation 1-1, variables a1 to a4 can each be independent integers from 0 to 10. Variable a1 represents the number of R1s. When a1 is an integer of 2 or greater than 2, two or more R1s can be the same or different from each other. Variable a2 represents the number of R2s. When a2 is an integer of 2 or greater than 2, two or more R2s can be the same or different from each other. Variable a3 represents the number of R3s. When a3 is an integer of 2 or greater than 2, two or more R3s can be the same or different from each other. Variable a4 represents the number of R4s. When a4 is an integer of 2 or greater than 2, two or more R4s can be the same or different from each other.

[0095] In Equation 1-1, if a1 is an integer of 2 or greater than 2, two or more R1s may optionally be connected to each other to form an unsubstituted or at least one R1. 10a Replacement C3-C 60 Carbocyclic group, or unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, two or more of the two R2 groups may optionally be linked together to form an unsubstituted or substituted group, with at least one R2 group. 10a Replacement C3-C 60 Carbocyclic group, or unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, two or more of the three R3s may optionally be linked together to form an unsubstituted or substituted group, with at least one R3. 10a Replacement C3-C 60 Carbocyclic group, or unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, two or more of the four R4 groups, may optionally be linked together to form an unsubstituted or substituted group. 10a Replacement C3-C 60 Carbocyclic group, or unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic groups.

[0096] R in Equation 1-1 11 To R 14 Two or more adjacent groups may optionally be linked to each other to form an unsubstituted or R-shaped compound. 10a Replacement C3-C 60 Carbocyclic group, or unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic group. R 10a Q1 to Q3 and Q 31 To Q 33 Each is the same as described in this article.

[0097] Equation 1-1 can be expressed by Equation 1-1-1:

[0098] Formula 1-1-1

[0099]

[0100] In Equation 1-1-1,

[0101] CY1, CY2, X1 to X4, Y1, Y2, Ar1 to Ar 10R1, R2, a1, and a2 are each the same as those described in this paper.

[0102] R 3a and R 3b Each is the same as the description regarding R3, and

[0103] R 4a and R 4b Each is identical to the description regarding R4.

[0104] In the implementation plan, the equation 1-1 is derived from... The group represented can be one of the groups represented by formulas CY1-1 to CY1-10:

[0105]

[0106] Among them, in formulas CY1-1 to CY1-10,

[0107] Y 11 It can be O, S, Se, Te, N(R) 11a ), C(R 11a (R) 11b ) or Si(R 11a (R) 11b ),

[0108] R 1a To R 1h R 11a and R 11b Each can be the same as the description of R1.

[0109] * indicates the binding site with X1 in Equation 1-1, and

[0110] *' indicates the binding site with Y1 in Equation 1-1.

[0111] In the implementation plan, the equation 1-1 is derived from... The group represented can be one of the groups represented by formulas CY2-1 to CY2-10:

[0112]

[0113] Among them, in formulas CY2-1 to CY2-10,

[0114] Y 21 It can be O, S, Se, Te, N(R) 21a ), C(R 21a (R) 21b ) or Si(R 21a (R) 21b ),

[0115] R2a To R 2h R 21a and R 21b Each is the same as the description regarding R2.

[0116] * indicates the binding site with X3 in Equation 1-1, and

[0117] *' indicates the binding site with Y2 in Equation 1-1.

[0118] In the implementation scheme, equation 1-2 can be represented by equation 1-2-1 or equation 1-2-2:

[0119]

[0120] Among them, in equations 1-2-1 and 1-2-2,

[0121] X 11 To X 14 Each is the same as described in this article.

[0122] X 21 It can be N or C(R) 21 ), X 22 It can be N or C(R) 22 ), X 23 It can be N or C(R) 23 ), X 24 It can be N or C(R) 24 ), and X 25 It can be N or C(R) 25 ),

[0123] X 31 It can be N or C(R) 31 ), X 32 It can be N or C(R) 32 ), X 33 It can be N or C(R) 33 ), X 34 It can be N or C(R) 34 ), and X 35 It can be N or C(R) 35 ),

[0124] R 21 To R 25 and R 31 To R 35 Each and about R 10a The descriptions are the same.

[0125] R 21 To R 25 Two or more adjacent groups may optionally be linked to each other to form an unsubstituted or R-shaped compound.10a Replacement C3-C 60 Carbocyclic group, or unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, and

[0126] R 31 To R 35 Two or more adjacent groups may optionally be linked together to form an unsubstituted or R-shaped compound. 10a Replacement C3-C 60 Carbocyclic group, or unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic groups. The asterisks (*) in Formulas 1-2-1 and 1-2-2 represent binding sites with A1 in Formula 1, and R... 10a Same as described in this article.

[0127] For example, formula 1-2 can be a group selected from formulas 2-1 to 2-57:

[0128]

[0129]

[0130]

[0131]

[0132] Among them, in equations 2-1 to 2-57,

[0133] V1 to V4 can each be C or N independently.

[0134] Z1 to Z5 can each be independently:

[0135] Deuterium, -F, -Cl, -Br, -I, cyano group, C1-C 20 alkyl groups or C1-C 20 Alkoxy group;

[0136] C1-C groups, each substituted with deuterium, -CD3, -CD2H, -CDH2, -F, -CF3, -CF2H, -CFH2, -Cl, -CCl3, -CCl2H, -CClH2, -Br, -CBr3, -CBr2H, -CBrH2, -I, -CI3, -CI2H, -CIH2, cyano groups, or any combination thereof. 20 alkyl groups or C1-C 20 Alkoxy group;

[0137] Each unsubstituted or deuterated group, -CD3, -CD2H, -CDH2, -F, -CF3, -CF2H, -CFH2, -Cl, -CCl3, -CCl2H, -CClH2, -Br, -CBr3, -CBr2H, -CBrH2, -I, -CI3, -CI2H, -CIH2, cyano groups, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, terphenyl group, C1-C 20 Alkylphenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracene group, thiophene group, furanyl group, indole group, isoindole group, indole group, carbazole group, benzofuranyl group, benzothiophene group, benzothiophene group, dibenzofuranyl group, dibenzothiophene group, dibenzothiophene group, benzofluorenyl group, benzocarbazole group, naphthobenzofuranyl group, naphthobenzothiophene group, naphthobenzofuranyl group Thiolyl group, dibenzofluorenyl group, dibenzocarbazoyl group, dinaphthofuranyl group, dinaphthothienyl group, dinaphthothiolyl group, indolecarbazoyl group, indolecarbazoyl group, benzofuranocarbazoyl group, benzothiophenocarbazoyl group, benzothiolocarbazoyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, indazoleyl group, purine group, quinolinyl group, isoquinolinyl group, benzoquinoline Benzyl group, benzoisoquinolinyl group, phthalazinyl group, naphthidyl group, quinoxalinyl group, benzoquinoxalinyl group, quinazolinyl group, benzoquinoxalinyl group, phenazinyl group, acridineyl group, phenanthrololinyl group, phenazinyl group, phenoxazinyl group, phenthiazinyl group, phenoxthiazinyl group, benzimidazole group, benzothiazolyl group, benziisothiazolyl group, benzoxazolyl group, benziisoxazolyl group, triazole Benzyl group, tetrazolyl group, thiadiazolyl group, oxadiazolyl group, triazine group, imidazopyridyl group, imidazopyrimidinyl group, oxazolylpyridyl group, thiazopyridyl group, benzonaphthyl group, azafluorenyl group, azaspiro-difluorenyl group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group, azadibenzothiophenyl group, indolepyrroleyl group, indolepyrroleyl group, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32-C(=O)(Q) 31 -S(=O)2(Q) 31 -P(=O)(Q) 31 (Q) 32 ) or any combination thereof, substituted with cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, terphenyl group, C1-C 20 Alkylphenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthraceneyl group, thiophene group, furanyl group, indene group, isoindoleyl group, indoleyl group, carbazole group, benzofuranyl group, benzothiophene group, benzothiophene group, dibenzofuranyl group, dibenzothiophene group, dibenzothiophene group, benzofluorenyl group, benzocarbazole group, naphthobenzofuranyl group, naphthobenzothiophene group, naphthobenzo benzo[a]thiopyrrolyl group, dibenzo[a]fluorenyl group, dibenzo[a]carbazoleyl group, dinaphthofuranyl group, dinaphthothiophenyl group, dinaphthothiopyrrolyl group, indole[a]carbazoleyl group, indole[a]carbazoleyl group, benzo[a]furan[a]carbazoleyl group, benzo[a]thiophen[a]carbazoleyl group, benzo[a]thiopyrrol[a]carbazoleyl group, pyridyl group, pyrimidinyl group, pyridazinyl group, indazoleyl group, purineyl group, quinolinyl group, isoquinolinyl group, benzo[a]quinolone Phinyl group, benzisoquinolinyl group, phthalazinyl group, naphthidyl group, quinoxalinyl group, benzoquinoxalinyl group, quinazolinyl group, benzoquinazolinyl group, phenanthidyl group, acridineyl group, phenanthrololinyl group, phenazinyl group, phenoxazinyl group, phenthiazinyl group, phenoxthiazyl group, benzimizolyl group, benzothiazolyl group, benzisothiazolyl group, benzooxazolyl group, benzisooxazolyl group, Triazolyl group, tetrazolyl group, thiadiazolyl group, oxadiazolyl group, triazinyl group, imidazopyridyl group, imidazopyrimidyl group, oxazolylpyridyl group, thiazopyridyl group, benzonaphthyl group, azafluorenyl group, azaspiro-difluorenyl group, azacarbazoyl group, azadibenzofuranyl group, azadibenzothiophenyl group, azadibenzothiophenyl group, indenepyrroleyl group or indolepyrroleyl group; or

[0138] -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),

[0139] Among them, Q1 to Q3 and Q 31 To Q 33Each of these can be independently hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl group; cyano group; nitro group; C1-C 60 Alkyl group; C2-C 60 alkenyl group; C2-C 60 alkynyl group; C1-C 60 Alkoxy groups; or each unsubstituted or deuterated, -F, cyano groups, C1-C 60 Alkyl groups, C1-C 60 C3-C substituted with alkoxy groups, phenyl groups, biphenyl groups, or any combination thereof 60 Carbocyclic groups or C1-C 60 Heterocyclic groups,

[0140] e2 can be an integer from 0 to 2.

[0141] e3 can be an integer from 0 to 3.

[0142] e4 can be an integer from 0 to 4.

[0143] e5 can be an integer from 0 to 5.

[0144] e7 can be an integer from 0 to 7.

[0145] e11 can be an integer from 0 to 11, and

[0146] * indicates a binding site with an adjacent group.

[0147] In one embodiment, the heterocyclic compound may be selected from compound 1 to compound 110:

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154] Heterocyclic compounds represented by Formula 1-1 may contain at least one group represented by Formula 1-2 as a substituent in the core structure represented by Formula 1-1:

[0155]

[0156]

[0157] While not wishing to be bound by theory, when the hypothetical compound with the structure corresponding to Formula 1 does not contain the groups represented by Formulas 1-2 as described above, the B atom in the hypothetical compound can bind to a nucleophile through the empty p orbital of the B atom, causing the triangular bond structure of the B atom to transform into a tetrahedral structure, thus leading to the degradation of the electronic device using the hypothetical compound. However, the p orbital of the B atom in Formula 1 can be effectively protected by the groups represented by Formulas 1-2, and thus the triangular bond structure of the B atom in Formula 1 can be effectively maintained. Furthermore, although the heterocyclic compound represented by Formula 1 has a multiple resonance plane structure, the distance between molecules may increase through the groups represented by Formulas 1-2, leading to molecular aggregation and the generation of molecular excimers or molecular excimer complexes, and thus reducing the possibility of intermolecular interactions that may lead to reduced emission efficiency. Furthermore, in the heterocyclic compound represented by Formula 1, when X in Formula 1-2... 11 To X 14 When at least one atom in the compound is "N", for example, the stability of the boron compound can be significantly improved because the lone pair of electrons in the N atom of pyridine stabilizes the p orbital while exhibiting an electron-donating effect. Therefore, the emission efficiency and / or lifespan of electronic devices (e.g., light-emitting devices) containing heterocyclic compounds represented by Formula 1 can be improved.

[0158] By referring to the synthetic examples and / or embodiments provided below, those skilled in the art will recognize the synthetic method of the heterocyclic compound represented by Formula 1.

[0159] In some embodiments, the first electrode of the light-emitting device can be an anode, the second electrode of the light-emitting device can be a cathode, and the intermediate layer can further include a hole transport region located between the first electrode and the emitting layer and an electron transport region located between the emitting layer and the second electrode. The hole transport region can include a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer or any combination thereof, and the electron transport region can include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer or any combination thereof.

[0160] In one or more embodiments, a heterocyclic compound may be contained between the first and second electrodes of the light-emitting device. Therefore, the heterocyclic compound may be contained in an intermediate layer of the light-emitting device, for example, in an emitting layer of the intermediate layer. The emitting layer may emit red, green, blue, and / or white light. For example, the emitting layer may emit blue light. Blue light may have a maximum emission wavelength, for example, from about 400 nm to about 490 nm or from about 450 nm to about 470 nm. Because blue light has a maximum emission wavelength of about 450 nm to about 470 nm, it is possible to manufacture an organic light-emitting device with high color purity. In embodiments, the emitting layer may further comprise a host, and the amount of the host may be greater than the amount of the heterocyclic compound represented by Formula 1.

[0161] In embodiments, the light-emitting device may include a capping layer located outside the first electrode or outside the second electrode. For example, the capping layer may contain a heterocyclic compound represented by Formula 1. For example, the light-emitting device may further include at least one of a first capping layer located outside the first electrode and a second capping layer located outside the second electrode, and the heterocyclic compound represented by Formula 1 may be contained in at least one of the first capping layer and the second capping layer. Further details of the first capping layer and / or the second capping layer are the same as described herein. In one or more embodiments, the light-emitting device may further include: a first capping layer located outside the first electrode and containing a heterocyclic compound represented by Formula 1; a second capping layer located outside the second electrode and containing a heterocyclic compound represented by Formula 1; or a first capping layer and a second capping layer.

[0162] As used herein, the expression "(intermediate layer and / or capping layer) comprises at least one heterocyclic compound represented by Formula 1" can include cases where "(intermediate layer and / or capping layer) comprises the same heterocyclic compound represented by Formula 1" and cases where "(intermediate layer and / or capping layer) comprises two or more different heterocyclic compounds represented by Formula 1". For example, the intermediate layer and / or capping layer may comprise only compound 1 as a heterocyclic compound. In this respect, compound 1 may be present in the emitting layer of the light-emitting device. In one or more embodiments, the intermediate layer may comprise compound 1 and compound 2 as heterocyclic compounds. In this respect, compound 1 and compound 2 may be present in the same layer (e.g., both compound 1 and compound 2 may be present in the emitting layer) or in different layers (e.g., compound 1 may be present in the emitting layer and compound 2 may be present in the electron transport region).

[0163] According to another aspect of the invention, the electronic device including the light-emitting device may further include a thin-film transistor. In one or more embodiments, the electronic device may further include a thin-film transistor comprising a source electrode and a drain electrode, and a first electrode of the light-emitting device may be electrically connected to the source electrode or the drain electrode. In embodiments, the electronic device may further include a color filter, a color conversion layer, a touchscreen layer, a polarizing layer, or any combination thereof. Further details regarding the electronic device are the same as described herein.

[0164] According to embodiments of the present invention, the heterocyclic compound is represented by Formula 1. The specific description of Formula 1 is the same as that described herein.

[0165] Figure 1 Description

[0166] Figure 1 This is a schematic cross-sectional view of an embodiment of a light-emitting device constructed according to the principles of the present invention.

[0167] Specifically, Figure 1 This is a schematic cross-sectional view of the light-emitting device 10 according to an embodiment. The light-emitting device 10 includes a first electrode 110, an intermediate layer 130, and a second electrode 150.

[0168] In the following text, we will discuss... Figure 1 The structure of the light-emitting device 10 according to the embodiment and an exemplary method of manufacturing the light-emitting device 10 are described.

[0169] First electrode 110

[0170] exist Figure 1 In this embodiment, the substrate may additionally be located below the first electrode 110 or above the second electrode 150. A glass substrate or a plastic substrate may be used as the substrate. In one or more embodiments, the substrate may be a flexible substrate and may comprise a plastic with excellent heat resistance and durability, such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or any combination thereof.

[0171] The first electrode 110 can be formed, for example, by depositing or sputtering a material for forming the first electrode 110 on a substrate. When the first electrode 110 is an anode, the material for forming the first electrode 110 can be a high work function material that promotes hole injection.

[0172] The first electrode 110 can be a reflective electrode, a semi-transparent reflective electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, the material used to form the first electrode 110 can include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof. In one or more embodiments, when the first electrode 110 is a semi-transparent reflective electrode or a reflective electrode, magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof can be used as the material for forming the first electrode.

[0173] The first electrode 110 may have a single-layer structure consisting 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.

[0174] Middle layer 130

[0175] The intermediate layer 130 may be located on the first electrode 110. The intermediate layer 130 may include an emitter layer. The intermediate layer 130 may further include a hole transport region disposed between the first electrode 110 and the emitter layer and an electron transport region disposed between the emitter layer and the second electrode 150.

[0176] In addition to various organic materials, the intermediate layer 130 may further comprise metal-containing compounds (e.g., organometallic compounds), inorganic materials (e.g., quantum dots), etc. In one or more embodiments, the intermediate layer 130 may include: i) two or more emission units sequentially stacked between the first electrode 110 and the second electrode 150, and ii) a charge generation layer located between the two or more emission units. When the intermediate layer 130 includes emission units and a charge generation layer as described above, the light-emitting device 10 may be a tandem light-emitting device.

[0177] Hole transport region in intermediate layer 130

[0178] The hole transport region can have: i) a single-layer structure consisting of a single layer made of a single material, ii) a single-layer structure consisting of a single layer made of multiple different materials, or iii) a multi-layer structure including multiple layers containing different materials. The hole transport region can include a hole injection layer, a hole transport layer, an emission assist layer, an electron blocking layer, or any combination thereof.

[0179] For example, the hole transport region may have a multilayer structure including a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission auxiliary layer structure, a hole injection layer / emission auxiliary layer structure, a hole transport layer / emission auxiliary layer structure, or a hole injection layer / hole transport layer / electron blocking layer structure, wherein, in each structure, the layers are stacked sequentially from the first electrode 110.

[0180] The hole transport region may contain a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:

[0181] Formula 201

[0182]

[0183] Formula 202

[0184]

[0185] Among them, in equations 201 and 202,

[0186] L 201 To L 204 Each is independently unsubstituted or by at least one R 10a Replacement of divalent C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Substituted divalent C1-C 60 Heterocyclic groups,

[0187] L 205 It can be *-O-*', *-S-*', or *-N(Q) 201 )-*', unsubstituted or by at least one R 10a Replacement C1-C 20 alkylene groups, unsubstituted or with at least one R 10a Replacement C2-C 20 alkenyl groups, unsubstituted or with at least one R 10a Replacement of divalent C3-C 60 Carbocyclic group, or unsubstituted or with at least one R 10a Substituted divalent C1-C 60 Heterocyclic groups,

[0188] xa1 to xa4 are each an independent integer from 0 to 5.

[0189] xa5 is an integer from 0 to 10.

[0190] R 201 To R 204 and Q 201 Each is independently unsubstituted or by at least one R 10aReplacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups,

[0191] R 201 and R 202 Optionally via a single bond, unsubstituted, or by at least one R 10a Substituted C1-C5 alkylene groups or unsubstituted or substituted with at least one R 10a The substituted C2-C5 alkenyl groups are linked together to form unsubstituted or substituted groups with at least one R group. 10a Replacement C8-C 60 Polycyclic groups (e.g., carbazole groups, etc.) (e.g., compound HT16),

[0192] R 203 and R 204 Optionally via a single bond, unsubstituted, or by at least one R 10a Substituted C1-C5 alkylene groups or unsubstituted or substituted with at least one R 10a The substituted C2-C5 alkenyl groups are linked together to form unsubstituted or substituted groups with at least one R group. 10a Replacement C8-C 60 Polycyclic groups, wherein R 10a Same as described in this article, and

[0193] na1 can be an integer from 1 to 4.

[0194] In one or more embodiments, each of Formula 201 and Formula 202 may contain at least one of the groups represented by Formula CY201 to Formula CY217.

[0195]

[0196] The variable R in equations CY201 to CY217 10b and R 10c Regarding R 10a The descriptions are the same, CY ring 201 To CY 204 Each can be C3-C independently. 20 Carbocyclic groups or C1-C 20 Heterocyclic groups, and at least one hydrogen atom in formulas CY201 to CY217 may be unsubstituted or substituted with R. 10a Replace, where R 10a Same as described in this article.

[0197] In the implementation plan, the ring CY in formulas CY201 to CY217 201 To CY204 Each group can be a phenyl group, a naphthol group, a phenanthrene group, or an anthracene group independently. In one or more embodiments, each of formulas 201 and 202 may contain at least one of the groups represented by formulas CY201 to CY203.

[0198] In one or more embodiments, formula 201 may comprise at least one group represented by formulas CY201 to CY203 and at least one group represented by formulas CY204 to CY217. In one or more embodiments, xa1 in formula 201 is 1, R 201 It is a group represented by one of the formulas CY201 to CY203, xa2 can be 0, and R 202 It may be a group represented by one of the formulas CY204 to CY217. In one or more embodiments, each of formulas 201 and 202 may not contain a group represented by one of the formulas CY201 to CY203. In one or more embodiments, each of formulas 201 and 202 may not contain a group represented by one of the formulas CY201 to CY203, but may contain at least one group represented by one of the formulas CY204 to CY217. In one or more embodiments, each of formulas 201 and 202 may not contain a group represented by one of the formulas CY201 to CY217.

[0199] In the implementation scheme, the hole transport region may comprise compounds HT1 to HT46, 4,4',4”-tris[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), 1-N,1-N-bis[4-(diphenylamino)phenyl]-4-N,4-N-diphenylphenyl-1,4-diamine (TDATA), 4,4',4”-tris[2-naphthyl(phenyl)amino]triphenylamine (2-TNATA), bis(naphth-1-yl)-N,N'-bis(phenyl) Benzidine (NPB or NPD), N4,N4'-bis(naphthyl-2-yl)-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (β-NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenylbenzidine (TPD), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-9,9-spirodifluorene-2,7-diamine (spiro-TPD), N2,N7-bis-1-naphthyl-N2,N7-diphenyl-9,9 '-spirobis[9H-fluorene]-2,7-diamine (spiro-NPB), N,N'-di(1-naphthyl)-N,N'-diphenyl-2,2'-dimethyl-(1,1'-biphenyl)-4,4'-diamine (methylated-NPB), 4,4'-cyclohexylbis[N,N-bis(4-methylphenyl)aniline] (TAPC), N,N,N',N'-tetra(3-methylphenyl)-3,3'-dimethylbenzidine (HMTPD), 4,4',4”-tris(N-carbamate) One or any combination thereof from the following: 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), 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi):

[0200]

[0201]

[0202]

[0203]

[0204]

[0205] The thickness of the hole transport region can be approximately to approximately For example, about to approximately 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 can be approximately to approximately For example, about to approximately Furthermore, the thickness of the hole transport layer can be approximately to approximately For example, about to approximately When the thicknesses of the hole transport region, hole injection layer, and hole transport layer are within these ranges, satisfactory hole transport characteristics can be obtained without a significant increase in driving voltage.

[0206] The emission assist layer can increase light emission efficiency by compensating for the optical resonant distance according to the wavelength of the light emitted by the emission layer, and the electron blocking layer can block the leakage of electrons from the emission layer to the hole transport region. Materials that can be contained in the hole transport region can be included in both the emission assist layer and the electron blocking layer.

[0207] p-dopants

[0208] In addition to these materials, the hole transport region may further comprise a charge-generating material for improving conductivity. The charge-generating 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-generating material). The charge-generating material may be, for example, a p-dopant. In one or more embodiments, the lowest unoccupied molecular orbital (LUMO) level of the p-dopant may be about -3.5 eV or less than -3.5 eV.

[0209] In one or more embodiments, the p-doper may include quinone derivatives, cyano-containing compounds, compounds containing elements EL1 and EL2, or any combination thereof. Examples of quinone derivatives are tetracyanoquinone dimethyl ether (TCNQ), 2,3,5,6-tetrafluoro-7,7',8,8'-tetracyanoquinone dimethyl ether (F4-TCNQ), etc. Examples of cyano-containing compounds are 1,4,5,8,9,12-hexaazabenzophenanthrene-hexacarboxynitrile (HAT-CN) and compounds represented by the following formula 221.

[0210]

[0211] Equation 221

[0212]

[0213] In Equation 221, R 221 To R 223 Each can be independently unsubstituted or by at least one R. 10a Replacement C3-C 60The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups, and R 221 To R 223 One or more of them may be independently substituted with a cyano group; -F; -Cl; -Br; -I; or a C1-C group substituted with a cyano group, -F, -Cl, -Br, -I, or any combination thereof. 20 Alkyl groups; or C3-C groups substituted with any combination thereof 60 Carbocyclic groups or C1-C 60 Heterocyclic groups, wherein R 10a Same as described in this article. In compounds containing elements EL1 and EL2, element EL1 can be a metal, a metalloid, or any combination thereof, and element EL2 can be a nonmetal, a metalloid, or any combination thereof.

[0214] Examples of metals 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.); and 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 (C), etc.). (e.g., o), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au), etc.); later transition metals (e.g., zinc (Zn), indium (In), tin (Sn), etc.); and lanthanides (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.).

[0215] Examples of metalloids are silicon (Si), antimony (Sb), and tellurium (Te). Examples of nonmetals are oxygen (O) and halogens (e.g., F, Cl, Br, I, etc.). In one or more embodiments, examples of compounds containing elements EL1 and EL2 are metal oxides, metal halides (e.g., metal fluorides, metal chlorides, metal bromides, or metal iodides), metalloid halides (e.g., metalloid fluorides, metalloid chlorides, metalloid bromides, or metalloid iodides), metal tellurides, or any combination thereof.

[0216] Examples of metal oxides are tungsten oxides (e.g., WO, W₂O₃, WO₂, WO₃, W₂O₅, etc.), vanadium oxides (e.g., VO, V₂O₃, VO₂, V₂O₅, etc.), molybdenum oxides (e.g., MoO, Mo₂O₃, MoO₂, MoO₃, Mo₂O₅, etc.), and rhenium oxides (e.g., ReO₃, etc.). Examples of metal halides are alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, and lanthanide metal halides.

[0217] Examples of alkali metal halides are LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, and CsI. Examples of alkaline earth metal halides are BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2, SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, BeI2, MgI2, CaI2, SrI2, and BaI2.

[0218] Examples of transition metal halides 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.), and tantalum halides (e.g., TaF3, TaCl3, TaB). rhenium halides (e.g., CrF3, 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.), and rhenium halides (e.g., ReF2, ReCl2, ReBr2). Iron halides (e.g., FeF2, FeCl2, FeBr2, FeI2), ruthenium halides (e.g., RuF2, RuCl2, RuBr2, RuI2), osmium halides (e.g., OsF2, OsCl2, OsBr2, OsI2), cobalt halides (e.g., CoF2, CoCl2, CoBr2, CoI2), rhodium halides (e.g., RhF2, RhCl2, RhBr2, RhI2), iridium halides (e.g., IrF2, IrCl2, IrB2). (e.g., r2, 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.), copper halides (e.g., CuF, CuCl, CuBr, CuI, etc.), silver halides (e.g., AgF, AgCl, AgBr, AgI, etc.) and gold halides (e.g., AuF, AuCl, AuBr, AuI, etc.).

[0219] Examples of late transition metal halides are zinc halides (e.g., ZnF₂, ZnCl₂, ZnBr₂, ZnI₂, etc.), indium halides (e.g., InI₃, etc.), and tin halides (e.g., SnI₂, etc.). Examples of lanthanide metal halides are YbF, YbF₂, YbF₃, SmF₃, YbCl, YbCl₂, YbCl₃, SmCl₃, YbBr, YbBr₂, YbBr₃, SmBr₃, YbI, YbI₂, YbI₃, and SmI₃. Examples of metal halides are antimony halides (e.g., SbCl₅, etc.).

[0220] Examples of metal tellurides include alkali metal tellurides (e.g., Li₂Te, Na₂Te, K₂Te, Rb₂Te, Cs₂Te, etc.), alkaline earth metal tellurides (e.g., BeTe, MgTe, CaTe, SrTe, BaTe, etc.), and transition metal tellurides (e.g., TiTe₂, ZrTe₂, HfTe₂, V₂Te₃, Nb₂Te₃, Ta₂Te₃, Cr₂Te₃, Mo₂Te₃, W₂Te₃, MnTe, TcTe, ReTe, Fe₂Te). Te, 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.).

[0221] emission layer in intermediate layer 130

[0222] When the light-emitting device 10 is a full-color light-emitting device, the emitting layer can be patterned into a red emitting layer, a green emitting layer, and / or a blue emitting layer, depending on the sub-pixel. In one or more embodiments, the emitting layer may have a stacked structure of two or more layers selected from red, green, and blue emitting layers, wherein the two or more layers are in contact with or spaced apart from each other. In one or more embodiments, the emitting layer may contain two or more materials selected from red-emitting, green-emitting, and blue-emitting materials, wherein the two or more materials are mixed with each other in a single layer to emit white light. For example, the emitting layer may emit blue light.

[0223] In an embodiment, the emitter layer may comprise a heterocyclic compound represented by Formula 1 as described above. The emitter layer may comprise a host and a dopant. In an embodiment, the dopant may comprise a heterocyclic compound represented by Formula 1 as described above. In this respect, in addition to the heterocyclic compound represented by Formula 1, the dopant may comprise a phosphorescent dopant, a fluorescent dopant, or any combination thereof. The phosphorescent and fluorescent dopants that may be further included in the emitter layer, in addition to the heterocyclic compound represented by Formula 1, are the same as those described below.

[0224] Based on 100 parts by weight of the host material, the amount of dopant in the emission layer can be from about 0.01 parts by weight to about 15 parts by weight. In one or more embodiments, the emission layer may comprise quantum dots. The emission layer may comprise a delayed fluorescence material. The delayed fluorescence material may act as either the host or the dopant in the emission layer. The thickness of the emission layer may be approximately... to approximately For example, about to approximately When the thickness of the emitting layer is within these ranges, excellent light emission characteristics can be obtained without a significant increase in driving voltage.

[0225] main body

[0226] The main body may include, for example, a carbazole-containing compound, an anthracene-containing compound, or any combination thereof. In embodiments, the main body may include a compound represented by the following formula 301:

[0227] Formula 301

[0228] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21

[0229] In Equation 301,

[0230] Ar 301 Each can be independently unsubstituted or by at least one R. 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups,

[0231] L 301 Each can be independently unsubstituted or by at least one R. 10a Replacement of divalent C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Substituted divalent C1-C 60 Heterocyclic groups,

[0232] xb11 can be 1, 2, or 3.

[0233] xb1 can be an integer from 0 to 5.

[0234] R 301 It can be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, unsubstituted or with at least one R 10a Replacement C1-C 60 alkyl groups, unsubstituted or with at least one R 10a Replacement C2-C 60 alkenyl groups, unsubstituted or with at least one R 10a Replacement C2-C 60The alkynyl group, unsubstituted or with at least one R 10a Replacement C1-C 60 alkoxy group, unsubstituted or with at least one R 10a Replacement C3-C 60 Carbocyclic groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, -Si(Q) 301 (Q) 302 (Q) 303 -N(Q) 301 (Q) 302 -B(Q) 301 (Q) 302 -C(=O)(Q) 301 -S(=O)2(Q) 301 ) or -P(=O)(Q 301 (Q) 302 ),

[0235] xb21 can be an integer from 1 to 5, and

[0236] Where R 10a Same as described in this article, and Q 301 To Q 303 Same as the description regarding Q1.

[0237] For example, when xb11 in equation 301 is 2 or greater than 2, two or more Ar 301 They can be linked to each other via single bonds. In one or more embodiments, the body may include a compound represented by formula 301-1, a compound represented by formula 301-2, or any combination thereof:

[0238] Formula 301-1

[0239]

[0240] Formula 301-2

[0241]

[0242] In Equations 301-1 and 301-2,

[0243] Ring A 301 To Ring A 304 Each can be independently unsubstituted or by at least one R. 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups, wherein R 10aAs described in this article,

[0244] X 301 It can be O, S, N-[(L 304 ) xb4 -R 304 ]、C(R 304 (R) 305 ) or Si(R 304 (R) 305 ),

[0245] xb22 and xb23 can each be 0, 1, or 2 independently.

[0246] L 301 xb1 and R 301 Each is independently identical to the description in this article.

[0247] L 302 To L 304 Each independently and about L 301 The descriptions are the same.

[0248] xb2 to xb4 are each independently identical to the description of xb1, and

[0249] R 302 To R 305 and R 311 To R 314 Each independently and about R 301 The descriptions are the same.

[0250] In one or more embodiments, the body may include alkaline earth metal complexes, post-transition metal complexes, or any combination thereof. In one or more embodiments, the body may include Be complexes (e.g., compound H55), Mg complexes, Zn complexes, or any combination thereof.

[0251] In the embodiments, the main body may include one or any combination of compounds H1 to H124, 9,10-bis(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthyl-2-yl)anthracene (MADN), 9,10-bis(2-naphthyl)-2-tert-butyl-anthracene (TBADN), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 1,3-bis(carbazolyl-9-yl)benzene (mCP), and 1,3,5-tris(carbazolyl-9-yl)benzene (TCP):

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258] Phosphorescent dopants

[0259] Phosphorescent dopants may contain at least one transition metal as the center metal. Phosphorescent dopants may contain monodentate, bidentate, tripentate, tetradentate, pentadentate, hexadentate ligands, or any combination thereof. Phosphorescent dopants may be electrically neutral. For example, phosphorescent dopants may include organometallic compounds represented by Formula 401:

[0260] Formula 401

[0261] M(L 401 ) xc1 (L 402 ) xc2

[0262] Formula 402

[0263]

[0264] In Equations 401 and 402,

[0265] 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)).

[0266] L 401 The ligand can be represented by Equation 402, and xc1 can be 1, 2, or 3, where when xc1 is 2 or greater than 2, there are two or more L... 401 They can be the same or different from each other.

[0267] L 402 It can be an organic ligand, and xc2 can be 0, 1, 2, 3, or 4, and when xc2 is 2 or greater than 2, two or more L... 402 They can be the same or different from each other.

[0268] X 401 and X 402 It can be either nitrogen or carbon, each independently.

[0269] Ring A 401 And Ring A 402 Each can be C3-C independently. 60Carbocyclic groups or C1-C 60 Heterocyclic groups,

[0270] T 401 It can be a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q) 411 )-*'、*-C(Q 411 (Q) 412 )-*'、*-C(Q 411 )=C(Q 412 )-*'、*-C(Q 411 ) = *' or * = C = *',

[0271] X 403 and X 404 These can be chemical bonds (e.g., covalent or coordinate bonds), O, S, N (Q) independently. 413 ), B(Q) 413 ), P(Q 413 ), C(Q 413 (Q) 414 ) or Si(Q 413 (Q) 414 ),

[0272] Q 411 To Q 414 Each is the same as described in Q1.

[0273] R 401 and R 402 Each of these groups can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 20 alkyl groups, unsubstituted or with at least one R 10a Replacement C1-C 20 alkoxy group, unsubstituted or with at least one R 10a Replacement C3-C 60 Carbocyclic groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, -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 ),

[0274] R 10a Same as described in this article, and Q 401 To Q 403 Each is the same as described in Q1.

[0275] xc11 and xc12 can each be an integer from 0 to 10 independently, and

[0276] T 401 In Equation 402, * and *' represent binding sites with adjacent atoms, and in Equation 402, * and *' represent binding sites with M in Equation 401.

[0277] For example, in equation 402, i)X 401 It can be nitrogen, and X 402 It can be carbon, or ii)X 401 and X 402 Each of them can be nitrogen.

[0278] In one or more embodiments, when xc1 in equation 401 is 2 or greater than 2, two or more L 401 The two rings A in 401 It can be optionally via T as a linking group 402 They are connected to each other, and the two rings A 402 Optionally via T as a linking group 403 They are interconnected (see compounds PD1 through PD4 and PD7). The group T 402 and T 403 Each and about T 401 The descriptions are the same.

[0279] The group L in Formula 401 402 It can be an organic ligand. For example, L... 402 It may include halogen groups, diketone groups (e.g., acetylacetonate groups), carboxylic acid groups (e.g., pyridine carboxylate groups), -C (=O) groups, isonitrile groups, -CN groups, phosphorus-containing groups (e.g., phosphine groups, phosphite groups, etc.) or any combination thereof.

[0280] Phosphorescent dopants may include, for example, one or any combination of compounds PD1 to PD39:

[0281]

[0282]

[0283]

[0284] Fluorescent dopants

[0285] Fluorescent dopant may include compounds containing amine groups, compounds containing styrene groups, or any combination thereof. In one or more embodiments, the fluorescent dopant may include a compound represented by Formula 501:

[0286] Formula 501

[0287]

[0288] In Equation 501,

[0289] Ar 501 R 501 and R 502 Each can be independently unsubstituted or by at least one R. 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups,

[0290] L 501 To L 503 Each can be independently unsubstituted or by at least one R. 10a Replacement of divalent C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Substituted divalent C1-C 60 Heterocyclic groups, wherein R 10a As described in this article,

[0291] xd1 to xd3 can each be independently 0, 1, 2, or 3, and

[0292] xd4 can be 1, 2, 3, 4, 5, or 6.

[0293] In one or more embodiments, Ar in Formula 501 501 It can be a fused cyclic group consisting of three or more monocyclic groups fused together (e.g., anthracene group, ...). (group or pyrene group).

[0294] In one or more embodiments, xd4 in Formula 501 can be 2.

[0295] In one or more embodiments, the fluorescent dopant may include: one of compounds FD1 to FD36; DPVBi; DPAVBi; or any combination thereof.

[0296]

[0297]

[0298]

[0299] Electron transport region in intermediate layer 130

[0300] The electron transport region can have: i) a single-layer structure consisting of a single layer made of a single material, ii) a single-layer structure consisting of a single layer made of multiple different materials, or iii) a multi-layer structure including multiple layers containing different materials. The electron transport region can include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0301] In the implementation scheme, the electron transport region may have an electron transport layer / electron injection layer structure, a hole blocking layer / electron transport layer / electron injection layer structure, an electron control layer / electron transport layer / electron injection layer structure, or a buffer layer / electron transport layer / electron injection layer structure, wherein, for each structure, the constituent layers are stacked sequentially from the emission layer.

[0302] In the implementation, the electron transport region (e.g., a buffer layer, hole blocking layer, electron control layer, or electron transport layer in the electron transport region) may contain C1-C containing at least one nitrogen with π-deficient electrons. 60 Metal-free compounds with cyclic groups.

[0303] In an implementation, the electron transport region may comprise a compound represented by the following formula 601:

[0304] Formula 601

[0305] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21

[0306] In Equation 601,

[0307] Ar 601 Each can be independently unsubstituted or by at least one R. 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups,

[0308] L 601 Each can be independently unsubstituted or by at least one R. 10a Replacement of divalent C3-C 60The carbocyclic group is either unsubstituted or has at least one R group. 10a Substituted divalent C1-C 60 Heterocyclic groups, wherein R 10a As described in this article,

[0309] xe11 can be 1, 2, or 3.

[0310] xe1 can be 0, 1, 2, 3, 4, or 5.

[0311] R 601 It can be unsubstituted or replaced by at least one R 10a Replacement C3-C 60 Carbocyclic groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, -Si(Q) 601 (Q) 602 (Q) 603 -C(=O)(Q) 601 -S(=O)2(Q) 601 ) or -P(=O)(Q 601 (Q) 602 ),

[0312] Q 601 To Q 603 Same as described regarding Q1,

[0313] xe21 can be 1, 2, 3, 4, or 5, and

[0314] Ar 601 L 601 and R 601 One or more of them can be independently unsubstituted or by at least one R 10a Substituted C1-C nitrogen containing π-electron-deficient atoms 60 Cyclic groups.

[0315] For example, when xe11 in equation 601 is 2 or greater than 2, two or more Ar 601 It can be connected via a single key. In one or more embodiments, Ar in Formula 601 601 The anthracene group may be substituted or unsubstituted. In embodiments, the electron transport region may comprise a compound represented by formula 601-1:

[0316] Formula 601-1

[0317]

[0318] In Equation 601-1,

[0319] X614 It can be N or C(R) 614 ), X 615 It can be N or C(R) 615 ), X 616 It can be N or C(R) 616 ), X 614 To X 616 One or more of them can be N,

[0320] L 611 To L 613 Regarding L 601 The descriptions are the same.

[0321] xe611 to xe613 are the same as those described regarding xe1.

[0322] R 611 To R 613 Regarding R 601 The same description, and

[0323] R 614 To R 616 Each of these can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 20 Alkyl groups, C1-C 20 alkoxy group, unsubstituted or with at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups, wherein R 10a Same as described herein. For example, xe1 and xe611 to xe613 in Equations 601 and 601-1 can each be 0, 1 or 2 independently.

[0324] The electron transport region may contain compounds ET1 to ET45, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), tris-(8-hydroxyquinoline)aluminum (Alq3), bis(2-methyl-8-quinoline-N1,O8)-(1,1'-biphenyl-4-ol)aluminum (BAlq), 3-(biphenyl-4-ol)aluminum (BAlq), and others. One or any combination of the following: (1-(4-tert-butylphenyl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), 4-(naphthyl-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), biphenyl[4-(triphenylsilyl)phenyl]phosphine oxide (TSPO1), and 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBI):

[0325]

[0326]

[0327]

[0328] The thickness of the electron transport region can be approximately to approximately For example, about to approximately 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, hole blocking layer, or electron control layer can be independently approximately [missing information]. to approximately For example, about to approximately Furthermore, the thickness of the electron transport layer can be approximately to approximately For example, about to approximately When the thicknesses of the buffer layer, hole blocking layer, electronic control layer, electron transport layer, and / or electron transport layer are within these ranges, satisfactory electron transport characteristics can be obtained without a significant increase in driving voltage.

[0329] In addition to the materials described above, the electron transport region (e.g., the electron transport layer within the electron transport region) may further comprise a metal-containing material. The metal-containing material may include alkali metal complexes, alkaline earth metal complexes, or any combination thereof. The metal ion of the alkali metal complex may be Li, Na, K, Rb, or Cs ions, and the metal ion of the alkaline earth metal complex may be Be, Mg, Ca, Sr, or Ba ions. The ligands coordinated to the metal ions of the alkali metal or alkaline earth metal complex may include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthrene, cyclopentadiene, or any combination thereof.

[0330] For example, metal-containing materials may include Li complexes. Li complexes may include, for example, compounds ET-D1 (lithium hydroxyquinoline, LiQ) or ET-D2:

[0331]

[0332] The electron transport region may include an electron injection layer that facilitates the injection of electrons from the second electrode 150. The electron injection layer may be in direct contact with the second electrode 150.

[0333] The electron injection layer may have: i) a single-layer structure consisting of a single layer composed of a single material, ii) a single-layer structure consisting of a single layer composed of a plurality of different materials, or iii) a multi-layer structure including a plurality of layers containing different materials.

[0334] The electron injection layer may 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. The alkali metal may include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.

[0335] The alkali metal-containing compound, the alkaline earth metal-containing compound, and the rare earth metal-containing compound may be oxides, halides (e.g., fluorides, chlorides, bromides or iodides) or tellurides of alkali metals, alkaline earth metals and rare earth metals, or any combination thereof.

[0336] The alkali metal-containing compound may include an alkali metal oxide (e.g., Li₂O, Cs₂O or K₂O), an alkali metal halide (e.g., LiF, NaF, CsF, KF, LiI, NaI, CsI or KI), or any combination thereof. The alkaline earth metal-containing compound may include an alkaline earth metal compound, such as BaO, SrO, CaO, Ba x Sr 1-x O (x is a real number satisfying the condition of 0<x<1), Ba x Ca 1-x O (x is a real number satisfying the condition of 0<x<1), and the like. The rare earth metal-containing compound may include YbF₃, ScF₃, Sc₂O₃, Y₂O₃, Ce₂O₃, GdF₃, TbF₃, YbI₃, ScI₃, TbI₃, or any combination thereof. In one or more embodiments, the rare earth metal-containing compound may include lanthanide metal tellurides. Examples of the lanthanide metal tellurides are 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.

[0337] Alkali metal complexes, alkaline earth metal complexes, and rare earth metal complexes may contain i) one of the ions of an alkali metal, an alkaline earth metal, and a rare earth metal, and ii) as a ligand attached to a metal ion, such as hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthrene, cyclopentadiene, or any combination thereof.

[0338] The electron injection layer may consist of alkali metals, alkaline earth metals, rare earth metals, alkali metal-containing compounds, alkaline earth metal-containing compounds, rare earth metal-containing compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof, as described above. In one or more embodiments, the electron injection layer may further comprise an organic material (e.g., a compound represented by Formula 601).

[0339] In one or more embodiments, the electron-injected layer may consist of: i) an alkali metal-containing compound (e.g., an alkali metal halide); ii) a) an alkali metal-containing compound (e.g., an alkali metal halide); and b) an alkali metal, alkaline earth metal, rare earth metal, or any combination thereof. In one or more embodiments, the electron-injected layer may be a KI:Yb co-deposited layer, an RbI:Yb co-deposited layer, etc.

[0340] When the electron injection layer further contains organic materials, alkali metals, alkaline earth metals, rare earth metals, alkali metal-containing compounds, alkaline earth metal-containing compounds, rare earth metal-containing compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof can be uniformly or non-uniformly dispersed in the matrix containing organic materials.

[0341] The thickness of the electron injection layer can be approximately to approximately And for example, about to approximately When the thickness of the electron injection layer is within the range described above, the electron injection layer can have satisfactory electron injection characteristics without a significant increase in driving voltage.

[0342] Second electrode 150

[0343] The second electrode 150 may be located on the intermediate layer 130 having such a structure. The second electrode 150 may be a cathode serving as an electron injection electrode, and may be made of metals, alloys, conductive compounds, or any combination thereof, each having a low work function.

[0344] In one or more embodiments, the second electrode 150 may comprise 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 reflective electrode, or a reflective electrode. The second electrode 150 may have a single-layer structure or a multilayer structure comprising two or more layers.

[0345] Cover layer

[0346] The first cover layer may be located outside the first electrode 110, and / or the second cover layer may be located outside the second electrode 150. Specifically, the light-emitting device 10 may have a structure in which the first cover layer, the first electrode 110, the intermediate layer 130, and the second electrode 150 are stacked sequentially in a predetermined order, or a structure in which the first cover layer, the first electrode 110, the intermediate layer 130, the second electrode 150, and the second cover layer are stacked sequentially in a predetermined order.

[0347] The light generated in the emitting layer of the intermediate layer 130 of the light-emitting device 10 can be led outward through the first electrode 110 (which is a semi-transparent reflective electrode or a transmissive electrode) and the first cover layer, or the light generated in the emitting layer of the intermediate layer 130 of the light-emitting device 10 can be led outward through the second electrode 150 (which is a semi-transparent reflective electrode or a transmissive electrode) and the second cover layer.

[0348] While not wishing to be bound by theory, the first and second capping layers can increase the external emission efficiency based on the principle of constructive interference. Therefore, the light extraction efficiency of the light-emitting device 10 is increased, thereby improving its emission efficiency. Each of the first and second capping layers may contain a material having a refractive index of about 1.6 or greater (at 589 nm).

[0349] The first and second capping layers can each be independently an organic capping layer containing organic materials, an inorganic capping layer containing inorganic materials, or an organic-inorganic composite capping layer containing both organic and inorganic materials.

[0350] At least one of the first and second capping layers may independently comprise a carbocyclic compound, a heterocyclic compound, an amine-containing compound, a porphyrin derivative, a phthalocyanine derivative, a naphthylphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compound, heterocyclic compound, and amine-containing compound may optionally be substituted with substituents containing O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In one or more embodiments, at least one of the first and second capping layers may independently comprise an amine-containing compound.

[0351] In one or more embodiments, at least one of the first and second capping layers may each independently contain a compound represented by formula 201, a compound represented by formula 202, or any combination thereof.

[0352] In one or more embodiments, at least one of the first and second capping layers may each independently comprise one of compounds HT28 to HT33, one of compounds CP1 to CP6, N4,N4'-bis(naphthyl-2-yl)-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (β-NPB), or any combination thereof:

[0353]

[0354] electronic devices

[0355] The light-emitting device 10 can be included in various electronic devices. In one or more embodiments, the electronic device including the light-emitting device can be a light-emitting device, a verification device, etc.

[0356] In addition to the light-emitting device 10, the electronic device (e.g., the light-emitting device) may further include: i) a color filter, ii) a color conversion layer, or iii) a color filter and a color conversion layer. The color filter and / or the color conversion layer may be located in at least one direction of travel of the light emitted from the light-emitting device 10. In one or more embodiments, the light emitted from the light-emitting device 10 may be blue light or white light. The light-emitting device 10 may be the same as described above. In one or more embodiments, the color conversion layer may comprise quantum dots. The quantum dots may be, for example, as described herein.

[0357] An electronic device may include a first substrate. The first substrate may include a plurality of sub-pixel regions, a color filter may include a plurality of color filter regions corresponding to the sub-pixel regions, and a color conversion layer may include a plurality of color conversion regions corresponding to the sub-pixel regions.

[0358] A pixel definition layer may be located between sub-pixel regions to define each of the sub-pixel regions. A color filter may further include a plurality of color filter regions and a light-blocking pattern located between the color filter regions, and a color conversion layer may further include a plurality of color conversion regions and a light-blocking pattern located between the color conversion regions.

[0359] A color filter region (or color conversion region) may include a first region emitting a first color light, a second region emitting a second color light, and / or a third region emitting a third color light, wherein the first, second, and / or third color light may have different maximum emission wavelengths from each other. In one or more embodiments, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. In one or more embodiments, the color filter region (or color conversion region) may contain quantum dots. Specifically, the first region may contain red quantum dots, the second region may contain green quantum dots, and the third region may not contain quantum dots. The quantum dots are the same as those described herein. The first, second, and / or third regions may each contain a scatterer.

[0360] In one or more embodiments, the light-emitting device 10 can emit first light, a first region can absorb the first light to emit a first first color light, a second region can absorb the first light to emit a second first color light, and a third region can absorb the first light to emit a third first color light. In this respect, the first, second, and third first color lights can have different maximum emission wavelengths. Specifically, the first light can be blue light, the first first color light can be red light, the second first color light can be green light, and the third first color light can be blue light.

[0361] In addition to the light-emitting device 10 described above, the electronic device may further include a thin-film transistor. The thin-film transistor may include a source electrode, a drain electrode, and an active layer, wherein either the source electrode or the drain electrode may be electrically connected to either the first electrode or the second electrode of the light-emitting device 10.

[0362] Thin-film transistors can further include gate electrodes, gate insulating films, etc. The active layer can contain crystalline silicon, amorphous silicon, organic semiconductors, oxide semiconductors, etc.

[0363] The electronic device may further include a sealing portion for sealing the light-emitting device 10. The sealing portion and / or color conversion layer may be disposed between the color filter and the light-emitting device 10. The sealing portion allows light from the light-emitting device 10 to be guided to the outside while simultaneously preventing ambient air and moisture from penetrating into the light-emitting device 10. The sealing portion may be a sealing substrate comprising a transparent glass substrate or a plastic substrate. The sealing portion may be a thin-film encapsulation layer comprising at least one of an organic layer and an inorganic layer. When the sealing portion is a thin-film encapsulation layer, the electronic device may be flexible.

[0364] Depending on the application of the electronic device, various functional layers may additionally be located on the sealing portion, in addition to color filters and / or color conversion layers. Functional layers may include a touchscreen layer, a polarization layer, etc. The touchscreen layer may be a pressure-sensitive touchscreen layer, a capacitive touchscreen layer, or an infrared touchscreen layer. The verification device may be, for example, a biometric verification device that verifies an individual using biometric information from a living organism (e.g., fingertips, pupils, etc.). In addition to the light-emitting device 10, the verification device may further include a biometric information collector.

[0365] Electronic devices can take the form of or be used in the following ways: various displays, light sources, lighting equipment, personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic notebooks, electronic dictionaries, video game consoles, medical instruments (e.g., electronic thermometers, blood pressure monitors, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram displays, ultrasound diagnostic devices, or endoscopic displays), fish finders, various measuring instruments, meters (e.g., instruments for vehicles, aircraft, and ships), projectors, etc.

[0366] Figure 2 and Figure 3 Description

[0367] Figure 2 This is a schematic cross-sectional view of an embodiment of a light-emitting device including a light-emitting device constructed according to the principles of the present invention.

[0368] Figure 2 The light-emitting device 180 includes a substrate 100, a thin-film transistor (TFT) 200, a light-emitting device 10, and a package 300 that seals the light-emitting device 10.

[0369] The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. A buffer layer 210 may be formed on the substrate 100. The buffer layer 210 can prevent impurities from penetrating through the substrate 100 and can provide a substantially flat surface on the substrate 100.

[0370] TFT 200 may be located on buffer layer 210. TFT 200 may include active layer 220, gate electrode 240, source electrode 260 and drain electrode 270.

[0371] The active layer 220 may contain inorganic semiconductors (such as silicon or polysilicon), organic semiconductors or oxide semiconductors, and may include source region, drain region and channel region.

[0372] 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. An interlayer insulating film 250 is located on the gate electrode 240. The interlayer insulating film 250 may be placed 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.

[0373] 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 and drain regions of the active layer 220, and the source electrode 260 and the drain electrode 270 may contact the exposed portions of the source and drain regions of the active layer 220.

[0374] TFT 200 is electrically connected to light-emitting device 10 to drive light-emitting device 10, and may be covered by passivation layer 280. Passivation layer 280 may include an inorganic insulating film, an organic insulating film, or any combination thereof. Light-emitting device 10 is provided on passivation layer 280. Light-emitting device 10 may include a first electrode 110, an intermediate layer 130, and a second electrode 150.

[0375] The first electrode 110 may be formed on the passivation layer 280. The passivation layer 280 does not completely cover the drain electrode 270 and exposes a portion of the drain electrode 270, and the first electrode 110 is connected to the exposed portion of the drain electrode 270.

[0376] A pixel defining layer 290 containing insulating material may be located on the first electrode 110. The pixel defining layer 290 exposes an area of ​​the first electrode 110, and an intermediate layer 130 may be formed in the exposed area of ​​the first electrode 110. The pixel defining layer 290 may be a polyimide or polyacrylic acid organic film. At least some layers of the intermediate layer 130 may extend beyond the upper portion of the pixel defining layer 290 to be positioned as a common layer.

[0377] The second electrode 150 may be located on the intermediate layer 130, and a capping layer 170 may be additionally formed on the second electrode 150. The capping layer 170 may be formed to cover the second electrode 150.

[0378] The encapsulation portion 300 may be located on the cover layer 170. The encapsulation portion 300 may be located on the light-emitting device 10 to protect the light-emitting device from moisture or oxygen. The encapsulation portion 300 may include an inorganic film comprising silicon nitride (SiN). x ), silicon oxide (SiO) x Indium tin oxide, indium zinc oxide, or any combination thereof; an organic membrane comprising polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, acrylic resin (e.g., polymethyl methacrylate, polyacrylic acid, etc.), epoxy resin (e.g., aliphatic glycidyl ether (AGE), etc.) or any combination thereof; or any combination of inorganic and organic membranes.

[0379] Figure 3 This is a schematic cross-sectional view of another embodiment of a light-emitting device including a light-emitting device constructed according to the principles of the present invention.

[0380] Figure 3 Light-emitting device 190 and Figure 2 The light-emitting device 180 is the same, but the light-shielding pattern 500 and the functional area 400 are additionally located on the encapsulation portion 300. The functional area 400 may be: i) a color filter area, ii) a color conversion area, or iii) a combination of a color filter area and a color conversion area. In one or more embodiments, including Figure 3 The light-emitting device 10 in the light-emitting device 190 can be a series light-emitting device.

[0381] Manufacturing method

[0382] Layers comprising a hole transport region, an emission layer, and layers comprising an electron transport region can be formed in a specific region by using one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, and laser-induced thermal imaging.

[0383] When forming layers constituting hole transport regions, emission regions, and electron transport regions by vacuum deposition, the deposition temperature can be from about 100°C to about 500°C, and the deposition time can be from about 10°C to about 500°C, depending on the material to be included in the layers and the structure of the layers. -8 To about 10 -3 The vacuum degree and about / seconds to approximately Deposition is carried out at a deposition rate of / second.

[0384] Definition of terminology

[0385] As used herein, the term "intermediate layer" refers to a single layer and / or all layers between the first electrode and the second electrode of the light-emitting device. The phrase "(intermediate layer and / or capping layer) contains a fused cyclic compound represented by Formula 1" can be interpreted as meaning that "(intermediate layer and / or capping layer) contains at least one identical fused cyclic compound represented by Formula 1 or (intermediate layer and / or capping layer) contains two or more different fused cyclic compounds represented by Formula 1".

[0386] As used in this article, the term "energy level" can be expressed as "electron volt" and abbreviated as "eV".

[0387] As used herein, the term “atom” may mean an element or its corresponding group bonded to one or more other atoms.

[0388] The terms “hydrogen” and “deuterium” refer to their respective atoms and corresponding groups, with the deuterium group abbreviated as “-D”, and the terms “-F, -Cl, -Br and -I” are the groups of fluorine, chlorine, bromine and iodine, respectively.

[0389] As used herein, substituents for monovalent groups (e.g., alkyl groups) can also be substituents for the corresponding divalent groups (e.g., alkylene groups).

[0390] As used in this article, the term "C3-C" 60 A "carbocyclic group" refers to a cyclic group consisting solely of carbon as the cyclic atom and having 3 to 60 (e.g., 3 to 30, 3 to 20, 3 to 15, 3 to 10, or 3 to 5) carbon atoms, and as used herein by the term "C1-C". 60 A "heterocyclic group" refers to a cyclic group having 1 to 60 (e.g., 1 to 30, 1 to 20, 1 to 15, 1 to 10, or 1 to 5) carbon atoms and further having heteroatoms other than carbon (e.g., 1 to 15, 1 to 10, 1 to 5, or 1 to 3 heteroatoms) as cyclic atoms. (C3-C) 60 Carbocyclic groups and C1-C 60 Heterocyclic groups can be monocyclic groups, each consisting of a single ring, or polycyclic groups in which two or more rings are fused together. For example, C1-C 60 Heterocyclic groups have 3 to 61 cyclic atoms.

[0391] As used in this article, "cyclic group" can include C3-C 60 Carbocyclic groups and C1-C 60 Heterocyclic groups.

[0392] As used in this article, “π-electron-rich C3-C” 60"Cyclic group" refers to a cyclic group having 3 to 60 (e.g., 3 to 30, 3 to 20, 3 to 15, 3 to 10, or 3 to 5) carbon atoms and not containing *-N=*' as a cyclic moiety, and as used herein by the term "C1-C containing π-electron-deficient nitrogen". 60 A "cyclic group" refers to a heterocyclic group having 1 to 60 (e.g., 1 to 30, 1 to 20, 1 to 15, 1 to 10, or 1 to 5) carbon atoms and containing *-N=*' as the cyclic part.

[0393] For example, C3-C 60 The carbocyclic group can be i) a group T1G, or ii) a fused cyclic group in which two or more groups T1G are fused together, such as cyclopentadienyl group, adamantyl group, norbornel group, phenyl group, pentanene group, naphthyl group, chamomile ring group, indole group, acenaphthene group, phenanthrene group, phenanthrene group, anthracene group, fluoranthene group, benzo[a]phenanthrene group, pyrene group, etc. Group, perylene group, pentaphenyl group, heptadene group, tetraphenyl group, styrene group, hexaphenyl group, pentaphenyl group, rutin group, styrene group, ovoid group, indene group, fluorene group, spiro-difluorene group, benzo[a]fluorene group, ind[a]phenanthrene group or ind[a]anthracene group.

[0394] C1-C 60The heterocyclic group can be i) a group T2G, ii) a fused cyclic group in which two or more groups T2G are fused together, or iii) a fused cyclic group in which at least one group T2G and at least one group T1G are fused together, for example, a pyrrole group, a thiophene group, a furan group, an indole group, a benzo[a]indole group, a naph[a]indole group, an isoindole group, a benzo[a]isoindole group, a naph[a]isoindole group, or a benzo[a]thiophene group. Benzothiophene group, benzofuran group, carbazole group, dibenzothiophene group, dibenzothiophene group, dibenzofuran group, indole-carbazole group, indole-carbazole group, benzofuran-carbazole group, benzothiophene-carbazole group, benzothiophene-carbazole group, benzoindole-carbazole group, benzocarbazole group, benzonaphthofuran group, benzonaphthothiophene group, benzonaphthothiophene group, benzofuran-dibenzofuran group, benzofuran Benzo[2,3-benzothiophene], benzo[2,3-benzothiophene], pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, oxadiazole group, thiazole group, isothiazole group, thiaazole group, isothiazole group, thiadiazole group, benzo[2,3-benzopyrazole], benzimidazole group, benzo[2,3-benzoxazole], benzimidazole group, benzo[2,3-benzoxazole], benzo[2,3-benzoxazole], benzo[2,3-benzoxazole], benzo[2,3-benzoxazole], benzo[2,3-benzoxazole], pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group Groups, including benzoquinoline group, benzoisoquinoline group, quinoxaloline group, benzoquinoxaloline group, quinazoline group, benzoquinazoline group, phenanthrene group, cycloline group, phthalazine group, naphthidine group, imidazopyridine group, imidazopyrimidine group, imidazotriazine group, imidazopyrazine group, imidazopyridazine group, azacarbazole group, azafluorene group, azadibenzothiophene group, azadibenzothiophene group, azadibenzofuran group, etc.

[0395] C3-C rich in π electrons 60 The cyclic group can be i) a group T1G, ii) a fused cyclic group in which two or more groups T1G are fused together, iii) a group T3G, iv) a fused cyclic group in which two or more groups T3G are fused together, or v) a fused cyclic group in which at least one group T3G and at least one group T1G are fused together, for example, C3-C 60Carbocyclic groups, 1H-pyrrole groups, thiorrole groups, borocyclopentadienyl groups, 2H-pyrrole groups, 3H-pyrrole groups, thiophene groups, furan groups, indole groups, benzoindole groups, naphthoindole groups, isoindole groups, benzoisoindole groups, naphthoisoindole groups, benzothiorrole groups, benzothiophene groups, benzofuran groups, carbazole groups, dibenzothiorrole groups, dibenzothiophene groups, dibenzofuran groups, indole-carbazole groups, indole-carbazole groups, benzofuran-carbazole groups, benzothiophene-carbazole groups, benzothiorrole-carbazole groups, benzoindole-carbazole groups, benzocarbazole groups, benzonaphthofuran groups, benzonaphthophene groups, benzonaphthorrole groups, benzofuran-dibenzofuran groups, benzofuran-dibenzothiophene groups, benzothiophene-dibenzothiophene groups, etc.

[0396] C1-C containing nitrogen lacking π electrons 60 The cyclic group can be i) a group T4G, ii) a fused cyclic group in which two or more groups T4G are fused together, iii) a fused cyclic group in which at least one group T4G and at least one group T1G are fused together, iv) a fused cyclic group in which at least one group T4G and at least one group T3G are fused together, or v) a fused cyclic group in which at least one group T4G, at least one group T1G, and at least one group T3G are fused together, for example, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, oxadiazole group, thiazole group, isothiazole group, thiadiazole group, benzopyrazole group. Groups, including benzimidazole group, benzioxazole group, benziisooxazole group, benzithiazole group, benziisothiazole group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, benziquinoline group, benziisoquinoline group, quinoxaline group, benziquinoxaline group, quinazoline group, benziquinazoline group, phenanthrene group, cinnamoline group, phthalazine group, naphthidine group, imidazopyridine group, imidazopyrimidine group, imidazotriazine group, imidazopyrazine group, imidazopyridazine group, azacarbazole group, azafluorene group, azadibenzothiophene group, azadibenzothiophene group, azadibenzofuran group, etc.

[0397] The group T1G can be a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclobutene group, a cyclopentene group, a cyclopentadiene group, a cyclohexene group, a cyclohexadiene group, a cycloheptene group, adamantane group, norbornane (or bicyclo[2.2.1]heptane) group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group, or a phenyl group.

[0398] The group T2G can be a furan group, thiophene group, 1H-pyrrole group, thiorrole group, borocyclopentadiene group, 2H-pyrrole group, 3H-pyrrole group, imidazole group, pyrazole group, triazole group, tetraazole group, oxazole group, isoxazole group, oxadiazole group, thiazole group, isothiazole group, thiadiazole group, azathirrole group, azaboroxadiene group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, tetraazine group, pyrrolidinyl group, imidazolidinyl group, dihydropyrrole group, piperidine group, tetrahydropyridine group, dihydropyridine group, hexahydropyrimidine group, tetrahydropyrimidine group, dihydropyrimidine group, piperazine group, tetrahydropyrazine group, dihydropyrazine group, tetrahydropyridazine group, or dihydropyridazine group.

[0399] The group T3G can be a furan group, a thiophene group, a 1H-pyrrole group, a thiophene group, or a borocyclopentadiene group.

[0400] The group T4G can be a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetraazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azathirrole group, an azaboranecyclopentadiene group, a pyridine group, a pyrazine group, a pyridazine group, a triazine group, or a tetraazine group.

[0401] As used in this article, "cyclic group, C3-C" 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, π-electron-rich C3-C 60 Cyclic groups or C1-C atoms containing nitrogen lacking π electrons 60 "Cyclic group" refers to a group, monovalent group, or polyvalent group (e.g., divalent group, trivalent group, tetravalent group, etc.) fused with any cyclic group, depending on the structure of the formula associated with the use of the term. In embodiments, "phenyl group" can be a benzo[a] group, phenyl group, phenylene group, etc., which can be readily understood by those skilled in the art from the structure of a formula including "phenyl group".

[0402] Unit price C3-C 60 Carbocyclic groups and monovalent C1-C 60 Examples of heterocyclic groups are C3-C. 10 Cycloalkyl groups, C1-C 10 Heterocyclic alkyl groups, C3-C 10 cycloalkenyl groups, C1-C 10 Heterocyclic alkenyl groups, C6-C 60 aryl group, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups, and divalent C3-C 60Carbocyclic groups and divalent C1-C 60 Examples of heterocyclic groups are C3-C. 10 Cycloalkyl groups, C1-C 10 heterocyclic alkyl groups, C3-C 10 Cycloalkylene groups, C1-C 10 heterocyclic alkenyl groups, C6-C 60 arylene groups, C1-C 60 Hypoaryl groups, divalent non-aromatic fused polycyclic groups, and divalent non-aromatic fused heterocyclic groups.

[0403] As used in this article, the term "C1-C" 60 An "alkyl group" refers to a straight-chain or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms (e.g., 1 to 30, 1 to 20, 1 to 15, 1 to 10, or 1 to 5), and examples include methyl groups, ethyl groups, n-propyl groups, isopropyl groups, n-butyl groups, sec-butyl groups, isobutyl groups, tert-butyl groups, n-pentyl groups, tert-pentyl groups, neopentyl groups, isopentyl groups, and sec-pentyl groups. Groups, 3-pentyl group, secondary isopentyl group, n-hexyl group, isohexyl group, secondary hexyl group, tert-hexyl group, n-heptyl group, isoheptyl group, secondary hexyl group, tert-heptyl group, n-octyl group, isooctyl group, secondary octyl group, tert-octyl group, n-nonyl group, isononyl group, secondary nonyl group, tert-nonyl group, n-decyl group, isodecyl group, secondary decyl group, and tert-decyl group. As used herein, the term "C1-C" is similar to the terminology used in this document. 60 "alkylene group" refers to a group that has a corresponding C1-C2 group. 60 Alkyl groups are divalent groups in structure.

[0404] As used in this article, the term "C2-C" 60 "Alkenyl group" refers to the group located at C2-C. 60 An alkyl group is a monovalent hydrocarbon group having at least one carbon-carbon double bond at its middle or end, and examples of such groups are vinyl groups, propenyl groups, and butenyl groups. As used herein, the term "C2-C" is used... 60 "Ideinyl group" refers to a group that has a corresponding C2-C group. 60 The structure of an alkenyl group is a divalent group.

[0405] As used in this article, the term "C2-C" 60 "Alkyne group" refers to the group located at C2-C. 60 An alkyl group is a monovalent hydrocarbon group having at least one carbon-carbon triple bond at its middle or end, and examples include ethynyl and propynyl groups. As used herein, the term "C2-C" is used... 60 "Imyynyl group" refers to a group that has a corresponding C2-C group. 60The structure of an alkynyl group is a divalent group.

[0406] As used in this article, the term "C1-C" 60 "Alkoxy group" refers to the group consisting of -OA 101 (where A) 101 It is C1-C 60 Alkyl groups are monovalent groups, and examples of them include methoxy groups, ethoxy groups and isopropoxy groups.

[0407] As used in this article, the term "C3-C" 10 "Cycloalkyl group" refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and examples of such groups are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel alkyl (or bicyclic [2.2.1]heptyl), bicyclic [1.1.1]pentyl, bicyclic [2.1.1]hexyl, and bicyclic [2.2.2]octyl. As used herein, the term "C3-C" is also relevant. 10 "Cycloalkylene group" refers to a group that has a corresponding C3-C4 group. 10 A divalent group in the structure of a cycloalkyl group.

[0408] As used in this article, the term "C1-C" 10 "Heterocyclic alkyl group" refers to a monovalent cyclic group that further comprises at least one heteroatom other than a carbon atom (where the number of heteroatoms can be 1 to 5 or 1 to 3, e.g., 1, 2, 3, 4 or 5) as a cyclic atom and has 1 to 10 carbon atoms, and examples are 1,2,3,4-oxatriazole alkyl groups, tetrahydrofuranyl groups, and tetrahydrothiophenyl groups. The term "C1-C" as used herein is also relevant. 10 "Heterocyclic alkyl group" refers to a group that has a corresponding C1-C2 group. 10 A divalent group in the structure of a heterocyclic alkyl group.

[0409] The terminology used in this article is C3-C. 10 A cycloalkenyl group is a monovalent cyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and lacking aromaticity; examples include cyclopentenyl, cyclohexenyl, and cycloheptenyl groups. As used herein, the term "C3-C" is used in conjunction with this terminology. 10 "Iridyl group" refers to a group that has a corresponding C3-C... 10 The structure of a cycloalkenyl group is a divalent group.

[0410] As used in this article, the term "C1-C" 10A "heterocyclic alkenyl group" refers to a monovalent cyclic group having at least one heteroatom (the number of heteroatoms can be 1 to 5 or 1 to 3, for example 1, 2, 3, 4 or 5) other than a carbon atom as cyclic atoms, 1 to 10 carbon atoms, and at least one double bond (e.g., a carbon-carbon double bond) in its cyclic structure. C1-C 10 Examples of heterocyclic alkenyl groups include 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothiophenyl groups. As used herein, the term "C1-C..." 10 "Heterocyclic alkenyl group" refers to a group that has a corresponding C1-C... 10 The structure of a heterocyclic alkenyl group is a divalent group.

[0411] As used in this article, the term "C6-C" 60 "Aryl group" refers to a monovalent group having a carbocyclic aromatic system containing 6 to 60 carbon atoms (e.g., 6 to 30, 6 to 20, 6 to 15, 6 to 10, or 6 to 8), and as used herein by the term "C6-C". 60 "Aromatic group" refers to a divalent group in a carbocyclic aromatic system having 6 to 60 carbon atoms (e.g., 6 to 30, 6 to 20, 6 to 15, 6 to 10, or 6 to 8). C6-C 60 Examples of aryl groups include phenyl groups, pentanenyl groups, naphthyl groups, chamomile cycloyl groups, indoleyl groups, acenaphthenic groups, phenanthreneyl groups, anthraceneyl groups, fluoranthraceneyl groups, benzo[a]phenanthreneyl groups, and pyreneyl groups. Peryl group, peryl group, pentaphenyl group, heptalenyl group, tetraphenyl group, fusyl group, hexaphenyl group, pentaphenyl group, rutinyl group, keratyl group, and ovoidyl group. When C6-C 60 aryl groups and C6-C 60 When each of the aryl groups comprises two or more rings, the rings may be fused together.

[0412] As used in this article, the term "C1-C" 60 A "heteroaryl group" refers to a monovalent group in a heterocyclic aromatic system having at least one heteroatom (e.g., 1 to 15, 1 to 10, 1 to 5, or 1 to 3 heteroatoms) other than carbon atoms as cyclic atoms and 1 to 60 carbon atoms (e.g., 1 to 30, 1 to 20, 1 to 15, 1 to 10, or 1 to 5). The term "C1-C" is used herein. 60A "hybrid aryl group" refers to a divalent group in a heterocyclic aromatic system having at least one heteroatom (e.g., 1 to 15, 1 to 10, 1 to 5, or 1 to 3 heteroatoms) other than carbon atoms as cyclic atoms and 1 to 60 carbon atoms (e.g., 1 to 30, 1 to 20, 1 to 15, 1 to 10, or 1 to 5). C1-C 60 Examples of heteroaryl groups are pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, benzo[a]quinolinyl, isoquinolinyl, benzo[a]isoquinolinyl, quinoxalinyl, benzo[a]quinoxalinyl, quinazolinyl, benzo[a]quinazolinyl, phenanthrolinel, phthalazinyl, and naphthidyl. When C1-C 60 heteroaryl groups and C1-C 60 When each of the heteroaryl groups comprises two or more rings, the rings can be fused together.

[0413] As used herein, the term "monovalent nonaromatic fused polycyclic group" refers to a monovalent group (e.g., having 8 to 60 (e.g., 8 to 30, 8 to 20, 8 to 15, or 8 to 10) carbon atoms) having two or more rings fused together, having only carbon atoms as cyclic atoms, and lacking aromaticity throughout its molecular structure. Examples of monovalent nonaromatic fused polycyclic groups are indenyl, fluorenyl, spiro-difluorenyl, benzo[a]fluorenyl, indo[a]phenanthrene, and indo[a]anthrayl groups. As used herein, the term "divalent nonaromatic fused polycyclic group" refers to a divalent group having a structure corresponding to that of a monovalent nonaromatic fused polycyclic group.

[0414] As used herein, the term "monovalent nonaromatic fused heterocyclic group" refers to a monovalent group (e.g., having 1 to 60 (e.g., 1 to 30, 1 to 20, 1 to 15, 1 to 10, or 1 to 5) carbon atoms) having two or more rings fused together, at least one heteroatom other than carbon atoms (e.g., 1 to 15, 1 to 10, 1 to 5, or 1 to 3 heteroatoms) as cyclic atoms and being nonaromatic throughout its molecular structure. Examples of monovalent non-aromatic fused heterocyclic groups include pyrrolyl groups, thiophenyl groups, furanyl groups, indole groups, benzoindole groups, naphthoindole groups, isoindole groups, benzoisoindole groups, naphthoisoindole groups, benzothiolyl groups, benzothiphenyl groups, benzofuranyl groups, carbazole groups, dibenzothiolyl groups, dibenzothiphenyl groups, dibenzofuranyl groups, azacarbazoleyl groups, azafluorenyl groups, azadibenzothiolyl groups, azadibenzothiphenyl groups, azadibenzofuranyl groups, pyrazolyl groups, imidazoleyl groups, triazoleyl groups, tetraazoleyl groups, oxazolyl groups, isoxazolyl groups, thiolyl groups, isothiazolyl groups, and oxadiazoleyl groups. Thiadiazolyl group, benzopyrazolyl group, benzoimidazolyl group, benzooxazolyl group, benzothiazolyl group, benzooxadiazolyl group, benzothiadiazolyl group, imidazopyridyl group, imidazopyrimidine group, imidazotriazinyl group, imidazopyrazinyl group, imidazopyridazinyl group, indolecarbazoyl group, indolocarbazoyl group, benzofuranocarbazoyl group, benzothiophenocarbazoyl group, benzothiophenocarbazoyl group, benzoindolocarbazoyl group, benzocarbazoyl group, benzonaphthiophenyl group, benzonaphthiophenyl group, benzofuranodibenzofuranyl group, benzofuranodibenzothiophenyl group and benzothiophenodibenzothiophenyl group. As used in this article, the term "divalent nonaromatic fused heterocyclic group" refers to a divalent group having a structure corresponding to a monovalent nonaromatic fused heterocyclic group.

[0415] As used in this article, the term "C6-C" 60 "Aryloxy group" indicates -OA 102 (where A) 102 It is C6-C 60 (aryl group), and as used herein by the term "C6-C" 60 "Aryl thio group" indicates -SA 103 (where A) 103 It is C6-C 60 (aryl group).

[0416] The term "C7-C" used in this article 60 "Arylalkyl group" refers to -A 104 A105 (where A) 104 It can be C1-C 54 alkylene groups, and A 105 It can be C6-C 59 (aryl group), and the term C2-C used herein. 60 "Heteroarylalkyl group" refers to -A 106 A 107 (where A) 106 It can be C1-C 59 alkylene groups, and A 107 It can be C1-C 59 (Heteroaryl groups).

[0417] As used in this article, the term "R" 10a " refers to:

[0418] Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group or nitro group;

[0419] Each of the following is an unsubstituted or replaced group: -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 aryloxy group, C6-C 60 aryl thioyl groups, -Si(Q) 11 (Q) 12 (Q) 13 -N(Q) 11 (Q) 12 -B(Q) 11 (Q) 12 -C(=O)(Q) 11 -S(=O)2(Q) 11 -P(=O)(Q) 11 (Q) 12 C1-C substituted by (or any combination thereof) 60 Alkyl groups, C2-C 60 alkenyl groups, C2-C 60 alkynyl group or C1-C 60 Alkoxy group;

[0420] Each of the following groups is unsubstituted or replaced: -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 60 Alkyl groups, C2-C 60 alkenyl groups, C2-C 60 alkynyl group, C1-C 60 alkoxy group, C3-C 60Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 aryloxy group, C6-C 60 aryl thioyl groups, -Si(Q) 21 (Q) 22 (Q) 23 -N(Q) 21 (Q) 22 -B(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q) 21 -P(=O)(Q) 21 (Q) 22 C3-C substituted by any combination thereof 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 aryloxy group, or C6-C 60 aryl thioyl group; or

[0421] -Si(Q 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 ) or -P(=O)(Q 31 (Q) 32 ),

[0422] The groups Q1 to Q3 and Q used in this article 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 These can be, independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl group; cyano group; nitro group; C1-C 60 Alkyl group; C2-C 60 alkenyl group; C2-C 60 alkynyl group; C1-C 60 Alkoxy groups; each unsubstituted or replaced by deuterium, -F, cyano groups, C1-C 60 Alkyl groups, C1-C 60 C3-C substituted with alkoxy groups, phenyl groups, biphenyl groups, or any combination thereof 60 Carbocyclic groups or C1-C 60Heterocyclic groups.

[0423] As used in this article, the term "heteroatom" refers to any atom other than a carbon atom. Examples of heteroatoms are O, S, N, P, Si, B, Ge, Se, and any combination thereof.

[0424] The term "third-row transition metals" used in this article includes hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), and gold (Au).

[0425] As used herein, the term "Ph" refers to a phenyl group, the term "Me" refers to a methyl group, the term "Et" refers to an ethyl group, and the term "tert-Bu" or "Bu" refers to a tert-Bu. t "" refers to the tert-butyl group, and the term "OMe" refers to the methyl methacrylate group.

[0426] As used in this article, the term "biphenyl group" refers to a "phenyl group substituted with a phenyl group." In other words, a "biphenyl group" is a group with a C6-C6 bond. 60 The aryl group is a substituted phenyl group.

[0427] As used in this article, the term "terphenyl group" refers to a "phenyl group substituted with a biphenyl group." In other words, a "terphenyl group" is a phenyl group with a C6-C substituted group. 60 C6-C substituted with aryl group 60 The aryl group is a substituted phenyl group.

[0428] The abbreviation "eq." means "molar equivalent".

[0429] Unless otherwise defined, as used herein, the symbols * and *' each refer to the binding site with an adjacent atom in the corresponding formula or part.

[0430] The statement "use B instead of A" means using the same molar equivalent of B to replace the same molar equivalent of A.

[0431] Example

[0432] Synthesis Example 1: Synthesis of Compound 1

[0433]

[0434] Synthesis of intermediate compound 1-a

[0435] Under an argon atmosphere, 5-chloro-N1,N1,N3,N3-tetraphenylphenyl-1,3-diamine (50 g, 112 mmol), 2-(pyridin-2-yl)aniline (19 g, 112 mmol), sodium tert-butoxide (32 g, 336 mmol), tri-tert-butylphosphine (5 mL, 11.2 mmol), and tris(dibenzylacetone)dipalladium(O)Pd2dba3 (5.12 g, 5.6 mmol) were added to a 2 L flask and dissolved in 1 L of o-xylene. The reaction solution was stirred at 140 °C for 12 h. After cooling, water (1 L) and ethyl acetate (300 mL) were added to extract and collect the organic layer, which was then dried and filtered using magnesium sulfate (MgSO4). The filtered solution was placed under reduced pressure to remove the solvent, and the resulting solid was purified and separated by column chromatography using silica gel and dichloromethane (CH2Cl2) and hexane as developing solvents to obtain intermediate compound 1-a (white solid, 41 g, 64%). The obtained white solid was identified as intermediate compound 1-a by ESI-LCMS.

[0436] ESI-LCMS: [M] + :C 41 H 32 N4.580.2612.

[0437] Synthesis of intermediate compound 1-b

[0438] Under an argon atmosphere, compound 1-a (40 g, 69 mmol), 3-bromo-iodobenzene (19.5 g, 69 mmol), sodium tert-butoxide (20 g, 207 mmol), 2,2'-bis(diphenylphosphine)-1,1'-binaphthyl (BINAP, 4.3 g in 7.0 mmol), and Pd2dba3 (3.1 g, 3.5 mmol) were added to a 2 L flask and dissolved in 700 mL of toluene. The reaction solution was stirred at 100 °C for 12 h. After cooling, water (1 L) and ethyl acetate (300 mL) were added to extract and collect the organic layer, which was dried over MgSO4 and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain intermediate compound 1-b (white solid, 36 g, 72%). The obtained white solid was identified as intermediate compound 1-b by ESI-LCMS.

[0439] ESI-LCMS: [M] + :C 47 H 35 N4Br.734.2020.

[0440] Synthesis of intermediate compound 1-c

[0441] Under an argon atmosphere, 5-chloro-N1,N1,N3,N3-tetraphenylphenyl-1,3-diamine (50 g, 112 mmol), aniline (10.7 g, 112 mmol), sodium tert-butoxide (32 g, 336 mmol), tri-tert-butylphosphine (5 mL, 11.2 mmol), and Pd2dba3 (3.1 g, 3.5 mmol) were added to a 2 L flask and dissolved in 1 L of o-xylene. The reaction solution was stirred at 140 °C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added to extract and collect the organic layer, which was dried over MgSO4 and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain intermediate compound 1-c (white solid, 38 g, 68 wt.%). The obtained white solid was identified as intermediate compound 1-c by ESI-LCMS.

[0442] ESI-LCMS: [M] + :C 36 H 29 N3.503.2412.

[0443] Synthesis of intermediate compound 1-d

[0444] Under an argon atmosphere, compound 1-b (30 g, 41 mmol), compound 1-c (20.5 g, 41 mmol), sodium tert-butoxide (12 g, 123 mmol), tri-tert-butylphosphine (2.0 mL, 4.2 mmol), and Pd₂dba₃ (1.9 g, 2.1 mmol) were added to a 2 L flask and dissolved in 400 mL of toluene. The reaction solution was stirred at 100 °C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added to extract and collect the organic layer, which was then dried over MgSO₄ and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH₂Cl₂ and hexane as developing solvents to obtain intermediate compound 1-d (white solid, 29 g, 62%). The obtained white solid was identified as intermediate compound 1-d by ESI-LCMS.

[0445] ESI-LCMS: [M] + :C 83 H 63 N7.1157.5437.

[0446] Synthesis of Compound 1

[0447] Compound 1-d (29 g, 25 mmol) was added to a 1 L flask under an argon atmosphere, dissolved in 500 mL of o-dichlorobenzene, and cooled to 0 °C in an ice-water container. Boron tribromide (5 equivalents) was slowly added dropwise to the reaction solution, the temperature was slowly increased to room temperature, and the reaction solution was stirred for 20 min. The reaction solution was heated to 180 °C and stirred for 12 h. After cooling, triethylamine (5 mL) was slowly added dropwise to terminate the reaction, and the solvent was removed under reduced pressure. The obtained solid was washed with methanol (MeOH) and purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain compound 1 (yellow solid, 2.6 g, 9%). The obtained yellow solid was analyzed by electrospray ionization-liquid chromatography-mass spectrometry (ESI-LCMS) and proton nuclear magnetic resonance (PMR). 1 Identified as compound 1 by H-NMR.

[0448] ESI-LCMS: [M] + :C 83 H 57 B2N7.1173.4936.

[0449] 1 H-NMR(400MHz, CDCl3):10.46(s,1H),9.94(d,2H),9.31(d,1H),8.37(d,1H),8 .20(d,2H),7.39(m,3H),7.24(m,18H),7.03(m,27H),6.83(s,1H),6.49(m,4H).

[0450] Synthesis Example 2: Synthesis of Compound 17

[0451]

[0452] Synthesis of intermediate compound 17-a

[0453] Under an argon atmosphere, 2,6-dibromoaniline (30 g, 120 mmol), (6-(tert-butyl)pyridin-2-yl)boronic acid (45 g, 250 mmol), potassium carbonate (50 g, 360 mmol), and tetra(triphenylphosphine)palladium(O) (4.1 g of Pd(PPh3)4, 3.6 mmol) were added to a 2 L flask and dissolved in 1 L of toluene and 250 mL of water. The reaction solution was stirred at 120 °C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added to extract and collect the organic layer, which was dried over MgSO4 and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to give intermediate compound 17-a (white solid, 24 g, 57%). The obtained white solid was analyzed by ESI-LCMS and... 1 H-NMR identified it as compound 17-a.

[0454] ESI-LCMS: [M] + :C 24 H 29 N3.359.2424.

[0455] 1 H-NMR (400MHz, CDCl3): 9.30 (d, 2H), 8.30 (s, 2H), 7.73 (d, 2H), 7.29 (d, 2H), 7.19 (t, 1H), 1.35 (s, 18H).

[0456] Synthesis of intermediate compound 17-b

[0457] Under an argon atmosphere, 5-chloro-N1,N1,N3,N3-tetraphenylphenyl-1,3-diamine (50 g, 112 mmol), compound 17-a (40 g, 112 mmol), sodium tert-butoxide (32 g, 336 mmol), tri-tert-butylphosphine (5.1 mL, 11.2 mmol), and Pd2dba3 (5.1 g, 5.6 mmol) were added to a 2 L flask and dissolved in 1 L of o-xylene. The reaction solution was stirred at 140 °C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added to extract and collect the organic layer, which was dried over MgSO4 and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain intermediate compound 17-b (white solid, 36 g, 42%). The obtained white solid was identified by ESI-LCMS as intermediate compound 17-b.

[0458] ESI-LCMS: [M] + :C 54 H 51 N5.769.4049.

[0459] Synthesis of intermediate compound 17-c

[0460] Under an argon atmosphere, compound 17-b (35 g, 45 mmol), 3-bromo-iodobenzene (63 g, 227 mmol), sodium tert-butoxide (13 g, 135 mmol), tri-tert-butylphosphine (4.0 mL, 4.6 mmol), and Pd₂dba₃ (2.0 g, 2.3 mmol) were added to a 2 L flask and dissolved in 450 mL of o-xylene. The reaction solution was stirred at 160 °C for 36 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added to extract and collect the organic layer, which was dried over MgSO₄ and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH₂Cl₂ and hexane as developing solvents to obtain intermediate compound 17-c (white solid, 21 g, 51%). The obtained white solid was identified as intermediate compound 17-c by ESI-LCMS.

[0461] ESI-LCMS: [M] + :C 60 H 54 N5Br.923.3119.

[0462] Synthesis of intermediate compound 17-d

[0463] Under an argon atmosphere, compound 17-c (20 g, 22 mmol), compound 1-c (11 g, 22 mmol), sodium tert-butoxide (6.3 g, 66 mmol), tri-tert-butylphosphine (1.0 mL, 2.2 mmol), and Pd₂dba₃ (1.0 g, 1.1 mmol) were added to a 2 L flask and dissolved in 220 mL of toluene. The reaction solution was stirred at 100 °C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added to extract and collect the organic layer, which was then dried over MgSO₄ and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH₂Cl₂ and hexane as developing solvents to obtain intermediate compound 17-d (white solid, 21.6 g, 73%). The obtained white solid was identified as intermediate compound 17-d by ESI-LCMS.

[0464] ESI-LCMS: [M]+ :C 96 H 82 N8.1346.6071.

[0465] Synthesis of Compound 17

[0466] Compound 17-d (20 g, 14 mmol) was added to a 1 L flask under an argon atmosphere, dissolved in 500 mL of o-dichlorobenzene, and cooled to 0 °C in an ice-water container. Boron tribromide (5 equivalents) was slowly added dropwise to the reaction solution, the temperature was slowly increased to room temperature, and the reaction solution was stirred for 20 min. The reaction solution was heated to approximately 180 °C and stirred for 12 h. After cooling, triethylamine (5 mL) was slowly added dropwise to terminate the reaction, and the solvent was removed under reduced pressure. The obtained solid was washed with MeOH and purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain compound 17 (yellow solid, 1.4 g, 7%). The obtained yellow solid was analyzed by ESI-LCMS and... 1 H-NMR identified it as compound 17.

[0467] ESI-LCMS: [M] + :C 96 H 76 B2N8.1362.6617.

[0468] 1 H-NMR(400MHz, CDCl3):10.52(s,1H),9.83(d,2H),9.41(d,2H),7.39(t,1H),7.31(m, 2H),7.24(m,16H),7.08(m,21H),7.01(t,2H),6.83(s,1H),6.77(d,2H),6.49(m,4H).

[0469] Synthesis Example 3: Synthesis of Compound 31

[0470]

[0471] Synthesis of intermediate compound 31-a

[0472] Under an argon atmosphere, 3-bromo(1,1'-biphenyl)-2-amine (30 g, 120 mmol), (5-(tert-butyl)pyridin-2-yl)boronic acid (45 g, 250 mmol), potassium carbonate (50 g, 360 mmol), and Pd(PPh3)4 (4.1 g, 3.6 mmol) were added to a 2 L flask and dissolved in 1 L of toluene and 250 mL of water. The reaction solution was stirred at 120 °C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added to extract and collect the organic layer, which was dried over MgSO4 and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain intermediate compound 31-a (white solid, 23 g, 77%). The obtained white solid was analyzed by ESI-LCMS and... 1 H-NMR identified it as compound 31-a.

[0473] ESI-LCMS: [M] + :C 17 H 14 N2.246.1238.

[0474] 1 H-NMR (400MHz, CDCl3): 9.30 (d, 1H), 8.37 (d, 1H), 8.09 (d, 1H), 7.42 (m, 4H), 7.08 (m, 4H), 6.90 (t, 1H).

[0475] Synthesis of intermediate compound 31-b

[0476] Under an argon atmosphere, compound 31-a (30 g, 121 mmol), 5-chloro-N1,N1,N3,N3-tetraphenylphenyl-1,3-diamine (54 g, 121 mmol), sodium tert-butoxide (35 g, 363 mmol), tri-tert-butylphosphine (5.5 mL, 12 mmol), and Pd2dba3 (5.5 g, 6.0 mmol) were added to a 2 L flask and dissolved in 1 L of o-xylene. The reaction solution was stirred at 140 °C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added to extract and collect the organic layer, which was dried over MgSO4 and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain intermediate compound 31-b (white solid, 43 g, 58%). The obtained white solid was identified by ESI-LCMS as intermediate compound 31-b.

[0477] ESI-LCMS: [M] + :C 47 H 36 N4.656.2912.

[0478] Synthesis of intermediate compound 31-c

[0479] Under an argon atmosphere, compound 31-b (40 g, 60 mmol), 3-bromo-iodobenzene (85 g, 300 mmol), sodium tert-butoxide (58 g, 600 mmol), tri-tert-butylphosphine (2.7 mL, 6 mmol), and Pd₂dba₃ (2.7 g, 3.0 mmol) were added to a 2 L flask and dissolved in 500 mL of o-xylene. The reaction solution was stirred at 140 °C for 36 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added to extract and collect the organic layer, which was dried over MgSO₄ and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH₂Cl₂ and hexane as developing solvents to obtain intermediate compound 31-c (white solid, 30 g, 62%). The obtained white solid was identified as intermediate compound 31-c by ESI-LCMS.

[0480] ESI-LCMS: [M] + :C 53 H 39 N4Br.810.2492.

[0481] Synthesis of intermediate compound 31-d

[0482] Under an argon atmosphere, Mg (0.88 g, 37 mmol) was added to a 1 L flask and dissolved in 150 mL of anhydrous THF. A catalytic amount of I₂ (50 mg) was added, and the mixture was cooled when the color changed from black to gray upon heating to 60 °C. The reaction solution was cooled to 0 °C using an ice-water container, and compound 31-c (30 g, 37 mmol) was added and stirred for 30 min. The reaction solution was then heated to 80 °C and stirred for 30 min, and selenium (3 equivalents) was added, while stirring at the same temperature for 2 h. After cooling, the reaction solution was poured into 1 L of ice water, and 1 N HCl was added dropwise to adjust the pH. Ethyl acetate (300 mL) was added for extraction and collection of the organic layer, which was then dried and filtered using MgSO₄. The filtered solution was placed under reduced pressure to remove the solvent, and the resulting solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvents to obtain intermediate compound 31-d (white solid, 11.4 g, 38%). The obtained white solid was identified as intermediate compound 31-d by ESI-LCMS.

[0483] ESI-LCMS: [M] + :C 53 H 40 N4Se.812.1299.

[0484] Synthesis of intermediate compound 31-e

[0485] Under an argon atmosphere, compound 31-d (11 g, 13 mmol), 1,3-dibromo-5-iodobenzene (4.9 g, 13 mmol), CuI (2.5 g, 13 mmol), 2-pyridinecarboxylic acid (1.6 g, 13 mmol), and K3PO4 (14 g, 65 mmol) were added to a 1 L flask and dissolved in 150 mL of dimethylformamide (DMF). The reaction solution was stirred at 160 °C for 12 hours, poured into diatomaceous earth (sold under the trade name CELITE by Imerys Minerals California, Inc., San Jose, California, hereinafter “diatomaceous earth”), and filtered. Ethyl acetate (300 mL) was added to the mixture for extraction and collection of the organic layer, which was then dried over MgSO4 and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvents to obtain intermediate compound 31-e (white solid, 8.4 g, 62%). The obtained white solid was identified as intermediate compound 31-e by ESI-LCMS.

[0486] ESI-LCMS: [M] + :C 59 H 42 N4SeBr2.1044.0917.

[0487] Synthesis of intermediate compound 31-f

[0488] Under an argon atmosphere, compound 31-e (8 g, 7.6 mmol), N-phenyl-2-(pyridin-2-yl)aniline (3.7 g, 15 mmol), sodium tert-butoxide (2.2 g, 23 mmol), tri-tert-butylphosphine (0.4 mL, 6.8 mmol), and Pd2dba3 (0.34 g, 3.4 mmol) were added to a 2 L flask and dissolved in 100 mL of toluene. The reaction solution was stirred at 140 °C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added to extract and collect the organic layer, which was dried over MgSO4 and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain intermediate compound 31-f (white solid, 7.5 g, 72%). The obtained white solid was identified as intermediate compound 31-f by ESI-LCMS.

[0489] ESI-LCMS: [M] + :C 93 H 68 N8Se.1376.4669.

[0490] Synthesis of Compound 31

[0491] Compound 31-f (7.5 g, 5.4 mmol) was added to a 1 L flask under an argon atmosphere, dissolved in 200 mL of o-dichlorobenzene, and cooled to 0 °C in an ice-water container. Boron tribromide (5 equivalents) was slowly added dropwise to the reaction solution, the temperature was slowly increased to room temperature, and the reaction solution was stirred for 20 min. The reaction solution was heated to 180 °C and stirred for 12 h. After cooling, triethylamine (5 mL) was slowly added dropwise to terminate the reaction, and the solvent was removed under reduced pressure. The obtained solid was washed with MeOH and purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain compound 31 (yellow solid, 0.8 g, 11%). The obtained yellow solid was analyzed by ESI-LCMS and... 1 H-NMR identified it as compound 31.

[0492] ESI-LCMS: [M] + :C 93 H62 B2N8Se.1395.4434.

[0493] 1 H-NMR(400MHz, CDCl3):10.26(s,1H),9.65(d,2H),9.41(d,2H),9.31(d,2H),8.37(d,3H),8. 20(m,1H),7.39(m,10H),7.24(m,12H),7.08(m,24H),6.77(s,1H),7.01(t,2H),6.49(s,2H).

[0494] Synthesis Example 4: Synthesis of Compound 37

[0495]

[0496] Synthesis of intermediate compound 37-a

[0497] Under an argon atmosphere, 5-fluoro-N1,N1,N3,N3-tetraphenylbenzene-1,3-diamine (50 g, 116 mmol), resorcinol (6.4 g, 58 mmol), and potassium hydroxide (KOH) (6.5 g, 116 mmol) were added to a 2 L flask and dissolved in 1 L of dimethyl sulfoxide (DMSO). The reaction solution was stirred at 180 °C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added to extract and collect the organic layer, which was then dried over MgSO4 and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain intermediate compound 37-a (white solid, 34 g, 64%). The obtained white solid was identified as intermediate compound 37-a by ESI-LCMS.

[0498] ESI-LCMS: [M] + :C 66 H 50 N4O2.930.3912.

[0499] Synthesis of intermediate compound 37-b

[0500] Compound 37-a (30 g, 32 mmol) was added to a 1 L flask under an argon atmosphere and dissolved in 300 mL of anhydrous oxacyclopentane (THF). After cooling to -78 °C, n-butyllithium (n-BuLi) (1.2 equivalents) was slowly added over 30 minutes. The reaction solution was then heated to room temperature and stirred for 2 hours, cooled again to -78 °C, and trimethyl borate (1.5 equivalents) was added, followed by stirring at room temperature for 12 hours. The reaction was terminated by adding 300 mL of 0.1 N hydrochloric acid (HCl), and ethyl acetate (300 mL) was added to collect the organic layer. The reaction solution was dried over MgSO4 and filtered. The solvent was removed from the filtered solution under reduced pressure, and the obtained solid was recrystallized from hexane to give intermediate compound 37-b (white solid, 16 g, 55%). The obtained white solid was identified as intermediate compound 37-b by ESI-LCMS.

[0501] ESI-LCMS: [M] + :C 66 H 51 N4O4B.974.4001.

[0502] Synthesis of intermediate compound 37-c

[0503] Under an argon atmosphere, compound 37-b (16 g, 16 mmol), 2,2'-(2-bromo-1,3-phenylene)dipyridine (5.1 g, 16 mmol), potassium carbonate (6.6 g, 48 mmol), and Pd(PPh3)4 (0.55 g, 0.5 mmol) were added to a 1 L flask and dissolved in 150 mL of toluene and 50 mL of water. The reaction solution was stirred at 120 °C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added to extract and collect the organic layer, which was dried over MgSO4 and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain intermediate compound 37-c (white solid, 14 g, 74%). The obtained white solid was identified as intermediate compound 37-c by ESI-LCMS.

[0504] ESI-LCMS: [M] + :C 82 H 60 N6O2.1160.4884.

[0505] Synthesis of Compound 37

[0506] Compound 37-c (14 g, 12 mmol) was added to a 1 L flask under an argon atmosphere, dissolved in 300 mL of o-dichlorobenzene, and cooled to 0 °C in an ice-water container. Boron tribromide (5 equivalents) was slowly added dropwise to the reaction solution, the temperature was slowly increased to room temperature, and the reaction solution was stirred for 20 min. The reaction solution was heated to 180 °C and stirred for 12 h. After cooling, triethylamine (5 mL) was slowly added dropwise to terminate the reaction, and the solvent was removed under reduced pressure. The obtained solid was washed with MeOH and purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain compound 37 (yellow solid, 1.7 g, 12%). The obtained yellow solid was analyzed by ESI-LCMS and... 1 H-NMR identified it as compound 37.

[0507] ESI-LCMS: [M] + :C 82 H 54 B2N6O2.1176.0157.

[0508] 1 H-NMR(400MHz, CDCl3):10.31(s,1H),9.42(d,2H),8.45(d,2H),8.37(d,2H),7.83(t, 1H),7.38(m,4H),7.24(m,12H),7.08(m,12H),6.90(m,9H),6.83(t,1H),6.52(d,4H).

[0509] Synthesis Example 5: Synthesis of Compound 41

[0510]

[0511] Synthesis of intermediate compound 41-a

[0512] Under an argon atmosphere, 3,5-dibromo-fluorobenzene (50 g, 197 mmol), resorcinol (10 g, 90 mmol), and KOH (11.7 g, 180 mmol) were added to a 2 L flask and dissolved in 1 L of DMSO. The reaction solution was stirred at 180 °C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added to extract and collect the organic layer, which was then dried over MgSO4 and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvents to obtain intermediate compound 41-a (white solid, 22 g, 43%). The obtained white solid was analyzed by ESI-LCMS and... 1H-NMR identified it as intermediate compound 41-a.

[0513] ESI-LCMS: [M] + :C 18 H 10 Br4O2.573.7473.

[0514] 1 H-NMR (400MHz, CDCl3): 7.70 (s, 2H), 7.28 (m, 5H), 7.00 (d, 2H), 6.52 (s, 1H).

[0515] Synthesis of intermediate compound 41-b

[0516] Under an argon atmosphere, compound 41-a (20 g, 35 mmol), N-phenyl-2-(pyridin-2-yl)aniline (51 g, 207 mmol), sodium tert-butoxide (10 g, 105 mmol), tri-tert-butylphosphine (0.4 mL, 7.0 mmol), and Pd2dba3 (0.34 g, 3.5 mmol) were added to a 2 L flask and dissolved in 500 mL of toluene. The reaction solution was stirred at 110 °C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added to extract and collect the organic layer, which was dried over MgSO4 and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain intermediate compound 41-b (white solid, 22.5 g, 52%). The obtained white solid was identified as intermediate compound 41-b by ESI-LCMS.

[0517] ESI-LCMS: [M] + :C 86 H 62 N8O2.1238.5001.

[0518] Synthesis of Compound 41

[0519] Compound 41-b (20 g, 16 mmol) was added to a 1 L flask under an argon atmosphere, dissolved in 500 mL of o-dichlorobenzene, and cooled to 0 °C in an ice-water container. Boron tribromide (5 equivalents) was slowly added dropwise to the reaction solution, the temperature was slowly increased to room temperature, and the reaction solution was stirred for 20 min. The reaction solution was heated to 180 °C and stirred for 12 h. After cooling, triethylamine (5 mL) was slowly added dropwise to terminate the reaction, and the solvent was removed under reduced pressure. The obtained solid was washed with MeOH and purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain compound 41 (yellow solid, 1.6 g, 8%). The obtained yellow solid was analyzed by ESI-LCMS and... 1 H-NMR identified it as compound 41.

[0520] ESI-LCMS: [M] + :C 86 H 56 B2N8O2.1254.4644.

[0521] 1 H-NMR (400MHz, CDCl3): 10.78(s,1H),9.87(d,2H),9.31(d,4H),8.37(d,4H),7.39(m,12H),7.21(m,8H),7.04(m,24H),6.65(s,1H),6.50(d,4H).

[0522] Synthesis Example 6: Synthesis of Compound 50

[0523]

[0524] Synthesis of intermediate compound 50-a

[0525] Under an argon atmosphere, 3,5-dibromo-fluorobenzene (23 g, 90 mmol), phenol (8.5 g, 90 mmol), and KOH (11.7 g, 180 mmol) were added to a 2 L flask and dissolved in 1 L of DMSO. The reaction solution was stirred at 180 °C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added to extract and collect the organic layer, which was then dried over MgSO4 and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain intermediate compound 50-a (white solid, 22.6 g, 77%). The obtained white solid was analyzed by ESI-LCMS and... 1 H-NMR identified it as intermediate compound 50-a.

[0526] ESI-LCMS: [M] + :C 12 H8Br2O.325.8924.

[0527] Synthesis of intermediate compound 50-b

[0528] Under an argon atmosphere, 2,6-dibromoaniline (30 g, 120 mmol), 2-pyridineboronic acid (29 g, 240 mmol), potassium carbonate (50 g, 360 mmol), and Pd(PPh3)4 (4.1 g, 3.6 mmol) were added to a 2 L flask and dissolved in 1 L of toluene and 250 mL of water. The reaction solution was stirred at 120 °C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added to extract and collect the organic layer, which was dried over MgSO4 and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain intermediate compound 50-b (white solid, 24 g, 81%). The obtained white solid was identified as intermediate compound 50-b by ESI-LCMS.

[0529] ESI-LCMS: [M] + :C 16 H 13 N3.247.1114.

[0530] Synthesis of intermediate compound 50-c

[0531] Under an argon atmosphere, compounds 50-a (26 g, 80 mmol), 50-b (20 g, 80 mmol), sodium tert-butoxide (23 g, 240 mmol), tri-tert-butylphosphine (3.6 mL, 8.0 mmol), and Pd₂dba₃ (3.6 g, 4 mmol) were added to a 2 L flask and dissolved in 800 mL of toluene. The reaction solution was stirred at 110 °C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added to extract and collect the organic layer, which was then dried over MgSO₄ and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH₂Cl₂ and hexane as developing solvents to obtain intermediate compound 50-c (white solid, 22.4 g, 67%). The obtained white solid was identified as intermediate compound 50-c by ESI-LCMS.

[0532] ESI-LCMS: [M] + :C22 H 16 N3OBr.417.0443.

[0533] Synthesis of intermediate compound 50-d

[0534] Under an argon atmosphere, compound 50-c (20 g, 48 mmol), phenyl-1,3-dithiophenol (3.4 g, 24 mmol), cuprous iodide (CuI) (4.5 g, 24 mmol), 2-pyridinecarboxylic acid (3 g, 24 mmol), and K3PO4 (17 g, 72 mmol) were added to a 1 L flask and dissolved in 500 mL of DMF. The reaction solution was stirred at 160 °C for 12 hours, poured into diatomaceous earth, and filtered. Ethyl acetate (300 mL) was added to the solution for extraction and collection of the organic layer, which was dried over MgSO4 and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvents to obtain intermediate compound 50-d (white solid, 15 g, 58%). The obtained white solid was identified as intermediate compound 50-d by ESI-LCMS.

[0535] ESI-LCMS: [M] + :C 74 H 52 N6S2O2.1120.3636.

[0536] Synthesis of Compound 50

[0537] Compound 50-d (20 g, 13 mmol) was added to a 1 L flask under an argon atmosphere, dissolved in 500 mL of o-dichlorobenzene, and cooled to 0 °C in an ice-water container. Boron tribromide (5 equivalents) was slowly added dropwise to the reaction solution, the temperature was slowly increased to room temperature, and the reaction solution was stirred for 20 min. The reaction solution was heated to 180 °C and stirred for 12 h. After cooling, triethylamine (5 mL) was slowly added dropwise to terminate the reaction, and the solvent was removed under reduced pressure. The obtained solid was washed with MeOH and purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain compound 50 (yellow solid, 0.9 g, 6%). The obtained yellow solid was analyzed by ESI-LCMS and... 1 H-NMR identified it as compound 50.

[0538] ESI-LCMS: [M] + :C 74 H 46 B2N6O2S2.1136.3336.

[0539] 1 H-NMR (400MHz, CDCl3): 10.56(s,1H),9.76(d,2H),9.41(d,4H),8.37(d,4H),7.41(m,6H),7.27(m,8H),7.12(m,14H),6.88(s,2H).

[0540] Synthesis Example 7: Synthesis of Compound 55

[0541]

[0542] Synthesis of intermediate compound 55-a

[0543] Under an argon atmosphere, [1,1':3',1”-terphenyl]-2'-amine (30 g, 122 mmol), 5-chloro-N1,N1,N3,N3-tetraphenylphenyl-1,3-diamine (58 g, 122 mmol), sodium tert-butoxide (35 g, 363 mmol), tri-tert-butylphosphine (5.5 mL, 12 mmol), and Pd2dba3 (5.5 g, 6.0 mmol) were added to a 2 L flask and dissolved in 1 L of o-xylene. The reaction solution was stirred at 140 °C for 1 minute. After 2 hours of cooling, water (1 L) and ethyl acetate (300 ml) were added to extract and collect the organic layer, which was then dried over MgSO4 and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain intermediate compound 55-a (white solid, 44.8 g, 66%). The obtained white solid was identified as intermediate compound 55-a by ESI-LCMS.

[0544] ESI-LCMS: [M] + :C 48 H 37 N3.655.3001.

[0545] Synthesis of intermediate compound 55-b

[0546] Under an argon atmosphere, compound 55-a (40 g, 61 mmol), 3-bromo-iodobenzene (170 g, 610 mmol), sodium tert-butoxide (17.5 g, 183 mmol), tri-tert-butylphosphine (2.8 mL, 6.1 mmol), and Pd₂dba₃ (2.8 g, 3.1 mmol) were added to a 2 L flask and dissolved in 200 mL of o-xylene. The reaction solution was stirred at 140 °C for 36 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added to extract and collect the organic layer, which was dried over MgSO₄ and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH₂Cl₂ and hexane as developing solvents to obtain intermediate compound 55-b (white solid, 22 g, 45%). The obtained white solid was identified as intermediate compound 55-b by ESI-LCMS.

[0547] ESI-LCMS: [M] + :C 54 H 40 N3Br.809.2412.

[0548] Synthesis of intermediate compound 55-c

[0549] Under an argon atmosphere, compound 55-b (22 g, 27 mmol), 1,3,5-dichlorobenzylthiophenol (4.9 g, 27 mmol), CuI (5.1 g, 27 mmol), 2-pyridinecarboxylic acid (3.3 g, 27 mmol), and K3PO4 (20 g, 81 mmol) were added to a 1 L flask and dissolved in 250 mL of DMF. The reaction solution was stirred at 160 °C for 12 hours, poured into diatomaceous earth, and filtered. Ethyl acetate (300 mL) was added to the solution for extraction and collection of the organic layer, which was dried over MgSO4 and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvents to obtain intermediate compound 55-c (white solid, 14 g, 56%). The obtained white solid was identified as intermediate compound 55-c by ESI-LCMS.

[0550] ESI-LCMS: [M] + :C 60 H 43 N3Cl2S.907.2612.

[0551] Synthesis of intermediate compound 55-d

[0552] Under an argon atmosphere, compound 55-c (14 g, 15 mmol), N-phenyl-2-(pyridin-2-yl)aniline (3.8 g, 15 mmol), sodium tert-butoxide (43.5 g, 45 mmol), tri-tert-butylphosphine (1.5 mL, 1.4 mmol), and Pd2dba3 (0.7 g, 0.8 mmol) were added to a 1 L flask and dissolved in 150 mL of o-xylene. The reaction solution was stirred at 140 °C for 36 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added to extract and collect the organic layer, which was dried over MgSO4 and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain intermediate compound 55-d (white solid, 15 g, 77%). The obtained white solid was identified as intermediate compound 55-d by ESI-LCMS.

[0553] ESI-LCMS: [M] + :C 94 H 69 N7S.1327.5353.

[0554] Synthesis of Compound 55

[0555] Compound 55-d (15 g, 11 mmol) was added to a 1 L flask under an argon atmosphere, dissolved in 500 mL of o-dichlorobenzene, and cooled to 0 °C in an ice-water container. Boron tribromide (5 equivalents) was slowly added dropwise to the reaction solution, the temperature was slowly increased to room temperature, and the reaction solution was stirred for 20 min. The reaction solution was heated to 180 °C and stirred for 12 h. After cooling, triethylamine (5 mL) was slowly added dropwise to terminate the reaction, and the solvent was removed under reduced pressure. The obtained solid was washed with MeOH and purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain compound 55 (yellow solid, 1.2 g, 8%). The obtained yellow solid was analyzed by ESI-LCMS and... 1 H-NMR identified it as compound 55.

[0556] ESI-LCMS: [M] + :C 94 H 63 B2N7S.1343.5001. 1H-NMR(400MHz, CDCl3):10.43(s,1H),9.58(d,2H),9.31(d,2H),8.37(d,2H),8.20(d, 2H),7.76(s,1H),7.41(m,7H),7.25(m,13H),7.12(m,17H),6.57(s,1H),6.49(s,2H).

[0557] Synthesis Example 8: Synthesis of Compound 57

[0558]

[0559] Synthesis of intermediate compound 57-a

[0560] Under an argon atmosphere, compound 55-b (30 g, 37 mmol), aniline (3.5 g, 37 mmol), sodium tert-butoxide (10.6 g, 111 mmol), tri-tert-butylphosphine (1.7 mL, 3.8 mmol), and Pd2dba3 (1.7 g, 1.9 mmol) were added to a 1 L flask and dissolved in 400 mL of o-xylene. The reaction solution was stirred at 140 °C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added to extract and collect the organic layer, which was dried over MgSO4 and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain intermediate compound 57-a (white solid, 20 g, 68%). The obtained white solid was identified as intermediate compound 57-a by ESI-LCMS.

[0561] ESI-LCMS: [M] + :C 60 H 46 N4.822.3734.

[0562] Synthesis of intermediate compound 57-b

[0563] Under an argon atmosphere, compound 57-a (20 g, 24 mmol), 1,3-dichloro-5-bromobenzene (3.5 g, 37 mmol), sodium tert-butoxide (6.9 g, 72 mmol), tri-tert-butylphosphine (1.1 mL, 2.4 mmol), and Pd₂dba₃ (1.1 g, 1.2 mmol) were added to a 1 L flask and dissolved in 250 mL of o-xylene. The reaction solution was stirred at 140 °C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added to extract and collect the organic layer, which was dried over MgSO₄ and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH₂Cl₂ and hexane as developing solvents to obtain intermediate compound 57-b (white solid, 15 g, 65%). The obtained white solid was identified as intermediate compound 57-b by ESI-LCMS.

[0564] ESI-LCMS: [M] + :C 66 H 48 N4Cl2.966.3311.

[0565] Synthesis of intermediate compound 57-c

[0566] Under an argon atmosphere, compound 57-b (15 g, 15 mmol), N-phenyl-2-(pyridin-2-yl)aniline (7.6 g, 30 mmol), sodium tert-butoxide (4.3 g, 45 mmol), tri-tert-butylphosphine (0.7 mL, 1.6 mmol), and Pd2dba3 (0.7 g, 0.8 mmol) were added to a 1 L flask and dissolved in 150 mL of o-xylene. The reaction solution was stirred at 140 °C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added to extract and collect the organic layer, which was dried over MgSO4 and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain intermediate compound 57-c (white solid, 12 g, 59%). The obtained white solid was identified as intermediate compound 57-c by ESI-LCMS.

[0567] ESI-LCMS: [M] + :C 100 H 74 N8.1386.5997.

[0568] Synthesis of Compound 57

[0569] Compound 57-c (12 g, 8 mmol) was added to a 1 L flask under an argon atmosphere, dissolved in 500 mL of o-dichlorobenzene, and cooled to 0 °C in an ice-water container. Boron tribromide (5 equivalents) was slowly added dropwise to the reaction solution, the temperature was slowly increased to room temperature, and the reaction solution was stirred for 20 min. The reaction solution was heated to 180 °C and stirred for 12 h. After cooling, triethylamine (5 mL) was slowly added dropwise to terminate the reaction, and the solvent was removed under reduced pressure. The obtained solid was washed with MeOH and purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain compound 57 (yellow solid, 1.1 g, 9%). The obtained yellow solid was analyzed by ESI-LCMS and... 1 H-NMR identified it as compound 57.

[0570] ESI-LCMS: [M] + :C 100 H 68 B2N8.1402.5554.

[0571] 1 H-NMR(400MHz, CDCl3):10.59(s,1H),9.68(d,2H),9.31(d,2H),8.37(d,2H),8.20(d,2H),7 .76(s,1H),7.43(m,9H),7.27(m,21H),7.12(m,17H),7.03(m,7H),6.83(s,1H),6.49(s,4H).

[0572] Synthesis Example 9: Synthesis of Compound 82

[0573]

[0574] Synthesis of intermediate compound 82-a

[0575] Under an argon atmosphere, compound 55-b (30 g, 37 mmol), 2-aminobiphenyl (6.3 g, 37 mmol), sodium tert-butoxide (10.6 g, 111 mmol), tri-tert-butylphosphine (1.7 mL, 3.8 mmol), and Pd2dba3 (1.7 g, 1.9 mmol) were added to a 1 L flask and dissolved in 400 mL of o-xylene. The reaction solution was stirred at 140 °C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added to extract and collect the organic layer, which was dried over MgSO4 and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain intermediate compound 82-a (white solid, 24 g, 74%). The obtained white solid was identified as intermediate compound 82-a by ESI-LCMS.

[0576] ESI-LCMS: [M] + :C 66 H 50 N4.898.4006.

[0577] Synthesis of intermediate compound 82-b

[0578] Under an argon atmosphere, compound 82-a (24 g, 27 mmol), 1,3-dichloro-5-bromobenzene (6 g, 27 mmol), sodium tert-butoxide (7.8 g, 81 mmol), tri-tert-butylphosphine (1.2 mL, 2.8 mmol), and Pd₂dba₃ (1.2 g, 1.4 mmol) were added to a 1 L flask and dissolved in 300 mL of o-xylene. The reaction solution was stirred at 100 °C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added to extract and collect the organic layer, which was dried over MgSO₄ and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH₂Cl₂ and hexane as developing solvents to obtain intermediate compound 82-b (white solid, 18 g, 65%). The obtained white solid was identified as intermediate compound 82-b by ESI-LCMS.

[0579] ESI-LCMS: [M] + :C 72 H 52 N4Cl2.1042.2437.

[0580] Synthesis of intermediate compound 82-c

[0581] Under an argon atmosphere, compound 82-b (18 g, 17 mmol), N-phenyl-[1,1'-biphenyl]-2-amine (8.5 g, 34 mmol), sodium tert-butoxide (4.9 g, 51 mmol), tri-tert-butylphosphine (1.0 mL, 1.8 mmol), and Pd2dba3 (0.8 g, 0.9 mmol) were added to a 1 L flask and dissolved in 200 mL of o-xylene. The reaction solution was stirred at 140 °C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added to extract and collect the organic layer, which was dried over MgSO4 and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain intermediate compound 82-c (white solid, 17 g, 71%). The obtained white solid was identified as intermediate compound 82-c by ESI-LCMS.

[0582] ESI-LCMS: [M] + :C 108 H 80 N6.1460.6318.

[0583] Synthesis of Compound 82

[0584] Compound 82-c (17 g, 12 mmol) was added to a 1 L flask under an argon atmosphere, dissolved in 500 mL of o-dichlorobenzene, and cooled to 0 °C in an ice-water container. Boron tribromide (5 equivalents) was slowly added dropwise to the reaction solution, the temperature was slowly increased to room temperature, and the reaction solution was stirred for 20 min. The reaction solution was heated to 180 °C and stirred for 12 h. After cooling, triethylamine (5 mL) was slowly added dropwise to terminate the reaction, and the solvent was removed under reduced pressure. The obtained solid was washed with MeOH and purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain compound 82 (yellow solid, 1.9 g, 11%). The obtained yellow solid was analyzed by ESI-LCMS and... 1 H-NMR identified it as compound 82.

[0585] ESI-LCMS: [M] + :C 108 H 74 B2N6.1476.6551.

[0586] 1H-NMR(400MHz, CDCl3):10.36(s,1H),9.22(d,2H),8.20(d,2H),8.10(d,3H),7. 43(m,13H),7.24(m,16H),7.12(m,20H),7.01(m,7H),6.87(s,1H),6.52(s,4H).

[0587] Synthesis Example 10: Synthesis of Compound 83

[0588]

[0589] Synthesis of intermediate compound 83-a

[0590] Under an argon atmosphere, 3,5-dibromochlorobenzene (18 g, 111 mmol), N-phenyl-[1,1'-biphenyl]-2-amine (54 g, 222 mmol), sodium tert-butoxide (32 g, 333 mmol), tri-tert-butylphosphine (5.0 mL, 11 mmol), and Pd2dba3 (5.1 g, 5.5 mmol) were added to a 2 L flask and dissolved in 1 L of o-xylene. The reaction solution was stirred at 100 °C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added to extract and collect the organic layer, which was dried over MgSO4 and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain intermediate compound 83-a (white solid, 50 g, 75%). The obtained white solid was identified by ESI-LCMS as intermediate compound 83-a.

[0591] ESI-LCMS: [M] + :C 42 H 31 N2Cl.598.2201.

[0592] Synthesis of intermediate compound 83-b

[0593] Under an argon atmosphere, compound 83-a (50 g, 83 mmol), aniline (8 g, 83 mmol), sodium tert-butoxide (24 g, 249 mmol), tri-tert-butylphosphine (4 mL, 8.4 mmol), and Pd2dba3 (3.8 g, 4.2 mmol) were added to a 2 L flask and dissolved in 800 mL of o-xylene. The reaction solution was stirred at 140 °C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added to extract and collect the organic layer, which was dried over MgSO4 and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain intermediate compound 83-b (white solid, 38 g, 71%). The obtained white solid was identified as intermediate compound 83-b by ESI-LCMS.

[0594] ESI-LCMS: [M] + :C 48 H 37 N3.655.3001.

[0595] Synthesis of intermediate compound 83-c

[0596] Under an argon atmosphere, compound 83-a (50 g, 83 mmol), [1,1':3',1”-terphenyl]-2'-amine (20 g, 83 mmol), sodium tert-butoxide (24 g, 249 mmol), tri-tert-butylphosphine (4 ml, 8.4 mmol), and Pd2dba3 (3.8 g, 4.2 mmol) were added to a 2 L flask and dissolved in 800 ml of o-xylene. The reaction solution was stirred at 140 °C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 ml) were added to extract and collect the organic layer, which was dried over MgSO4 and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain intermediate compound 83-c (white solid, 49 g, 73%). The obtained white solid was identified as intermediate compound 83-c by ESI-LCMS.

[0597] ESI-LCMS: [M] + :C 60 H 45 N3.807.3535.

[0598] Synthesis of intermediate compound 83-d

[0599] Under an argon atmosphere, compound 83-c (45 g, 55 mmol), 3-bromo-iodobenzene (15.8 g, 55 mmol), sodium tert-butoxide (16 g, 165 mmol), tri-tert-butylphosphine (2.5 mL, 5.6 mmol), and Pd₂dba₃ (2.5 g, 2.8 mmol) were added to a 2 L flask and dissolved in 800 mL of o-xylene. The reaction solution was stirred at 100 °C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added to extract and collect the organic layer, which was dried over MgSO₄ and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH₂Cl₂ and hexane as developing solvents to obtain intermediate compound 83-d (white solid, 35 g, 67%). The obtained white solid was identified as intermediate compound 83-d by ESI-LCMS.

[0600] ESI-LCMS: [M] + :C 66 H 48 N3Br.961.2738.

[0601] Synthesis of intermediate compound 83-e

[0602] Under an argon atmosphere, compounds 83-d (35 g, 36 mmol), 83-b (23.6 g, 36 mmol), sodium tert-butoxide (10 g, 108 mmol), tri-tert-butylphosphine (1.6 mL, 3.6 mmol), and Pd₂dba₃ (1.6 g, 1.8 mmol) were added to a 2 L flask and dissolved in 800 mL of o-xylene. The reaction solution was stirred at 140 °C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added to extract and collect the organic layer, which was then dried over MgSO₄ and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH₂Cl₂ and hexane as developing solvents to obtain intermediate compound 83-e (white solid, 32 g, 59%). The obtained white solid was identified as intermediate compound 83-e by ESI-LCMS.

[0603] ESI-LCMS: [M] + :C 114 H 84 N6.1536.6656.

[0604] Synthesis of Compound 83

[0605] Compound 83-e (32 g, 20 mmol) was added to a 1 L flask under an argon atmosphere, dissolved in 500 mL of o-dichlorobenzene, and cooled to 0 °C in an ice-water container. Boron tribromide (5 equivalents) was slowly added dropwise to the reaction solution, the temperature was slowly increased to room temperature, and the reaction solution was stirred for 20 min. The reaction solution was heated to 180 °C and stirred for 12 h. After cooling, triethylamine (5 mL) was slowly added dropwise to terminate the reaction, and the solvent was removed under reduced pressure. The obtained solid was washed with MeOH and purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain compound 83 (yellow solid, 2.2 g, 7%). The obtained yellow solid was analyzed by ESI-LCMS and... 1 H-NMR identified it as compound 83.

[0606] ESI-LCMS: [M] + :C 114 H 78 B2N6.1552.4437.

[0607] 1 H-NMR (400MHz, CDCl3): 10.17(s,1H),9.33(d,2H),8.22(d,2H),8.13(d,4H),7.41(m,23H),7.24(m,20H),7.08(m,18H),6.91(s,1H),6.43(s,4H).

[0608] Synthesis Example 11: Synthesis of Compound 85

[0609]

[0610] Synthesis of intermediate compound 85-a

[0611] Under an argon atmosphere, 3,5-dibromochlorobenzene (35 g, 111 mmol), N-phenyl-[1,1':3',1”-terphenyl]-2'-amine (36 g, 111 mmol), sodium tert-butoxide (32 g, 333 mmol), tri-tert-butylphosphine (5.1 ml, 11 mmol), and Pd2dba3 (5.1 g, 5.6 mmol) were added to a 2 L flask and dissolved in 1 L of o-xylene. The reaction solution was stirred at 100 °C for 12 hours. After cooling... Subsequently, water (1 L) and ethyl acetate (300 mL) were added to extract and collect the organic layer, which was then dried and filtered using MgSO4. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvents to obtain intermediate compound 85-a (white solid, 55 g, 67%). The obtained white solid was identified as intermediate compound 85-a by ESI-LCMS.

[0612] ESI-LCMS: [M] + :C 54 H 39 N2Cl.750.2812.

[0613] Synthesis of intermediate compound 85-b

[0614] Under an argon atmosphere, compound 85-a (55 g, 73 mmol), aniline (7 g, 111 mmol), sodium tert-butoxide (21 g, 219 mmol), tri-tert-butylphosphine (3.3 mL, 7.2 mmol), and Pd2dba3 (3.3 g, 3.6 mmol) were added to a 2 L flask and dissolved in 700 mL of o-xylene. The reaction solution was stirred at 140 °C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added to extract and collect the organic layer, which was dried over MgSO4 and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain intermediate compound 85-b (white solid, 38 g, 64%). The obtained white solid was identified as intermediate compound 85-b by ESI-LCMS.

[0615] ESI-LCMS: [M] + :C 60 H 45 N3.807.3515.

[0616] Synthesis of intermediate compound 85-c

[0617] Under an argon atmosphere, compound 85-b (30 g, 37 mmol), compound 55-b (30 g, 37 mmol), sodium tert-butoxide (10 g, 111 mmol), tri-tert-butylphosphine (1.7 mL, 3.6 mmol), and Pd2dba3 (1.7 g, 1.8 mmol) were added to a 2 L flask and dissolved in 400 mL of o-xylene. The reaction solution was stirred at 140 °C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added to extract and collect the organic layer, which was then dried over MgSO4 and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain intermediate compound 85-c (white solid, 24 g, 48%). The obtained white solid was identified as intermediate compound 85-c by ESI-LCMS.

[0618] ESI-LCMS: [M] + :C 114 H 84 N6.1536.6123.

[0619] Synthesis of Compound 85

[0620] Compound 85-c (24 g, 15 mmol) was added to a 1 L flask under an argon atmosphere, dissolved in 500 mL of o-dichlorobenzene, and cooled to 0 °C in an ice-water container. Boron tribromide (5 equivalents) was slowly added dropwise to the reaction solution, and the temperature was slowly increased to room temperature. The reaction solution was heated to 180 °C and stirred for 12 hours. After cooling, triethylamine (5 mL) was slowly added dropwise to terminate the reaction, and the solvent was removed under reduced pressure. The obtained solid was washed with MeOH and purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain compound 85 (yellow solid, 1.8 g, 8%). The obtained yellow solid was analyzed by ESI-LCMS and... 1 H-NMR identified it as compound 85.

[0621] ESI-LCMS: [M] + :C 114 H 78 B2N6.1552.6512.

[0622] 1H-NMR (400MHz, CDCl3): 10.22(s,1H),9.27(d,2H),8.25(d,6H),7.36(m,21H),7.21(m,14H),7.02(m,29H),6.88(s,1H),6.47(s,4H).

[0623] Synthesis Example 12: Synthesis of Compound 97

[0624]

[0625] Synthesis of intermediate compound 97-a

[0626] Under an argon atmosphere, 1,3-dibromo-5-chlorobenzene (30 g, 111 mmol), 4'-(tert-butyl)-N-phenyl-[1,1'-biphenyl]-2-amine (67 g, 222 mmol), sodium tert-butoxide (32 g, 333 mmol), tri-tert-butylphosphine (5 ml, 11 mmol), and Pd2dba3 (5.1 g, 5.6 mmol) were added to a 2 L flask and dissolved in 1 L of o-xylene. The reaction solution was stirred at 100 °C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 ml) were added to extract and collect the organic layer, which was dried over MgSO4 and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain intermediate compound 97-a (white solid, 46 g, 59%). The obtained white solid was identified by ESI-LCMS as intermediate compound 97-a.

[0627] ESI-LCMS: [M] + :C 50 H 47 N2Cl.710.3336.

[0628] Synthesis of intermediate compound 97-b

[0629] Under an argon atmosphere, compound 97-a (45 g, 63 mmol), aniline (6.1 g, 63 mmol), sodium tert-butoxide (18 g, 190 mmol), tri-tert-butylphosphine (3 ml, 6.4 mmol), and Pd2dba3 (2.9 g, 3.2 mmol) were added to a 2 L flask and dissolved in 600 ml of o-xylene. The reaction solution was stirred at 140 °C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 ml) were added to extract and collect the organic layer, which was then dried over MgSO4 and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain intermediate compound 97-b (white solid, 35 g, 72%). The obtained white solid was identified as intermediate compound 97-b by ESI-LCMS.

[0630] ESI-LCMS: [M] + :C 56 H 53 N3.767.4321.

[0631] Synthesis of intermediate compound 97-c

[0632] Under an argon atmosphere, compound 97-a (30 g, 42 mmol), [1,1':3',1”-terphenyl]-2'-amine (10 g, 42 mmol), sodium tert-butoxide (12 g, 126 mmol), tri-tert-butylphosphine (2 ml, 4.2 mmol), and Pd2dba3 (1.9 g, 2.1 mmol) were added to a 2 L flask and dissolved in 400 ml of o-xylene. The reaction solution was stirred at 140 °C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 ml) were added to extract and collect the organic layer, which was dried over MgSO4 and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain intermediate compound 97-c (white solid, 20 g, 54%). The obtained white solid was identified as intermediate compound 97-c by ESI-LCMS.

[0633] ESI-LCMS: [M] + :C 67 H 59 N3.905.4731.

[0634] Synthesis of intermediate compound 97-d

[0635] Under an argon atmosphere, compound 97-c (20 g, 22 mmol), 3-bromo-iodobenzene (10 g, 22 mmol), sodium tert-butoxide (6.4 g, 66 mmol), tri-tert-butylphosphine (1 ml, 2.2 mmol), and Pd₂dba₃ (1.0 g, 1.1 mmol) were added to a 1 L flask and dissolved in 250 ml of o-xylene. The reaction solution was stirred at 100 °C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 ml) were added to extract and collect the organic layer, which was dried over MgSO₄ and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH₂Cl₂ and hexane as developing solvents to obtain intermediate compound 97-d (white solid, 16 g, 71%). The obtained white solid was identified as intermediate compound 97-d by ESI-LCMS.

[0636] ESI-LCMS: [M] + :C 74 H 64 N3Br.1073.2917.

[0637] Synthesis of intermediate compound 97-e

[0638] Under an argon atmosphere, compounds 97-d (15 g, 14 mmol), 97-b (9.2 g, 14 mmol), sodium tert-butoxide (4 g, 42 mmol), tri-tert-butylphosphine (0.6 mL, 1.4 mmol), and Pd₂dba₃ (0.6 g, 0.7 mmol) were added to a 1 L flask and dissolved in 150 mL of o-xylene. The reaction solution was stirred at 100 °C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added to extract and collect the organic layer, which was then dried over MgSO₄ and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH₂Cl₂ and hexane as developing solvents to obtain intermediate compound 97-e (white solid, 16 g, 66%). The obtained white solid was identified as intermediate compound 97-e by ESI-LCMS.

[0639] ESI-LCMS: [M] + :C 130 H 116 N6.1760.9331.

[0640] Synthesis of Compound 97

[0641] Compound 97-e (15 g, 8.5 mmol) was added to a 1 L flask under an argon atmosphere, dissolved in 500 mL of o-dichlorobenzene, and cooled to 0 °C in an ice-water container. Boron tribromide (5 equivalents) was slowly added dropwise to the reaction solution, and the temperature was slowly increased to room temperature. The reaction solution was heated to 180 °C and stirred for 12 hours. After cooling, triethylamine (5 mL) was slowly added dropwise to terminate the reaction, and the solvent was removed under reduced pressure. The obtained solid was washed with MeOH and purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain compound 97 (yellow solid, 1.2 g, 8%). The obtained yellow solid was analyzed by ESI-LCMS and... 1 H-NMR identified it as compound 97.

[0642] ESI-LCMS: [M] + :C 130 H 110 B2N6.1776.8997.

[0643] 1 H-NMR (400MHz, CDCl3): 10.34(s,1H),9.41(d,2H),8.12(d,4H),7.44(m,32H),7.24(m,21H),7.00(m,9H),6.84(s,1H),6.52(s,4H),1.33(s,36H).

[0644] Synthesis Example 13: Synthesis of Compound 101

[0645]

[0646] Synthesis of intermediate compound 101-a

[0647] Under an argon atmosphere, compound 83-b (30 g, 46 mmol), 3-bromo-iodobenzene (13 g, 46 mmol), sodium tert-butoxide (13 g, 138 mmol), tri-tert-butylphosphine (2.2 mL, 4.6 mmol), and Pd₂dba₃ (2.1 g, 2.3 mmol) were added to a 2 L flask and dissolved in 500 mL of o-xylene. The reaction solution was stirred at 140 °C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added to extract and collect the organic layer, which was dried over MgSO₄ and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH₂Cl₂ and hexane as developing solvents to obtain intermediate compound 101-a (white solid, 21 g, 56%). The obtained white solid was identified as intermediate compound 101-a by ESI-LCMS.

[0648] ESI-LCMS: [M] + :C 54 H 40 N3Br.809.2434.

[0649] Synthesis of intermediate compound 101-b

[0650] Under an argon atmosphere, 5-chloro-N1,N1,N3,N3-tetraphenylphenyl-1,3-diamine (30 g, 67 mmol), 4,4”-di-tert-butyl-[1,1':3',1”-tert-phenyl]-2'-amine (24 g, 67 mmol), sodium tert-butoxide (19 g, 201 mmol), tri-tert-butylphosphine (6 ml, 6.8 mmol), and Pd2dba3 (3 g, 3.4 mmol) were added to a 2 L flask and dissolved in 500 ml of o-xylene. The reaction solution was stirred at 140 °C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 ml) were added to extract and collect the organic layer, which was then dried and filtered using MgSO4. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvents to obtain intermediate compound 101-b (white solid, 37 g, 72%). The obtained white solid was identified as intermediate compound 101-b by ESI-LCMS.

[0651] ESI-LCMS: [M] + :C 56 H 56 N3.767.4119.

[0652] Synthesis of intermediate compound 101-c

[0653] Under an argon atmosphere, compounds 101-a (20 g, 25 mmol), 101-b (19 g, 25 mmol), sodium tert-butoxide (7.2 g, 75 mmol), tri-tert-butylphosphine (1.2 mL, 2.6 mmol), and Pd₂dba₃ (1.1 g, 1.3 mmol) were added to a 2 L flask and dissolved in 250 mL of o-xylene. The reaction solution was stirred at 140 °C for 12 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added to extract and collect the organic layer, which was then dried over MgSO₄ and filtered. The filtered solution was placed under reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH₂Cl₂ and hexane as developing solvents to obtain intermediate compound 101-c (white solid, 23.5 g, 65%). The obtained white solid was identified as intermediate compound 101-c by ESI-LCMS.

[0654] ESI-LCMS: [M] + :C 110 H 52 N6.1497.2331.

[0655] Synthesis of Compound 101

[0656] Compound 101-c (20 g, 8.5 mmol) was added to a 1 L flask under an argon atmosphere, dissolved in 500 mL of o-dichlorobenzene, and cooled to 0 °C in an ice-water container. Boron tribromide (5 equivalents) was slowly added dropwise to the reaction solution, and the temperature was slowly increased to room temperature. The reaction solution was heated to 180 °C and stirred for 12 hours. After cooling, triethylamine (5 mL) was slowly added dropwise to terminate the reaction, and the solvent was removed under reduced pressure. The obtained solid was washed with MeOH and purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain compound 101 (yellow solid, 1 g, 10%). The obtained yellow solid was analyzed by ESI-LCMS and... 1 H-NMR identified it as compound 101.

[0657] ESI-LCMS: [M] + :C 110 H 86 B2N6.1512.7171.

[0658] 1H-NMR(400MHz, CDCl3):10.29(s,1H),9.23(d,2H),8.21(d,2H),8.10(d,2H),7.39(m,1 5H),7.24(m,10H),7.08(m,14H),7.00(m,5H),6.81(s,1H),6.47(s,4H),1.37(s,18H).

[0659] Proton NMR of the compounds synthesized according to Synthesis Examples 1 to 13 1 H NMR and matrix-assisted laser desorption / ionization time-of-flight mass spectrometry (MALDI-TOF MS) are shown in Table 1.

[0660] By referring to the synthetic routes and source materials described above, those skilled in the art can readily recognize methods for synthesizing compounds other than those shown in Synthesis Examples 1 to 13.

[0661] Table 1

[0662]

[0663]

[0664] Example 1

[0665] As the anode, it will have 15Ω / cm 2 The glass substrate on which the ITO electrode was formed (a product of Corning Inc. of Corning New York (hereinafter “Corning Inc”)) was cut to a size of 50 mm × 50 mm × 0.7 mm, sonicated with isopropanol and pure water for 5 minutes each, and then cleaned by exposure to ultraviolet light and ozone for 30 minutes. The resulting structure was then mounted into a vacuum deposition apparatus.

[0666] The compound NPD is deposited on the anode to form a structure with... A hole injection layer of a certain thickness is formed, and compound HT6 is deposited on the hole injection layer to form a hole injection layer with [missing information]. A hole transport layer of a certain thickness was formed, and the compound CzSi was deposited on the hole transport layer to form a hole transport layer with a certain thickness. A launch auxiliary layer of a certain thickness.

[0667] Compound mCP (the host) and compound 1 (the dopant) were co-deposited on the emission-assisted layer at a weight ratio of 99:1 to form a layer with... The thickness of the emission layer.

[0668] Subsequently, compound TSPO1 was deposited on the emitter layer to form a structure with... A hole-blocking layer of a certain thickness is formed by depositing the compound TPBI on the hole-blocking layer to create a hole-blocking layer. A thick electron transport layer is formed by depositing the compound lithium fluoride (LiF) on the electron transport layer to create an electron transport layer with... An electron-injection layer of a certain thickness is used to deposit elemental Al onto the electron-injection layer to form a layer with... A cathode of a certain thickness was formed, and compound HT28 was deposited on the electrode to form a cathode with a thickness of [missing information]. A thick covering layer is applied to complete the manufacturing of the light-emitting device.

[0669]

[0670] Examples 2 to 13 and Comparative Examples 1 to 3

[0671] The organic light-emitting device was manufactured in the same manner as in Example 1, but when forming the emission layer, the corresponding compounds shown in Table 2 were used instead of compound 1 as dopants.

[0672] Example 14

[0673] As the anode, it will have 15Ω / cm 2 The glass substrate (Corning Incorporated) on which the ITO electrode is formed is cut to a size of 50 mm × 50 mm × 0.7 mm, sonicated with isopropanol and pure water for 5 minutes each, and then cleaned by exposure to ultraviolet light and ozone for 30 minutes. The resulting structure is then mounted into a vacuum deposition apparatus.

[0674] The compound NPD is deposited on the anode to form a structure with... A hole injection layer of a certain thickness was formed, and compound HT45 was deposited on the hole injection layer to form a hole injection layer with [missing information]. A hole transport layer of a certain thickness was formed, and the compound CzSi was deposited on the hole transport layer to form a hole transport layer with a certain thickness. A launch auxiliary layer of a certain thickness.

[0675] Compounds H39 and H37 (5:5 weight ratio) used as the host mixture, compound PD26 used as a metal phosphorescent dopant, and compound 55 used as a dopant were co-deposited on the emission-assisted layer to form a layer with… The thickness of the emission layer.

[0676] Subsequently, compound TSPO1 was deposited on the emitter layer to form a structure with... A hole-blocking layer of a certain thickness is formed by depositing the compound TPBi on the hole-blocking layer to create a hole-blocking layer. An electron transport layer of a certain thickness is formed by depositing the compound LiF on the electron transport layer to form an electron transport layer with... An electron-injection layer of a certain thickness is used to deposit elemental Al onto the electron-injection layer to form a layer with... A cathode of a certain thickness was formed, and compound HT28 was deposited on the electrode to form a cathode with a thickness of [missing information]. A thick covering layer is applied to complete the manufacturing of the light-emitting device.

[0677]

[0678] Examples 15 to 21 and Comparative Examples 4 to 6

[0679] The light-emitting device was manufactured in the same manner as in Example 14, but the corresponding compounds shown in Table 3 were used for the host and dopant used as hole transport materials.

[0680] Example 22

[0681] As the anode, it will have 15Ω / cm 2 The glass substrate (Corning Incorporated) on which the ITO electrode is formed is cut to a size of 50 mm × 50 mm × 0.7 mm, sonicated with isopropanol and pure water for 5 minutes each, and then cleaned by exposure to ultraviolet light and ozone for 30 minutes. The resulting structure is then mounted into a vacuum deposition apparatus.

[0682] The compound NPD is deposited on the anode to form a structure with... A hole injection layer of a certain thickness was formed, and compound HT45 was deposited on the hole injection layer to form a hole injection layer with [missing information]. A hole transport layer of a certain thickness was formed, and the compound CzSi was deposited on the hole transport layer to form a hole transport layer with a certain thickness. A launch auxiliary layer of a certain thickness.

[0683] Compounds H39 and H37 (5:5 weight ratio) used as the host mixture, compound PD26 used as a metal phosphorescent dopant, and compound 17 used as a dopant were co-deposited on the emission-assisted layer to form a layer with… The thickness of the emission layer.

[0684] Subsequently, compound TSPO1 was deposited on the emitter layer to form a structure with... A hole-blocking layer of a certain thickness is formed, and compound ET1 is deposited on the hole-blocking layer to form An electron transport layer of a certain thickness is formed by depositing the compound LiF on the electron transport layer to form an electron transport layer with... An electron-injection layer of a certain thickness is used to deposit elemental Al onto the electron-injection layer to form a layer with... A cathode of a certain thickness was formed, and compound HT28 was deposited on the electrode to form a cathode with a thickness of [missing information]. A thick covering layer is applied to complete the manufacturing of the light-emitting device.

[0685]

[0686]

[0687] Examples 23 to 29, and Comparative Examples 7 and 8

[0688] The light-emitting device was manufactured in the same manner as in Example 22, but the corresponding compounds shown in Table 4 were used for the host and dopant used as hole transport materials.

[0689] Evaluation Example 2

[0690] The luminance of the organic light-emitting devices manufactured according to Examples 1 to 29 and Comparative Examples 1 to 8 was measured at 1,000 candela per square meter (cd / A or cd / m²) using a source meter (sold by Tektronix, Inc. of Beaverton, Oregon under the trade name Keithley MU 236) and a luminance meter sold by PhotoResearch Inc. of Los Angeles, California under the trade name PR650. 2 The driving voltage, emission efficiency (cd / A), and emission color are given in volts (V) at the given conditions. 95 The lifespan is the time taken to reach 95% of the initial brightness, measured in hours at 100 mA per square centimeter.

[0691] The results are shown in Tables 2 to 4.

[0692] Table 2

[0693]

[0694]

[0695] Table 3

[0696]

[0697] Table 4

[0698]

[0699] Table 2 shows that the light-emitting devices of Examples 1 to 13 emit blue light with a wavelength range of 450 nm to 470 nm, and have significantly and unexpectedly improved characteristics compared with the light-emitting devices of Comparative Examples 1 to 3, including lower driving voltage, higher emission efficiency and longer lifespan.

[0700] Table 3 shows that the light-emitting devices of Examples 14 to 21 emit blue light with a wavelength range of 450 nm to 470 nm, and have significantly and unexpectedly improved characteristics compared with the light-emitting devices of Comparative Examples 4 to 6, including lower driving voltage, higher emission efficiency and longer lifespan.

[0701] Table 4 shows that the light-emitting devices of Examples 22 to 29 emit blue light with a wavelength range of 450 nm to 470 nm, and have significantly and unexpectedly improved characteristics compared with the light-emitting devices of Comparative Examples 7 and 8, including lower driving voltage, higher emission efficiency and longer lifespan.

[0702] Although we do not wish to be bound by theory, because the light-emitting device contains a heterocyclic compound represented by Formula 1, the light-emitting device can have a low driving voltage, high emission efficiency and high external quantum efficiency, and can be used to manufacture high-quality electronic devices.

[0703] While certain embodiments and implementations have been described herein, other embodiments and modifications will be apparent from this specification. Therefore, the inventive concept is not limited to such embodiments, but rather to the broader scope of the appended claims and the various obvious modifications and equivalent arrangements that will be apparent to those skilled in the art.

Claims

1. A light-emitting device, comprising: First electrode; The second electrode facing the first electrode; as well as An intermediate layer comprising an emission layer is disposed between the first electrode and the second electrode, wherein The intermediate layer comprises a heterocyclic compound of formula 1: Formula 1 Formula 1-1 Formula 1-2 Among them, in Equation 1, Equation 1-1 and Equation 1-2, A1 is a group of formula 1-1. B1 is a group of formula 1-2. n1 is an integer from 1 to 10. CY1 to CY4 are each independently C5-C 30 Carbocyclic groups or C1-C 30 Heterocyclic groups, Y1 and Y2 are each independently B, P (=O), or P (=S). X1 is O, S, Se, Te, N(Ar1), Al(Ar1) or P(Ar1), X2 is O, S, Se, Te, N(Ar2), Al(Ar2), or P(Ar2). X3 is O, S, Se, Te, N(Ar3), Al(Ar3) or P(Ar3), X4 is O, S, Se, Te, N(Ar4), Al(Ar4) or P(Ar4), Ar1 to Ar 10 Each of these is independently a binding site with B1 in Formula 1, a hydrogen group, a deuterium group, a -F group, a -Cl group, a -Br group, a -I group, a hydroxyl group, a cyano group, a nitro group, an unsubstituted group, or a group with at least one R. 10a Replacement C1-C 60 alkyl groups, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkenyl groups, unsubstituted or with at least one R 10a Replacement C2-C 60 The alkynyl group, unsubstituted or with at least one R 10a Replacement C1-C 60 alkoxy group, unsubstituted or with at least one R 10a Replacement C3-C 60 Carbocyclic groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, unsubstituted or with at least one R 10a Replacement C6-C 60 aryloxy group, unsubstituted or with at least one R 10a Replacement C6-C 60 Aryl thiols, -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), Ar1 to Ar 10 At least one of them is a binding site for B1 in Formula 1. T 11 It is unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups, X 11 Is it N or C(R)? 11 ), X 12 Is it N or C(R)? 12 ), X 13 Is it N or C(R)? 13 ), and X 14 Is it N or C(R)? 14 ), R1 to R4 and R 11 To R 14 Each of these groups is independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, unsubstituted or substituted with at least one R. 10a Replacement C1-C 60 alkyl groups, unsubstituted or with at least one R 10a Replacement C2-C 60 alkenyl groups, unsubstituted or with at least one R 10a Replacement C2-C 60 The alkynyl group, unsubstituted or with at least one R 10a Replacement C1-C 60 alkoxy group, unsubstituted or with at least one R 10a Replacement C3-C 60 Carbocyclic groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, unsubstituted or with at least one R 10a Replacement C6-C 60 aryloxy group, unsubstituted or with at least one R 10a Replacement C6-C 60 Aryl thiols, -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), a1 to a4 are each an integer from 0 to 10, independent of each other. When a1 is an integer of 2 or greater than 2, two or more R1s are optionally connected to each other to form an unsubstituted or at least one R1. 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups, When a2 is an integer of 2 or greater than 2, two or more R2s are optionally connected to each other to form an unsubstituted or at least one R2. 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups, When a3 is an integer of 2 or greater than 2, two or more R3s are optionally connected to each other to form an unsubstituted or at least one R3. 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups, When a4 is an integer of 2 or greater than 2, two or more R4s are optionally connected to each other to form an unsubstituted or at least one R4. 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups, R 11 To R 14 Two or more adjacent groups in the form are optionally linked to each other to form an unsubstituted or R-shaped compound. 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups, In Equation 1-2 It is the binding site with A1 in Formula 1, and R 10a yes: Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group or nitro group; Each of the following is independent and unsubstituted or replaced by deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 aryloxy group, C6-C 60 aryl thioyl groups, -Si(Q) 11 (Q) 12 (Q) 13 -N(Q) 11 (Q) 12 -B(Q) 11 (Q) 12 -C(=O)(Q) 11 -S(=O)2(Q) 11 -P(=O)(Q) 11 (Q) 12 C1-C substituted by (or any combination thereof) 60 Alkyl groups, C2-C 60 alkenyl groups, C2-C 60 alkynyl group or C1-C 60 Alkoxy group; Each of the following is independent and unsubstituted or replaced by deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 60 Alkyl groups, C2-C 60 alkenyl groups, C2-C 60 alkynyl group, C1-C 60 alkoxy group, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 aryloxy group, C6-C 60 aryl thioyl groups, -Si(Q) 21 (Q) 22 (Q) 23 -N(Q) 21 (Q) 22 -B(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q) 21 -P(=O)(Q) 21 (Q) 22 C3-C replaced by any combination thereof 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 aryloxy group or C6-C 60 aryl thioyl group; or -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)₂(Q 31 ), or -P(=O)(Q 31 )(Q 32 ), Among them, Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each of the following is independent of the others: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl group; cyano group; nitro group; C1-C 60 Alkyl group; C2-C 60 alkenyl group; C2-C 60 alkynyl group; C1-C 60 Alkoxy groups; each independently unsubstituted or replaced by deuterium, -F, cyano groups, C1-C 60 Alkyl groups, C1-C 60 C3-C substituted with alkoxy groups, phenyl groups, biphenyl groups, or any combination thereof 60 Carbocyclic groups or C1-C 60 Heterocyclic groups.

2. The light-emitting device of claim 1, wherein the heterocyclic compound of formula 1 is contained in the emitting layer.

3. The light-emitting device of claim 2, wherein the organometallic compound of formula 401 is further contained in the emitting layer: Formula 401 M(L 401 ) xc1 (L 402 ) xc2 Formula 402 in, In Equations 401 and 402, M is a transition metal. L 401 It is a ligand of formula 402, and xc1 is 1, 2, or 3, wherein when xc1 is 2 or 3, there are two or more L... 401 Whether they are the same or different, L 402 It is an organic ligand, xc2 is 0, 1, 2, 3 or 4, and when xc2 is 2, 3 or 4, there are two or more L... 402 Whether they are the same or different, X 401 and X 402 Each is either nitrogen or carbon, independent of the others. Ring A 401 And Ring A 402 Each is independent of the others, namely C3-C. 60 Carbocyclic groups or C1-C 60 Heterocyclic groups, T 401 It is a single key. -O- '、 -S- '、 -C(=O)- '、 -N(Q 411 )- '、 -C(Q 411 (Q) 412 )- '、 -C(Q 411 )=C(Q 412 )- '、 -C(Q 411 )= 'or =C= ', X 403 and X 404 Each of these bonds is independent of the others: covalent bond, coordinate bond, O, S, N (Q). 413 ), B(Q) 413 ), P(Q 413 ), C(Q 413 (Q) 414 ) or Si(Q 413 (Q) 414 ), Q 411 To Q 414 They each have the same meaning as Q1 in claim 1, independent of each other. R 401 and R 402 Each of these groups is independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, unsubstituted or substituted with at least one R. 10a Replacement C1-C 20 alkyl groups, unsubstituted or with at least one R 10a Replacement C1-C 20 alkoxy group, unsubstituted or with at least one R 10a Replacement C3-C 60 Carbocyclic groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, -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 ), Q 401 To Q 403 Each having independently possesses Q1 as described in claim 1. xc11 and xc12 are each independent integers from 0 to 10, and T 401 In and Each represents a bonding site with an adjacent atom, and in Formula 402 and Each of these is a binding site for M in Equation 401.

4. The light-emitting device of claim 2, wherein the emitting layer is configured to emit blue light.

5. The light-emitting device of claim 2, wherein the emitting layer further comprises a body, and the weight of the body is greater than the weight of the heterocyclic compound of formula 1.

6. The light-emitting device of claim 5, wherein the host comprises two different host compounds.

7. The light-emitting device of claim 5, wherein the main body comprises a hole transport main compound and an electron transport main compound.

8. The light-emitting device of claim 1, wherein the intermediate layer further includes a hole transport region between the first electrode and the emitting layer and an electron transport region between the emitting layer and the second electrode. The hole transport region includes a hole injection layer, a hole transport layer, an emission assist layer, an electron blocking layer, or any combination thereof, and The electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.

9. The light-emitting device of claim 8, wherein the emitting layer comprises a heterocyclic compound of formula 1. The hole transport region comprises the compound of formula 201, the compound of formula 202, or any combination thereof: Formula 201 Formula 202 in, In equations 201 and 202, L 201 To L 204 Each is independent of the others and is either unsubstituted or controlled by at least one R. 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups, L 205 yes -O- '、 -S- '、 -N(Q 201 )- ', unsubstituted or by at least one R 10a Replacement C1-C 20 alkylene groups, unsubstituted or with at least one R 10a Replacement C2-C 20 alkenyl groups, unsubstituted or with at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups, xa1 to xa4 are each an integer from 0 to 5, which are independent of each other. xa5 is an integer from 0 to 10. R 201 To R 204 and Q 201 Each is independent of the others and is either unsubstituted or controlled by at least one R. 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups, R 201 and R 202 Optionally via a single bond, unsubstituted, or by at least one R 10a Substituted C1-C5 alkylene groups or unsubstituted or substituted with at least one R 10a The substituted C2-C5 alkenyl groups are linked together to form unsubstituted or substituted groups with at least one R group. 10a Replacement C8-C 60 Polycyclic groups, R 203 and R 204 Optionally via a single bond, unsubstituted, or by at least one R 10a Substituted C1-C5 alkylene groups or unsubstituted or substituted with at least one R 10a The substituted C2-C5 alkenyl groups are linked together to form unsubstituted or substituted groups with at least one R group. 10a Replacement C8-C 60 Polycyclic groups, L 205 In and Each is a binding site in Equation 202. na1 is an integer from 1 to 4.

10. The light-emitting device of claim 9, wherein each of formulas 201 and 202 comprises at least one group of formulas CY201 to CY217: in, In formulas CY201 to CY217 CY 201 To CY 204 Each is independent of the others, namely C3-C. 20 Carbocyclic groups or C1-C 20 Heterocyclic groups, At least one hydrogen atom in formulas CY201 to CY217 is unsubstituted or replaced by R. 10a Replacement, and R 10a R 10b and R 10c Each is independent of the others: Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group or nitro group; Each of the following is independent and unsubstituted or replaced by deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 aryloxy group, C6-C 60 aryl thioyl groups, -Si(Q) 11 (Q) 12 (Q) 13 -N(Q) 11 (Q) 12 -B(Q) 11 (Q) 12 -C(=O)(Q) 11 -S(=O)2(Q) 11 -P(=O)(Q) 11 (Q) 12 C1-C substituted by (or any combination thereof) 60 Alkyl groups, C2-C 60 alkenyl groups, C2-C 60 alkynyl group or C1-C 60 alkoxy group; Each of the following is independent and unsubstituted or replaced by deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 60 Alkyl groups, C2-C 60 alkenyl groups, C2-C 60 alkynyl group, C1-C 60 alkoxy group, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 aryloxy group, C6-C 60 aryl thioyl groups, -Si(Q) 21 (Q) 22 (Q) 23 -N(Q) 21 (Q) 22 -B(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q) 21 -P(=O)(Q) 21 (Q) 22 C3-C replaced by any combination thereof 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 aryloxy group or C6-C 60 aryl thioyl group; or -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)₂(Q 31 ), or -P(=O)(Q 31 )(Q 32 ), Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each of the following is independent of the others: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl group; cyano group; nitro group; C1-C 60 Alkyl group; C2-C 60 alkenyl group; C2-C 60 alkynyl group; C1-C 60 Alkoxy groups; each independently unsubstituted or replaced by deuterium, -F, cyano groups, C1-C 60 Alkyl groups, C1-C 60 C3-C substituted with alkoxy groups, phenyl groups, biphenyl groups, or any combination thereof 60 Carbocyclic groups or C1-C 60 Heterocyclic groups.

11. The light-emitting device of claim 8, wherein the emitting layer comprises a heterocyclic compound of formula 1. The electron transport region comprises a compound of formula 601: Formula 601 [On 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 in, In Equation 601, Ar 601 Each is independent of the others and is either unsubstituted or controlled by at least one R. 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups, L 601 Each is independent of the others and is either unsubstituted or controlled by at least one R. 10a Replacement of divalent C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Substituted divalent C1-C 60 Heterocyclic groups, xe11 is 1, 2, or 3. xe1 is 0, 1, 2, 3, 4, or 5. R 601 It is unsubstituted or by at least one R 10a Replacement C3-C 60 Carbocyclic groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, -Si(Q) 601 (Q) 602 (Q) 603 -C(=O)(Q) 601 -S(=O)2(Q) 601 ) or -P(=O)(Q 601 (Q) 602 ), xe21 is 1, 2, 3, 4, or 5. Ar 601 L 601 and R 601 One or more of them are each independently unsubstituted or by at least one R 10a Substituted C1-C nitrogen containing π-electron-deficient atoms 60 Cyclic groups, and R 10a yes: Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group or nitro group; Each of the following is independent and unsubstituted or replaced by deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 aryloxy group, C6-C 60 aryl thioyl groups, -Si(Q) 11 (Q) 12 (Q) 13 -N(Q) 11 (Q) 12 -B(Q) 11 (Q) 12 -C(=O)(Q) 11 -S(=O)2(Q) 11 -P(=O)(Q) 11 (Q) 12 C1-C substituted by (or any combination thereof) 60 Alkyl groups, C2-C 60 alkenyl groups, C2-C 60 alkynyl group or C1-C 60 alkoxy group; Each of the following is independent and unsubstituted or replaced by deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, C1-C 60 Alkyl groups, C2-C 60 alkenyl groups, C2-C 60 alkynyl group, C1-C 60 alkoxy group, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 aryloxy group, C6-C 60 aryl thioyl groups, -Si(Q) 21 (Q) 22 (Q) 23 -N(Q) 21 (Q) 22 -B(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q) 21 -P(=O)(Q) 21 (Q) 22 C3-C replaced by any combination thereof 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 aryloxy group or C6-C 60 aryl thioyl group; or -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ), or -P(=O)(Q 31 )(Q 32 ), Q 11 To Q 13 Q 21 To Q 23 Q 31 To Q 33 and Q 601 To Q 603 Each of the following is independent of the others: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl group; cyano group; nitro group; C1-C 60 Alkyl group; C2-C 60 alkenyl group; C2-C 60 alkynyl group; C1-C 60 Alkoxy groups; each independently unsubstituted or replaced by deuterium, -F, cyano groups, C1-C 60 Alkyl groups, C1-C 60 C3-C substituted with alkoxy groups, phenyl groups, biphenyl groups, or any combination thereof 60 Carbocyclic groups or C1-C 60 Heterocyclic groups.

12. The light-emitting device of claim 11, wherein the electron transport layer in the electron transport region comprises a compound of formula 601, and The electron transport layer further comprises a metallic material.

13. The light-emitting device of claim 12, wherein the material comprises a post-transition metal complex, an alkali metal complex, an alkaline earth metal complex, or any combination thereof.

14. The light-emitting device as claimed in claim 1, wherein Y1 and Y2 are each B.

15. The light-emitting device as claimed in claim 1, wherein formula 1-2 has formula 1-2-1 or formula 1-2-2: Equation 1-2-1 Equation 1-2-2 in, In equations 1-2-1 and 1-2-2, X 11 To X 14 Each independently possesses the same characteristics as X in claim 1. 11 To X 14 Same meaning, X 21 Is it N or C(R)? 21 ), X 22 Is it N or C(R)? 22 ), X 23 Is it N or C(R)? 23 ), X 24 Is it N or C(R)? 24 ), and X 25 Is it N or C(R)? 25 ), X 31 Is it N or C(R)? 31 ), X 32 Is it N or C(R)? 32 ), X 33 Is it N or C(R)? 33 ), X 34 Is it N or C(R)? 34 ), and X 35 Is it N or C(R)? 35 ), R 21 To R 25 and R 31 To R 35 Each independently possesses R as described in claim 1 10a The meaning, It has the meaning as described in claim 1. R 21 To R 25 Two or more adjacent groups in the form are optionally linked to each other to form an unsubstituted or R-shaped compound. 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups, and R 31 To R 35 Two or more adjacent groups in the form are optionally linked to each other to form an unsubstituted or R-shaped compound. 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups.

16. The light-emitting device as claimed in claim 1, wherein formula 1-2 is one of formulas 2-1 to 2-57: in, In equations 2-1 to 2-57, V1 to V4 are each independently either C or N. Z1 to Z5 are each independent of each other: Deuterium, -F, -Cl, -Br, -I, cyano group, C1-C 20 alkyl groups or C1-C 20 Alkoxy group; C1-C groups, each independently substituted with deuterium, -CD3, -CD2H, -CDH2, -F, -CF3, -CF2H, -CFH2, -Cl, -CCl3, -CCl2H, -CClH2, -Br, -CBr3, -CBr2H, -CBrH2, -I, -CI3, -CI2H, -CIH2, cyano groups, or any combination thereof. 20 alkyl groups or C1-C 20 Alkoxy group; Each independently of the other, unsubstituted or deuterated, -CD3, -CD2H, -CDH2, -F, -CF3, -CF2H, -CFH2, -Cl, -CCl3, -CCl2H, -CClH2, -Br, -CBr3, -CBr2H, -CBrH2, -I, -CI3, -CI2H, -CIH2, cyano groups, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, terphenyl group, C1-C 20 Alkylphenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracene group, thiophene group, furanyl group, indole group, isoindole group, indole group, carbazole group, benzofuranyl group, benzothiophene group, benzothiophene group, dibenzofuranyl group, dibenzothiophene group, dibenzothiophene group, benzofluorenyl group, benzocarbazole group, naphthobenzofuranyl group, naphthobenzothiophene group, naphthobenzofuranyl group Thiolyl group, dibenzofluorenyl group, dibenzocarbazoyl group, dinaphthofuranyl group, dinaphthothienyl group, dinaphthothiolyl group, indolecarbazoyl group, indolecarbazoyl group, benzofuranocarbazoyl group, benzothiophenocarbazoyl group, benzothiolocarbazoyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, indazoleyl group, purine group, quinolinyl group, isoquinolinyl group, benzoquinoline Benzyl group, benzoisoquinolinyl group, phthalazinyl group, naphthidyl group, quinoxalinyl group, benzoquinoxalinyl group, quinazolinyl group, benzoquinoxalinyl group, phenazinyl group, acridineyl group, phenanthrololinyl group, phenazinyl group, phenoxazinyl group, phenthiazinyl group, phenoxthiazinyl group, benzimidazole group, benzothiazolyl group, benziisothiazolyl group, benzoxazolyl group, benziisoxazolyl group, triazole Benzyl group, tetrazolyl group, thiadiazolyl group, oxadiazolyl group, triazine group, imidazopyridyl group, imidazopyrimidinyl group, oxazolylpyridyl group, thiazopyridyl group, benzonaphthyl group, azafluorenyl group, azaspiro-difluorenyl group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group, azadibenzothiophenyl group, indolepyrroleyl group, indolepyrroleyl group, -Si(Q) 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 -P(=O)(Q) 31 (Q) 32 ) or any combination thereof, substituted with cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, terphenyl group, C1-C 20 Alkylphenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthraceneyl group, thiophene group, furanyl group, indene group, isoindoleyl group, indoleyl group, carbazole group, benzofuranyl group, benzothiophene group, benzothiophene group, dibenzofuranyl group, dibenzothiophene group, dibenzothiophene group, benzofluorenyl group, benzocarbazole group, naphthobenzofuranyl group, naphthobenzothiophene group, naphthobenzo benzo[a]thiopyrrolyl group, dibenzo[a]fluorenyl group, dibenzo[a]carbazoleyl group, dinaphthofuranyl group, dinaphthothiophenyl group, dinaphthothiopyrrolyl group, indole[a]carbazoleyl group, indole[a]carbazoleyl group, benzo[a]furan[a]carbazoleyl group, benzo[a]thiophen[a]carbazoleyl group, benzo[a]thiopyrrol[a]carbazoleyl group, pyridyl group, pyrimidinyl group, pyridazinyl group, indazoleyl group, purineyl group, quinolinyl group, isoquinolinyl group, benzo[a]quinolone Phinyl group, benzisoquinolinyl group, phthalazinyl group, naphthidyl group, quinoxalinyl group, benzoquinoxalinyl group, quinazolinyl group, benzoquinazolinyl group, phenanthidyl group, acridineyl group, phenanthrololinyl group, phenazinyl group, phenoxazinyl group, phenthiazinyl group, phenoxthiazyl group, benzimizolyl group, benzothiazolyl group, benzisothiazolyl group, benzooxazolyl group, benzisooxazolyl group, Triazolyl group, tetrazolyl group, thiadiazolyl group, oxadiazolyl group, triazinyl group, imidazopyridyl group, imidazopyrimidyl group, oxazolylpyridyl group, thiazopyridyl group, benzonaphthyl group, azafluorenyl group, azaspiro-difluorenyl group, azacarbazoyl group, azadibenzofuranyl group, azadibenzothiophenyl group, azadibenzothiophenyl group, indenepyrroleyl group or indolepyrroleyl group; or -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), Among them, Q1 to Q3 and Q 31 To Q 33 Each of these groups independently represents hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl group; cyano group; nitro group; C1-C 60 Alkyl group; C2-C 60 alkenyl group; C2-C 60 alkynyl group; C1-C 60 Alkoxy groups; each independently unsubstituted or replaced by deuterium, -F, cyano groups, C1-C 60 Alkyl groups, C1-C 60 C3-C substituted with alkoxy groups, phenyl groups, biphenyl groups, or any combination thereof 60 Carbocyclic groups or C1-C 60 Heterocyclic groups, e2 is an integer between 0 and 2. e3 is an integer from 0 to 3. e4 is an integer from 0 to 4. e5 is an integer from 0 to 5. e7 is an integer from 0 to 7. e11 is an integer from 0 to 11, and Indicates the binding site with adjacent groups.

17. The light-emitting device as claimed in claim 1, wherein formula 1-1 has formula 1-1-1: Formula 1-1-1 in, In equation 1-1-1, CY1, CY2, X1 to X4, Y1, Y2, Ar1 to Ar 10 R1, R2, a1, and a2 independently have the same meaning as in claim 1. R 3a and R 3b Each of them independently has the same meaning as R3 in claim 1, and R 4a and R 4b They each have the same meaning as R4 in claim 1, and are independent of each other.

18. The light-emitting device of claim 1, wherein the light-emitting device further includes a covering layer outside the first electrode or the second electrode, and The capping layer comprises one or more carbocyclic compounds, heterocyclic compounds, amine-based compounds, porphyrin derivatives, phthalocyanine derivatives, naphthalene phthalocyanine derivatives, alkali metal complexes, alkaline earth metal complexes, or any combination thereof.

19. An electronic device comprising the light-emitting device according to any one of claims 1 to 18.

20. The electronic device of claim 19, further comprising a thin-film transistor, wherein... 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 at least one of the source electrode and the drain electrode of the thin-film transistor.

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