Organometallic compound, light-emitting device including the same, and electronic device

Abstract

An organometallic compound represented by Formula 1, a light-emitting device comprising the organometallic compound, and an electronic device comprising the light-emitting device are provided: [Formula 1] Each substituent in Formula 1 is the same as that described in the specification.

Description

[0001] Cross-references to related applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2021-0037436, filed with the Korean Intellectual Property Office on March 23, 2021, the entire contents of which are incorporated herein by reference. Technical Field

[0003] The implementation scheme relates to organometallic compounds, light-emitting devices comprising said organometallic compounds, and electronic devices comprising said light-emitting devices. Background Technology

[0004] Organic light-emitting devices (OLEDs) are self-emitting devices that offer wide viewing angles, high contrast, short response times, and superior characteristics in brightness, driving voltage, and response speed compared to devices in related fields, while also producing full-color images.

[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] It should be understood that this background section is intended to provide some useful context for understanding the art. However, this background section may also include ideas, concepts, or knowledge that were not known or understood by a person skilled in the art prior to the relevant valid application date of the subject matter disclosed herein. Summary of the Invention

[0007] An organometallic compound is provided, which results in a light-emitting device having characteristics of low driving voltage, high brightness, high luminous efficiency and long lifespan due to the inclusion of the organometallic compound, as well as an electronic device including the light-emitting device.

[0008] Other aspects will be set forth in part in the description which follows and will be apparent in part from the description, or may be learned by practice of embodiments of this disclosure.

[0009] The organometallic compound according to the embodiments of this disclosure can be represented by Formula 1.

[0010] [Formula 1]

[0011]

[0012] In Equation 1,

[0013] M1 and M2 can each be independently platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm).

[0014] A1 to A4 and B1 to B4 can each be independently C5-C 60 Carbocyclic groups or C1-C 60 Heterocyclic groups,

[0015] Y 10 To Y 12 Y 20 To Y 22 Y 30 To Y 32 Y 40 To Y 42 Y 50 To Y 52 Y 60 To Y 62 Y 70 To Y 72 and Y 80 To Y 82 Each can be C or N independently.

[0016] T1 and T2 can each be a single bond, *-O-*', *-S-*', *-C(R1)(R2)-*', *-C(R1)=*', *=C(R1)-*', *-C(R1)=C(R2)-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R1)-*', *-N(R1)-*', *-P(R1)-*', *-Si(R1)(R2)-*', or *-Ge(R1)(R2)-*'.

[0017] L 10 It can be unsubstituted or replaced 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,

[0018] a10 can be 1, 2, 3, 4, or 5.

[0019] R1, R2, R 10 R 20 R 30 R 40 R 50 R60 R 70 and R 80 Each of these groups can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone 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 10 Cycloalkyl groups, unsubstituted or with at least one R 10a Replacement C1-C 10 Heterocyclic alkyl groups, unsubstituted or with at least one R 10a Replacement C3-C 10 Cycloalkenyl groups, unsubstituted or with at least one R 10a Replacement C1-C 10 Heterocyclic alkenyl groups, unsubstituted or with at least one R 10a Replacement C6-C 60 aryl group, 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 group, unsubstituted or with at least one R 10a Replacement C1-C 60 heteroaryl groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Heteroaryl groups, unsubstituted or with at least one R 10a Replacement C1-C 60 heteroaryl thiols, unsubstituted or with at least one R 10a Substituted monovalent non-aromatic fused polycyclic groups, unsubstituted or substituted with at least one R 10a Substituted monovalent nonaromatic fused heterocyclic groups, -Si(Q 41 (Q) 42 (Q) 43 -N(Q) 41 (Q) 42 -B(Q) 41 (Q) 42 -C(=O)(Q) 41 -S(=O)2(Q) 41 ) or -P(=O)(Q 41 (Q) 42 ),

[0020] R1, R2, R 10 R 20 R 30 R 40 R 50 R 60 R 70 and R 80 Two adjacent substituents in the form can optionally be connected to each other to form an unsubstituted or substituted form 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,

[0021] b10, b20, b30, b40, b50, b60, b70, and b80 can each independently be 1, 2, 3, 4, 5, 6, 7, or 8.

[0022] * and *' represent the binding sites with adjacent atoms, and

[0023] R 10a It could be:

[0024] Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group or nitro group;

[0025] 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 thiols, C1-C 60 heteroaryloxy groups, C1-C 60 heteroaryl thiols, -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;

[0026] 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 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 aryloxy group, C6-C 60 aryl thiols, C1-C 60 heteroaryloxy groups, C1-C 60 heteroaryl thiols, -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, C6-C 60 aryl thiols, C1-C 60 heteroaryloxy groups or C1-C 60 heteroaryl thiols; or

[0027] -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 ),

[0028] Q 11 To Q 13 Q 21 To Q 23 Q 31 To Q 33 And Q41 To Q 43 Each 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.

[0029] In the implementation scheme, M1 and M2 can each be Pt or Pd independently.

[0030] In the implementation scheme, A1 to A4 can each be a 5-membered heterocyclic group independently or can each be a polycyclic C1-C containing a 5-membered heterocyclic group independently. 30 Heterocyclic groups.

[0031] In the implementation scheme, A1 and A4 may each be independently a group represented by one of Formulas 3-1 to 3-3 as explained below, and A2 and A3 may each be independently a group represented by one of Formulas 3-4 and 3-5 as explained below.

[0032] In the implementation plan, M1 and Y 10 The key between them can be a coordinate key, M1 and Y 20 The bond between them can be a coordinate bond, M2 and Y 30 The bond between them can be a coordinate bond, M2 and Y 40 The key between them can be a coordinate key, M1 and Y 50 The bond between them can be a covalent bond, M1 and Y 60 The bond between them can be a covalent bond, M2 and Y 70 The bond between them can be a covalent bond, or a bond between M2 and Y. 80 The bonds between them can be covalent bonds.

[0033] In the implementation scheme, T1 and T2 can each be *-O-*' or *-S-*' independently.

[0034] In the implementation plan, L 10 It can be unsubstituted or replaced by at least one R 10a Replacement C1-C 20 alkylene groups, unsubstituted or with at least one R 10a Replacement C2-C20 alkenyl groups, unsubstituted or with at least one R 10a Replacement C2-C 20 The ynyl group, unsubstituted or with at least one R 10a Replacement C3-C 10 Cycloalkyl groups, unsubstituted or with at least one R 10a Replacement C1-C 10 Heterocyclic alkyl groups, unsubstituted or with at least one R 10a Replacement C3-C 10 Cycloalkylene groups, unsubstituted or with at least one R 10a Replacement C1-C 10 Heterocyclic alkenyl groups, unsubstituted or with at least one R 10a Replacement C6-C 60 arylene groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Heteroaryl groups, unsubstituted or with at least one R 10a Substituted divalent non-aromatic fused polycyclic groups, or unsubstituted or substituted with at least one R 10a Substituted divalent nonaromatic fused heterocyclic groups.

[0035] In the implementation plan, L 10 It can be a group represented by one of the formulas 4-1 to 4-3 as explained below.

[0036] In the implementation plan, R1, R2, R 10 R 20 R 30 R 40 R 50 R 60 R 70 and R 80 These can be, independently: hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, C1-C 20 alkyl groups or C1-C 20 An alkoxy group; or a C1-C group, each substituted with a deuterium, -F, -Cl, -Br, -I, cyano group, phenyl group, biphenyl group, or any combination thereof. 20 alkyl groups or C1-C 20 An alkoxy group; or a group represented by one of formulas 5-1 to 5-26 and 6-1 to 6-55 as explained below. R1, R2, R 10 R 20 R 30 R 40 R 50 R 60 R70 and R 80 Two or more adjacent groups may optionally be connected to each other to form a cyclopentyl group, a cyclohexyl group, a phenyl group, a naphthyl group, a fluorene group, a pyridine group, a pyrimidine group, a triazine group, or a carbazole group.

[0037] In an embodiment, the organometallic compound may be represented by one of Formulas 11-1 to 11-3 as explained below.

[0038] In an embodiment, the organometallic compound may be electrically neutral.

[0039] In an embodiment, the organometallic compound may be one of compounds BD1 to BD104, as explained below.

[0040] Another aspect of this disclosure provides a light-emitting device that may include a first electrode, a second electrode facing the first electrode, an intermediate layer disposed between the first electrode and the second electrode and including an emitting layer, and the organometallic compound.

[0041] In this embodiment, the first electrode may be an anode, the second electrode may be a cathode, and the intermediate layer may further include a hole transport region disposed between the first electrode and the emitter layer, and an electron transport region disposed between the emitter layer and the second electrode. The hole transport region may include a hole injection layer, a hole transport layer, an emitter auxiliary layer, an electron blocking layer, or any combination thereof, and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0042] In an implementation, the emitter layer may contain the organometallic compound.

[0043] In an embodiment, the emitter layer may comprise a host and a dopant, and the dopant may comprise the organometallic compound.

[0044] In an embodiment, the hole transport region may further comprise a p-dopant having a lowest unoccupied molecular orbital (LUMO) energy level equal to or less than about -3.5 eV.

[0045] In an embodiment, the electron transport region may include the electron transport layer and the electron injection layer. At least one of the electron transport layer and the electron injection layer may contain alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof.

[0046] Another aspect of this disclosure provides an electronic device that may include a light-emitting device.

[0047] In one embodiment, the electronic device may further include a thin-film transistor. The thin-film transistor may include a source electrode and a drain electrode, and the first electrode of the light-emitting device may be electrically connected to the source electrode or the drain electrode. Attached Figure Description

[0048] The above and other aspects and features of this disclosure will become more apparent from the detailed description of embodiments thereof with reference to the accompanying drawings, in which:

[0049] Figure 1 This is a schematic cross-sectional view of the light-emitting device according to the implementation scheme;

[0050] Figure 2 It is a schematic cross-sectional view of an electronic device according to the implementation scheme; and

[0051] Figure 3 It is a schematic cross-sectional view of an electronic device according to the implementation scheme. Detailed Implementation

[0052] This disclosure will now be described more fully below with reference to the accompanying drawings, in which embodiments are illustrated. However, this disclosure may be implemented in various forms and should not be construed as being limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully communicate the scope of this disclosure to those skilled in the art.

[0053] In the accompanying drawings, the size, thickness, scale, and dimensions of the components may be enlarged for ease of description and clarity. The same numbers throughout refer to the same components.

[0054] In the description, it should be understood that when an element (or area, layer, component, etc.) is described as being "on," "connected to," or "attached to" another element, it can be directly on, directly connected to, or directly attached to the other element, or one or more intermediate elements may exist therein. In a similar sense, when an element (or area, layer, component, etc.) is described as "covering" another element, it can directly cover the other element, or one or more intermediate elements may exist therein.

[0055] In the description, when an element is "directly on" another element, "directly connected to" another element, or "directly linked to" another element, there is no intermediate element. For example, "directly on" can mean setting two layers or two elements without any additional elements in between, such as adhesive elements.

[0056] As used herein, expressions such as “a”, “an” and “the” used for the singular are intended to also include the plural form, unless the context clearly indicates otherwise.

[0057] As used herein, the term “and / or” includes any and all combinations of one or more of the related listed items. For example, “A and / or B” can be understood to mean “A, B, or A and B”. The terms “and” and “or” can be used in the sense of conjunctions or antonymous conjunctions and can be understood as equivalent to “and / or”.

[0058] In the specification and claims, for purposes of meaning and interpretation, the term "at least one of..." is intended to include the meaning of "at least one selected from the group consisting of...". For example, "at least one of A and B" can be understood to mean "A, B, or A and B". When preceding a list of elements, the term "at least one of..." modifies the entire list of elements without modifying any individual element in the list.

[0059] When implementing different schemes, the specific process sequence may differ from the described order. For example, two processes described as consecutive may be performed substantially simultaneously, or they may be performed in the reverse order of their description.

[0060] It should be understood that although the terms first, second, etc., may be used herein to describe various elements, these elements should not be limited by these terms. These terms are used only to distinguish one element from another. Therefore, without departing from the teachings of this disclosure, a first element may be referred to as a second element. Similarly, without departing from the scope of this disclosure, a second element may be referred to as a first element.

[0061] As used herein, the term "intermediate layer" refers to a single layer or multiple layers between the first electrode and the second electrode of the light-emitting device.

[0062] For ease of description, the spatial relative terms “below,” “under,” “lower,” “above,” “upper,” etc., may be used herein to describe the relationship between one element or component and another, as illustrated in the accompanying drawings. It should be understood that the spatial relative terms are intended to cover different orientations of the device during use or operation, other than those depicted in the drawings. For example, where the device illustrated in the drawings is flipped, a device located “below” or “under” another device may be placed “above” another device. Thus, the exemplary term “below” can include both a lower position and an upper position. The device may also be oriented in other directions, and therefore the spatial relative terms may be interpreted differently depending on the orientation.

[0063] As used herein, the terms “about” or “approximately” include a specified value and mean within an acceptable range of deviation from the value as determined by a person skilled in the art taking into account the relevant measurements and errors associated with the measurement of the quantity (i.e., limitations of the measurement system). For example, “about” may mean within one or more standard deviations, or within ±20%, ±10%, or ±5% of the specified value.

[0064] It should be understood that the terms “comprises,” “comprising,” “includes,” “including,” “have,” “having,” “contains,” “containing,” etc., are intended to indicate the presence of the features, integers, steps, operations, elements, components, or combinations thereof specified in this disclosure, but do not exclude the presence or addition of one or more other features, integers, steps, operations, elements, components, or combinations thereof.

[0065] Unless otherwise defined or implied herein, all terms used (including technical and scientific terms) have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure pertains. It should be further understood that terms (e.g., those defined in common dictionaries) should be interpreted as having a meaning consistent with their meaning in the context of the relevant field and should not be interpreted in an idealized or overly formal sense unless expressly defined in the specification.

[0066] According to aspects of this disclosure, organometallic compounds can be represented by Formula 1:

[0067] [Formula 1]

[0068]

[0069] In Equation 1, M1 and M2 can each be independently platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), or thulium (Tm).

[0070] In the implementation scheme, M1 and M2 can each be Pt or Pd independently.

[0071] In Equation 1, A1 to A4 and B1 to B4 can each be independently C5-C. 60 Carbocyclic groups or C1-C 60 Heterocyclic groups.

[0072] In the implementation scheme, A1 to A4 can each be a 5-membered heterocyclic group independently or can each be a polycyclic C1-C containing a 5-membered heterocyclic group independently. 30 Heterocyclic groups.

[0073] In the implementation scheme, A1 to A4 and B1 to B4 can each independently be a phenyl group, naphthyl group, anthracene group, phenanthrene group, chamomile ring group, benzo[a]phenanthrene group, pyrene group, etc. Groups, cyclopentadienyl group, 1,2,3,4-tetrahydronaphthyl group, furan group, thiophene group, thiophene group, indene group, fluorene group, indole group, carbazole group, benzofuran group, dibenzofuran group, benzothiophene group, dibenzothiophene group, benzothiophene group, dibenzothiophene group, indolepyridine group, indolepyridine group, benzofuranpyridine group, benzothiophenepyridine group, benzothiophenepyridine group, indolepyrimidine group, indolepyrimidine group, benzofuranpyrimidine group, benzothiophenepyrimidine group, benzothiophenepyrimidine group, dihydropyridine group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazolinine group, phenanthrenepyridine group, pyrrole group, pyrazolyl group The group includes: imidazole group, 2,3-dihydroimidazolium group, triazole group, 2,3-dihydrotriazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, pyrazolopyridine group, furanopyrazole group, thienopyrazole group, benzimidazole group, 2,3-dihydrobenzimidazole group, imidazopyridine group, 2,3-dihydroimidazopyridine group, furanopyrazole group, thienopyrazole group, imidazopyrimidine group, 2,3-dihydroimidazopyrimidine group, imidazopyrazine group, 2,3-dihydroimidazopyrazine group, benzoxazole group, benzothiazole group, benzooxadiazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group or 5,6,7,8-tetrahydroquinoline group.

[0074] In the implementation scheme, A1 to A4 can each independently be a pyrrole group, a pyrazole group, an imidazole group, a 2,3-dihydroimidazolium group, a triazole group, a 2,3-dihydrotriazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a pyrazolium group, a furanopyrazole group, a thiophene pyrazole group, a benzimidazole group, a 2,3-dihydrobenzimidazole group, an imidazopyridine group, a 2,3-dihydroimidazopyridine group, a furanopyrazole group, a thiophene pyridine group, a furanopyrazole group, a thiophene pyrazole group, an imidazopyrimidine group, a 2,3-dihydroimidazopyrimidine group, an imidazopyrazine group, a 2,3-dihydroimidazopyrazine group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, or a benzothiadiazole group.

[0075] In the implementation plan, B1 to B4 can each independently be a phenyl group, a naphthyl group, a phenanthrene group, a fluoranthene group, a benzo[a]phenanthrene group, a pyrene group, etc. Group, imidazole group, 2,3-dihydroimidazolium group, imidazopyrimidine group, benzimidazole group, indene group, fluorene group, spiro-difluorene group, benzo[fluorene] group, dibenzo[fluorene] group, indole group, pyridine group, pyrimidine group, carbazole group, benzo[carbazole] group, dibenzo[carbazole] group, azacarbazole group, furan group, benzo[furan] group, dibenzo[furan] group, azadibenzo[furan] group, naphtho[furan] group, benzo[naphtho[furan] group, dinaphtho[furan] group, thiophene group, benzo[thiophene] group, dibenzo[thiophene] group, azadibenzo[thiophene] group, naphtho[thiophene] group, benzo[naphtho[thiophene] group or dinaphtho[thiophene] group.

[0076] In the implementation scheme, A1 to A4 and B1 to B4 can each be independently represented by a group from Formula 2-1 to Formula 2-43.

[0077]

[0078]

[0079]

[0080] In equations 2-1 to 2-43,

[0081] X 21 To X 23 Each can be C(Z) independently. 24 ) or C-*, where X 21 To X 23 At least two of them can be C-*.

[0082] X 24 It can be N-*, and X 25 and X 26Each can be C(Z) independently. 24 ) or C-*, where X 25 and X 26 At least one of them can be C-*,

[0083] X 27 and X 28 They can be N and N(Z) independently. 25 ) or N-*, and X 29 It can be C(Z) 24 ) or C-*. X 27 and X 28 At least one of them can be N-*, and X 29 It can be C-*; or X 27 and X 28 Each can be N-*, and X 29 It can be C(Z) 24 ),

[0084] Z 21 To Z 25 They can be independently related to R. 10 The descriptions are the same.

[0085] c21 can be 1, 2, or 3.

[0086] c22 can be 1, 2, 3, 4 or 5.

[0087] c23 can be 1, 2, 3, or 4.

[0088] c24 can be 1 or 2, and

[0089] * indicates a binding site with an adjacent atom.

[0090] In the implementation plan, Z in Equations 2-1 to 2-43 21 To Z 25 These can be, independently: hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, C1-C 20 alkyl groups or C1-C 20 Alkoxy group;

[0091] C1-C groups each substituted with deuterium, -F, -Cl, -Br, -I, cyano group, phenyl group, biphenyl group, or any combination thereof 20 alkyl groups or C1-C 20 Alkoxy group;

[0092] Phenyl group, biphenyl group, triphenyl group, pentanyl group, indole group, naphthyl group, chamomile cycloyl group, indoleyl group, acenaphthenic group, fluorenyl group, spiro-difluorenyl group, benzo[a]fluorenyl group, dibenzo[a]fluorenyl group, carbazole group, acridine group, dibenzofuranyl group, dibenzothiophenyl group, benzo[a]carbazoleyl group or dibenzo[a]carbazoleyl group;

[0093] Each is associated with a deuterium, -F, -Cl, -Br, -I, cyano group, or C1-C group. 20 Alkyl groups, C1-C 20 Alkoxy group, phenyl group, biphenyl group or any combination thereof substituted with phenyl group, biphenyl group, terphenyl group, pentanenyl group, indole group, naphthyl group, chamomile cycloyl group, indoleyl group, acenaphthenic group, fluorenyl group, spiro-difluorenyl group, benzo[a]fluorenyl group, dibenzo[a]fluorenyl group, carbazole group, acridine group, dibenzofuranyl group, dibenzothiophenyl group, benzo[a]carbazoleyl group or dibenzo[a]carbazoleyl group; or

[0094] -Si(Q 41 (Q) 42 (Q) 43 ) or -N(Q 41 (Q) 42 Q 41 Q 42 and Q 43 Each can be independently identical to that described in this specification.

[0095] In the implementation scheme, A1 to A4 can each be independently represented by one of the groups from Formula 2-10 to Formula 2-43.

[0096] In the implementation scheme, A1 and A4 can each be independently represented by a group of one of formulas 3-1 to 3-3, and A2 and A3 can each be independently represented by a group of one of formulas 3-4 and 3-5.

[0097]

[0098] In equations 3-1 to 3-5,

[0099] X 31 To X 39 Each can be C(Z) independently. 32 ) or N,

[0100] Z 31 and Z 32 They can be independently related to R. 10 The same description, and

[0101] *, *', and *" each represent a binding site with an adjacent atom.

[0102] In the implementation plan, Z in Equations 3-1 to 3-5 31 and Z 32 These can be, independently: hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, C1-C 20 alkyl groups or C1-C 20 Alkoxy group;

[0103] C1-C groups each substituted with deuterium, -F, -Cl, -Br, -I, cyano group, phenyl group, biphenyl group, or any combination thereof 20 alkyl groups or C1-C 20 Alkoxy group;

[0104] Phenyl group, biphenyl group, triphenyl group, pentanyl group, indole group, naphthyl group, chamomile cycloyl group, indoleyl group, acenaphthenic group, fluorenyl group, spiro-difluorenyl group, benzo[a]fluorenyl group, dibenzo[a]fluorenyl group, carbazole group, acridine group, dibenzofuranyl group, dibenzothiophenyl group, benzo[a]carbazoleyl group or dibenzo[a]carbazoleyl group;

[0105] Each is associated with a deuterium, -F, -Cl, -Br, -I, cyano group, or C1-C group. 20 Alkyl groups, C1-C 20 Alkoxy group, phenyl group, biphenyl group or any combination thereof substituted with phenyl group, biphenyl group, terphenyl group, pentanenyl group, indole group, naphthyl group, chamomile cycloyl group, indoleyl group, acenaphthenic group, fluorenyl group, spiro-difluorenyl group, benzo[a]fluorenyl group, dibenzo[a]fluorenyl group, carbazole group, acridine group, dibenzofuranyl group, dibenzothiophenyl group, benzo[a]carbazoleyl group or dibenzo[a]carbazoleyl group; or

[0106] -Si(Q 41 (Q) 42 (Q) 43 ) or -N(Q 41 (Q) 42 ), where Q 41 Q 42 and Q 43 Each can be independently identical to that described in this specification.

[0107] In Equation 1, Y 10 To Y 12 Y 20 To Y 22 Y 30 To Y 32 Y 40 To Y42 Y 50 To Y 52 Y 60 To Y 62 Y 70 To Y 72 and Y 80 To Y 82 Each can be either C or N independently.

[0108] In the implementation plan, Y 50 Y 60 Y 70 and Y 80 Each can be C.

[0109] In the implementation plan, Y 10 and Y 20 Each can be C.

[0110] In the implementation plan, M1 and Y 10 The key between them can be a coordinate key, M1 and Y 20 The bond between them can be a coordinate bond, M2 and Y 30 The bond between them can be a coordinate bond, M2 and Y 40 The key between them can be a coordinate key, M1 and Y 50 The bond between them can be a covalent bond, M1 and Y 60 The bond between them can be a covalent bond, M2 and Y 70 The bond between them can be a covalent bond, or a bond between M2 and Y. 80 The bonds between them can be covalent bonds.

[0111] In Equation 1, T1 and T2 can each be a single bond, *-O-*', *-S-*', *-C(R1)(R2)-*', *-C(R1)=*', *=C(R1)-*', *-C(R1)=C(R2)-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R1)-*', *-N(R1)-*', *-P(R1)-*', *-Si(R1)(R2)-*', or *-Ge(R1)(R2)-*'.

[0112] In the implementation scheme, T1 and T2 can each be *-O-*' or *-S-*' independently.

[0113] In Equation 1, L 10 It can be unsubstituted or replaced 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.

[0114] In the implementation plan, L 10 It can be unsubstituted or replaced 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 C2-C 20 The ynyl group, unsubstituted or with at least one R 10a Replacement C3-C 10 Cycloalkyl groups, unsubstituted or with at least one R 10a Replacement C1-C 10 Heterocyclic alkyl groups, unsubstituted or with at least one R 10a Replacement C3-C 10 Cycloalkylene groups, unsubstituted or with at least one R 10a Replacement C1-C 10 Heterocyclic alkenyl groups, unsubstituted or with at least one R 10a Replacement C6-C 60 arylene groups, unsubstituted or with at least one R 10a Replacement C1-C 60 Heteroaryl groups, unsubstituted or with at least one R 10a Substituted divalent non-aromatic fused polycyclic groups, or unsubstituted or substituted with at least one R 10a Substituted divalent nonaromatic fused heterocyclic groups.

[0115] In the implementation plan, L 10 It can be: phenylene group, pentylene group, indenyl group, naphthyl group, chamomile cycloyl group, heptylene group, adamantyl group, acenaphthene group, fluorene group, spiro-difluorene group, spiro-fluorene-benzofuranyl group, benzo[a]fluorene group, dibenzo[a]fluorene group, phenanthroline group, anthracene group, fluorenyl anthracene group, benzo[a]phenanthrene group, pyrene group, etc. Benzyl group, tetraphenyl group, puryl group, peryl group, pentaphenyl group, hexaphenyl group, pentaphenyl group, rubidyl group, styrophenyl group, pyrrolyl group, thiophene group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyridinyl group, iso-indoleyl group, indoleyl group, indazoleyl group, purineyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthidyl group Group, quinoxalinyl group, quinoxalinyl group, phenanthrenepyridine group, phenanthrene-rheinyl group, phenanthrenepyridine group, phenanthrenepyridine group, benzoimidazole group, benzofuranyl group, benzothiophene group, isobenzothiazolyl group, benzooxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiaphenyl group, dibenzothiarolyl group, benzocarbazolyl group, dibenzocarbazolyl group, thiazolyldiazolyl group, imidazopyridyl group or imidazopyrimidinyl group; or

[0116] Each is associated with a deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, or C1-C group. 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, pentanenyl group, indole group, naphthyl group, chamomile cycloyl group, heptanenyl group, indoleyl group, acenaphthenic group, fluorenyl group, spiro-difluorenyl group, benzo[a]fluorenyl group, dibenzo[a]fluorenyl group, phenanthreneyl group, anthraceneyl group, fluoranthraceneyl group, benzo[a]phenanthreneyl group, pyrene group, Benzyl group, tetraphenyl group, furanyl group, perylyl group, pentaphenyl group, hexaphenyl group, pentaphenyl group, rutinyl group, kosyl group, ovoidyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazole group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, isoindoleyl group, indoleyl group, indazole group, purine group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthidyl group, quin Oxalinyl group, quinazolinyl group, cyclolinyl group, carbazole group, phenanthridine group, acridine group, phenanthroline group, phenazinyl group, benzimidazole group, benzofuranyl group, benzothiophene group, isobenzothiazolyl group, benzooxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophene group, dibenzothiophene group, benzocarbazole group, dibenzocarbazole group, thiadiazolyl group, imidazopyridyl group, imidazopyrimidine 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 The substituted groups (or any combination thereof) include phenylene groups, pentylene groups, indenyl groups, naphthyl groups, chamomile cycloyl groups, heptylene groups, adamantyl groups, acenaphthene groups, fluorene groups, spiro-difluorene groups, spiro-fluorene-benzofuranyl groups, benzo[a]fluorene groups, dibenzo[a]fluorene groups, phenanthroline groups, anthracene groups, fluorenyl anthracene groups, benzo[a]phenanthrene groups, pyrene groups, etc. Benzyl group, tetraphenyl group, puryl group, peryl group, pentaphenyl group, hexaphenyl group, pentaphenyl group, rubidyl group, styrophenyl group, pyrrolyl group, thiophene group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyridazinyl group, isoindoleyl group, indoleyl group, indazoleyl group, purineyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthidine The following groups are included: quinoxalinyl group, quinoxalinyl group, quinoxalinyl group, quinoxalinyl group, carbazoyl group, phenanthridine group, acridine group, phenanthridine group, benzimidazole group, benzifuranyl group, benzithiophene group, isobenzothiazolyl group, benzioxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiaphenyl group, dibenzothiarolyl group, benzicarbazolyl group, dibenzocarbazolyl group, thiazodiazole group, imidazopyridyl group, or imidazopyrimidine group.

[0117] In the implementation plan, Q 31 To Q 33 Each can be C1-C independently. 10 Alkyl groups, C1-C 10 alkoxy groups, phenyl groups, C1-C 10 Alkyl groups substituted with phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, pyridyl groups, pyrimidinyl groups, triazine groups, quinolinyl groups, or isoquinolinyl groups.

[0118] In the implementation plan, L 10 It can be a group represented by one of Formulas 4-1 to 4-3:

[0119]

[0120] In equations 4-1 to 4-3,

[0121] Y 91 It can be C(R) 91 ) or N, Y 92 It can be C(R) 92 ) or N, Y 93 It can be C(R) 93 ) or N, and Y 94 It can be C(R) 94 ) or N,

[0122] R91 To R 94 They can be independently related to R. 10a The same description, and

[0123] * and *' each represent a bonding site with an adjacent atom. R 10a It can be the same as described in this specification.

[0124] In Equation 1, a10 can be 1, 2, 3, 4 or 5.

[0125] In the implementation scheme, a10 can be 1 or 2.

[0126] In the implementation scheme, a10 can be 1.

[0127] In Equation 1, R1, R2, R 10 R 20 R 30 R 40 R 50 R 60 R 70 and R 80 Each of these groups can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amido group, hydrazine group, hydrazone 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 10 Cycloalkyl groups, unsubstituted or with at least one R 10a Replacement C1-C 10 Heterocyclic alkyl groups, unsubstituted or with at least one R 10a Replacement C3-C 10 Cycloalkenyl groups, unsubstituted or with at least one R 10a Replacement C1-C 10 Heterocyclic alkenyl groups, unsubstituted or with at least one R 10a Replacement C6-C 60 aryl group, 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 group, unsubstituted or with at least one R 10a Replacement C1-C 60 heteroaryl groups, unsubstituted or with at least one R 10aReplacement C1-C 60 Heteroaryl groups, unsubstituted or with at least one R 10a Replacement C1-C 60 heteroaryl thiols, unsubstituted or with at least one R 10a Substituted monovalent non-aromatic fused polycyclic groups, unsubstituted or substituted with at least one R 10a Substituted monovalent nonaromatic fused heterocyclic groups, -Si(Q 41 (Q) 42 (Q) 43 -N(Q) 41 (Q) 42 -B(Q) 41 (Q) 42 -C(=O)(Q) 41 -S(=O)2(Q) 41 ) or -P(=O)(Q 41 (Q) 42 ),as well as

[0128] R1, R2, R 10 R 20 R 30 R 40 R 50 R 60 R 70 and R 80 Two adjacent substituents in the form can optionally be connected to each other to form an unsubstituted or substituted form 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.

[0129] In the implementation plan, R1, R2, R 10 R 20 R 30 R 40 R 50 R 60 R 70 and R 80 Each of these can be independently: hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, or cyano group;

[0130] C1-C 20 Alkyl groups, C2-C 20 alkenyl groups, C2-C 20 alkynyl group or C1-C 20 Alkoxy group;

[0131] Each is replaced by deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, pyridyl group, pyrimidinyl 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 C1-C substituted by (or any combination thereof) 20 Alkyl groups, C2-C 20 alkenyl groups, C2-C 20 alkynyl group or C1-C 20 Alkoxy group;

[0132] Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, pentanenyl group, indole group, naphthyl group, fluorenyl group, spiro-difluorenyl group, benzo[a]fluorenyl group, dibenzo[a]fluorenyl group, phenanthroline group, anthraceneyl group, fluoranthraceneyl group, benzo[a]phenanthryl group, pyrene group, Benzyl group, pyrrolyl group, furanyl group, thiophenyl group, imidazole group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indoleyl group, indazole group, purine group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthidyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, Carbazolyl group, phenanthridine group, acridine group, phenanthrolinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, benzothiazolyl group, isobenzothiazolyl group, benzooxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridyl group or imidazopyrimidinyl group; or

[0133] Each is associated with a deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, or C1-C group. 20 Alkyl groups, C2-C 20 alkenyl groups, C2-C 20 alkynyl group, C1-C 20 Alkoxy groups, cyclopentyl groups, cyclohexyl groups, cycloheptyl groups, cyclooctyl groups, adamantyl groups, norbornyl groups, norbornenyl groups, cyclopentenyl groups, cyclohexenyl groups, cycloheptenyl groups, phenyl groups, pentanenyl groups, indole groups, naphthyl groups, fluorenyl groups, spiro-difluorenyl groups, benzo[a]fluorenyl groups, dibenzo[a]fluorenyl groups, phenanthroline groups, anthraceneyl groups, fluoranthraceneyl groups, benzo[a]phenanthreneyl groups, pyrene groups, Benzyl group, pyrrolyl group, furanyl group, thiophenyl group, imidazole group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indoleyl group, indazole group, purine group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthidyl group, quinoxalinyl group, quinazolinyl group, cyclophosphinyl group, carbazole Benzyl group, phenanthridine group, acridine group, phenanthrolinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, benzothiazolyl group, isobenzothiazolyl group, benzooxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazine group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazole group, dibenzocarbazole group, imidazopyridyl group, imidazopyrimidine 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 The cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, pentanenyl group, indole group, naphthyl group, fluorenyl group, spiro-difluorenyl group, benzo[a]fluorenyl group, dibenzo[a]fluorenyl group, phenanthyl group, anthraceneyl group, fluoranthraceneyl group, benzo[a]phenanthryl group, pyrene group, or any combination thereof substituted with the following groups: Benzyl group, pyrrolyl group, furanyl group, thiophenyl group, imidazole group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indoleyl group, indazole group, purine group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthidyl group, quinoxalinyl group, quinazolinyl group, zonalyl group Carbazolyl group, phenanthridine group, acridine group, phenanthrolinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, benzothiazolyl group, isobenzothiazolyl group, benzooxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazine group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridyl group or imidazopyrimidine group,

[0134] In the implementation plan, Q 31 To Q 33 They can be hydrogen, deuterium, -F, -Cl, -Br, -I, cyano groups, C1-C, or any of these groups independently. 20 Alkyl groups, C2-C 20 alkenyl groups, C2-C 20 alkynyl group, C1-C 20 alkoxy group, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocyclic alkyl groups, C3-C 10 cycloalkenyl groups, C1-C 10 Heterocyclic alkenyl groups, C6-C 20 aryl group, C1-C 20 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, biphenyl groups, or terphenyl groups.

[0135] In the implementation plan, R1, R2, R 10 R 20 R 30 R 40 R 50 R 60 R 70 and R 80 These can be, independently: hydrogen, 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, -F, -Cl, -Br, -I, cyano group, phenyl group, biphenyl group, or any combination thereof 20 alkyl groups or C1-C 20 alkoxy group; or

[0137] A group represented by one of formulas 5-1 to 5-26 and 6-1 to 6-55.

[0138]

[0139]

[0140]

[0141]

[0142] In equations 5-1 to 5-26 and equations 6-1 to 6-55,

[0143] X 51 and X 52 Each can be independently O, S, C(Z) 53 (Z) 54 ), N(Z 53 ) or Si(Z 53 (Z) 54 ),

[0144] Z 51 To Z 54 They can be independently related to R. 10a The descriptions are the same.

[0145] e2 can be 1 or 2.

[0146] e3 can be 1, 2, or 3.

[0147] e4 can be 1, 2, 3, or 4.

[0148] e5 can be 1, 2, 3, 4, or 5.

[0149] e6 can be 1, 2, 3, 4, 5, or 6.

[0150] e7 can be 1, 2, 3, 4, 5, 6, or 7.

[0151] e9 can be 1, 2, 3, 4, 5, 6, 7, 8, or 9, and

[0152] * indicates a binding site with an adjacent atom.

[0153] In the implementation scheme, Z in Equations 5-1 to 5-26 and Equations 6-1 to 6-55 51 To Z54 Each of these groups can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, C1-C 20 Alkyl groups, C2-C 20 alkenyl groups, C2-C 20 alkynyl group, C1-C 20 Alkoxy group, phenyl group, biphenyl group, triphenyl group, naphthyl group, fluorenyl group, spiro-difluorenyl group, phenanthryl group, anthracene group, benzophenanthryl group, pyridyl group, pyrimidinyl group, carbazole group or triazine group.

[0154] In the implementation plan, R1, R2, R 10 R 20 R 30 R 40 R 50 R 60 R 70 and R 80 Two or more adjacent substituents may optionally be connected to each other to form a cyclopentyl group, a cyclohexyl group, a phenyl group, a naphthyl group, a fluorene group, a pyridine group, a pyrimidine group, a triazine group, or a carbazole group.

[0155] In Equation 1, b10, b20, b30, b40, b50, b60, b70, and b80 can each be 1, 2, 3, 4, 5, 6, 7, or 8 independently.

[0156] In the implementation plan, b10, b20, b30, b40, b50, b60, b70, and b80 can each be 1, 2, 3, or 4 independently.

[0157] In the implementation plan, b10, b20, b30, b40, b50, b60, b70 and b80 can each be 1 or 2 independently.

[0158] In Equation 1, * and *' each represent a binding site with an adjacent atom.

[0159] R 10a It could be:

[0160] Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group or nitro group;

[0161] 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-C60 aryl thiols, C1-C 60 heteroaryloxy groups, C1-C 60 heteroaryl thiols, -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;

[0162] 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 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 aryloxy group, C6-C 60 aryl thiols, C1-C 60 heteroaryloxy groups, C1-C 60 heteroaryl thiols, -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, C6-C 60 aryl thiols, C1-C 60 heteroaryloxy groups or C1-C60 heteroaryl thiols; or

[0163] -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 ),

[0164] Q 11 To Q 13 Q 21 To Q 23 Q 31 To Q 33 and Q 41 To Q 43 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.

[0165] In the implementation scheme, the organometallic compound may be represented by one of formulas 11-1 to 11-3:

[0166] [Equation 11-1]

[0167]

[0168] [Equation 11-2]

[0169]

[0170] [Equation 11-3]

[0171]

[0172] In equations 11-1 to 11-3,

[0173] Y 23 It can be C(R) 23 ) or N, Y 24 It can be C(R) 24 ) or N, Y 25 It can be C(R) 25 ) or N, Y 26 It can be C(R) 26 ) or N, Y 27 It can be C(R) 27 ) or N, Y 28 It can be C(R) 28 ) or N, Y 33 It can be C(R) 33 ) or N, Y 34 It can be C(R) 34 ) or N, Y 35 It can be C(R) 35 ) or N, Y 36 It can be C(R) 36 ) or N, Y 37 It can be C(R) 37 ) or N, and Y 38 It can be C(R) 38 ) or N,

[0174] R 23 To R 28 Each can be independently related to R in Equation 1 20 The same description, and

[0175] R 33 To R 38 Each can be independently related to R in Equation 1 30 The descriptions are the same, and Y 10 To Y 12 Y 40 To Y 42 Y 50 To Y 52 Y 60 To Y 62 Y 70 To Y 72 Y 80 To Y 82 R 10 R 40 R 50 R 60 R 70 R 80 A1, A4, B1 to B4, M1, M2, T1, T2, b10, b40, b50, b60, b70, b80, a10 and L 10 Each can be independently identical to that described in this specification.

[0176] In the implementation scheme, the organometallic compound may be one selected from compounds BD1 to BD104:

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186] In the implementation scheme, the organometallic compound may be electrically neutral.

[0187] Organometallic compounds represented by Formula 1 can contain two metal atoms, and ligands coordinated to the metal atoms can be linked together to form a rigid structure that results in excellent molecular stability. Because organometallic compounds represented by Formula 1 have a structure in which the angles of the ligands are tilted relative to the metal atoms, the formation of excitons can be suppressed. Therefore, light-emitting devices using organometallic compounds can have low driving voltages and excellent brightness, luminous efficiency, and lifespan.

[0188] Organometallic compounds can emit blue light. In specific embodiments, the organometallic compounds can emit blue light with a maximum emission wavelength of about 430 nm to about 470 nm (bottom emission CIE). x,y The color coordinates are from 0.05 to 0.06, but the embodiments of this disclosure are not limited thereto. Therefore, the organometallic compound represented by Formula 1 can be used to manufacture a light-emitting device that emits blue light.

[0189] By referring to the embodiments provided below, those skilled in the art will recognize the method for synthesizing organometallic compounds represented by Formula 1.

[0190] At least one of such organometallic compounds represented by Formula 1 can be used between a pair of electrodes of the light-emitting device. In an embodiment, the organometallic compound can be contained in the emission layer. The organometallic compound contained in the emission layer can act as a dopant. In an embodiment, the organometallic compound represented by Formula 1 can be used as a material for a capping layer located outside a pair of electrodes of the light-emitting device.

[0191] Therefore, a light-emitting device is provided, which may include a first electrode, a second electrode facing the first electrode, an intermediate layer disposed between the first electrode and the second electrode and including an emitting layer, and at least one organometallic compound represented by Formula 1.

[0192] The expression “(intermediate layer) contains at least one organometallic compound” as used herein can include cases where “(intermediate layer) contains the same organometallic compound represented by Formula 1” and cases where “(intermediate layer) contains two or more different organometallic compounds represented by Formula 1”.

[0193] In one embodiment, the intermediate layer may contain only compound BD1 as an organometallic compound. In this case, compound BD1 may be present in the emitting layer of the light-emitting device. In another embodiment, the intermediate layer may contain both compound BD1 and compound BD2 as organometallic compounds. In this case, compound BD1 and compound BD2 may be present in the same layer (e.g., both compound BD1 and compound BD2 may be present in the emitting layer) or in different layers (e.g., compound BD1 may be present in the emitting layer, and compound BD2 may be present in the electron transport region).

[0194] In the implementation scheme, 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 hole blocking layer, an electron transport layer, an electron injection layer or any combination thereof.

[0195] As used herein, the term "intermediate layer" refers to a single layer or all layers between the first and second electrodes of the light-emitting device. Materials included in the "intermediate layer" are not limited to organic materials.

[0196] In one embodiment, the emitter layer may comprise an organometallic compound represented by Formula 1. In another embodiment, the emitter layer may comprise a host and a dopant, and the dopant may comprise an organometallic compound represented by Formula 1. The amount of the host in the emitter layer may be greater than the amount of the organometallic compound in the emitter layer.

[0197] In one embodiment, based on 100 parts by weight of the emitter layer, the amount of the subject can be from about 0.1 parts by weight to about 99 parts by weight. In another embodiment, based on 100 parts by weight of the emitter layer, the amount of the subject can be from about 0.5 parts by weight to about 95 parts by weight. For example, based on 100 parts by weight of the emitter layer, the amount of the subject can be from about 0.1 parts by weight to about 90 parts by weight.

[0198] The emitting layer can emit red, green, blue, and / or white light. In one embodiment, the emitting layer can emit blue light with a maximum emission wavelength of about 410 nm to about 500 nm.

[0199] In one embodiment, the hole transport region may include an electron blocking layer, and the electron blocking layer may contain an organometallic compound; or the electron transport region may include a hole blocking layer, and the hole blocking layer may contain an organometallic compound.

[0200] In an implementation, the hole transport region may contain a p-dopant having a lowest unoccupied molecular orbital (LUMO) energy level equal to or less than about -3.5 eV.

[0201] In the implementation scheme, the electron transport region may include an electron transport layer and an electron injection layer, and at least one of the electron transport layer and the electron injection layer may contain alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof.

[0202] Another aspect of this disclosure provides an electronic device that may include a light-emitting device. The electronic device may further include a thin-film transistor. In an embodiment, 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 an embodiment, 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 in the specification.

[0203] [ Figure 1 [Description]

[0204] 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.

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

[0206] [First Electrode 110]

[0207] exist Figure 1 In this embodiment, the substrate may be further included below the first electrode 110 or above the second electrode 150. The substrate may be a glass substrate or a plastic substrate. In an embodiment, the substrate may be a flexible substrate and may contain a plastic with excellent heat resistance and durability, such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or any combination thereof.

[0208] The first electrode 110 can be formed, for example, by depositing or sputtering a material for forming the first electrode 110 onto a substrate. When the first electrode 110 is an anode, the material used to form the first electrode 110 can be a high work function material that promotes hole injection.

[0209] 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 an embodiment, 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.

[0210] The first electrode 110 may have a structure consisting of a single layer or a structure comprising multiple layers. In an embodiment, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO.

[0211] [Middle Layer 130]

[0212] Intermediate layer 130 may be disposed on first electrode 110. Intermediate layer 130 may include emitter layer.

[0213] The intermediate layer 130 may further include a hole transport region between the first electrode 110 and the emitter layer and an electron transport region between the emitter layer and the second electrode 150.

[0214] In addition to various organic materials, the intermediate layer 130 may further contain metal-containing compounds (e.g., organometallic compounds), inorganic materials (e.g., quantum dots), etc.

[0215] In an embodiment, the intermediate layer 130 may include two or more light-emitting units stacked sequentially between the first electrode 110 and the second electrode 150, and a charge-generating layer between the two or more light-emitting units. When the intermediate layer 130 includes two or more light-emitting units and a charge-generating layer as described above, the light-emitting device 10 may be a series light-emitting device.

[0216] [Hole transport region in intermediate layer 130]

[0217] Hole transport regions can have a single-layer structure consisting of layers made of a single material, a single-layer structure consisting of layers made of different materials, or a multi-layer structure including layers containing different materials.

[0218] The hole transport region may include a hole injection layer, a hole transport layer, an emission assist layer, an electron blocking layer, or any combination thereof.

[0219] In the implementation, 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 from the first electrode 110 in their respective prescribed order, but the implementation is not limited to this.

[0220] The hole transport region may contain a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:

[0221] [Formula 201]

[0222]

[0223] [Equation 202]

[0224]

[0225] In equations 201 and 202,

[0226] L 201 To L 204 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,

[0227] L 205 It can be *-O-*', *-S-*', or *-N(Q) 201 )-*', unsubstituted or by at least one R10a 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,

[0228] xa1 to xa4 can each be an integer from 0 to 5 independently.

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

[0230] R 201 To R 204 and Q 201 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] R 201 and R 202 It can be 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),

[0232] R 203 and R 204 It can be 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, and

[0233] na1 can be an integer from 1 to 4. * and *' each represent a binding site with an adjacent atom. R 10a It can be the same as described in this specification.

[0234] In an embodiment, each of Formula 201 and Formula 202 may contain at least one of the groups represented by Formula CY201 to Formula CY217.

[0235]

[0236] In equations CY201 to CY217, R 10b and R 10c They can be independently related to 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. R 10a It can be the same as described in this specification.

[0237] In the implementation plan, the ring CY in formulas CY201 to CY217 201 To CY 204 Each group can be an independent phenyl group, naphthol group, phenanthrene group, or anthracene group.

[0238] In an embodiment, each of Formula 201 and Formula 202 may contain at least one of the groups represented by Formula CY201 to Formula CY203.

[0239] In an embodiment, formula 201 may include at least one of the groups represented by formulas CY201 to CY203 and at least one of the groups represented by formulas CY204 to CY217.

[0240] In the implementation scheme, in equation 201, xa1 can be 1, R 201 It can be a group represented by one of the formulas CY201 to CY203, xa2 can be 0, and R 202 It can be a group represented by one of the formulas CY204 to CY207.

[0241] In the implementation, each of Formula 201 and Formula 202 may not contain a group represented by one of Formulas CY201 to CY203.

[0242] In the embodiments, each of Formulas 201 and 202 may not contain a group represented by one of Formulas CY201 to CY203, but may contain at least one of the groups represented by Formulas CY204 to CY217.

[0243] In the implementation, each of Formula 201 and Formula 202 may not contain a group represented by one of Formulas CY201 to CY217.

[0244] In the implementation scheme, the hole transport region may comprise one or any combination of compounds HT1 to HT46, m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated-NPB, TAPC, HMTPD, 4,4',4”-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), and polyaniline / poly(4-styrenesulfonate) (PANI / PSS):

[0245]

[0246]

[0247]

[0248]

[0249]

[0250] The thickness of the hole transport region can be approximately to approximately For example, the thickness of the hole transport region can be approximately 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 Furthermore, the thickness of the hole transport layer can be approximately to approximately For example, the thickness of the hole injection layer can be to approximately For example, the thickness of the hole transport layer can be approximately 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.

[0251] 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.

[0252] [p-dopant]

[0253] In addition to these materials, the hole transport region may further contain charge-generating materials to improve conductivity. The charge-generating materials may be uniformly or non-uniformly dispersed in the hole transport region (e.g., in the form of a single layer composed of charge-generating materials).

[0254] The charge-generating material can be, for example, a p-doped agent.

[0255] In the implementation, the lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant can be equal to or less than about -3.5 eV.

[0256] In the embodiments, the p-dopant may include quinone derivatives, compounds containing cyano groups, compounds containing elements EL1 and EL2, or any combination thereof.

[0257] Examples of quinone derivatives may include TCNQ and F4-TCNQ.

[0258] Examples of compounds containing a cyano group may include HAT-CN and compounds represented by formula 221.

[0259]

[0260] [Equation 221]

[0261]

[0262] In Equation 221,

[0263] R 221 To R 223 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 10a It may be the same as described in this specification, and

[0264] R 221 To R 223At least one of them can be a C1-C 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.

[0265] In a compound 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.

[0266] Examples of metals can include alkali metals (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); alkaline earth metals (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), etc.); transition metals (e.g., titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (… Co, rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au), etc.; 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.).

[0267] Examples of metalloids can include silicon (Si), antimony (Sb), and tellurium (Te).

[0268] Examples of nonmetals can include oxygen (O) and halogens (e.g., F, Cl, Br, I, etc.).

[0269] In the embodiments, examples of compounds containing elements EL1 and EL2 may include metal oxides, metal halides (e.g., metal fluorides, metal chlorides, metal bromides, or metal iodides), quasi-metal halides (e.g., quasi-metal fluorides, quasi-metal chlorides, quasi-metal bromides, or quasi-metal iodides), metal tellurides, or any combination thereof.

[0270] Examples of metal oxides may include tungsten oxides (e.g., WO, W2O3, WO2, WO3, W2O5, etc.), vanadium oxides (e.g., VO, V2O3, VO2, V2O5, etc.), molybdenum oxides (e.g., MoO, Mo2O3, MoO2, MoO3, Mo2O5, etc.) and rhenium oxides (e.g., ReO3, etc.).

[0271] Examples of metal halides can include alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, and lanthanide metal halides.

[0272] Examples of alkali metal halides may include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, and CsI.

[0273] Examples of alkaline earth metal halides may include BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2, SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, BeI2, MgI2, CaI2, SrI2, and BaI2.

[0274] Examples of transition metal halides can 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, T...). (e.g., aBr3, TaI3, etc.) chromium halides (e.g., CrF3, CrCl3, CrBr3, CrI3, etc.), molybdenum halides (e.g., MoF3, MoCl3, MoBr3, MoI3, etc.), tungsten halides (e.g., WF3, WCl3, WBr3, WI3, etc.), manganese halides (e.g., MnF2, MnCl2, MnBr2, MnI2, etc.), technetium halides (e.g., TcF2, TcCl2, TcBr2, TcI2, etc.), rhenium halides (e.g., ReF2, ReCl2, ReBr...) 2. ReI2, etc.), iron halides (e.g., FeF2, FeCl2, FeBr2, FeI2, etc.), ruthenium halides (e.g., RuF2, RuCl2, RuBr2, RuI2, etc.), osmium halides (e.g., OsF2, OsCl2, OsBr2, OsI2, etc.), cobalt halides (e.g., CoF2, CoCl2, CoBr2, CoI2, etc.), rhodium halides (e.g., RhF2, RhCl2, RhBr2, RhI2, etc.), iridium halides (e.g., IrF2, IrCl2, Ir... Nickel halides (e.g., NiF2, NiCl2, NiBr2, NiI2), palladium halides (e.g., PdF2, PdCl2, PdBr2, PdI2), platinum halides (e.g., PtF2, PtCl2, PtBr2, PtI2), copper halides (e.g., CuF, CuCl, CuBr, CuI), silver halides (e.g., AgF, AgCl, AgBr, AgI), and gold halides (e.g., AuF, AuCl, AuBr, AuI).

[0275] Examples of post-transition metal halides may include zinc halides (e.g., ZnF2, ZnCl2, ZnBr2, ZnI2, etc.), indium halides (e.g., InI3, etc.) and tin halides (e.g., SnI2, etc.).

[0276] Examples of lanthanide metal halides may include YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3, SmCl3, YbBr, YbBr2, YbBr3, SmBr3, YbI, YbI2, YbI3, and SmI3.

[0277] Examples of metal halide halides can include antimony halides (e.g., SbCl5, etc.).

[0278] Examples of metal tellurides can 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, F₂Te, etc.). (eTe, 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.).

[0279] [Emitting layer in intermediate layer 130]

[0280] The light-emitting device according to the embodiment may include an emitting layer in the intermediate layer. The emitting layer may be the same as described above, or the same as described below regarding the light-emitting device.

[0281] 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 an embodiment, the emitting layer may have a stacked structure of two or more layers selected from red, green, and blue emitting layers, wherein the two or more layers may be in contact with each other or may be spaced apart from each other. In an embodiment, 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.

[0282] The emitting layer may comprise a host and dopants. Dopants may include phosphorescent dopants, fluorescent dopants, or any combination thereof.

[0283] Based on 100 parts by weight of the host, the amount of dopant in the emitter layer can be from about 0.01 parts by weight to about 15 parts by weight.

[0284] In the implementation scheme, the emitter layer may contain quantum dots.

[0285] The emission layer may contain delayed fluorescence material. The delayed fluorescence material can act as either the host or a dopant in the emission layer.

[0286] The thickness of the emission layer can be approximately to approximately For example, the thickness of the emission layer can be approximately to approximately When the thickness of the emitting layer is within this range, excellent light emission characteristics can be obtained without a significant increase in driving voltage.

[0287] [main body]

[0288] The main body may include a compound represented by formula 301:

[0289] [Formula 301]

[0290] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21

[0291] In Equation 301,

[0292] Ar 301 It can be unsubstituted or replaced 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 group, L 301 It can be unsubstituted or replaced 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,

[0293] xb11 can be 1, 2, or 3.

[0294] xb1 can be an integer from 0 to 5.

[0295] 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 ),

[0296] xb21 can be an integer from 1 to 5, and

[0297] Q 301 To Q 303 Each can be independently identical to the description regarding Q1. R 10a It can be the same as described in this specification.

[0298] In the implementation scheme, when xb11 in formula 301 is 2 or greater than 2, two or more Ar 301 They can be connected to each other via a single key.

[0299] In the implementation scheme, the main body may include a compound represented by formula 301-1, a compound represented by formula 301-2, or any combination thereof:

[0300] [Formula 301-1]

[0301]

[0302] [Formula 301-2]

[0303]

[0304] In Equations 301-1 and 301-2,

[0305] 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-C60 Heterocyclic groups,

[0306] X 301 It can be O, S, N[(L 304 ) xb4 -R 304 ]、C(R 304 (R) 305 ) or Si(R 304 (R) 305 ),

[0307] xb22 and xb23 can each be 0, 1, or 2 independently.

[0308] L 301 xb1 and R 301 Each can be the same as described in the instruction manual.

[0309] L 302 To L 304 They can be independently related to L 301 The descriptions are the same.

[0310] xb2 to xb4 can each be independently identical to the description of xb1, and

[0311] R 302 To R 305 and R 311 To R 314 They can be independently related to R. 301 The descriptions are the same. R 10a It can be the same as described in this specification.

[0312] In the embodiments, the main body may include alkaline earth metal complexes, post-transition metal complexes, or any combination thereof. In the embodiments, the main body may include Be complexes (e.g., compound H55), Mg complexes, Zn complexes, or any combination thereof.

[0313] 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(9-carbazolyl)benzene (mCP), and 1,3,5-tris(carbazolyl-9-yl)benzene (TCP):

[0314]

[0315]

[0316]

[0317]

[0318]

[0319]

[0320]

[0321] [Phosphorescent dopant]

[0322] Phosphorescent dopants may contain at least one transition metal as the center metal.

[0323] Phosphorescent dopants may include monodentate ligands, dipentate ligands, tridentate ligands, tetradentate ligands, pentadentate ligands, hexadentate ligands, or any combination thereof.

[0324] Phosphorescent dopants can be electrically neutral.

[0325] In the implementation scheme, the phosphorescent dopant may include an organometallic compound represented by formula 401:

[0326] [Formula 401]

[0327] M(L 401 ) xc1 (L 402 ) xc2

[0328] [Formula 402]

[0329]

[0330] In Equations 401 and 402,

[0331] 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)).

[0332] 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.

[0333] L 402 It can be an organic ligand, and xc2 can be 0, 1, 2, 3, or 4, wherein when xc2 is 2 or greater than 2, there are two or more L... 402 They can be the same or different from each other.

[0334] X 401 and X 402 They can be nitrogen (N) or carbon (C) independently.

[0335] Ring A 401 And Ring A 402 Each can be C3-C independently. 60 Carbocyclic groups or C1-C 60 Heterocyclic groups,

[0336] 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 = *',

[0337] 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 ),

[0338] Q 411 To Q 414 Each can be independently identical to the description regarding Q1.

[0339] 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 ),

[0340] Q 401 To Q 403 Each can be independently identical to the description regarding Q1.

[0341] xc11 and xc12 can each be an integer from 0 to 10 independently, and

[0342] In Equation 402, * and *' each represent a binding site with M in Equation 401. 10a It can be the same as described in this specification.

[0343] In the implementation plan, in formula 402, X 401 It can be nitrogen, and X 402 It can be carbon, or X. 401 and X 402 Each of them can be nitrogen.

[0344] In the implementation scheme, 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 It can be optionally via T as a linking group 403 They are interconnected (see compounds PD1 through PD4 and PD7). T 402 and T 403 They can be independently related to T 401 The descriptions are the same.

[0345] L in Equation 401 402 It can be an organic ligand. In the implementation scheme, L... 402 It may include halogen groups, diketone groups (e.g., acetylacetonate groups), carboxylic acid groups (e.g., pyridine carboxylate groups), -C (=O), isonitrile groups, -CN, phosphorus-containing groups (e.g., phosphine groups, phosphite groups, etc.) or any combination thereof.

[0346] Phosphorescent dopants may include, for example, one or any combination of compounds PD1 to PD25:

[0347]

[0348] [Fluorescent dopant]

[0349] Fluorescent dopants may include compounds containing amine groups, compounds containing styrene groups, or any combination thereof.

[0350] In an embodiment, the fluorescent dopant may include a compound represented by formula 501:

[0351] [Formula 501]

[0352]

[0353] In Equation 501,

[0354] 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 group, 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 It may be the same as described in this specification.

[0355] xd1 to xd3 can each be independently 0, 1, 2, or 3, and

[0356] xd4 can be 1, 2, 3, 4, 5, or 6.

[0357] In the implementation scheme, 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).

[0358] In the implementation scheme, xd4 in formula 501 can be 2.

[0359] In the implementation scheme, the fluorescent dopant may include one or any combination of compounds FD1 to FD36, DPVBi, DPAVBi:

[0360]

[0361]

[0362]

[0363] [Delayed fluorescence materials]

[0364] The emission layer may contain delayed fluorescence material.

[0365] In the specification, the delayed fluorescence material may be selected from compounds that can emit delayed fluorescence based on the delayed fluorescence emission mechanism.

[0366] Depending on the type of other materials contained in the emission layer, the delayed fluorescence material contained in the emission layer can act as either a host or a dopant.

[0367] In this embodiment, the energy difference between the triplet level (eV) and the singlet level (eV) of the delayed fluorescent material can be from about 0 eV to about 0.5 eV. When the energy difference between the triplet level (eV) and the singlet level (eV) of the delayed fluorescent material satisfies the range described above, an upconversion from the triplet to the singlet state of the delayed fluorescent material can occur effectively, and thus the luminous efficiency of the light-emitting device 10 can be improved.

[0368] In the implementation scheme, the delayed fluorescence material may include at least one electron donor (e.g., a π-electron-rich C3-C). 60 Cyclic groups (e.g., carbazole groups) and at least one electron acceptor (e.g., sulfoxide groups, cyano groups, or C1-C groups containing nitrogen lacking π electrons). 60 Materials containing cyclic groups, and C8-C materials containing two or more cyclic groups that share boron (B) in combination. 60 Materials with polycyclic groups.

[0369] Examples of delayed fluorescence materials may include at least one of compounds DF1 to DF9:

[0370]

[0371] [Quantum dot]

[0372] The emitter layer can contain quantum dots.

[0373] In the specification, quantum dots can be crystals of semiconductor compounds and can include any material capable of emitting light of various wavelengths depending on the size of the crystal.

[0374] The diameter of a quantum dot can be, for example, from about 1 nm to about 10 nm.

[0375] Quantum dots can be synthesized through wet chemical processes, metal-organic chemical vapor deposition, molecular beam epitaxy, or any similar process.

[0376] According to the wet chemical process, precursor materials are mixed with organic solvents to grow quantum dot crystals. During crystal growth, the organic solvent naturally acts as a dispersant coordinated on the surface of the quantum dot crystals and controls the crystal growth. This allows the growth of quantum dot particles to be performed more easily and with lower cost than vapor deposition methods (such as metal-organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE)).

[0377] Quantum dots can include group II-VI semiconductor compounds, group III-V semiconductor compounds, group III-VI semiconductor compounds, group I-III-VI semiconductor compounds, group IV-VI semiconductor compounds, group IV elements or compounds, or any combination thereof.

[0378] Examples of group II-VI semiconductor compounds may include binary compounds, such as CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, or MgS; ternary compounds, such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, or MgZnS; quaternary compounds, such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, or HgZnSTe; or any combination thereof.

[0379] Examples of group III-V semiconductor compounds may include: binary compounds, such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, or InSb; ternary compounds, such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, or InPSb; quaternary compounds, such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, or InAlPSb; or any combination thereof. Group III-V semiconductor compounds may further contain group II elements. Examples of further group III-V semiconductor compounds containing group II elements may include InZnP, InGaZnP, or InAlZnP.

[0380] Examples of III-VI semiconductor compounds may include binary compounds such as GaS, GaSe, Ga2Se3, GaTe, InS, InSe, In2S3, In2Se3, or InTe; ternary compounds such as InGaS3 or InGaSe3; or any combination thereof.

[0381] Examples of group I-III-VI semiconductor compounds may include ternary compounds such as AgInS, AgInS2, CuInS, CuInS2, CuGaO2, AgGaO2, or AgAlO2; or any combination thereof.

[0382] Examples of group IV-VI semiconductor compounds may include binary compounds, such as SnS, SnSe, SnTe, PbS, PbSe, or PbTe; ternary compounds, such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, or SnPbTe; quaternary compounds, such as SnPbSSe, SnPbSeTe, or SnPbSTe; or any combination thereof.

[0383] Group IV elements or compounds can include single-element materials, such as Si or Ge; binary compounds, such as SiC or SiGe; or any combination thereof.

[0384] Each element contained in a multi-element compound (e.g., binary, ternary, and quaternary compounds) may exist in the particles at a uniform or non-uniform concentration.

[0385] Quantum dots can have a single structure or a core-shell structure. In the case of a quantum dot with a single structure, the concentration of each element contained within the corresponding quantum dot can be uniform. In embodiments, the materials contained in the core and the materials contained in the shell can be different from each other.

[0386] The shell of a quantum dot can be a protective layer to prevent chemical denaturation of the nucleus and maintain its semiconductor properties, and / or a charging layer to impart electrophoretic properties to the quantum dot. The shell can be single-layered or multi-layered. The interface between the nucleus and the shell can have a concentration gradient, where the concentration of elements present in the shell decreases towards the center of the nucleus.

[0387] Examples of shells for quantum dots can include oxides of metals, oxides of quasi-metals, oxides of nonmetals, semiconductor compounds, or combinations thereof. Examples of oxides of metals, quasi-metals, or nonmetals can include binary compounds (e.g., SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, or NiO); ternary compounds (e.g., MgAl2O4, CoFe2O4, NiFe2O4, or CoMn2O4); or any combination thereof. Examples of semiconductor compounds can include group II-VI semiconductor compounds, group III-V semiconductor compounds, group III-VI semiconductor compounds, group I-III-VI semiconductor compounds, group IV-VI semiconductor compounds, or any combination thereof as described herein. In the embodiments, the semiconductor compound may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or any combination thereof.

[0388] The full width at half maximum (FWHM) of the emission wavelength spectrum of quantum dots can be equal to or less than about 45 nm. For example, the FWHM of the emission wavelength spectrum of quantum dots can be equal to or less than about 40 nm. For example, the FWHM of the emission wavelength spectrum of quantum dots can be equal to or less than about 30 nm. Within these ranges, color purity or color gamut can be increased. Light emitted by quantum dots can be emitted in all directions, and a wide viewing angle can be improved.

[0389] Quantum dots can be spherical nanoparticles, pyramidal nanoparticles, multi-armed nanoparticles, cubic nanoparticles, nanotubes, nanowires, nanofibers, or nanoplates.

[0390] Since the band gap can be adjusted by controlling the size of the quantum dots, light with various wavelength bands can be obtained from the quantum dot emission layer. Therefore, by using quantum dots of different sizes, light-emitting devices that emit light of various wavelengths can be realized. For example, the size of the quantum dots can be selected to emit red, green, and / or blue light. The size of the quantum dots can be configured to emit white light by combining various colors of light.

[0391] [Electron transport region in intermediate layer 130]

[0392] The electron transport region can have a single-layer structure consisting of layers made of a single material, a single-layer structure consisting of layers made of different materials, or a multi-layer structure including layers containing different materials.

[0393] 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.

[0394] 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. For each structure, the constituent layers can be stacked from the emission layer in their respective prescribed order, but the implementation scheme is not limited to this.

[0395] The electron transport region (e.g., a buffer layer, hole blocking layer, electron control layer, or electron transport layer within the electron transport region) may contain C1-C atoms with at least one π-electron-deficient nitrogen atom. 60 Metal-free compounds with cyclic groups.

[0396] In the implementation scheme, the electron transport region may contain a compound represented by formula 601:

[0397] [Formula 601]

[0398] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21

[0399] In Equation 601,

[0400] Ar 601 It can be unsubstituted or replaced 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 group, L 601It can be unsubstituted or replaced 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,

[0401] xe11 can be 1, 2, or 3.

[0402] xe1 can be 0, 1, 2, 3, 4, or 5.

[0403] 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 ), Q 601 To Q 603 Each can be independently identical to the description regarding Q1.

[0404] xe21 can be 1, 2, 3, 4, or 5, and

[0405] It can satisfy at least one of the following conditions: Ar 601 It is unsubstituted or by at least one R 10a Substituted C1-C nitrogen containing π-electron-deficient atoms 60 Cyclic groups; R 601 It is unsubstituted or by at least one R 10a Substituted C1-C nitrogen containing π-electron-deficient nitrogen 60 Cyclic groups; and L 601 It is unsubstituted or by at least one R 10a Substituted divalent nitrogen with π-electron deficiency C1-C 60 Cyclic group. R 10a It can be the same as described in this specification.

[0406] In the implementation scheme, when xe11 in formula 601 is 2 or greater than 2, two or more Ar 601 They can be connected to each other via a single key.

[0407] In the implementation scheme, Ar in Formula 601 601It can be a substituted or unsubstituted anthracene group.

[0408] In the implementation scheme, the electron transport region may comprise a compound represented by formula 601-1:

[0409] [Formula 601-1]

[0410]

[0411] In Equation 601-1,

[0412] X 614 It can be N or C(R) 614 ), X 615 It can be N or C(R) 615 ), X 616 It can be N or C(R) 616 ), and X 614 To X 616 At least one of them can be N,

[0413] L 611 To L 613 They can be independently related to L 601 The descriptions are the same.

[0414] xe611 to xe613 can each be independently identical to the description concerning xe1.

[0415] R 611 To R 613 They can be independently related to R. 601 The same description, and

[0416] 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 group. R 10a It can be the same as described in this specification.

[0417] In the implementation scheme, xe1 in Formula 601 and xe611 to xe613 in Formula 601-1 can each be 0, 1 or 2 independently.

[0418] The electron transport region may contain one or any combination of compounds ET1 to ET45, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, TAZ, and NTAZ.

[0419]

[0420]

[0421]

[0422]

[0423] The thickness of the electron transport region can be approximately to approximately For example, the thickness of the electron transport region can be approximately 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 Furthermore, the thickness of the electron transport layer can be approximately to approximately For example, the thickness of the buffer layer, hole blocking layer, or electronic control layer can each be approximately [missing information]. to approximately For example, the thickness of the electron transport layer can be approximately to approximately When the thicknesses of the buffer layer, hole blocking layer, electronic control layer, and / or electron transport layer are within these ranges, satisfactory electron transport characteristics can be obtained without a significant increase in driving voltage.

[0424] In addition to the materials described above, the electron transport region (e.g., the electron transport layer in the electron transport region) may further contain a metallic material.

[0425] Metal-containing materials may include alkali metal complexes, alkaline earth metal complexes, or any combination thereof. The metal ion in an alkali metal complex may be Li, Na, K, Rb, or Cs ions, and the metal ion in an alkaline earth metal complex may be Be, Mg, Ca, Sr, or Ba ions. Ligands coordinating with 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.

[0426] In this embodiment, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (Liq) or compound ET-D2:

[0427]

[0428] 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.

[0429] The electron injection layer can have a structure consisting of layers made of a single material, a structure consisting of layers made of different materials, or a multilayer structure including layers containing different materials.

[0430] The electron injection layer may contain 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.

[0431] Alkali metals may include Li, Na, K, Rb, Cs, or any combination thereof. Alkali earth metals may include Mg, Ca, Sr, Ba, or any combination thereof. Rare earth metals may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.

[0432] Compounds containing alkali metals, compounds containing alkaline earth metals, and compounds containing rare earth metals may include 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.

[0433] Alkali metal compounds may include alkali metal oxides (e.g., Li₂O, Cs₂O, or K₂O), alkali metal halides (e.g., LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI), or any combination thereof. Alkali earth metal compounds may include alkaline earth metal oxides, such as BaO, SrO, CaO, Ba...x Sr 1-x O (where x is a real number satisfying the condition 0 < x < 1), Ba x Ca 1-x O (where x is a real number satisfying the condition 0 < x < 1), etc. Compounds containing rare earth metals may include YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, ScI3, TbI3, or any combination thereof. In an embodiment, the compound containing rare earth metals may include lanthanide metal tellurides. Examples of lanthanide metal tellurides may include LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La2Te3, Ce2Te3, Pr2Te3, Nd2Te3, Pm2Te3, Sm2Te3, Eu2Te3, Gd2Te3, Tb2Te3, Dy2Te3, Ho2Te3, Er2Te3, Tm2Te3, Yb2Te3, and Lu2Te3.

[0434] Alkali metal complexes, alkaline earth metal complexes, and rare earth metal complexes may contain: one of ions of alkali metals, ions of alkaline earth metals, and ions of rare earth metals; and ligands bonded to the metal ions, such as hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxyphenyl oxadiazole, hydroxyphenyl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzimidazole, hydroxyphenyl benzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.

[0435] The electron injection layer may be composed of: alkali metals, alkaline earth metals, rare earth metals, compounds containing alkali metals, compounds containing alkaline earth metals, compounds containing rare earth metals, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof as described above. In an embodiment, the electron injection layer may further contain an organic material (e.g., a compound represented by Formula 601).

[0436] In an embodiment, the electron injection layer may be composed of: a compound containing an alkali metal (e.g., an alkali metal halide); or a compound containing an alkali metal (e.g., an alkali metal halide), and an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof. In an embodiment, the electron injection layer may be a KI:Yb co-deposited layer, a RbI:Yb co-deposited layer, etc.

[0437] 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.

[0438] The thickness of the electron injection layer can be approximately to approximately For example, the thickness of the electron injection layer can be approximately to approximately When the thickness of the electron injection layer is within this range, satisfactory electron injection characteristics can be obtained without a significant increase in driving voltage.

[0439] [Second electrode 150]

[0440] The second electrode 150 can be disposed on the intermediate layer 130 having such a structure. The second electrode 150 can be a cathode serving as an electron injection electrode, and can be made of metals, alloys, conductive compounds, or any combination thereof, each having a low work function.

[0441] The second electrode 150 may contain 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 transmission electrode, a semi-transmissive reflection electrode, or a reflection electrode.

[0442] The second electrode 150 may have a single-layer structure or a multi-layer structure including two or more layers.

[0443] [Overlay]

[0444] 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. For example, 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 in this prescribed 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 in this prescribed order.

[0445] 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 may be a semi-transparent reflective electrode or a transmissive electrode) and through the first cover layer. 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 may be a semi-transparent reflective electrode or a transmissive electrode) and through the second cover layer.

[0446] The first and second capping layers can each increase the external luminous efficiency based on the principle of constructive interference. Therefore, the light emission efficiency of the light-emitting device 10 can be increased, thereby improving the luminous efficiency of the light-emitting device 10.

[0447] Each of the first and second capping layers may contain a material having a refractive index equal to or greater than about 1.6 (at a wavelength of about 589 nm).

[0448] 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.

[0449] 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 be optionally substituted with substituents containing O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In an embodiment, at least one of the first and second capping layers may independently comprise an amine-containing compound.

[0450] In the implementation scheme, at least one of the first capping layer and the second capping layer may each independently contain a compound represented by formula 201, a compound represented by formula 202, or any combination thereof.

[0451] In the implementation scheme, at least one of the first capping layer and the second capping layer may each independently contain one of compounds HT28 to HT33, one of compounds CP1 to CP6, β-NPB, or any combination thereof:

[0452]

[0453] [membrane]

[0454] The organometallic compound represented by Formula 1 can be contained in various films. Therefore, according to another aspect, films containing organometallic compounds represented by Formula 1 can be provided. The film can be, for example, an optical component (or light control device) (e.g., a color filter, color conversion component, capping layer, light emission efficiency enhancement layer, selective light absorption layer, polarization layer, or layer containing quantum dots), a light blocking component (e.g., a light reflecting layer or a light absorbing layer), or a protective layer (e.g., an insulating layer or a dielectric layer).

[0455] [Electronic Devices]

[0456] The light-emitting device can be included in various electronic devices. In this embodiment, the electronic device including the light-emitting device can be a light-emitting device, a verification device, etc.

[0457] In addition to the light-emitting device, the electronic device (e.g., the light-emitting device) may further include a color filter, a color conversion layer, or a color filter and a color conversion layer. The color filter and / or color conversion layer may be located in at least one direction of travel of the light emitted from the light-emitting device. In embodiments, the light emitted from the light-emitting device may be blue light or white light. The light-emitting device may be the same as described above. In embodiments, the color conversion layer may comprise quantum dots. Quantum dots may be, for example, quantum dots as described herein.

[0458] An electronic device may include a first substrate. The first substrate may include sub-pixels, color filters may include color filter regions corresponding to the sub-pixels, and color conversion layers may include color conversion regions corresponding to the sub-pixels.

[0459] A pixel definition layer can be located between subpixels to define each of the subpixels.

[0460] The color filter may further include a color filter area and a light-blocking pattern located between the color filter areas, and the color conversion layer may include a color conversion area and a light-blocking pattern located between the color conversion areas.

[0461] The 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 an embodiment, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. In an embodiment, the color filter region (or color conversion region) may contain quantum dots. For example, 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 may be the same as those described in the specification. Each of the first, second, and / or third regions may further contain a scattering agent.

[0462] In this embodiment, the light-emitting device can emit first light, a first region can absorb the first light to emit a 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 from each other. For example, the first light can be blue light, the first color light can be red light, the second color light can be green light, and the third color light can be blue light.

[0463] In addition to the light-emitting device described above, the electronic device may further include a thin-film transistor. The thin-film transistor may include a source electrode, a drain electrode, and an active layer, wherein 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.

[0464] Thin-film transistors may further include gate electrodes, gate insulating films, etc.

[0465] The active layer can contain crystalline silicon, amorphous silicon, organic semiconductors, oxide semiconductors, etc.

[0466] The electronic device may further include a sealing portion for sealing the light-emitting device. The sealing portion and / or color conversion layer may be located between the color filter and the light-emitting device. The sealing portion allows light from the light-emitting device to be led out to the outside while simultaneously preventing ambient air and / or moisture from penetrating into the light-emitting device. 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 / or an inorganic layer. When the sealing portion is a thin-film encapsulation layer, the electronic device may be flexible.

[0467] 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. Examples of functional layers may include touchscreen layers, polarization layers, verification devices, 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.).

[0468] In addition to the light-emitting device, the verification device may further include a biometric information collector.

[0469] Electronic devices can be used in a variety of displays, such as 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 endoscope displays), fish finders, various measuring instruments, meters (e.g., instruments for vehicles, aircraft, and ships), projectors, etc.

[0470] [ Figure 2 and Figure 3 [Description]

[0471] Figure 2 This is a schematic cross-sectional view of an electronic device according to an embodiment of the present disclosure.

[0472] Figure 2 The electronic device includes a substrate 100, a thin-film transistor (TFT), a light-emitting device, and a package 300 that seals the light-emitting device.

[0473] The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. A buffer layer 210 may be located on the substrate 100. The buffer layer 210 can prevent impurities from penetrating through the substrate 100 and can provide a flat surface on the substrate 100.

[0474] The TFT can be located on the buffer layer 210. The TFT may include an active layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.

[0475] 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.

[0476] 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.

[0477] An intermediate insulating film 250 may be located on the gate electrode 240. The intermediate insulating film 250 may be located between the gate electrode 240 and the source electrode 260 to insulate the gate electrode 240 from the source electrode 260, and between the gate electrode 240 and the drain electrode 270 to insulate the gate electrode 240 from the drain electrode 270.

[0478] 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.

[0479] The TFT is electrically connected to the light-emitting device to drive the light-emitting device and may be covered by a passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or any combination thereof. The light-emitting device is provided on the passivation layer 280. The light-emitting device may include a first electrode 110, an intermediate layer 130, and a second electrode 150.

[0480] The first electrode 110 may be located on the passivation layer 280. The passivation layer 280 may not completely cover the drain electrode 270 and may expose a portion of the drain electrode 270, and the first electrode 110 may be electrically connected to the exposed portion of the drain electrode 270.

[0481] A pixel defining layer 290 containing insulating material may be located on the first electrode 110. The pixel defining layer 290 may expose a portion of the first electrode 110, and an intermediate layer 130 may be formed in the exposed portion of the first electrode 110. The pixel defining layer 290 may be a polyimide or polyacrylic acid organic film. Although in Figure 2 Although not shown, at least some layers of intermediate layer 130 may extend beyond the upper portion of pixel-defined layer 290 to provide the form of a common layer.

[0482] The second electrode 150 may be disposed on the intermediate layer 130, and a cover layer 170 may be additionally formed on the second electrode 150. The cover layer 170 may be formed to cover the second electrode 150.

[0483] The encapsulation portion 300 may be located on the cover layer 170. The encapsulation portion 300 may be located on the light-emitting device to protect it from moisture and / 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.

[0484] Figure 3 This is a schematic cross-sectional view of an electronic device according to an embodiment of the present disclosure.

[0485] Figure 3 electronic devices and Figure 2The electronic device is the same, but the light-shielding pattern 500 and the functional area 400 are additionally located on the package portion 300. The functional area 400 may be a color filter area, a color conversion area, or a combination of a color filter area and a color conversion area. In the embodiment, it includes... Figure 3 The light-emitting device in an electronic device can be a series of light-emitting devices.

[0486] [Manufacturing Method]

[0487] 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.

[0488] When forming layers including hole transport regions, emitter layers, and electron transport regions by vacuum deposition, the deposition temperature can be from about 100°C to about 500°C, depending on the material to be included in the layers to be formed and the structure of the layers to be formed, and the deposition time can be from about 10°C to about 500°C. -8 To about 10 -3 The vacuum degree and about to approximately Deposition occurs at a certain deposition rate.

[0489] [Definition of the term]

[0490] As used in this article, the term "C3-C" 60 A "carbocyclic group" can be a cyclic group consisting solely of carbon as the cyclic atom and having 3 to 60 carbon atoms (e.g., 3 to 30, 3 to 20, or 3 to 10 carbon atoms), and as used herein by the term "C1-C". 60 A "heterocyclic group" can be a cyclic group having 1 to 60 carbon atoms (e.g., 1 to 30, 1 to 20, or 1 to 10 carbon atoms) and further having at least one heteroatom other than carbon as a cyclic atom. C3-C 60 Carbocyclic groups and C1-C 60 The heterocyclic group can be a monocyclic group, each consisting of a single ring, or a polycyclic group in which two or more rings are fused together. In the embodiment, C1-C 60 Heterocyclic groups can have 3 to 61 cyclic atoms, for example, 3 to 30, 3 to 20 or 3 to 10 cyclic atoms.

[0491] As used herein, the term "cyclic group" can include C3-C 60 Carbocyclic groups and C1-C 60 Heterocyclic groups.

[0492] As used in this article, “π-electron-rich C3-C” 60 A "cyclic group" can be having three to sixty carbon atoms (e.g., 3 to 30, 3 to 20, or 3 to 10 carbon atoms) and may not contain a cyclic group with *-N=*' as a cyclic moiety, and as used herein, "C1-C containing π-electron-deficient nitrogen". 60 A "cyclic group" can be a heterocyclic group having one to sixty carbon atoms (e.g., one to 30, one to 20, or one to 10 carbon atoms) and can contain a *-N=*' as a cyclic moiety.

[0493] In the implementation plan,

[0494] C3-C 60 The carbocyclic group can be a T1 group or a fused cyclic group in which two or more T1 groups are fused together (e.g., 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.). Groups, perylene groups, pentaphenyl groups, heptadiene groups, tetraphenyl groups, styrene groups, hexaphenyl groups, pentaphenyl groups, rutin groups, argentinium groups, ovoid groups, indene groups, fluorene groups, spiro-difluorene groups, benzo[a]fluorene groups, ind[a]phenanthrene groups, or ind[a]anthracene groups),

[0495] C1-C 60The heterocyclic group can be a T2 group, a fused cyclic group in which two or more T2 groups are fused together, or a fused cyclic group in which at least one T2 group and at least one T1 group are fused together (e.g., pyrrole group, thiophene group, furan group, indole group, benzo[a]indole group, naphtho[a]indole group, isoindole group, benzo[a]isoindole group, naphtho[a]isoindole group, benzo[a]thiophene ... Furan group, carbazole group, dibenzothiophene group, dibenzofuran group, indole-carbazole group, indolo-carbazole group, benzofuran-carbazole group, benzothiophene-carbazole group, benzothiophene-carbazole group, benzoindolo-carbazole group, benzocarbazole group, benzonaphthiofuran group, benzonaphthiophene group, benzonaphthiophene group, benzofuran-dibenzofuran group, benzofuran-dibenzothiophene group Groups, benzothiophene, dibenzothiophene group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, oxadiazole group, thiazole group, isothiazole group, thiaazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benziisoxazole group, benzothiazole group, benziisothiazole group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, benzo[…] Quinoline group, benzoisoquinoline group, quinoxaloline group, benzoquinoxaloline group, quinazoline group, benzoquinazoline 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.

[0496] C3-C rich in π electrons 60 The cyclic group can be a T1 group, a fused cyclic group in which two or more T1 groups are fused together, a T3 group, a fused cyclic group in which two or more T3 groups are fused together, or a fused cyclic group in which at least one T3 group and at least one T1 group are fused together (e.g., C3-C). 60Carbocyclic groups, 1H-pyrrole groups, thiorrole groups, borocyclopentadiene 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, benzonaphthothiophene groups, benzonaphthorrole groups, benzofuran-dibenzofuran groups, benzofuran-dibenzothiophene groups, benzothiophene-dibenzothiophene groups, etc.

[0497] C1-C containing nitrogen lacking π electrons 60 The cyclic group can be a T4 group, a fused cyclic group in which two or more T4 groups are fused together, a fused cyclic group in which at least one T4 group and at least one T1 group are fused together, a fused cyclic group in which at least one T4 group and at least one T3 group are fused together, or a fused cyclic group in which at least one T4 group, at least one T1 group, and at least one T3 group are fused together (e.g., pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, oxadiazole group, thiazole group, isothiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group). The following groups are listed: azole group, benzisoxazole group, benzothiazole group, benzisothiazole group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, benzoquinoline group, benzoisoquinoline group, quinoxaline group, benzoquinoxaline group, quinazoline group, benzoquinazoline group, phenanthrene group, cinnamyl 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.

[0498] Wherein the T1 group 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.

[0499] The T2 group can be a furan group, thiophene group, 1H-pyrrole group, thiorrole group, borocyclopentadienyl 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, azaborhexacyclopentadienyl group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, tetraazine group, pyrrolidinyl group, imidazoalkyl 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.

[0500] The T3 group can be a furan group, a thiophene group, a 1H-pyrrole group, a thiophene group, or a borocyclopentadiene group, and

[0501] The T4 group 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 azathiazole group, an azaboranecyclopentadiene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or a tetraazine group.

[0502] As used in this article, the terms "cyclic group" and "C3-C" are similar to those used in this article. 60 "Carbon ring group", "C1-C" 60 Heterocyclic groups, π-electron-rich C3-C 60 "Cyclic group" or "C1-C containing nitrogen lacking π electrons" 60 The term "cyclic group" can be a group fused with any cyclic group or a multivalent group (e.g., a divalent group, a trivalent group, a tetravalent group, etc.) depending on the structure of the formula associated with the use of the term. In embodiments, "phenyl group" can be a benzo[a] group, a phenyl group, a phenylene group, etc., which can be readily understood by those skilled in the art from the structure of a formula including "phenyl group".

[0503] Unit price C3-C 60 Carbocyclic groups and monovalent C1-C 60 Examples of heterocyclic groups may include 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-C60 Carbocyclic groups and divalent C1-C 60 Examples of heterocyclic groups may include 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 nonaromatic fused polycyclic groups, and divalent nonaromatic fused heterocyclic groups.

[0504] As used in this article, the term "C1-C" 60 An "alkyl group" can be a straight-chain or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms (e.g., 1 to 30, 1 to 20, or 1 to 10 carbon atoms), and examples may 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, sec-pentyl groups, 3-pentyl groups, sec-isopentyl groups, n-hexyl groups, isohexyl groups, sec-hexyl groups, tert-hexyl groups, n-heptyl groups, isoheptyl groups, sec-heptyl groups, tert-heptyl groups, n-octyl groups, isooctyl groups, sec-octyl groups, tert-octyl groups, n-nonyl groups, isononyl groups, sec-nonyl groups, tert-nonyl groups, n-decyl groups, isodel groups, sec-decyl groups, and tert-decyl groups. The term "C1-C" as used herein... 60 "alkylene group" can be a group with C1-C2... 60 Divalent groups with the same structure as alkyl groups.

[0505] As used in this article, the term "C2-C" 60 "Alkenyl group" can be C2-C 60 A monovalent hydrocarbon group having at least one carbon-carbon double bond at the middle or end of an alkyl group, and examples of such groups may include vinyl groups, propenyl groups, and butenyl groups. As used herein, the term "C2-C" is used... 60 "Ideinyl group" can be a group with C2-C 60 Divalent groups with the same structure as alkenyl groups.

[0506] As used in this article, the term "C2-C" 60 The "alkynyl group" can be at C2-C 60 A monovalent hydrocarbon group having at least one carbon-carbon triple bond at the middle or end of an alkyl group, and examples of such groups may include ethynyl and propynyl groups. As used herein, the term "C2-C" is used... 60 "Imyynyl group" can be a group with C2-C60 A divalent group with the same structure as the alkynyl group.

[0507] As used in this article, the term "C1-C" 60 The alkoxy group can be composed of -O(A 101 (where A) 101 It is C1-C 60 The alkyl group represents a monovalent group, and examples of such groups may include methoxy groups, ethoxy groups and isopropoxy groups.

[0508] As used in this article, the term "C3-C" 10 "Cycloalkyl group" can be a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and examples of such groups can include cyclopropyl groups, cyclobutyl groups, cyclopentyl groups, cyclohexyl groups, cycloheptyl groups, cyclooctyl groups, adamantyl groups, norbornel alkyl groups (or bicyclic [2.2.1]heptyl groups), bicyclic [1.1.1]pentyl groups, bicyclic [2.1.1]hexyl groups, and bicyclic [2.2.2]octyl groups. The term "C3-C" as used herein is also relevant. 10 "Cycloalkylene group" can be a group with C3-C6 groups. 10 A divalent group with the same structure as a cycloalkyl group.

[0509] As used in this article, the term "C1-C" 10 "Heterocyclic alkyl group" can be a monovalent cyclic group that further includes at least one heteroatom other than a carbon atom as a cyclic atom and has 1 to 10 carbon atoms, and examples of such groups can include 1,2,3,4-oxatriazole alkyl groups, tetrahydrofuranyl groups, and tetrahydrothiophenyl groups. The term "C1-C" as used herein is also relevant. 10 "Heterocyclic alkyl groups" can be those having a C1-C2 relationship. 10 Divalent groups with the same structure as heterocyclic alkyl groups.

[0510] As used in this article, the term "C3-C" 10 A "cycloalkenyl group" can be a monovalent cyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and being non-aromatic, and examples of such groups can include cyclopentenyl groups, cyclohexenyl groups, and cycloheptenyl groups. As used herein, the term "C3-C" is also relevant. 10 "Iridyl group" can be a group with C3-C 10 A divalent group with the same structure as the cycloalkenyl group.

[0511] As used in this article, the term "C1-C" 10A "heterocyclic alkenyl group" can be a monovalent cyclic group having at least one heteroatom other than a carbon atom as a cyclic atom, one to ten carbon atoms, and at least one double bond in its cyclic structure. C1-C 10 Examples of heterocyclic alkenyl groups may 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 groups" can be those having a C1-C2 relationship. 10 A divalent group with the same structure as a heterocyclic alkenyl group.

[0512] As used in this article, the term "C6-C" 60 An "aryl group" can be a monovalent group having a carbocyclic aromatic system containing 6 to 60 carbon atoms (e.g., 6 to 30, 6 to 20, or 6 to 10 carbon atoms), and as used herein by the term "C6-C". 60 An "arylene group" can be a divalent group having a carbocyclic aromatic system containing 6 to 60 carbon atoms (e.g., 6 to 30, 6 to 20, or 6 to 10 carbon atoms). C6-C 60 Examples of aryl groups may include phenyl groups, pentanenyl groups, naphthyl groups, chamomile cycloyl groups, indoleyl groups, acenaphthenic groups, phenanthreneyl groups, anthraceneyl groups, fluoranthraceneyl groups, benzo[a]phenanthreneyl groups, pyreneyl groups, etc. 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.

[0513] As used in this article, the term "C1-C" 60 A "heteroaryl group" can be a monovalent group having a heterocyclic aromatic system containing at least one heteroatom other than a carbon atom as a cyclic atom and 1 to 60 carbon atoms (e.g., 1 to 30, 1 to 20, or 1 to 10 carbon atoms). The term "C1-C" as used herein... 60 A "hybrid aryl group" can be a divalent group having a heterocyclic aromatic system containing at least one heteroatom other than a carbon atom as a cyclic atom and 1 to 60 carbon atoms (e.g., 1 to 30, 1 to 20, or 1 to 10 carbon atoms). C1-C 60Examples of heteroaryl groups may include pyridinyl groups, pyrimidinyl groups, pyrazinyl groups, pyridazinyl groups, triazinyl groups, quinolinyl groups, benzo[a]quinolinyl groups, isoquinolinyl groups, benzo[a]isoquinolinyl groups, quinoxalinyl groups, benzo[a]quinoxalinyl groups, quinazolinyl groups, benzo[a]quinazolinyl groups, cyclophosphinyl groups, phenanthrolinel groups, phthalazinyl groups, and naphthidyl groups. When C1-C 60 heteroaryl groups and C1-C 60 When each of the heteroaryl groups comprises two or more rings, the rings can be fused together.

[0514] As used herein, the term "monovalent nonaromatic fused polycyclic group" can be a monovalent group having two or more rings fused together, with only carbon atoms as cyclic atoms, and lacking aromaticity throughout its molecular structure (e.g., having 8 to 60 carbon atoms, such as 8 to 30, 8 to 20, or 8 to 10 carbon atoms). Examples of monovalent nonaromatic fused polycyclic groups can include indenyl groups, fluorenyl groups, spiro-difluorenyl groups, benzo[a]fluorenyl groups, inden[a]phenanthrene groups, and inden[a]anthrayl groups. As used herein, the term "divalent nonaromatic fused polycyclic group" can be a divalent group having the same structure as a monovalent nonaromatic fused polycyclic group.

[0515] As used herein, the term “monovalent nonaromatic fused heterocyclic group” can be a monovalent group having two or more rings fused together, at least one heteroatom other than a carbon atom as a cyclic atom, and no aromaticity throughout its molecular structure (e.g., having 1 to 60 carbon atoms, such as 1 to 30, 1 to 20, or 1 to 10 carbon atoms). Examples of monovalent non-aromatic fused heterocyclic groups may include pyrrolyl groups, thiophenyl groups, furanyl groups, indoleyl groups, benzoindoleyl groups, naphthoindoleyl groups, isoindoleyl groups, benzoisoindoleyl groups, naphthoisoindoleyl groups, benzothiophenyl groups, benzofuranyl groups, carbazoleyl groups, dibenzothiophenyl groups, dibenzothiophenyl groups, dibenzofuranyl groups, azacarbazoleyl groups, azafluorenyl groups, azadibenzothiophenyl groups, azadibenzothiophenyl groups, azadibenzofuranyl groups, pyrazolyl groups, imidazoleyl groups, triazoleyl groups, tetraazoleyl groups, oxazolyl groups, isoxazolyl groups, thiazolyl groups, isothiazolyl groups, and oxadiazoleyl groups. Group, thiadiazole group, benzopyrazolyl group, benzoimidazolyl group, benzooxazolyl group, benzothiazolyl group, benzooxadiazole group, benzothiadiazole 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 herein, the term "divalent nonaromatic fused heterocyclic group" can refer to a divalent group having the same structure as a monovalent nonaromatic fused heterocyclic group.

[0516] As used in this article, the term "C6-C" 60 The aryloxy group can be formed by -O(A 102 (where A) 102 It is C6-C 60 (aryl group) is used to indicate, and as used herein, the term "C6-C" is used. 60 The aryl thioyl group can be formed by -S(A 103 (where A) 103 It is C6-C 60 (Aromatic group) is used to indicate this.

[0517] As used in this article, the term "C7-C" 60 "Arylalkyl group" can be composed of -(A 104 (A) 105 (where A) 104It can be C1-C 54 alkylene groups, and A 105 It can be C6-C 59 (aryl group) is used, and as the term "C2-C" is used herein 60 "Heteroarylalkyl group" can be composed of -(A 106 (A) 107 (where A) 106 It can be C1-C 59 alkylene groups, and A 107 It can be C1-C 59 (represented by a heteroaryl group).

[0518] As used in this article, the term "R" 10a "Could be:

[0519] Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group or nitro group;

[0520] 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 thiols, C1-C 60 heteroaryloxy groups, C1-C 60 heteroaryl thiols, -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;

[0521] 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 60alkoxy group, C3-C 60 Carbocyclic groups, C1-C 60 Heterocyclic groups, C6-C 60 aryloxy group, C6-C 60 aryl thiols, C1-C 60 heteroaryloxy groups, C1-C 60 heteroaryl thiols, -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, C6-C 60 aryl thiols, C1-C 60 heteroaryloxy groups or C1-C 60 heteroaryl thiols; or

[0522] -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 ).

[0523] As used in this article, Q 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 60Alkoxy 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 60 Heterocyclic groups.

[0524] As used herein, the term "heteroatom" can be any atom other than a carbon or hydrogen atom, and the number of heteroatoms can be from 1 to 10, for example, 1, 2, 3, 4, or 5. Examples of heteroatoms can include O, S, N, P, Si, B, Ge, Se, or any combination thereof.

[0525] The term "third-row transition metals" as used in this article can include hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), gold (Au), etc.

[0526] As used herein, the term "Ph" refers to a phenyl group, "Me" refers to a methyl group, "Et" refers to an ethyl group, and "tert-Bu" or "Bu" refers to a tert-Bu group. t "" refers to the tert-butyl group, and as used herein, the term "OMe" refers to the methyl methacrylate group.

[0527] As used herein, the term "biphenyl group" can mean "a phenyl group substituted with a phenyl group." For example, a "biphenyl group" can be a group having a C6-C... 60 The aryl group is a substituted phenyl group.

[0528] As used herein, the term "terphenyl group" can mean "a phenyl group substituted with a biphenyl group." For example, a "terphenyl group" can be a phenyl group having a C6-C substituted group. 60 C6-C substituted with aryl group 60 The aryl group is a substituted phenyl group.

[0529] In this specification, unless otherwise defined, the symbols *, *' and *” used herein each represent a binding site with an adjacent atom in the corresponding formula or part.

[0530] The organometallic compound and the light-emitting device according to the embodiments will be described in detail below with reference to the embodiments. The phrase "using B instead of A" used to describe the embodiments means using an equimolar amount of B instead of A.

[0531] [Example]

[0532] Synthesis Example 1: Synthesis of Compound BD2

[0533]

[0534] (1) Synthesis of intermediate [1-1]

[0535] 21.0 g (62 mmol) of benzimidazole, 20.2 g (74 mmol) of 3-bromoanisole, 26.4 g (124 mmol) of tripotassium phosphate, 1,180 mg (6.2 mmol) of copper iodide, and 760 mg (6.2 mmol) of pyridinecarboxylic acid were added to a reaction vessel and suspended in 650 mL of dimethyl sulfoxide. The reaction mixture was heated and stirred at 160 °C for 12 hours. After the reaction was complete, the reaction mixture was cooled to room temperature and extracted with ethyl acetate. The extracted organic layer was washed with a saturated aqueous sodium chloride solution and dried over sodium sulfate. The residue obtained by removing the solvent was separated by column chromatography to obtain 21.2 g (40 mmol) of the intermediate [1-1].

[0536] (2) Synthesis of intermediates [1-2]

[0537] 21.2 g (40 mmol) of intermediate [1-1] was added to the reaction vessel and suspended in 400 mL of HCl / AcOH (4:1 volume ratio). The reaction temperature was raised to 120 °C and the reaction mixture was stirred for 12 hours. After the reaction was complete, the reaction mixture was cooled to room temperature and extracted with ethyl acetate. The extracted organic layer was washed with a saturated aqueous sodium chloride solution and dried over sodium sulfate. The residue obtained by removing the solvent was separated by column chromatography to obtain 15.3 g (32 mmol) of intermediate [1-2].

[0538] (3) Synthesis of intermediates [1-3]

[0539] 15.3 g (32 mmol) of intermediate [1-2], 12.1 g (35 mmol) of 1,3-dibromobenzene, 18.5 g (70 mmol) of tripotassium phosphate, 560 mg (3.2 mmol) of copper iodide, and 420 mg (3.5 mmol) of pyridinecarboxylic acid were added to a reaction vessel and suspended in 400 mL of dimethyl sulfoxide. The reaction mixture was heated and stirred at 160 °C for 12 hours. After the reaction was complete, the reaction mixture was cooled to room temperature and extracted with ethyl acetate. The organic layer extracted therefrom was washed with a saturated aqueous sodium chloride solution and dried over sodium sulfate. The residue obtained by removing the solvent therefrom was separated by column chromatography to obtain 14.5 g (28 mmol) of intermediate [1-3].

[0540] (4) Synthesis of intermediates [1-4]

[0541] 14.5 g (28 mmol) of intermediate [1-3], 3.0 g (28 mmol) of phenyl-1,2-diamine, 460 mg (0.5 mmol) of tris(dibenzylacetone)dipalladium, 480 mg (1.0 mmol) of 2-biscyclohexylphosphine-2',4',6'-triisopropylbiphenyl (Xphos), and 5.0 g (52 mmol) of sodium tert-butoxide were added to a reaction vessel and suspended in 260 mL of toluene. The reaction temperature was raised to 110 °C, and the reaction mixture was stirred for 6 hours. After the reaction was complete, the reaction mixture was cooled to room temperature and extracted with ethyl acetate. The organic layer extracted therefrom was washed with a saturated aqueous sodium chloride solution and dried over sodium sulfate. The residue obtained by removing the solvent therefrom was separated by column chromatography to obtain 14.2 g (19 mmol) of intermediate [1-4].

[0542] (5) Synthesis of intermediates [1-5]

[0543] 14.2 g (19 mmol) of intermediate [1-4], 2.1 g (9 mmol) of 1,4-dibromobenzene, 430 mg (0.4 mmol) of tris(dibenzylacetone)dipalladium, 450 mg (0.8 mmol) of XPhos, and 4.5 g (40 mmol) of sodium tert-butoxide were added to a reaction vessel and suspended in 250 mL of toluene. The reaction temperature was raised to 110 °C, and the reaction mixture was stirred for 6 hours. After the reaction was complete, the reaction mixture was cooled to room temperature and extracted with ethyl acetate. The extracted organic layer was washed with a saturated aqueous sodium chloride solution and dried over sodium sulfate. The residue obtained by removing the solvent was separated by column chromatography to obtain 3.1 g (5 mmol) of intermediate [1-5].

[0544] (6) Synthesis of intermediates [1-6]

[0545] 3.1 g (5 mmol) of intermediate [1-5], 20 mL (250 mmol) of triethyl orthoformate, and 3.5 g (35 mmol) of 35 wt% HCl solution were added to a reaction vessel, heated, and stirred at 80 °C for 12 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, and the residue obtained by removing the solvent was separated by column chromatography to obtain 3.2 g (4 mmol) of intermediate [1-6].

[0546] (7) Synthesis of intermediates [1-7] and [1-8]

[0547] 3.2 g (4 mmol) of intermediate [1-6] and 0.6 g (16 mmol) of iodomethane were added to the reaction vessel and suspended in 110 mL of dichloromethane. The reaction temperature was raised to 50 °C and the reaction mixture was stirred for 12 hours. After the reaction was complete, the reaction mixture was cooled to room temperature and extracted with ethyl acetate. The extracted organic layer was washed with a saturated aqueous sodium chloride solution and dried over sodium sulfate. The residue obtained by removing the solvent was separated by column chromatography to obtain 3.8 g (4 mmol) of intermediate [1-7]. Immediately afterwards, 2.3 g (14 mmol) of ammonium hexafluorophosphate was added to the reaction vessel and suspended in a solution of methanol and water in a 2:1 ratio. The reaction mixture was stirred at room temperature for 12 hours. The resulting solid was filtered and separated by column chromatography to obtain 3.5 g (3 mmol) of intermediate [1-8].

[0548] (8) Synthesis of compound BD2

[0549] 3.5 g (3 mmol) of intermediates [1-8], 1.0 g (4 mmol) of dichloro(1,5-cyclooctadiene)platinum, and 0.4 g (6 mmol) of sodium acetate were suspended in 100 mL of dioxane. The reaction mixture was heated and stirred at 110 °C for 72 hours. After the reaction was complete, the reaction mixture was cooled to room temperature and extracted with ethyl acetate. The extracted organic layer was washed with a saturated aqueous sodium chloride solution and dried over sodium sulfate. The residue obtained by removing the solvent was separated by column chromatography to obtain 0.7 g (1 mmol) of compound BD2.

[0550] Synthesis Example 2: Synthesis of Compound BD9

[0551]

[0552]

[0553] (1) Synthesis of intermediate [2-1]

[0554] 21.0 g (60 mmol) of 3,4-dimethylbenzimidazole, 20.2 g (72 mmol) of 3-bromoanisole, 26.4 g (124 mmol) of tripotassium phosphate, 1,180 mg (6.2 mmol) of copper iodide, and 760 mg (6.2 mmol) of pyridinecarboxylic acid were added to a reaction vessel and suspended in 650 mL of dimethyl sulfoxide. The reaction mixture was heated and stirred at 160 °C for 12 hours. After the reaction was complete, the reaction mixture was cooled to room temperature and extracted with ethyl acetate. The extracted organic layer was washed with a saturated aqueous sodium chloride solution and dried over sodium sulfate. The residue obtained by removing the solvent was separated by column chromatography to obtain 22.3 g (42 mmol) of the intermediate [2-1].

[0555] (2) Synthesis of intermediate [2-2]

[0556] 22.3 g (42 mmol) of intermediate [2-1] was added to the reaction vessel and suspended in 400 mL of HCl / AcOH (4:1 volume ratio). The reaction temperature was raised to 120 °C and the reaction mixture was stirred for 12 hours. After the reaction was complete, the reaction mixture was cooled to room temperature and extracted with ethyl acetate. The extracted organic layer was washed with a saturated aqueous sodium chloride solution and dried with sodium sulfate. The residue obtained by removing the solvent was separated by column chromatography to obtain 14.7 g (32 mmol) of intermediate [2-2].

[0557] (3) Synthesis of intermediate [2-3]

[0558] 14.7 g (32 mmol) of intermediate [2-2], 12.1 g (35 mmol) of 1,3-dibromobenzene, 18.5 g (70 mmol) of tripotassium phosphate, 560 mg (3.2 mmol) of copper iodide, and 420 mg (3.5 mmol) of pyridinecarboxylic acid were added to a reaction vessel and suspended in 400 mL of dimethyl sulfoxide. The reaction mixture was heated and stirred at 160 °C for 12 hours. After the reaction was complete, the reaction mixture was cooled to room temperature and extracted with ethyl acetate. The organic layer extracted therefrom was washed with a saturated aqueous sodium chloride solution and dried over sodium sulfate. The residue obtained by removing the solvent therefrom was separated by column chromatography to obtain 14.1 g (25 mmol) of intermediate [2-3].

[0559] (4) Synthesis of intermediate [2-4]

[0560] 14.1 g (25 mmol) of the intermediate [2-3], 3.0 g (28 mmol) of phenyl-1,2-diamine, 460 mg (0.5 mmol) of tris(dibenzylacetone)dipalladium, 480 mg (1.0 mmol) of Xphos and 5.0 g (52 mmol) of sodium tert-butoxide were added to a reaction vessel and suspended in 260 mL of toluene. The reaction temperature was raised to 110 °C and the reaction mixture was stirred for 6 hours. After the reaction was complete, the reaction mixture was cooled to room temperature and extracted with ethyl acetate. The organic layer extracted therefrom was washed with a saturated aqueous sodium chloride solution and dried over sodium sulfate. The residue obtained by removing the solvent therefrom was separated by column chromatography to obtain 14.0 g (18 mmol) of the intermediate [2-4].

[0561] (5) Synthesis of intermediate [2-5]

[0562] 14.0 g (18 mmol) of intermediate [2-4], 2.1 g (9 mmol) of 1,4-dibromobenzene, 430 mg (0.4 mmol) of tris(dibenzylacetone)dipalladium, 450 mg (0.8 mmol) of XPhos, and 4.5 g (40 mmol) of sodium tert-butoxide were added to a reaction vessel and suspended in 250 mL of toluene. The reaction temperature was raised to 110 °C, and the reaction mixture was stirred for 6 hours. After the reaction was complete, the reaction mixture was cooled to room temperature and extracted with ethyl acetate. The organic layer extracted therefrom was washed with a saturated aqueous sodium chloride solution and dried over sodium sulfate. The residue obtained by removing the solvent therefrom was separated by column chromatography to obtain 3.0 g (4 mmol) of intermediate [2-5].

[0563] (6) Synthesis of intermediates [2-6]

[0564] 3.0 g (4 mmol) of the intermediate [2-5], 20 mL (250 mmol) of triethyl orthoformate, and 3.5 g (35 mmol) of 35 wt% HCl solution were added to the reaction vessel, heated, and stirred at 80 °C for 12 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, and the residue obtained by removing the solvent was separated by column chromatography to obtain 2.9 g (3 mmol) of the intermediate [2-6].

[0565] (7) Synthesis of intermediates [2-7] and [2-8]

[0566] 2.9 g (3 mmol) of the intermediate [2-6] and 0.6 g (16 mmol) of iodomethane were added to the reaction vessel and suspended in 110 mL of dichloromethane. The reaction temperature was raised to 50 °C and the reaction mixture was stirred for 12 hours. After the reaction was complete, the reaction mixture was cooled to room temperature and extracted with ethyl acetate. The extracted organic layer was washed with a saturated aqueous sodium chloride solution and dried over sodium sulfate. The residue obtained by removing the solvent was separated by column chromatography to obtain 3.8 g (4 mmol) of the intermediate [2-7]. Immediately afterwards, 2.3 g (14 mmol) of ammonium hexafluorophosphate was added to the reaction vessel and suspended in a 2:1 solution of methanol and water. The reaction mixture was stirred at room temperature for 12 hours. The resulting solid was filtered and separated by column chromatography to obtain 3.6 g (3 mmol) of the intermediate [2-8].

[0567] (8) Synthesis of compound BD9

[0568] 3.6 g (3 mmol) of intermediate [2-8], 1.0 g (4 mmol) of dichloro(1,5-cyclooctadiene)platinum, and 0.4 g (6 mmol) of sodium acetate were suspended in 100 mL of dioxane. The reaction mixture was heated and stirred at 110 °C for 72 hours. After the reaction was complete, the reaction mixture was cooled to room temperature and extracted with ethyl acetate. The extracted organic layer was washed with a saturated aqueous sodium chloride solution and dried over sodium sulfate. The residue obtained by removing the solvent was separated by column chromatography to obtain 0.6 g (1 mmol) of compound BD9.

[0569] Synthesis Example 3: Synthesis of compounds BD1 to BD104

[0570] Compounds BD1 to BD104 were synthesized in essentially the same manner as compound BD2, but using different starting materials than compound BD2.

[0571] The compound synthesized according to the synthesis example 1 H NMR and MS / FAB are shown in Table 1.

[0572] [Table 1]

[0573]

[0574] Example 1

[0575] As the anode, a 15Ω / cm anode manufactured by Corning Inc. will be used. 2 The ITO-coated glass substrate was cut to dimensions of 50 mm × 50 mm × 0.7 mm, and then ultrasonicated with isopropanol and pure water for 5 minutes each, irradiated with ultraviolet (UV) light for 30 minutes, and exposed to ozone for cleaning. The resulting glass substrate was then loaded onto a vacuum deposition apparatus.

[0576] 2-TNATA, a compound in this field, was vacuum deposited on a substrate to form a structure with... A hole injection layer of a certain thickness is formed, and 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter referred to as NPB) as a hole transport compound is vacuum deposited on it to form a hole injection layer of a certain thickness. A hole transport layer of a certain thickness.

[0577] mCBP as the main component and 10 wt% of compound BD2 as a dopant were co-deposited on the hole transport layer to form a structure with The thickness of the emission layer.

[0578] TSPO1 was vacuum deposited onto the emitter layer to form a structure with... A hole-blocking layer of varying thickness was formed. Alq3 was deposited on the hole-blocking layer to create a hole-blocking layer with... An electron transport layer of a certain thickness will be deposited on which LiF, as a halide alkali metal, will be deposited to form an electron transport layer with... An electron-injected layer of a certain thickness, and Al vacuum deposition on the electron-injected layer to form a layer with... The thickness of the LiF / Al cathode electrode is used to complete the fabrication of the light-emitting device.

[0579]

[0580] Examples 2 to 5, and Comparative Examples 1 and 2

[0581] The light-emitting device was manufactured in the same manner as in Example 1, but when forming the emitting layer, the corresponding compounds shown in Table 2 were used instead of compound BD2 as dopants.

[0582]

[0583] Evaluation example

[0584] The driving voltage, current density, luminance, luminous efficiency, emission color, and emission wavelength of the light-emitting devices manufactured according to Examples 1 to 5, Comparative Examples 1 and 2 were measured using a Keithley SMU 236 and a luminance meter PR650, and the results are shown in Table 2.

[0585] [Table 2]

[0586]

[0587] Referring to Table 2, it was found that the light-emitting device according to the embodiment has a lower driving voltage and higher brightness and luminous efficiency than the light-emitting device of the comparative example.

[0588] The light-emitting device containing organometallic compounds according to the implementation scheme can have low driving voltage, high brightness and luminous efficiency, and long service life.

[0589] This document discloses embodiments, and although terminology is used, it is used and interpreted in a general and descriptive sense only, and not for limiting purposes. In some instances, as will be apparent to those skilled in the art, features, characteristics, and / or elements described with respect to embodiments may be used alone or in combination with features, characteristics, and / or elements described with respect to other embodiments, unless specifically indicated otherwise. Therefore, those skilled in the art will understand that various changes in form and detail may be made without departing from the spirit and scope of this disclosure as set forth in the claims.

Claims

1. An organometallic compound represented by Formula 1: [Formula 1] wherein in Formula 1, M1and M2are each independently platinum or palladium, wherein in Formula 3-2 and Formula 3-5, a10is 1, (R 10 ) b10 -A1and (R 40 ) b40 each -A4is independently a group represented by formula 3-2, (R 20 ) b20 -A2and (R 30 ) b30 -A3are each independently a group represented by formula 3-5: b10, b20, b30, b40, b50, b60, b70, and b80are each independently 1, 2, 3, 4, 5, 6, 7, or 8, and X 33 to X 36 each independently C(Z 32 ), Z 31 and Z 32 each independently is the same as described for R 10 ; and , ' and '' each represent a binding site to an adjacent atom; (R 50 ) b50 -B1, (R 60 ) b60 -B2, (R 70 ) b70 -B3, and (R 80 ) b80 each B4is independently a group represented by Formula 2-1 or Formula 2-3, ， wherein in formula 2-1 and formula 2-3, X 21 to X 23 each independently is C- , Z 21 and Z 22 each independently is the same as described for R 10 c21 is 1, 2, or 3, and represents a binding site to an adjacent atom, Y 11 , Y 12 , Y 21 , Y 22 , Y 31 , Y 32 , Y 41 and Y 42 each independently is N, Y 10 , Y 20 , Y 30 , Y 40 , Y 50 to Y 52 , Y 60 to Y 62 , Y 70 to Y 72 and Y 80 to Y 82 are each independently C, T1and T2are each independently -O- ' or -S- ', L 10 It is unsubstituted or by at least one R 10a Substituted phenylene groups, deuterium, -F, -CI, -Br, or -I. R 10 R 20 R 30 R 40 R 50 R 60 R 70 and R 80 Each is independently hydrogen, deuterium, -F, -Cl, -Br, -I, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 20 Alkyl groups or unsubstituted or with at least one R 10a Replacement C1-C 20 alkoxy group, 2. The organometallic compound of claim 1, wherein R 10a is: wherein in Formula 4-1 to Formula 4-3, 5. The organometallic compound of claim 1, wherein the organometallic compound is electrically neutral. the bond between M1and Y 10 is a coordination bond, the bond between M1and Y 20 is a coordination bond, The bond between M2 and Y 30 is a coordination bond, The bond between M2 and Y 40 is a coordination bond, the bond between M1and Y 50 is a covalent bond, the bond between M1and Y 60 is a covalent bond, the bond between M2and Y 70 is a covalent bond, and The bond between M2and Y 80 is a covalent bond.

3. The organometallic compound of claim 1, wherein L 10 is a group represented by one of formula 4-1 to formula 4-3:

6. The organometallic compound of claim 1, wherein the organometallic compound is one selected from the following compounds: Y 91 is C(R 91 ), Y 92 is C(R 92 ), Y 93 is C(R 93 ), Y 94 is C(R 94 ), R 91 to R 94 each independently is the same as described with respect to R 10a described above for R1in Formula 1, and and each represents a site of attachment to an adjacent atom.

4. The organometallic compound of claim 1, wherein R 10 , R 20 , R 30 , R 40 , R 50 , R 60 , R 70 and R 80 are each independently: hydrogen, deuterium, or C1-C6alkyl; 20 an alkyl group; or C1-C replaced by deuterium 20 Alkyl groups.

7. A light-emitting device comprising: a first electrode; 。 a second electrode facing the first electrode; an intermediate layer disposed between the first electrode and the second electrode and including an emission layer; and the organometallic compound of any one of claims 1 to 6.

8. The light-emitting device of claim 7, wherein the first electrode is an anode, the second electrode is a cathode, and the intermediate layer further includes: a hole transport region disposed between the first electrode and the emission layer and including a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or a combination thereof; and an electron transport region disposed between the emission layer and the second electrode and including a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

9. The light-emitting device of claim 7, wherein the emission layer comprises the organometallic compound.

10. The light-emitting device of claim 9, wherein the emission layer comprises a host and a dopant, and the dopant includes the organometallic compound.

11. The light-emitting device of claim 8, wherein the hole transport region further comprises a p-dopant having a lowest unoccupied molecular orbital energy level equal to or less than -3.5 eV.

12. The light-emitting device of claim 8, wherein the electron transport region includes the electron transport layer and the electron injection layer, and at least one of the electron transport layer and the electron injection layer comprises an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or a combination thereof.

13. An electronic device comprising the light-emitting device of any one of claims 7 to 12.

14. The electronic device of claim 13, wherein the electronic device further comprises 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 the source electrode or the drain electrode. ​ ​

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