Organometal compound, light emitting device including the same, and electronic device including the light emitting device

Abstract

Provided are an organometallic compound represented by Formula 1 wherein the detailed description of Formula 1 is as provided herein, a light-emitting device including the organometallic compound, and an electronic device including the light-emitting device.

Description

[0001] Cross-reference to related applications

[0002] This application claims priority and benefits to Korean Patent Application No. 10-2024-0167756, filed on November 21, 2024, with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field

[0003] This topic relates to organometallic compounds, light-emitting devices including said organometallic compounds, and electronic devices including said light-emitting devices. Background Technology

[0004] Among light-emitting devices, organic light-emitting devices (OLEDs) are self-emissive devices that offer improved characteristics in terms of viewing angle, response time, brightness, driving voltage, and response speed. Furthermore, OLEDs can produce full-color images.

[0005] In this example, the organic light-emitting device includes an anode, a cathode, and an intermediate layer disposed between the anode and cathode, including an emission layer. A hole transport region may be disposed between the anode and the emission layer, and an electron transport region may be disposed between the emission layer and the cathode. Holes supplied from the anode move towards the emission layer through the hole transport region, and electrons supplied from the cathode move towards the emission layer through the electron transport region. Holes and electrons recombine in the emission layer to generate excitons. Excitons transition from an excited state to the ground state, thereby producing light. Summary of the Invention

[0006] Provided are organometallic compounds, light-emitting devices comprising said organometallic compounds, and electronic devices comprising said light-emitting devices.

[0007] Other aspects will be set forth in part in the following detailed description, and will also be apparent in part from that detailed description, or may be learned through practice of the exemplary embodiments presented herein.

[0008] According to one aspect, organometallic compounds represented by Formula 1 are provided:

[0009] Formula 1

[0010]

[0011] In Equation 1,

[0012] M is either Pt or Pd.

[0013] X1 is C,

[0014] X2 to X4 are each independently C or N.

[0015] CY2 ring, CY ring 31 CY 32 CY4 and CY5 are independently C5-C 30 Carbocyclic groups or C1-C 30 Heterocyclic groups,

[0016] X 11 For N or C(R) 11 ), X 12 For N or C(R) 12 ), and X 13 For N or C(R) 13 ),

[0017] X 51 For N or C(R) 51 ), X 52 For N or C(R) 52 ), X 53 For N or C(R) 53 ), and X 54 For N or C(R) 54 ),

[0018] X 61 For N or C(R) 61 ), X 62 For N or C(R) 62 ), X 63 For N or C(R) 63 ), and X 64 For N or C(R) 64 ),

[0019] X 71 For N or C(R) 71 ), X 72 For N or C(R) 72 ), X 73 For N or C(R) 73 ), and X 74 For N or C(R) 74 ),

[0020] L1 is O, S, Se, N (R 101 ), C(R 101 (R) 102 ), or Si(R) 101 (R) 102 ),

[0021] L2, L3, and L4 are each independently a single bond, O, S, Se, N(R'), C(R')(R"), or Si(R')(R").

[0022] At least one of L2, L3, and L4 is O, S, Se, N(R'), C(R')(R"), or Si(R')(R"),

[0023] R2, R3, R4, R 11 To R 13 R 51 To R 54 R 61 To R 64 R 71 To R 74 R 101 R 102 R' and R" are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C1-C 60 Alkylthio, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 arylalkyl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -N(Q4)(Q5), -B(Q6)(Q7), -P(Q8)(Q9), or -P(=O)(Q8)(Q9),

[0024] a2 to a4 are each an independent integer from 0 to 20.

[0025] R 11 To R 13 Two or more may be optionally connected to each other to form an unreplaced or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups,

[0026] Two or more of R2s are optionally connected to each other to form a group that is not replaced or is occupied by at least one R. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups,

[0027] Two or more of a plurality of R3s are optionally connected to each other to form an unsubstituted or at least one R 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups,

[0028] Two or more of a plurality of R4s are optionally connected to each other to form an unsubstituted or at least one R 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups,

[0029] R 51 To R 54 Two or more may be optionally connected to each other to form an unreplaced or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups,

[0030] R 61 To R 64 Two or more may be optionally connected to each other to form an unreplaced or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups,

[0031] R71 To R 74 Two or more may be optionally connected to each other to form an unreplaced or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups,

[0032] R 101 and R 102 Optionally connected to each other to form an unreplaced or at least R 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups,

[0033] R' and R" are optionally connected to each other to form an unsubstituted or at least one R 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups,

[0034] R 10a For example, regarding R 11 As described,

[0035] Replacement C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C1-C 60 Alkylthio, substituted C3-C 10 cycloalkyl, substituted C1-C 10 Heterocyclic alkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 Aryl, substituted C7-C 60 Alkyl aryl, substituted C7-C 60 Arylalkyl, substituted C6-C 60 aryloxy groups, substituted C6-C 60 Arylthioyl, substituted C1-C 60 heteroaryl, substituted C2-C 60 Alkyl heteroaryl, substituted C2-C 60 Heteroarylalkyl, substituted C1-C 60 Heteroaryl groups, substituted C1-C 60At least one substituent of the heteroaryl thio group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heterocyclic group is:

[0036] Deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 alkoxy, or C1-C 60 Alkylthio;

[0037] Each of the following C1-C is replaced: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 alkoxy, or C1-C 60 Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 11 (Q) 12 (Q) 13 -Ge(Q) 11 (Q) 12 (Q) 13 -N(Q) 14 (Q) 15 -B(Q) 16 (Q) 17 -P(Q) 18 (Q) 19-P(=O)(Q) 18 (Q) 19 ), or combinations thereof;

[0038] Each of the following C3-Cs was not replaced or was replaced as follows 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid groups or their salts, sulfonic acid groups or their salts, phosphate groups or their salts, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 Arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 21 (Q) 22 (Q) 23 -Ge(Q) 21 (Q) 22 (Q) 23-N(Q) 24 (Q) 25 -B(Q) 26 (Q) 27 -P(Q) 28 (Q) 29 -P(=O)(Q) 28 (Q) 29 ), or combinations thereof;

[0039] -Si(Q 31 (Q) 32 (Q) 33 -Ge(Q) 31 (Q) 32 (Q) 33 -N(Q) 34 (Q) 35 -B(Q) 36 (Q) 37 -P(Q) 38 (Q) 39 ), or -P(=O)(Q 38 (Q) 39 );or

[0040] Its combination, and

[0041] Q1 to Q9, Q 11 To Q 19 Q 21 To Q 29 , and Q 31 To Q 39 Each independently is:

[0042] Hydrogen, deuterium, or -F; or

[0043] Each of the following C1-Cs was not replaced or was replaced as follows 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 Arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups: deuterium, -F, cyano, C1-C 60 Alkyl, C6-C 60 Aryl groups, or combinations thereof.

[0044] In Equation 1, i) when L2 is N(R'), R' is not connected to X. 54 and X 61 either of the following, ii) when L3 is N(R'), R' is not connected to X. 64 and X 71 either of the above, and iii) when L4 is N(R'), R' is not connected to X. 74 and X 11 Any one of them.

[0045] According to another aspect, the light-emitting device includes a first electrode, a second electrode, and an intermediate layer disposed between the first electrode and the second electrode, wherein the intermediate layer includes an emitting layer, and wherein the intermediate layer includes at least one organometallic compound represented by Formula 1.

[0046] According to another aspect, the electronic device includes the light-emitting device. Attached Figure Description

[0047] By combination Figure 1 The above and other aspects, features and advantages of some exemplary embodiments will become clearer from the following detailed description. Figure 1 This is a schematic cross-sectional view of an organic light-emitting device according to one or more embodiments. Detailed Implementation

[0048] Exemplary embodiments will now be described in further detail, examples of which are illustrated in the accompanying drawings, wherein the same reference numerals refer to the same elements throughout the specification. In this respect, the exemplary embodiments may take different forms and should not be construed as limited to the detailed description set forth herein. Therefore, exemplary embodiments are described in further detail below and with reference to the accompanying drawings only to illustrate certain aspects and features. As used herein, the term “and / or” includes any and all combinations of one or more of the associated enumerated items. Expressions such as “at least one of” modify the entire list of elements when preceding or following it, without modifying any individual element of the list.

[0049] The terminology used herein is for the purpose of describing one or more exemplary embodiments only and is not intended to be limiting. As used herein, the singular forms “a” and “the” are also intended to include the plural forms unless the context clearly indicates otherwise. The term “or” means “and / or”. It will be further understood that the terms “comprising” or “including” as used in this specification indicate the presence of the stated features, regions, integrals, steps, operations, elements, and / or components, but do not exclude the presence or addition of one or more additional features, regions, integrals, steps, operations, elements, components, and / or sets thereof.

[0050] It will be understood that although the terms first, second, third, etc., may be used herein to describe various elements, components, regions, layers, and / or portions, these elements, components, regions, layers, and / or portions should not be limited by these terms. These terms are used only to distinguish one element, component, region, layer, or portion from another. Therefore, without departing from the teachings of this embodiment, the first element, component, region, layer, or portion discussed below may be referred to as the second element, component, region, layer, or portion.

[0051] Exemplary embodiments are described herein with reference to cross-sectional views, which are schematic diagrams of idealized embodiments. Thus, deviations from the shapes shown in the figures will be anticipated as a result of, for example, manufacturing techniques and / or tolerances. Therefore, the embodiments described herein should not be construed as limited to the specific shapes of the regions illustrated herein, but rather include deviations in shape caused, for example, by manufacturing processes. For example, regions illustrated or described as flat may typically have rough and / or non-linear characteristics. Furthermore, sharp corners in the figures may be rounded. Therefore, the regions shown in the figures are schematic in nature and their shapes are not intended to illustrate the precise shape of the regions nor to limit the scope of the claims.

[0052] It will be understood that when an element is referred to as being "on" another element, it may be in direct contact with the other element or there may be an intermediate element between them. Conversely, when an element is referred to as being "directly on" another element, there is no intermediate element.

[0053] Unless otherwise defined, all terms used herein (including technical and scientific terms) have the same meaning as commonly understood by one of ordinary skill in the art to which this general inventive concept pertains. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having meanings consistent with their meanings in the context of this disclosure and the relevant field, and will not be interpreted in an idealized or overly formal sense unless expressly defined herein.

[0054] As used herein, “about” or “approximately” includes the stated value and means within an acceptable range of deviations from the specific value, as determined by a person skilled in the art taking into account the measurement in question and the errors associated with the measurement of the specific quantity (i.e., limitations of the measurement system). For example, “about” may mean within one or more standard deviations relative to the stated value, or within ±30%, 20%, 10%, or 5%.

[0055] One aspect provides organometallic compounds represented by Formula 1:

[0056] Formula 1

[0057] .

[0058] In Equation 1, M is either Pt or Pd.

[0059] In one or more embodiments, M may be Pt.

[0060] In Equation 1, X1 is C, and X2 to X4 are each independently C or N.

[0061] In one or more embodiments, X2 and X3 may each be C, and X4 may be N.

[0062] In one or more embodiments, the bonds between X1 and M and between X4 and M can each be coordinate bonds, and the bonds between X2 and M and between X3 and M can each be covalent bonds. That is, the organometallic compound can be electrically neutral.

[0063] Formula 1, where X1 represents a carbene and X4 is N, can be represented as Formula 1', where the charges of the two nitrogen atoms are as shown below (i.e., Formula 1, where X4 is N, can be the same as Formula 1'), and it is readily understood that the description of Formula 1, where X4 is N, can be applied to Formula 1':

[0064] Formula 1'

[0065] .

[0066] In Equation 1, rings CY2 and CY 31 CY 32 CY4 and CY5 are independently C5-C 30 Carbocyclic groups or C1-C 30 Heterocyclic groups.

[0067] In one or more embodiments, ring CY2, ring CY 31 CY 32The CY4 ring can be independently a phenyl group, naphthol group, phenanthrene group, pyridine group, pyrimidine group, pyridazine group, pyrazine group, triazine group, quinoline group, isoquinoline group, benzoquinoline group, or benzoisoquinoline group.

[0068] In one or more embodiments, ring CY2, ring CY 31 , and CY 32 Each group can be independently a phenyl group, naphthol group, phenanthrene group, pyridine group, pyrimidine group, pyrazine group, pyrazine group, triazine group, quinoline group, isoquinoline group, benzo[a]quinoline group, or benzo[a]isoquinoline group, and the ring CY4 can be a pyridine group, pyrimidine group, pyrazine group, pyrazine group, triazine group, quinoline group, isoquinoline group, benzo[a]quinoline group, or benzo[a]isoquinoline group.

[0069] In Equation 1, X 11 For N or C(R) 11 ), X 12 For N or C(R) 12 ), X 13 For N or C(R) 13 ), X 51 For N or C(R) 51 ), X 52 For N or C(R) 52 ), X 53 For N or C(R) 53 ), X 54 For N or C(R) 54 ), X 61 For N or C(R) 61 ), X 62 For N or C(R) 62 ), X 63 For N or C(R) 63 ), X 64 For N or C(R) 64 ), X 71 For N or C(R) 71 ), X 72 For N or C(R) 72 ), X 73 For N or C(R) 73 ), and X 74 For N or C(R) 74 R 11 To R 13 R 51 To R 54 R 61 To R 64 and R 71 To R 74 Each can be as described in this article.

[0070] In one or more embodiments, in Formula 1, X 11 It can be C(R) 11 ), X 12 It can be C(R) 12 ), X 13 It can be C(R) 13 ), X 51 It can be C(R) 51 ), X 52 It can be C(R) 52 ), X 53 It can be C(R) 53 ), X 54 It can be C(R) 54 ), X 61 It can be C(R) 61 ), X 62 It can be C(R) 62 ), X 63 It can be C(R) 63 ), X 64 It can be C(R) 64 ), X 71 It can be C(R) 71 ), X 72 It can be C(R) 72 ), X 73 It can be C(R) 73 ), and X 74 It can be C(R) 74 ).

[0071] In Equation 1, L1 represents O, S, Se, and N(R). 101 ), C(R 101 (R) 102 ), or Si(R) 101 (R) 102 ).

[0072] In one or more embodiments, L1 in Formula 1 may be O or S. 101 and R 102 Each can be as described in this article.

[0073] In Equation 1, L2, L3, and L4 are each independently a single bond, O, S, Se, N(R'), C(R')(R"), or Si(R')(R"), wherein at least one of L2, L3, and L4 (or "L2, L3, L4, or any combination thereof") is O, S, Se, N(R'), C(R')(R"), or Si(R')(R").

[0074] In one or more embodiments, at least one of L2, L3, and L4 in Formula 1 may be N(R').

[0075] In one or more embodiments, at least one of L2, L3, and L4 in Formula 1 may be O, S, or Se.

[0076] In one or more embodiments, at least one of L2, L3, and L4 in Formula 1 may be C(R')(R") or Si(R')(R").

[0077] In one or more embodiments, two of L2, L3, or L4 in Formula 1 may each be a single bond, and the remaining one of L2, L3, or L4 may not be a single bond.

[0078] In one or more embodiments, in Formula 1,

[0079] i) L2 and L3 are each single bonds, and L4 is O, S, Se, N(R'), C(R')(R"), or Si(R')(R"),

[0080] ii) L2 and L4 are each single bonds, and L3 is O, S, Se, N(R'), C(R')(R"), or Si(R')(R"), or

[0081] iii) L3 and L4 are each single bonds, and L2 is O, S, Se, N(R'), C(R')(R"), or Si(R')(R").

[0082] In Equation 1, i) when L2 is N(R'), R' is not connected to X. 54 and X 61 either of the following, ii) when L3 is N(R'), R' is not connected to X. 64 and X 71 either of them, and iii) when L4 is N(R'), R' is not connected to X. 74 and X 11 Either of them. That is, for example, compounds C3 and C4 described below cannot be included in Formula 1 described herein.

[0083] For example, in Equation 1, i) when L2 is N(R'), R' is not connected to X. 54 and X 61 ii) When L3 is N(R'), R' is not connected to X. 64 and X 71 And iii) when L4 is N(R'), R' is not connected to X. 74 and X 11 .

[0084] In Equation 1, R2, R3, R4, R 11 To R 13 R 51 To R 54 R61 To R 64 R 71 To R 74 R 101 R 102 R' and R" are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C 60 Alkyl groups (e.g., substituted or unsubstituted C1-C) 20 Alkyl), substituted or unsubstituted C2-C 60 Alkenyl (e.g., substituted or unsubstituted C2-C) 20 alkenyl), substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy groups (e.g., substituted or unsubstituted C1-C) 20 Alkoxy, substituted or unsubstituted C1-C 60 Alkylthio, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 Aryl (e.g., substituted or unsubstituted C6-C) 20 aryl), substituted or unsubstituted C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 arylalkyl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl groups (e.g., substituted or unsubstituted C1-C) 20 (heteroaryl), substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 The groups are heteroaryl thio groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -N(Q4)(Q5), -B(Q6)(Q7), -P(Q8)(Q9), or -P(=O)(Q8)(Q9). Q1 to Q9 are each as described herein.

[0085] In one or more embodiments, R2, R3, R4, R 11 To R 13 R 51 To R 54 R 61 To R 64 R 71 To R 74 R 101 R 102 R' and R" can each be independently defined as:

[0086] Hydrogen, deuterium, -F, or cyano;

[0087] Each of them was not replaced or replaced by deuterium, -F, cyano, C1-C 20 C1-C substituted with alkyl, phenyl, carbazole, or combinations thereof 20 Alkyl or C1-C 20 Alkoxy;

[0088] Each of the following C3-Cs was not replaced or was replaced as follows 10 Cycloalkyl, phenyl, naphthyl, pyridyl, furanyl, thiophene, benzofuranyl, benzothiophene, carbazole, dibenzofuranyl, or dibenzothiophene: deuterium, -F, cyano, C1-C 20 Alkyl, C1-C 20 Alkoxy, deuterated C1-C 20 Alkyl, fluorinated C1-C 20 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 Cycloalkyl, fluorinated C3-C 10 cycloalkyl, (C1-C 20 Alkyl)C3-C 10 Cycloalkyl, phenyl, deuterated phenyl, fluorophenyl, (C1-C 20 Alkyl)phenyl, naphthyl, pyridyl, furanyl, thiophene, benzofuranyl, benzothiophene, carbazole, dibenzofuranyl, dibenzothiophene, -Si(Q) 33 (Q) 34 (Q) 35 -Ge(Q) 33 (Q) 34 (Q) 35 ), or a combination thereof; or

[0089] -Si(Q3)(Q4)(Q5) or -Ge(Q3)(Q4)(Q5).

[0090] In one or more embodiments, R2, R3, R4, R 11 To R 13R 51 To R 54 R 61 To R 64 R 71 To R 74 R 101 R 102 R' and R" can each be independently defined as:

[0091] Hydrogen or deuterium; or

[0092] Each was not replaced or replaced by deuterium, C1-C 20 C1-C substituted with alkyl, phenyl, carbazole (e.g., N-carbazole), or combinations thereof 20 Alkyl, phenyl, or carbazolyl (e.g., N-carbazolyl).

[0093] As used in this article, the terms "each deuterated, C1-C" are as follows: 20 C1-C substituted with alkyl, phenyl, carbazole, or combinations thereof 20 Non-limiting examples of "alkyl, phenyl, or carbazole" may include:

[0094] C1-C replaced by at least one deuterium 20 alkyl,

[0095] C1-C substituted with at least one phenyl group 20 alkyl,

[0096] C1-C substituted with at least one deuterium and at least one phenyl group 20 alkyl,

[0097] C1-C substituted with at least one deuterium and at least one deuterated phenyl group (e.g., a fully deuterated phenyl group, etc.). 20 alkyl,

[0098] C1-C substituted with at least one phenyl group 20 Alkyl group, wherein the phenyl group is reacted with at least one deuterium and at least one C1-C alkyl group. 20 Alkyl groups, or combinations thereof, are substituted.

[0099] A phenyl group substituted with at least one deuterium,

[0100] by at least one C1-C 20 Alkyl-substituted phenyl,

[0101] Contains at least one deuterium and at least one C1-C 20 Alkyl-substituted phenyl,

[0102] C1-C replaced by at least one deuterium and at least one deuterium 20Alkyl-substituted phenyl groups (e.g., -CD3, CD2H, -CDH2, -CD2CD3, -CH2CD3, etc.),

[0103] by at least one C1-C 20 Alkyl group and at least one deuterated C1-C 20 Alkyl-substituted phenyl, or

[0104] A carbazolyl group substituted with at least one deuterium group.

[0105] In one or more embodiments, R2, R3, R4, R 11 To R 13 R 51 To R 54 R 61 To R 64 R 71 To R 74 R 101 R 102 R' and R" can each be independently defined as:

[0106] Hydrogen or deuterium;

[0107] Each of the following substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isonyl, sec-nonyl, tert-nonyl, n-decyl, isodel, sec-decyl, or tert-decyl: deuterium, phenyl, or combinations thereof; or

[0108] The phenyl or carbazoyl group, whether unsubstituted or substituted with the following: deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isonyl, sec-nonyl, tert-nonyl, n-decyl, isodel, sec-decyl, tert-decyl, or combinations thereof.

[0109] In one or more embodiments, the organometallic compound represented by Formula 1 may include deuterium, unsubstituted or substituted tert-butyl, or combinations thereof.

[0110] In Equation 1, a2 to a4 represent the quantities of R2 to R4, and each is an independent integer from 0 to 20, 0 to 15, 0 to 10, 0 to 6, 0 to 5, 0 to 4, or 0 to 3. a2 to a4 can each be determined based on ring CY2, ring CY... 31 CY32 The structure of ring CY4 is chosen in a variety of ways within the range described above. When a2 is 2 or greater, two or more R2s may be the same or different from each other; when a3 is 2 or greater, two or more R3s may be the same or different from each other; and when a4 is 2 or greater, two or more R4s may be the same or different from each other.

[0111] In one or more implementations, a2 can be an integer from 0 to 3.

[0112] In one or more implementations, a3 can be an integer from 0 to 6.

[0113] In one or more implementations, a4 can be an integer from 0 to 4.

[0114] In one or more embodiments, a2 may not be 0, and R2 may not be hydrogen.

[0115] In one or more embodiments, a4 may not be 0, and R4 may not be hydrogen.

[0116] In one or more embodiments, Equation 1 may satisfy at least one of the following conditions:

[0117] Condition 11

[0118] X 11 It is C(R) 11 ), and R 11 Not hydrogen

[0119] Condition 12

[0120] X 12 It is C(R) 12 ), and R 12 Not hydrogen

[0121] Condition 13

[0122] X 13 It is C(R) 13 ), and R 13 Not hydrogen

[0123] Condition 51

[0124] X 51 It is C(R) 51 ), and R 51 Not hydrogen

[0125] Condition 52

[0126] X 52 It is C(R) 52 ), and R 52 Not hydrogen

[0127] Condition 53

[0128] X 53 It is C(R) 53 ), and R 53 Not hydrogen

[0129] Condition 54

[0130] X 54 It is C(R) 54 ), and R 54 Not hydrogen

[0131] Condition 61

[0132] X 61 It is C(R) 61 ), and R 61 Not hydrogen

[0133] Condition 62

[0134] X 62 It is C(R) 62 ), and R 62 Not hydrogen

[0135] Condition 63

[0136] X 63 It is C(R) 63 ), and R 63 Not hydrogen

[0137] Condition 64

[0138] X 64 It is C(R) 64 ), and R 64 Not hydrogen

[0139] Condition 71

[0140] X 71 It is C(R) 71 ), and R 71 Not hydrogen

[0141] Condition 72

[0142] X 72 It is C(R) 72 ), and R 72 Not hydrogen

[0143] Condition 73

[0144] X 73 It is C(R) 73 ), and R 73 Not hydrogen

[0145] Condition 74

[0146] X 74 It is C(R)74 ), and R 74 It's not hydrogen.

[0147] R in conditions 11 to 13, 51 to 54, 61 to 64, and 71 to 74 11 To R 13 R 51 To R 54 R 61 To R 64 and R 71 To R 74 Each can be as described in this article.

[0148] In one or more embodiments, Formula 1 may satisfy at least one of conditions 51 to 54, at least one of conditions 61 to 64, at least one of conditions 71 to 74, or a combination thereof.

[0149] In one or more embodiments, Formula 1 may satisfy at least one of conditions 51 or 53.

[0150] In one or more embodiments, Formula 1 may satisfy at least one of conditions 62 or 63.

[0151] In one or more embodiments, Formula 1 may satisfy at least one of conditions 71 or 74.

[0152] In one or more embodiments, R in conditions 11 to 13, 51 to 54, 61 to 64, and 71 to 74 11 To R 13 R 51 To R 54 R 61 To R 64 and R 71 To R 74 Each can be independently:

[0153] Deuterium, -F, or cyano;

[0154] Each of them was not replaced or replaced by deuterium, -F, cyano, C1-C 20 C1-C substituted with alkyl, phenyl, carbazole, or combinations thereof 20 Alkyl or C1-C 20 Alkoxy;

[0155] Each of the following C3-Cs was not replaced or was replaced as follows 10 Cycloalkyl, phenyl, naphthyl, pyridyl, furanyl, thiophene, benzofuranyl, benzothiophene, carbazole, dibenzofuranyl, or dibenzothiophene: deuterium, -F, cyano, C1-C 20 Alkyl, C1-C 20 Alkoxy, deuterated C1-C 20Alkyl, fluorinated C1-C 20 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 Cycloalkyl, fluorinated C3-C 10 cycloalkyl, (C1-C 20 Alkyl)C3-C 10 Cycloalkyl, phenyl, deuterated phenyl, fluorophenyl, (C1-C 20 Alkyl)phenyl, naphthyl, pyridyl, furanyl, thiophene, benzofuranyl, benzothiophene, carbazole, dibenzofuranyl, dibenzothiophene, -Si(Q) 31 (Q) 32 (Q) 33 -Ge(Q) 31 (Q) 32 (Q) 33 ), or a combination thereof; or

[0156] -Si(Q1)(Q2)(Q3) or -Ge(Q1)(Q2)(Q3).

[0157] In Equation 1,

[0158] R 11 To R 13 Two or more may be optionally connected to each other to form an unreplaced or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups,

[0159] Two or more of R2s are optionally connected to each other to form a group that is not replaced or is occupied by at least one R. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups,

[0160] Two or more of a plurality of R3s are optionally connected to each other to form an unsubstituted or at least one R 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups,

[0161] Two or more of a plurality of R4s are optionally connected to each other to form an unsubstituted or at least one R 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10aReplacement C1-C 30 Heterocyclic groups,

[0162] R 51 To R 54 Two or more may be optionally connected to each other to form an unreplaced or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups,

[0163] R 61 To R 64 Two or more may be optionally connected to each other to form an unreplaced or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups,

[0164] R 71 To R 74 Two or more may be optionally connected to each other to form an unreplaced or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups,

[0165] R 101 and R 102 Optionally connected to each other to form an unreplaced or at least R 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups, and

[0166] R' and R" are optionally connected to each other to form an unsubstituted or at least one R 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic group. R 10a For example, regarding R 11 As described.

[0167] As can be seen from the definition in Equation 1, i) when L2 is N(R'), R' is not connected to X. 54 and X 61 either of the following, ii) when L3 is N(R'), R' is not connected to X.64 and X 71 either of them, and iii) when L4 is N(R'), R' is not connected to X. 74 and X 11 Either of them. That is, for example, compounds C3 and C4 described below cannot be included in Formula 1 described herein.

[0168] In one or more embodiments, the organometallic compound represented by Formula 1 can be represented by Formula 1-1:

[0169] Equation 1-1

[0170]

[0171] In Equation 1-1,

[0172] M, X1 to X4, X 11 To X 13 X 51 To X 54 X 61 To X 64 X 71 To X 74 L1 through L4 can each be as described in this article.

[0173] X 21 It can be N or C(R) 21 ), X 22 It can be N or C(R) 22 ), and X 23 It can be N or C(R) 23 ),

[0174] R 21 To R 23 Each can be as described regarding R2,

[0175] X 31 It can be N or C(R) 31 ), X 32 It can be N or C(R) 32 ), X 33 It can be N or C(R) 33 ), X 34 It can be N or C(R) 34 ), X 35 It can be N or C(R) 35 ), and X 36 It can be N or C(R) 36 ),

[0176] R 31 To R 36 Each can be as described regarding R3.

[0177] X41 It can be N or C(R) 41 ), X 42 It can be N or C(R) 42 ), X 43 It can be N or C(R) 43 ), and X 44 It can be N or C(R) 44 ),

[0178] R 41 To R 44 Each can be as described regarding R4.

[0179] R 11 To R 13 Two or more may optionally be connected to each other to form an unsubstituted or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups,

[0180] R 21 To R 23 Two or more may optionally be connected to each other to form an unsubstituted or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups,

[0181] R 31 To R 36 Two or more may optionally be connected to each other to form an unsubstituted or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups,

[0182] R 41 To R 44 Two or more may optionally be connected to each other to form an unsubstituted or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups, and

[0183] R 10a For example, regarding R 11 As described.

[0184] All descriptions of Equation 1 provided in this article can be applied to Equation 1-1.

[0185] In one or more embodiments, formula 1-1 may satisfy at least one of the following conditions:

[0186] Condition 21

[0187] X 21 It is C(R) 21 ), and R 21 Not hydrogen

[0188] Condition 22

[0189] X 22 It is C(R) 22 ), and R 22 Not hydrogen

[0190] Condition 23

[0191] X 23 It is C(R) 23 ), and R 23 Not hydrogen

[0192] Condition 31

[0193] X 31 It is C(R) 31 ), and R 31 Not hydrogen

[0194] Condition 32

[0195] X 32 It is C(R) 32 ), and R 32 Not hydrogen

[0196] Condition 33

[0197] X 33 It is C(R) 33 ), and R 33 Not hydrogen

[0198] Condition 34

[0199] X 34 It is C(R) 34 ), and R 34 Not hydrogen

[0200] Condition 35

[0201] X 35 It is C(R) 35 ), and R 35 Not hydrogen

[0202] Condition 36

[0203] X 36It is C(R) 36 ), and R 36 Not hydrogen

[0204] Condition 41

[0205] X 41 It is C(R) 41 ), and R 41 Not hydrogen

[0206] Condition 42

[0207] X 42 It is C(R) 42 ), and R 42 Not hydrogen

[0208] Condition 43

[0209] X 43 It is C(R) 43 ), and R 43 Not hydrogen

[0210] Condition 44

[0211] X 44 It is C(R) 44 ), and R 44 It's not hydrogen.

[0212] R in conditions 21 to 23, 31 to 36, and 41 to 44 21 To R 23 R 31 To R 36 and R 41 To R 44 Each can be as described in this article.

[0213] In one or more embodiments, Equation 1-1 may satisfy condition 42.

[0214] In one or more embodiments, Equation 1-1 may satisfy conditions 22 and 42.

[0215] In one or more embodiments, R in conditions 21 to 23, 31 to 36, and 41 to 44 21 To R 23 R 31 To R 36 and R 41 To R 44 Each can be independently:

[0216] Deuterium, -F, or cyano;

[0217] Each of them was not replaced or replaced by deuterium, -F, cyano, C1-C 20 C1-C substituted with alkyl, phenyl, carbazole, or combinations thereof20 Alkyl or C1-C 20 Alkoxy;

[0218] Each of the following C3-Cs was not replaced or was replaced as follows 10 Cycloalkyl, phenyl, naphthyl, pyridyl, furanyl, thiophene, benzofuranyl, benzothiophene, carbazole, dibenzofuranyl, or dibenzothiophene: deuterium, -F, cyano, C1-C 20 Alkyl, C1-C 20 Alkoxy, deuterated C1-C 20 Alkyl, fluorinated C1-C 20 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 Cycloalkyl, fluorinated C3-C 10 cycloalkyl, (C1-C 20 Alkyl)C3-C 10 Cycloalkyl, phenyl, deuterated phenyl, fluorophenyl, (C1-C 20 Alkyl)phenyl, naphthyl, pyridyl, furanyl, thiophene, benzofuranyl, benzothiophene, carbazole, dibenzofuranyl, dibenzothiophene, -Si(Q) 31 (Q) 32 (Q) 33 -Ge(Q) 31 (Q) 32 (Q) 33 ), or a combination thereof; or

[0219] -Si(Q1)(Q2)(Q3) or -Ge(Q1)(Q2)(Q3).

[0220] In one or more embodiments, the organometallic compound represented by Formula 1 may be one of compounds 1 to 420:

[0221]

[0222]

[0223]

[0224]

[0225]

[0226] 。

[0227] In Equation 1, L2, L3, and L4 are each independently a single bond, O, S, Se, N(R'), C(R')(R"), or Si(R')(R"), wherein at least one of L2, L3, and L4 is O, S, Se, N(R'), C(R')(R"), or Si(R')(R"). That is, a 10-membered ring, an 11-membered ring, or a 12-membered ring can be fused to the ring containing X1 and X in Equation 1 while sharing the nitrogen atom adjacent to X1. 11 To X 13 The ring (e.g., a benzimidazole ring) (see Formula 1 below). Thus, due to fusion with nitrogen atoms adjacent to X1, X1 and X2 are simultaneously fused together. 11 To X 13 The 10-membered, 11-membered, or 12-membered rings (e.g., benzimidazole rings) of Formula 1, where M is the central metal, can be effectively shielded and X1, as the carbene portion, can be stabilized, thereby improving the stability and rigidity of Formula 1. Furthermore, the electron-donating properties of the organometallic compound represented by Formula 1 can be improved, thereby improving the luminescence efficiency of the organometallic compound represented by Formula 1.

[0228] Formula 1"

[0229]

[0230] Furthermore, in Equation 1, i) when L2 is N(R'), R' is not connected to X. 54 and X 61 either of the following, ii) when L3 is N(R'), R' is not connected to X. 64 and X 71 either of them, and iii) when L4 is N(R'), R' is not connected to X. 74 and X 11 Either of them. That is, for example, compounds C3 and C4 described below cannot be included in Formula 1 described herein. As a result, compounds containing X1 and X2 are fused to Formula 1 while sharing the nitrogen atom adjacent to X1. 11 To X 13 The structural degrees of freedom of the 10-membered, 11-membered, or 12-membered ring (see Formula 1) of the ring (e.g., benzimidazole ring) can be relatively increased, and the angle of structural distortion (deformation) caused by the 10-membered, 11-membered, or 12-membered ring (see Formula 1) can be relatively reduced, thereby improving the structural stability of the organometallic compound represented by Formula 1.

[0231] The peak wavelength (also called emission peak wavelength, maximum emission peak wavelength, or maximum emission wavelength) of the peak with the maximum emission intensity in the emission spectrum of the organometallic compound represented by Formula 1 may be from about 440 nanometers (nm) to about 470 nm, from about 445 nm to about 470 nm, from about 450 nm to about 470 nm, from about 455 nm to about 470 nm, from about 460 nm to about 470 nm, from about 440 nm to about 465 nm, from about 445 nm to about 465 nm, from about 450 nm to about 465 nm, from about 455 nm to about 465 nm, or from about 460 nm to about 465 nm.

[0232] The half-width (FWHM) of the emission spectrum of the organometallic compound represented by Formula 1 can be about 5 nm to about 50 nm, about 5 nm to about 40 nm, about 5 nm to about 30 nm, about 5 nm to about 20 nm, about 10 nm to about 50 nm, about 10 nm to about 40 nm, about 10 nm to about 30 nm, about 10 nm to about 20 nm, about 15 nm to about 50 nm, about 15 nm to about 40 nm, about 15 nm to about 30 nm, or about 15 nm to about 24 nm.

[0233] The triplet (T1) energy levels of organometallic compounds represented by Formula 1 can be from about 2.00 eV to about 3.20 eV, from about 2.00 eV to about 3.00 eV, from about 2.00 eV to about 2.80 eV, from about 2.50 eV to about 3.20 eV, from about 2.50 eV to about 3.00 eV, or from about 2.50 eV to about 2.80 eV.

[0234] The highest occupied molecular orbital (HOMO) level, lowest unoccupied molecular orbital (LUMO) level, and T1 level of compounds 5, 8, 10, 49, 50, 53, 66, 68, 78, 81, 95, 96, 125, 140, 155, 190, 280, 334, 335, 340, and 395 were evaluated by density functional theory (DFT) using the Gaussian 09 program with molecular structure optimization obtained at the B3LYP level, and the results are shown in Table 1.

[0235] Table 1

[0236]

[0237] The methods for synthesizing the organometallic compounds represented by Formula 1 are as can be recognized by those skilled in the art and by referring to the synthesis examples provided below.

[0238] Therefore, each of the organometallic compounds represented by Formula 1 is suitable for use as a material for an intermediate layer of a light-emitting device, for example, a material for an emitting layer of the intermediate layer. Thus, on the other hand, a light-emitting device is provided, comprising: a first electrode; a second electrode; and an intermediate layer disposed between the first electrode and the second electrode, wherein the intermediate layer comprises an emitting layer, and wherein the intermediate layer comprises at least one organometallic compound represented by Formula 1.

[0239] Because the light-emitting device has an intermediate layer comprising at least one organometallic compound represented by Formula 1 as described herein, the light-emitting device can have excellent driving voltage, excellent external quantum efficiency, and a relatively narrow FWHM of the emission peak of the electroluminescence (EL) spectrum.

[0240] Organometallic compounds represented by Formula 1 can be used between electrode pairs in a light-emitting device. For example, an organometallic compound represented by Formula 1 can be included in an emitting layer. In this respect, the emitting layer may further include a host. The amount (e.g., by weight) of the host in the emitting layer may be greater than the amount (e.g., by weight) of the at least one organometallic compound represented by Formula 1. The emitting layer may emit red light, green light, and / or blue light. For example, an organometallic compound represented by Formula 1 may emit blue light.

[0241] In one or more embodiments, the CIEy value of the light emitted from the emission layer may be about 0.040 to about 0.170, about 0.050 to about 0.170, about 0.060 to about 0.170, about 0.040 to about 0.165, about 0.050 to about 0.165, or about 0.060 to about 0.165.

[0242] In one or more embodiments, the CIEy value of light emitted from an emitting layer comprising at least one organometallic compound represented by Formula 1 as an emitter may be about 0.130 to about 0.170, about 0.135 to about 0.170, about 0.140 to about 0.170, about 0.130 to about 0.165, about 0.135 to about 0.165, about 0.140 to about 0.165, about 0.130 to about 0.160, about 0.135 to about 0.160, or about 0.140 to about 0.160.

[0243] In one or more embodiments, the CIEy value of light emitted from an emitting layer comprising at least one organometallic compound represented by Formula 1 as a sensitizer may be about 0.070 to about 0.140, about 0.080 to about 0.140, about 0.090 to about 0.140, about 0.070 to about 0.135, about 0.080 to about 0.135, about 0.090 to about 0.135, about 0.100 to about 0.135, about 0.110 to about 0.135, about 0.120 to about 0.135, or about 0.125 to about 0.135.

[0244] In one or more embodiments, the maximum emission wavelength of light emitted from the emission layer may be about 440 nm to about 470 nm, about 445 nm to about 470 nm, about 450 nm to about 470 nm, about 455 nm to about 470 nm, about 460 nm to about 470 nm, about 440 nm to about 465 nm, about 445 nm to about 465 nm, about 450 nm to about 465 nm, about 455 nm to about 465 nm, or about 460 nm to about 465 nm.

[0245] The emission layer may further include a body. The body may be as described herein.

[0246] In one or more embodiments, the emission layer may have a configuration as described in the first or second embodiment:

[0247] First implementation of the emission layer

[0248] The emitting layer may include at least one organometallic compound represented by Formula 1, and the organometallic compound represented by Formula 1 may act as an emitter, for example, a phosphorescent emitter. That is, the organometallic compound represented by Formula 1 may be the emitter. For example, the ratio of the luminescent component emitted from the organometallic compound represented by Formula 1 to all luminescent components of the emitting layer may be about 80% or greater, about 85% or greater, about 90% or greater, or about 95% or greater. The light emitted from the organometallic compound represented by Formula 1 may be blue light. In addition to the at least one organometallic compound represented by Formula 1, the emitting layer may further include phosphorescent compounds, fluorescent compounds, or combinations thereof, each different from the organometallic compound represented by Formula 1. In this respect, the phosphorescent compound and / or fluorescent compound may act as a sensitizer or auxiliary dopant.

[0249] Second implementation of the emission layer

[0250] The emitting layer may include at least one organometallic compound represented by Formula 1, and the organometallic compound represented by Formula 1 may act as a sensitizer or as an auxiliary dopant. That is, the organometallic compound represented by Formula 1 may be a sensitizer or an auxiliary dopant. The emitting layer may further include an emitter different from the at least one organometallic compound represented by Formula 1. For example, the ratio of the luminescent component emitted from the emitter to all luminescent components of the emitting layer may be about 80% or greater, about 85% or greater, about 90% or greater, or about 95% or greater. The light emitted from the emitter may be blue light. The emitter may include a phosphorescent compound, a fluorescent compound, or a combination thereof that is different from the at least one organometallic compound represented by Formula 1.

[0251] In a second embodiment of the emitter layer, the amount of emitter may be about 1 part by weight to about 100 parts by weight, about 5 parts by weight to about 50 parts by weight, or about 10 parts by weight to about 20 parts by weight, based on 100 parts by weight of the at least one organometallic compound represented by Formula 1.

[0252] In a second embodiment of the emission layer, based on 100 parts by weight of the emission layer, the total amount of the at least one organometallic compound represented by Formula 1 and the emitter may be from about 1 part by weight to 30 parts by weight, from about 3 parts by weight to about 20 parts by weight, or from about 5 parts by weight to about 15 parts by weight.

[0253] In the second embodiment of the emitting layer, the fluorescent compound used as the emitter may not include transition metals.

[0254] In one or more embodiments, the fluorescent compound that can be used as an emitter in a second embodiment of the emitting layer may be a fluorescent material that does not include cyano (-CN), fluorine (-F), or combinations thereof.

[0255] In one or more embodiments, the fluorescent compound that can be used as the emitter in the second embodiment of the emission layer may include transient fluorescent compounds, delayed fluorescent compounds (e.g., thermally activated delayed fluorescent compounds), or combinations thereof.

[0256] In one or more embodiments, the fluorescent compound that can be used as an emitter in the second embodiment of the emitting layer may be a compound containing a fused ring, an amino compound, a styrene compound, a boron compound, or a combination thereof.

[0257] In one or more embodiments, the fluorescent compound that can be used as an emitter in the second embodiment of the emission layer can be a multiple resonance thermally activated delayed fluorescence compound.

[0258] In one or more embodiments, the fluorescent compound that can be used as an emitter in a second embodiment of the emitting layer may include i) an amine-containing fluorescent compound, and / or ii) a fused polycyclic fluorescent compound containing six-membered rings, including nitrogen and boron, fused together.

[0259] In one or more embodiments, the fluorescent compound that can be used as an emitter in a second embodiment of the emitting layer may include a naphthyl group, a fluorene group, a spirodifluorene group, a benzo[9,10]fluorene group, a dibenzo[9,10]fluorene group, a phenanthrene group, an anthracene group, a fluoranthene group, a benzo[9,10]phenanthrene group, a pyrene group, Group, tetraphenyl group (butanol group), Groups, Group, pentylenetetrazol group, indene-anthracene group, group represented by any one of formulas 501-1 to 501-21, or a combination thereof:

[0260]

[0261] .

[0262] In one or more embodiments, the fluorescent compound that can be used as an emitter in a second embodiment of the emitting layer may include a compound represented by formula 501A or 501B:

[0263]

[0264] In Equations 501A and 501B,

[0265] Ar 501 It can be a naphthyl group, fluorene group, spirodifluorene group, benzo[9,10]fluorene group, dibenzo[9,10]fluorene group, phenanthrene group, anthracene group, fluoranthene group, benzo[9,10]phenanthrene group, pyrene group, Group, tetraphenyl group, Groups, Group, pentylenetetrazolium group, indene-anthracene group, bianthracite group, or a group represented by any one of formulas 501-1 to 501-21,

[0266] R 511 It can be hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 Arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, or -Si(Q) 501 (Q) 502 (Q) 503 ),

[0267] xd5 can be an integer from 0 to 10.

[0268] L 501 To L 503 Each can be independently:

[0269] Single key; or

[0270] Each of the following C3-Cs was not replaced or was replaced as follows 10 Cycloalkylene, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkylene, C1-C 10 Heterocyclic alkenyl, C6-C 60 aryl, C1-C 60 Heteroaryl groups, divalent non-aromatic fused polycyclic groups, or divalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid groups or their salts, sulfonic acid groups or their salts, phosphate groups or their salts, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 Arylalkyl, C6-C 60Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 501 (Q) 502 (Q) 503 ), or a combination thereof,

[0271] xd1 to xd3 can each be 1, 2, or 3 independently.

[0272] R 501 and R 502 Each can be independently substituted or substituted with one of the following: phenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, pyrene. alkyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazole group, triazinyl, dibenzofuranyl, dibenzothiopheneyl, or dibenzothiopheneyl: deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, nitro, amino, amidoyl, hydrazyl, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 Arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 501 (Q) 502 (Q) 503), or a combination thereof,

[0273] Z 11 Each of the following can be C1-C that has not been replaced or has been replaced as follows: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 Arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid groups or their salts, sulfonic acid groups or their salts, phosphate groups or their salts, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 Arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q)501 (Q) 502 (Q) 503 ), or a combination thereof,

[0274] xd4 can be 1, 2, 3, 4, 5, or 6, and

[0275] Q 501 To Q 503 Each can be independently hydrogen, C1-C 60 Alkyl, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C6-C 60 Aryl, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups.

[0276] In one or more embodiments, the fluorescent compound may include a compound represented by formula 501A or 501B, wherein xd4 in formula 501A may be 1, 2, 3, 4, 5, or 6, and xd4 in formula 501B may be 2, 3, or 4.

[0277] In one or more embodiments, the fluorescent compound that can be used as an emitter in a second embodiment of the emitting layer may include a compound represented by formula 503-1 or 503-2:

[0278] Formula 503-1

[0279]

[0280] Formula 503-2

[0281]

[0282] In Equations 503-1 and 503-2,

[0283] Y 51 To Y 54 Each can be independently a single bond, O, S, N[(L 506 ) xd6 -R 506 ]、C[(L 506 ) xd6 -R 506 ][(L 507 ) xd7 -R 507 ], or Si[(L 506 ) xd6 -R 506 ][(L 507 ) xd7 -R 507 ],

[0284] m53 can be 0 or 1.

[0285] L 501 To L 507 Each can be as shown in L in Equation 501B 501 As described,

[0286] xd1 to xd7 can each be as described with respect to xd1 in Equation 501B.

[0287] R 501 To R 507 Each can be independently:

[0288] Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl, C1-C 20 alkoxy, or C1-C 20 Alkylthio;

[0289] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, pyrene alkyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazole group, triazinyl, dibenzofuranyl, or dibenzothiopheneyl; or

[0290] Each of the following substituted phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, pyrene alkyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, triazinyl, dibenzofuranyl, or dibenzothiopheneyl: deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazyl, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthracene, pyrene, alkyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, triazinyl, dibenzofuranyl, dibenzothiopheneyl, or combinations thereof,

[0291] xd21 and xd23 can each be independently 0, 1, 2, 3, or 4.

[0292] xd22 and xd24 can each be 0, 1, 2, or 3 independently.

[0293] xd25 can be 0, 1, or 2, and

[0294] R 501 To R 507 The two can optionally combine with each other to form a saturated or unsaturated ring.

[0295] The fluorescent compound may include, for example, at least one of compounds FD(1) to FD(16) or FD1 to FD14, or a combination thereof, but the embodiments are not limited thereto:

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303] .

[0304] The statements “(intermediate layer) comprises at least one organometallic compound represented by Formula 1” and “(intermediate layer) comprises at least one organometallic compound represented by Formula 1” are used interchangeably herein and may include cases in which “(intermediate layer) comprises the same organometallic compound represented by Formula 1” and cases in which “(intermediate layer) comprises two or more different organometallic compounds represented by Formula 1”.

[0305] In one or more embodiments, the intermediate layer may include only compound 1 as the at least one organometallic compound represented by formula 1. In this respect, compound 1 may be present in the emitting layer of the light-emitting device. In one or more embodiments, the intermediate layer may include both compound 1 and compound 2 as the at least one organometallic compound represented by formula 1. In this respect, compound 1 and compound 2 may be present in the same layer (e.g., both compound 1 and compound 2 may be present in the emitting layer).

[0306] The first electrode may be the anode of the hole injection electrode and the second electrode may be the cathode of the electron injection electrode; or the first electrode may be the cathode of the electron injection electrode and the second electrode may be the anode of the hole injection electrode.

[0307] In one or more embodiments, in the light-emitting device, the first electrode may be an anode, the second electrode may be a cathode, and the intermediate layer may further include a hole transport region disposed between the first electrode and the emitting layer, and an electron transport region disposed between the emitting layer and the second electrode, wherein the hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof, and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

[0308] As used herein, the term "intermediate layer" refers to a single layer or multiple layers disposed between the first and second electrodes of a light-emitting device. In addition to organic compounds, "intermediate layer" may also include organometallic complexes containing metals.

[0309] Figure 1 This is a schematic cross-sectional view of an organic light-emitting device 10, which is a light-emitting device according to one or more embodiments. Referring below... Figure 1 The structure and manufacturing method of an organic light-emitting device 10 according to one or more embodiments are described in further detail. The organic light-emitting device 10 may have a structure in which a first electrode 11, an intermediate layer 15, and a second electrode 19 are stacked sequentially in the stated order.

[0310] A substrate may be disposed below the first electrode 11 or on the second electrode 19. The substrate may be a conventional substrate used in organic light-emitting devices, such as a glass substrate or a transparent plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and / or water resistance.

[0311] The first electrode 11 can be formed, for example, by depositing or sputtering a material for forming the first electrode 11 onto a substrate. The first electrode 11 can be an anode. The material for forming the first electrode 11 can include a material with a high work function to facilitate hole injection. The first electrode 11 can be a reflective electrode, a semi-transparent semi-reflective electrode, or a transmissive electrode. The material for forming the first electrode 11 can be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), or zinc oxide (ZnO). In one or more embodiments, the material for forming the first electrode 11 can be a metal, such as magnesium (Mg), aluminum (Al), silver (Ag), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag).

[0312] The first electrode 11 may have a single-layer structure or a multi-layer structure comprising two or more layers. For example, the first electrode 11 may have a three-layer structure of ITO / Ag / ITO.

[0313] The intermediate layer 15 can be arranged on the first electrode 11.

[0314] The intermediate layer 15 may include an emission layer and may further include a hole transport region and an electron transport region.

[0315] The hole transport region can be arranged between the first electrode 11 and the emitter layer.

[0316] The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof.

[0317] The hole transport region may include a hole injection layer or a hole transport layer only. In one or more embodiments, the hole transport region may have a hole injection layer / hole transport layer structure, or a hole injection layer / hole transport layer / electron blocking layer structure, wherein the corresponding layers of each structure are stacked sequentially from the first electrode 11 in the stated order.

[0318] When the hole transport region includes a hole injection layer, the hole injection layer can be formed on the first electrode 11 by using one or more suitable methods such as vacuum deposition, spin coating, tape casting, Langmuir-Broguet (LB) deposition, etc., but the implementation is not limited to this.

[0319] When a hole injection layer is formed by vacuum deposition, the deposition conditions can vary depending on the compound used to form the hole injection layer, as well as the desired structure and thermal properties of the hole injection layer. For example, the deposition temperature can be from about 100°C to about 500°C, and the vacuum level can be about 10. -8 To about 10 -3 The deposition rate can be from about 0.01 Å / s to about 100 Å / s, but the implementation is not limited thereto.

[0320] When a hole injection layer is formed by spin coating, the coating conditions can vary depending on the compound used to form the hole injection layer, as well as the desired structure and thermal properties of the hole injection layer. For example, the coating rate can be from about 2,000 rpm to about 5,000 rpm, and the temperature at which the heat treatment is performed after coating to remove the solvent can be from about 80°C to about 200°C, but the implementation is not limited thereto.

[0321] The conditions for forming the hole transport layer and electron blocking layer can be the same as those for forming the hole injection layer.

[0322] The hole transport region may include at least one of the following: 4,4',4"-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4"-tri{N-(2-naphthyl)-N-phenylamino}-triphenylamine (2-TNATA), N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine (NPB), β-NPB, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD), spiro-TPD, spiro-NPB, methylated NPB, 4,4'-cyclohexylidene bis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD), α-NPD, 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-sulfonated styrene) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-sulfonated styrene) (PANI / PSS), compounds represented by formula 201, compounds represented by formula 202, or combinations thereof, but the embodiments are not limited thereto:

[0323]

[0324]

[0325]

[0326] Formula 201

[0327]

[0328] Formula 202

[0329] .

[0330] Ar in Equation 201 101 and Ar 102 Each can be independently an unsubstituted or substituted phenylene, cyclopentadienylene, indenylene, naphthylene, or phenylene. alkyl, heptadeneyl, acenaphthene, fluoreneyl, phenentheneyl, anthraceneyl, fluoreneyl, benzo[9,10]phenentheneyl, pyreneyl, phenentheneyl alkyl, tetraphenyl, alkyl Base, Asia alkyl, or pentanephenyl: deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 Arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thio groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, or combinations thereof.

[0331] In Equation 201, xa and xb can each be an integer from 0 to 5, or xa and xb can each be 0, 1, or 2. For example, xa can be 1 and xb can be 0, but the implementation is not limited to this.

[0332] R in Equations 201 and 202 101 To R 108 R 111 To R 119 and R 121 To R 124 Each can be independently:

[0333] Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl groups (e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl, etc.), C1-C 10 Alkyl groups (e.g., methoxy, ethoxy, propoxy, butoxy, pentoxy, etc.) or C1-C 10 Alkylthio;

[0334] Each of the following C1-C is replaced: 10Alkyl, C1-C 10 alkoxy, or C1-C 10 Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, or combinations thereof; or

[0335] Each of the following groups—either unsubstituted or substituted with: deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl, C1-C 10 Alkoxy, C1-C 10 Alkylthio group, or combinations thereof.

[0336] R in Equation 201 109 It can be phenyl, naphthyl, anthracene, or pyridyl, respectively, either unsubstituted or substituted with the following: deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, phenyl, naphthyl, anthraceneyl, pyridyl, or combinations thereof.

[0337] In one or more embodiments, the compound represented by formula 201 may be represented by formula 201A:

[0338] Formula 201A

[0339] .

[0340] R in Equation 201A 101 R 111 R 112 and R 109 Each can be as described in this article.

[0341] In one or more embodiments, the hole transport region may include one or a combination of compounds HT1 to HT20, but the embodiments are not limited thereto:

[0342]

[0343]

[0344]

[0345] .

[0346] The thickness of the hole transport region can be from about 100 Å to about 10,000 Å, for example, from about 100 Å to about 1,000 Å. When the hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof, the thickness of the hole injection layer can be from about 100 Å to about 10,000 Å, for example, from about 100 Å to about 1,000 Å, and the thickness of the hole transport layer can be from about 50 Å to about 2,000 Å, for example, from about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within the ranges described above, satisfactory hole transport characteristics can be obtained without a significant increase in driving voltage.

[0347] In addition to the materials described above, the hole transport region may further include a charge-generating material for improving conductivity. The charge-generating material may be uniformly or non-uniformly dispersed in the hole transport region.

[0348] The charge-generating material can be, for example, a p-doper. The p-doper can be a quinone derivative, a metal oxide, a cyano-containing compound, or a combination thereof, but the implementation is not limited thereto. For example, the p-doper may include quinone derivatives such as tetracyanoquinone dimethylane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethylane (F4-TCNQ), or F6-TCNNQ; metal oxides such as tungsten oxide or molybdenum oxide; cyano-containing compounds such as compound HT-D1; or combinations thereof, but the implementation is not limited thereto.

[0349]

[0350] .

[0351] Hole transport regions may include buffer layers.

[0352] The buffer layer can compensate for the optical resonant distance according to the wavelength of the light emitted from the emitting layer to improve efficiency.

[0353] When the hole transport region includes an electron blocking layer, the material used to form the electron blocking layer may include the materials used in the hole transport region as described above, the host material described below, or a combination thereof. For example, when the hole transport region includes an electron blocking layer, the material used to form the electron blocking layer may be mCP, which will be described below.

[0354] The emitter layer can be formed on the hole transport region by vacuum deposition, spin coating, casting, LB deposition, etc., but the implementation is not limited to these methods. When the emitter layer is formed by vacuum deposition or spin coating, the deposition or coating conditions can be similar to those used when forming the hole injection layer, although the deposition or coating conditions can vary depending on the material to be used.

[0355] The emitter layer may include a host and a dopant, and the dopant may include at least one organometallic compound represented by Formula 1 as described herein.

[0356] The main body may include at least one of the following: 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi), 3-tert-butyl-9,10-bis(naphthyl-2-yl)anthracene (TBADN), 9,10-bis(naphthyl-2-yl)anthracene (ADN) (also known as "DNA"), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 4,4'-bis(9-carbazolyl)-2,2'-dimethyl-biphenyl (CDBP), 1,3,5-tris(carbazol-9-yl)benzene (TCP), 1,3-bis(N-carbazolyl)benzene (mCP), compound H50, compound H51, compound H52, or combinations thereof, but the embodiments are not limited thereto:

[0357]

[0358]

[0359] .

[0360] When the organic light-emitting device is a full-color organic light-emitting device, the emitting layer can be patterned as a red emitting layer, a green emitting layer, and / or a blue emitting layer. In one or more embodiments, due to the stacked structure including red, green, and / or blue emitting layers, the emitting layer can emit white light, and various variations are possible.

[0361] When the emitter layer comprises a host and a dopant, the amount of dopant may be from about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host, but the implementation is not limited thereto.

[0362] The thickness of the emitting layer can be from about 100 Å to about 1,000 Å, for example from about 200 Å to about 600 Å. When the thickness of the emitting layer is within the range described above, excellent light emission characteristics can be obtained without a significant increase in driving voltage.

[0363] The electron transmission area can be arranged on the emission layer.

[0364] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

[0365] In one or more embodiments, the electron transport region may have a hole blocking layer / electron transport layer / electron injection layer structure, or an electron transport layer / electron injection layer structure, but the embodiments are not limited thereto. The electron transport layer may have a multilayer structure or a single-layer structure comprising two or more different materials.

[0366] The conditions for forming the hole blocking layer, electron transport layer, and electron injection layer that constitute the electron transport region can be the same as the conditions for forming the hole injection layer.

[0367] When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, at least one of the following: 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), or combinations thereof, but the embodiments are not limited thereto:

[0368] .

[0369] In one or more embodiments, the hole blocking layer may include the body described above, the material for forming the electron transport layer, the material for forming the electron injection layer, or a combination thereof, as described below.

[0370] The thickness of the hole blocking layer can be from about 20 Å to about 1,000 Å, for example from about 30 Å to about 600 Å. When the thickness of the hole blocking layer is within the range described above, excellent hole blocking characteristics can be obtained without a significant increase in driving voltage.

[0371] The electron transport layer may include at least one of the following: 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi), tris(8-hydroxyquinoline)aluminum (Alq3), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthyl-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), or combinations thereof, but the embodiments are not limited thereto:

[0372] .

[0373] In one or more embodiments, the electron transport layer may include one or a combination of compounds ET1 to ET25, but the embodiments are not limited thereto:

[0374]

[0375]

[0376]

[0377] .

[0378] The thickness of the electron transport layer can be from about 100 Å to about 1,000 Å, for example from about 150 Å to about 500 Å. When the thickness of the electron transport layer is within the range described above, satisfactory electron transport characteristics can be obtained without a significant increase in driving voltage.

[0379] In addition to the materials described above, the electron transport layer may further include metallic materials.

[0380] Metal-containing materials may include Li complexes. Li complexes may include, for example, compounds ET-D1 or ET-D2, but the embodiments are not limited thereto:

[0381] .

[0382] The electron transport region may also include an electron injection layer that facilitates the injection of electrons from the second electrode 19.

[0383] The electron-injected layer may include LiF, NaCl, CsF, Li2O, BaO, or combinations thereof.

[0384] The thickness of the electron injection layer can be from about 1 Å to about 100 Å, for example from about 3 Å to about 90 Å. When the thickness of the electron injection layer is within the range described above, satisfactory electron injection characteristics can be obtained without a significant increase in the driving voltage.

[0385] The second electrode 19 may be disposed on the intermediate layer 15. The second electrode 19 may be a cathode. The material used to form the second electrode 19 may be a metal, alloy, conductive compound, or combination thereof, each having a relatively low work function. For example, the material used to form the second electrode 19 may be lithium (Li), magnesium (Mg), aluminum (Al), silver (Ag), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag). In one or more embodiments, for the purpose of manufacturing a top-emitting light-emitting device, a transmissive electrode formed using ITO or IZO may be used as the second electrode 19, and various variations are possible.

[0386] The above text has already referenced Figure 1 Organic light-emitting devices are described, but implementation methods are not limited thereto.

[0387] According to another aspect, the light-emitting device can be included in various electronic devices. Therefore, an electronic device including the light-emitting device is provided.

[0388] In addition to the light-emitting device, the electronic device may further include i) a color filter, ii) a color conversion layer, or iii) a color filter and a color conversion layer. The color filter and / or color conversion layer may be arranged in at least one direction in which the light emitted from the light-emitting device travels. For example, the light emitted from the light-emitting device may be blue, green, or white light. The light-emitting device may be as described herein. In one or more embodiments, the color conversion layer may include quantum dots.

[0389] An electronic device may include a first substrate. The first substrate may include a plurality of sub-pixel regions, a color filter may include a plurality of color filter regions corresponding to the plurality of sub-pixel regions, and a color conversion layer may include a plurality of color conversion regions corresponding to the plurality of sub-pixel regions.

[0390] Pixel-defining films can be arranged between sub-pixel regions to define each sub-pixel region.

[0391] The color filter may further include a light-shielding (light-blocking) pattern disposed between the plurality of color filter regions, and the color conversion layer may further include a light-shielding pattern disposed between the plurality of color conversion regions.

[0392] In addition to the light-emitting devices described above, electronic devices may further include thin-film transistors. A 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.

[0393] Thin-film transistors may further include gate electrodes, gate insulating films, etc.

[0394] The active layer may include crystalline silicon, amorphous silicon, organic semiconductors, oxide semiconductors, etc.

[0395] The electronic device may further include a sealing portion for sealing the light-emitting device. The sealing portion may be disposed between the color filter and / or color conversion layer and the light-emitting device. The sealing portion allows light from the light-emitting device to be extracted to the outside while simultaneously preventing ambient air and moisture (humidity) 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 type of organic layer and / or inorganic layer. When the sealing portion is a thin-film encapsulation layer, the electronic device may be flexible.

[0396] Depending on the application of the electronic device, various functional layers may be arranged on the sealed portion in addition to color filters and / or color conversion layers. Examples of functional layers may include a touchscreen layer and a polarizing layer. The touchscreen layer may be a pressure-sensitive touchscreen layer, a capacitive touchscreen layer, or an infrared touchscreen layer.

[0397] In one or more embodiments, the electronic device may include a light-emitting device and a sealing portion for sealing the light-emitting device.

[0398] In one or more embodiments, a method is provided for manufacturing an electronic device including a light-emitting device and a sealing portion for sealing the light-emitting device, the method comprising:

[0399] Manufacturing light-emitting devices; and

[0400] Manufacture sealed parts to protect light-emitting devices from ambient air and moisture.

[0401] In one or more embodiments, the electronic device may be or can be applied to one of the following: flat panel display, curved display, computer monitor (display), medical monitor, television, billboard, indoor light, outdoor light, signal light, head-up display, fully or partially transparent display, flexible display, rollable display, foldable display, stretchable display, laser printer, telephone, mobile phone, tablet computer, phablet, personal digital assistant (PDA), wearable device (e.g., watch), laptop computer, personal computer, digital camera, camcorder, viewfinder, microdisplay, 3D display, virtual reality display, augmented reality display, vehicle, video wall including multiple displays tiled together, theater screen, stadium screen, phototherapy equipment, signage (signboard, notice board), electronic notebook, electronic dictionary, video game console, etc., but the embodiments are not limited thereto.

[0402] The light-emitting device can have excellent driving voltage and external quantum efficiency characteristics, and therefore, electronic devices including the light-emitting device can have high-quality characteristics such as high brightness, high resolution, and low power consumption.

[0403] On the other hand, a diagnostic composition comprising at least one organometallic compound represented by Formula 1 is provided.

[0404] Organometallic compounds represented by Formula 1 may be able to provide high luminescence efficiency, and therefore, diagnostic compositions comprising at least one organometallic compound represented by Formula 1 may have high diagnostic efficiency.

[0405] The diagnostic composition can be used in a variety of applications, including diagnostic kits, diagnostic reagents, biosensors, biomarkers, etc., but the implementation is not limited thereto.

[0406] As used in this article, the term "C1-C" 60 "Alkyl" refers to a straight-chain or branched monovalent group of a saturated aliphatic hydrocarbon having 1 to 60 carbon atoms, and as used herein, "C1-C..." 60 "alkylene" refers to a compound with C1-C2 atoms.60 Divalent groups with the same structure as alkyl groups.

[0407] In this article, C1-C 60 Alkyl groups can be C1-C 20 Alkyl groups, such as C1-C 10 Alkyl or C1-C6 alkyl. These alkyl groups can each be straight-chain or branched. In the case of branched alkyl groups, the lower limit of the carbon number range for each alkyl group becomes 3. C1-C 60 Alkyl, C1-C 20 Alkyl, and / or C1-C 10 Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodel. Sec-decyl, tert-decyl, etc.: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isonyl, sec-nonyl, tert-nonyl, n-decyl, isodel, sec-decyl, tert-decyl, or combinations thereof.

[0408] As used in this article, the term "C1-C" 60 "Alkoxy" refers to a compound with the formula -OA 101 (where A) 101 It is C1-C 60 Alkyl) monovalent groups, and as used herein, the term "C1-C 60 "Alkylthio" refers to a group with the formula -SA 102 (where A) 102 It is C1-C 60 Alkyl groups are monovalent groups.

[0409] C1-C 60 Alkoxy, C1-C 20 alkoxy, or C1-C 10 Non-limiting examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, pentoxy, etc.

[0410] As used in this article, the term "C2-C" 60 "Alkenyl" refers to a group formed by the synthesis of alkenyl groups from C2-C2. 60A hydrocarbon group formed by substituting at least one carbon-carbon double bond at the middle or end of an alkyl group, and non-limiting examples include vinyl, propenyl, butenyl, etc. As used herein, the term "C2-C" is used... 60 "Alkenyl" refers to a group that has a C2-C bond structure. 60 Divalent groups with the same structure as alkenyl groups.

[0411] As used in this article, the term "C2-C" 60 "Alkyne group" refers to a group formed by the combination of C2-C... 60 A hydrocarbon group formed by substituting at least one carbon-carbon triple bond into the middle or end of an alkyl group, and non-limiting examples include ethynyl, propynyl, etc. As used herein, the term "C2-C" is used in this context. 60 "Immyneyl" refers to a group that has a similar structure to C2-C2. 60 Divalent groups with the same structure as alkynyl groups.

[0412] As used in this article, the term "C3-C" 10 "Cycloalkyl" refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms as cyclic atoms, and as used herein in the term "C3-C". 10 "Cycloalkylene" refers to a compound with C3-C66 atoms. 10 Divalent groups with the same structure as cycloalkyl groups.

[0413] C3-C 10 Non-limiting examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl (norbornel), bicyclo[2.2.2]octyl, etc.

[0414] As used in this article, the term "C1-C" 10 "Heterocyclic alkyl" refers to a monovalent saturated cyclic group comprising at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a cyclic atom and 1 to 10 carbon atoms as cyclic atoms, and as used herein by the term "C1-C". 10 "Heterocyclic alkyl" refers to a compound with C1-C2 atoms. 10 Divalent groups with the same structure as heterocyclic alkyl groups.

[0415] C1-C 10 Non-limiting examples of heterocyclic alkyl groups include silylcyclopentyl, silylcyclohexyl, tetrahydrofuranyl, tetrahydro-2H-pyranyl, tetrahydrothiophenyl, etc.

[0416] As used in this article, the term "C3-C" 10"Cycloalkenyl" refers to a monovalent hydrocarbon cyclic group that includes 3 to 10 carbon atoms as cyclic atoms and at least one carbon-carbon double bond in its ring and is not aromatic, and non-limiting examples include cyclopentenyl, cyclohexenyl, cycloheptenyl, etc. As used herein, the term "C3-C" is also used. 10 "Biopylidene alkenyl" refers to a group that has a C3-C... 10 A divalent group with the same structure as a cycloalkenyl group.

[0417] As used in this article, the term "C1-C" 10 "Heterocyclic alkenyl" refers to a monovalent cyclic group that includes at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a cyclic atom, 1 to 10 carbon atoms as cyclic atoms, and at least one double bond, and is not aromatic. C1-C 10 Non-limiting examples of heterocyclic alkenyl groups include 2,3-dihydrofuranyl, 2,3-dihydrothiophenyl, etc., as used herein with the term "C1-C". 10 "Heterocyclic alkenyl" refers to a group that has a similar structure to C1-C1. 10 Divalent groups with the same structure as heterocyclic alkenyl groups.

[0418] As used in this article, the term "C6-C" 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic ring system with 6 to 60 carbon atoms as cyclic atoms, and as used herein in the term "C6-C". 60 "Arylene" refers to a divalent group in a carbocyclic aromatic ring system with 6 to 60 carbon atoms as cyclic atoms. (C6-C) 60 Non-limiting examples of aryl groups include phenyl, naphthyl, anthraceneyl, phenanthryl, pyrene, Base, etc. When C6-C 60 Aryl and C6-C 60 When each of the aryl groups comprises two or more rings, the rings may be fused together.

[0419] As used in this article, the term "C7-C" 60 "alkylaryl" refers to an alkyl group formed by at least one C1-C2 group. 54 Alkyl-substituted C6-C 59 Aryl. As used in this text, the term "C7-C" 60 "Arylalkyl" refers to an alkyl group consisting of at least one C6-C bond. 59 aryl-substituted C1-C 54 alkyl.

[0420] As used in this article, the term "C1-C" 60"Heteroaryl" refers to a monovalent heteroaryl ring group comprising a heteroaryl ring system having at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a cyclic atom and 1 to 60 carbon atoms as cyclic atoms, and as used herein by the term "C1-C". 60 "Hypo-heteroaryl" refers to a divalent group comprising a heteroaromatic ring system having at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a cyclic atom and 1 to 60 carbon atoms as cyclic atoms. C1-C 60 Non-limiting examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, etc. When C1-C... 60 heteroaryl and C1-C 60 When each heteroaryl group comprises two or more rings, the rings can be fused together.

[0421] As used in this article, the term "C2-C" 60 "alkyl heteroaryl" refers to an alkyl group formed by at least one C1-C2 group. 59 Alkyl-substituted C1-C 59 heteroaryl. As used in this text, the term "C2-C" is used in conjunction with... 60 "Heteroarylalkyl" refers to an alkyl group consisting of at least one C1-C2 group. 59 heteroaryl-substituted C1-C 59 alkyl.

[0422] As used in this article, the term "C6-C" 60 "Aryloxy group" refers to -OA 103 (where A) 103 It is C6-C 60 Aryl), and as used herein, the term "C6-C" 60 "Arylthio" refers to -SA 104 (where A) 104 It is C6-C 60 Aryl).

[0423] As used in this article, the term "C1-C" 60 "Heteroaryloxy" refers to -OA 105 (where A) 105 It is C1-C 60 (Heteroaryl), and as used herein, the term "C1-C 60 "Heteroary sulfide" refers to -SA 106 (where A) 106 It is C1-C 60 (Miscellaneous aromatics).

[0424] As used herein, the term "monovalent nonaromatic fused polycyclic group" refers to a monovalent group (e.g., having 8 to 60 carbon atoms) that has two or more rings fused together, has only carbon atoms as cyclic atoms, and is not aromatic in its entirety. Non-limiting examples of monovalent nonaromatic fused polycyclic groups include fluorene groups, etc. As used herein, the term "divalent nonaromatic fused polycyclic group" refers to a divalent group having the same structure as a monovalent nonaromatic fused polycyclic group.

[0425] As used herein, the term "monovalent nonaromatic fused heterocyclic group" refers to a monovalent group (e.g., having 1 to 60 carbon atoms) that has two or more fused rings, has heteroatoms selected from N, O, P, Si, S, Se, Ge, and B as cyclic atoms in addition to carbon atoms, and is not aromatic in its overall structure. Non-limiting examples of monovalent nonaromatic fused heterocyclic groups include carbazole groups, etc. As used herein, the term "divalent nonaromatic fused heterocyclic group" refers to a divalent group having the same structure as a monovalent nonaromatic fused heterocyclic group.

[0426] As used in this article, the term "C5-C" 30 A "carbocyclic group" refers to a saturated or unsaturated cyclic group that consists of only 5 to 30 carbon atoms as cyclic atoms. (C5-C) 30 The carbocyclic group can be a monocyclic or polycyclic group. "(Unsubstituted or substituted with at least one R)" 10a (Replacement) C5-C 30 Non-limiting examples of "carbocyclic groups" include (each unsubstituted or with at least one R) 10a Substituted) adamantyl group, norbornene group, bicyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo[2.2.1]heptane (norbornene) group, bicyclo[2.2.2]octyl group, cyclopentyl group, cyclohexyl group, cyclohexene group, phenyl group, naphthyl group, anthracene group, phenanthrene group, benzo[9,10]phenanthrene group, pyrene group, Groups such as 1,2,3,4-tetrahydronaphthalene group, cyclopentadienyl group, and fluorene group.

[0427] As used in this article, the term "C1-C" 30 A "heterocyclic group" refers to a saturated or unsaturated cyclic group that, in addition to 1 to 30 carbon atoms as cyclic atoms, has at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a cyclic atom. C1-C 30 Heterocyclic groups can be monocyclic or polycyclic. "(Unsubstituted or substituted with at least one R)" 10a (Replacement) C1-C 30Non-limiting examples of "heterocyclic groups" include (each not substituted or with at least one R) 10a Substituted thiophene group, furan group, pyrrole group, thiophene group, borocyclopentadien group, phosphacyclopentadien group, selenophene group, germanium heterocyclopentadien group, benzothiophene group, benzofuran group, indole group, benzothiophene group, benzoboron heterocyclopentadien group, benzophosphacyclopentadien group, benzoselenophene group, benzogermanium heterocyclopentadien group, dibenzothiophene group, dibenzofuran group, carbazole group, dibenzothiophene group, dibenzoboron heterocyclopentadien group, dibenzophosphacyclopentadien group, dibenzoselenophene group, dibenzogermanium heterocyclopentadien group, dibenzothiophene 5-oxide group, 9H-fluorene-9-one group, dibenzothiophene 5,5-dioxide group, azabenzothiophene group, azabenzofuran group, azaindole group, azaindene group, nitrogen The following groups are listed: benzothiophene group, azibabenzoborane group, azibabenzophosphacyclopentadiene group, azibabenzoselenophene group, azibabenzogeranecyclopentadiene group, azibadibenzothiophene group, azibadibenzofuran group, azibacarbazole group, azibafluorene group, azibadibenzothiophene group, azibadibenzoboranecyclopentadiene group, azibadibenzophosphacyclopentadiene group, azibadibenzoselenophene group, azibadibenzogeranecyclopentadiene group, azibadibenzothiophene 5-oxide group, aziba-9H-fluorene-9-one group, azibadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazolinine group, phenanthrene-rhein group, pyrazole group, imidazole group, triazole group. azole group, iso- azole group, thiazole group, isothiazole group, Diazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzo[] azole group, benzothiazole group, benzo[] Diazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group, 5,6,7,8-tetrahydroquinoline group, etc.

[0428] As used in this article, the term "fluorinated C1-C" 60 Alkyl (or fluorinated C1-C) 20 Alkyl groups, etc., and fluorinated C3-C groups. 10 "cycloalkyl", "fluorinated C1-C" 10 "Heterocyclic alkyl" and "fluorophenyl" refer to C1-C1 alkyl groups, respectively, that are substituted with at least one fluorine group (-F). 60 Alkyl (or C1-C) 20 Alkyl groups, etc., C3-C 10 cycloalkyl, C1-C 10Heterocyclic alkyl groups and phenyl groups. For example, the term "fluoroC1 alkyl (i.e., fluoromethyl)" includes -CF3, -CF2H, and -CFH2. "Fluoro-C1-C..." 60 Alkyl (or fluorinated C1-C) 20 Alkyl groups, etc., and fluorinated C3-C groups. 10 "cycloalkyl", "fluorinated C1-C" 10 "Heterocyclic alkyl" or "fluorophenyl" can be i) fully fluorinated C1-C 60 Alkyl (or fully fluorinated C1-C) 20 Alkyl groups, etc.), fully fluorinated C3-C 10 cycloalkyl, fully fluorinated C1-C 10 Heterocyclic alkyl groups or fully fluorinated phenyl groups, wherein all hydrogen atoms in each group are replaced by fluorine groups, or ii) partially fluorinated C1-C 60 Alkyl (or partially fluorinated C1-C) 20 Alkyl groups, etc.), and some fluorinated C3-C groups. 10 Cycloalkyl, partially fluorinated C1-C 10 Heterocyclic alkyl groups or partially fluorophenyl groups, wherein not all hydrogen atoms in each group are replaced by fluorine groups.

[0429] As used in this article, “deuterated C1-C” 60 Alkyl (or deuterated C1-C) 20 Alkyl groups, etc., and deuterated C3-C 10 "Cycloalkyl", "Deuterated C1-C" 10 "Heterocyclic alkyl" and "deuterated phenyl" refer to C1-C1 alkyl groups respectively substituted with at least one deuterium. 60 Alkyl (or C1-C) 20 Alkyl groups, etc., C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl groups and phenyl groups. For example, the term "deuterated C1 alkyl (i.e., deuterated methyl)" includes -CD3, -CD2H, and -CDH2. "Deuterated C1-C..." 60 Alkyl (or deuterated C1-C) 20 Alkyl groups, etc., and deuterated C3-C 10 "Cycloalkyl", "Deuterated C1-C" 10 "Heterocyclic alkyl" or "deuterated phenyl" can be i) fully deuterated C1-C 60 Alkyl (or fully deuterated C1-C) 20 Alkyl groups, etc., fully deuterated C3-C 10 Cycloalkyl, fully deuterated C1-C 10 Heterocyclic alkyl groups, or fully deuterated phenyl groups, wherein all hydrogen atoms in each group are replaced by deuterium, or ii) partially deuterated C1-C 60Alkyl (or partially deuterated C1-C) 20 Alkyl groups, etc., and partially deuterated C3-C 10 cycloalkyl, partially deuterated C1-C 10 Heterocyclic alkyl groups, or partially deuterated phenyl groups, wherein not all hydrogen atoms in each group are replaced by deuterium.

[0430] As used in this article, the term "(C1-C" is similar to the term "(C1-C)" 20 "alkyl)'X' group" refers to a group formed by at least one C1-C2 group. 20 Alkyl-substituted 'X' groups. For example, as used herein, the term "(C1-C1)" 20 Alkyl)C3-C 10 "Cycloalkyl" refers to a compound formed by at least one C1-C2 group. 20 Alkyl-substituted C3-C 10 Cycloalkyl, and as used herein, the term "(C1-C1)" 20 "alkyl)phenyl" refers to a compound formed by at least one C1-C2 bond. 20 Alkyl-substituted phenyl groups. An example of (C1 alkyl)phenyl is tolyl.

[0431] As used herein, the terms "azaindole group, azabenzoboranecyclopentadienyl group, azabenzophosphacyclopentadienyl group, azaindene group, azabenzothiophene group, azabenzogermanium cyclopentadienyl group, azabenzothiophene group, azabenzoselenene group, azabenzofuran group, azacarbazole group, azadibenzoboranecyclopentadienyl group, azadibenzophosphacyclopentadienyl group, azafluorene group, azadibenzothiophene group, azadibenzogermanium cyclopentadienyl group, azadibenzothiophene group, azadibenzoselenene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluorene-9-one group, and azadibenzothiophene 5,5-dioxide group" are used in this document. These refer to the following heterocyclic groups, which have the same skeleton as "indole group, benzoboron heterocyclopentadienyl group, benzophosphonocyclopentadienyl group, indene group, benzothiophene group, benzogermanium heterocyclopentadienyl group, benzothiophene group, benzoselenene group, benzofuran group, carbazole group, dibenzoboron heterocyclopentadienyl group, dibenzophosphonocyclopentadienyl group, fluorene group, dibenzothiophene group, dibenzogermanium heterocyclopentadienyl group, dibenzothiophene group, dibenzoselenene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluorene-9-one group, and dibenzothiophene 5,5-dioxide group", wherein in each group, at least one carbon atom selected from the cyclic carbon atom is replaced by a nitrogen atom.

[0432] Replacement C5-C 30 Carbocyclic groups, substituted C1-C 30 Heterocyclic groups, substituted C1-C60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C1-C 60 Alkylthio, substituted C3-C 10 cycloalkyl, substituted C1-C 10 Heterocyclic alkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 Aryl, substituted C7-C 60 Alkyl aryl, substituted C7-C 60 Arylalkyl, substituted C6-C 60 aryloxy groups, substituted C6-C 60 Arylthioyl, substituted C1-C 60 heteroaryl, substituted C2-C 60 Alkyl heteroaryl, substituted C2-C 60 Heteroarylalkyl, substituted C1-C 60 Heteroaryl groups, substituted C1-C 60 At least one substituent of the heteroaryl thio group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heterocyclic group can each independently be:

[0433] Deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 alkoxy, or C1-C 60 Alkylthio;

[0434] Each of the following C1-C is replaced: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 alkoxy, or C1-C 60 Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C3-C 10 cycloalkyl, C1-C10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 11 (Q) 12 (Q) 13 -Ge(Q) 11 (Q) 12 (Q) 13 -N(Q) 14 (Q) 15 -B(Q) 16 (Q) 17 -P(Q) 18 (Q) 19 -P(=O)(Q) 18 (Q) 19 ), or combinations thereof;

[0435] C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups;

[0436] Each of the following C3-C is replaced: 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid groups or their salts, sulfonic acid groups or their salts, phosphate groups or their salts, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 Arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 21 (Q) 22 (Q) 23 -Ge(Q) 21 (Q) 22 (Q) 23 -N(Q) 24 (Q) 25 -B(Q) 26 (Q) 27 -P(Q) 28 (Q) 29 -P(=O)(Q) 28 (Q) 29 ), or combinations thereof;

[0437] -Si(Q 31 (Q) 32 (Q) 33-Ge(Q) 31 (Q) 32 (Q) 33 -N(Q) 34 (Q) 35 -B(Q) 36 (Q) 37 -P(=O)(Q) 38 (Q) 39 ), or -P(Q 38 (Q) 39 );or

[0438] Its combination.

[0439] The Q1 to Q9, Q described in this article 11 To Q 19 Q 21 To Q 29 , and Q 31 To Q 39 Each can be independently:

[0440] Hydrogen, deuterium, or -F; or

[0441] Each of the following C1-Cs was not replaced or was replaced as follows 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 Arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups: deuterium, -F, cyano, C1-C 60 Alkyl, C6-C 60 Aryl groups, or combinations thereof.

[0442] Hereinafter, the organometallic compound and light-emitting device represented by Formula 1 according to exemplary embodiments will be described in further detail with reference to synthesis examples and embodiments. However, the embodiments are not limited thereto. The phrase "using B instead of A" used in describing the synthesis examples means that, in molar equivalents, the amount of A used is the same as the amount of B used.

[0443] Example

[0444] Synthesis Example 1 (Compound 5)

[0445]

[0446]

[0447] Synthesis of compound 5E

[0448] Compound 5A (8.00 g, 27.0 mmol), compound 5B (16.2 g, 32.4 mmol), tetrakis(triphenylphosphine)palladium(0)(Pd(PPh3)4) (3.12 g, 2.70 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos) (2.22 g, 5.40 mmol), and K2CO3 (7.47 g, 54.0 mmol) were added to a round-bottom flask and combined with 1,4-dioxane / H2O (120 mL / 30 mL). The mixture was then stirred under reflux at 110 °C for 16 hours. After the reaction was complete, the temperature was lowered to room temperature, and ethyl acetate and a saturated aqueous solution of ammonium chloride were added to the reaction mixture to obtain an organic layer. The organic layer was extracted with ethyl acetate, dried over anhydrous MgSO4, and then filtered. The filtrate obtained was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 9.0 g (57% yield) of compound 5E.

[0449] Liquid chromatography-mass spectrometry (LC-MS): 589.27 [M+H] + .

[0450] Synthesis of compound 5F

[0451] Compound 5E (9.0 g, 15.3 mmol) and K₂CO₃ (6.34 g, 45.9 mmol) were added to a round-bottom flask and combined with dimethylformamide (DMF) (160 mL). The mixture was then stirred at 100 °C for 13 hours. After the reaction was complete, the temperature was lowered to room temperature, and ethyl acetate and a saturated aqueous solution of ammonium chloride were added to the reaction mixture to obtain an organic layer. The organic layer was extracted with ethyl acetate, dried over anhydrous MgSO₄, and then filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 4.2 g (48% yield) of compound 5F.

[0452] LC-MS: 568.27 [M+H] + .

[0453] Synthesis of compound 5G

[0454] Compound 5F (4.20 g, 7.39 mmol), carbon-supported palladium (Pd / C) (10 wt% carbon-supported Pd, 0.79 g, 0.74 mmol), and ammonium formate (9.31 g, 148 mmol) were added to a round-bottom flask and combined with ethanol (EtOH) (75 mL). The mixture was then stirred under reflux at 80 °C for 13 h. After the reaction was complete, the temperature was lowered to room temperature, and ethyl acetate and a saturated aqueous solution of ammonium chloride were added to the reaction mixture to obtain an organic layer. The organic layer was extracted with ethyl acetate, dried over anhydrous MgSO4, and then filtered. The filtrate obtained was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 3.39 g (85% yield) of compound 5G.

[0455] LC-MS: 538.29 [M+H] + .

[0456] Synthesis of compound 5I

[0457] Compound 5G (3.39 g, 6.29 mmol), compound 5H (3.11 g, 6.61 mmol), tris(dibenzylacetone)dipalladium(O)(Pd2(dba)3) (0.58 g, 0.63 mmol), SPhos (0.52 g, 1.26 mmol), and sodium tert-butoxide (NaOtBu) (0.91 g, 9.44 mmol) were added to a round-bottom flask and combined with toluene (65 mL). The mixture was then stirred under reflux at 110 °C for 13 h. After the reaction was complete, the temperature was lowered to room temperature, and ethyl acetate and a saturated aqueous solution of ammonium chloride were added to the reaction mixture to obtain an organic layer. The organic layer was extracted with ethyl acetate, dried over anhydrous MgSO4, and then filtered. The filtrate obtained was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 5.2 g (89% yield) of compound 5I.

[0458] LC-MS: 929.47 [M+H] + .

[0459] Synthesis of compound 5J

[0460] Compound 5I (5.2 g, 5.60 mmol) was added to a round-bottom flask and mixed with triethyl orthoformate (50 mL), followed by the addition of 35% hydrochloric acid (0.58 mL, 6.72 mmol). The mixture was then stirred at 80 °C for 3 hours. After the reaction was complete, the temperature was lowered to room temperature, and the reaction mixture was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 5.19 g (95% yield) of compound 5J.

[0461] Synthesis of Compound 5

[0462] Compound 5J (5.19 g, 5.32 mmol), K₂PtCl₄ (2.52 g, 5.85 mmol), and sodium acetate (NaOAc) (1.57 g, 16.0 mmol) were added to a round-bottom flask and combined with dioxane (100 mL). The mixture was then stirred under reflux at 100 °C for 12 hours. After the reaction was complete, the temperature was lowered to room temperature, and ethyl acetate and a saturated aqueous solution of ammonium chloride were added to the reaction mixture to obtain an organic layer. The organic layer was extracted with ethyl acetate, dried over anhydrous MgSO₄, and then filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 3.4 g (56% yield) of compound 5.

[0463] LC-MS: 1132.28 [M+H] + .

[0464] Synthesis Example 2 (Compound 125)

[0465]

[0466]

[0467] Synthesis of compound 125C

[0468] Compound 125A (10.0 g, 20.9 mmol), compound 125B (5.8 g, 31.4 mmol), Pd(PPh3)4 (2.42 g, 2.09 mmol), SPhos (1.72 g, 4.18 mmol), and K2CO3 (5.78 g, 41.8 mmol) were added to a round-bottom flask and combined with 1,4-dioxane / H2O (80 mL / 20 mL). The mixture was then stirred under reflux at 110 °C for 16 hours. After the reaction was complete, the temperature was lowered to room temperature, and ethyl acetate and a saturated aqueous solution of ammonium chloride were added to the reaction mixture to obtain an organic layer. The organic layer was extracted with ethyl acetate, dried over anhydrous MgSO4, and then filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 7.50 g (67% yield) of compound 125C.

[0469] LC-MS: 538.05 [M+H] + .

[0470] Synthesis of Compound 125E

[0471] Compound 125C (7.50 g, 13.9 mmol), compound 125D (8.51 g, 20.9 mmol), Pd(PPh3)4 (1.61 g, 1.39 mmol), SPhos (1.14 g, 2.79 mmol), and K2CO3 (3.85 g, 27.9 mmol) were added to a round-bottom flask and combined with 1,4-dioxane / H2O (60 mL / 15 mL). The mixture was then stirred under reflux at 110 °C for 16 hours. After the reaction was complete, the temperature was lowered to room temperature, and ethyl acetate and a saturated aqueous solution of ammonium chloride were added to the reaction mixture to obtain an organic layer. The organic layer was extracted with ethyl acetate, dried over anhydrous MgSO4, and then filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 8.50 g (83% yield) of compound 125E.

[0472] LC-MS: 739.35 [M+H] + .

[0473] Synthesis of compound 125F

[0474] Compound 125E (8.5 g, 11.5 mmol) and K₂CO₃ (4.77 g, 34.5 mmol) were added to a round-bottom flask and combined with DMF (120 mL). The mixture was then stirred at 100 °C for 16 hours. After the reaction was complete, the temperature was lowered to room temperature, and ethyl acetate and a saturated aqueous solution of ammonium chloride were added to the reaction mixture to obtain an organic layer. The organic layer was extracted with ethyl acetate, dried over anhydrous MgSO₄, and then filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 5.30 g (64% yield) of compound 125F.

[0475] LC-MS: 719.36 [M+H] + .

[0476] Synthesis of Compound 125G

[0477] Compound 125F (5.30 g, 7.37 mmol), Pd / C (10 wt% carbon-supported Pd, 0.78 g, 0.74 mmol), and ammonium formate (9.30 g, 147 mmol) were added to a round-bottom flask and combined with ethanol (75 mL). The mixture was then stirred under reflux at 80 °C for 4 hours. After the reaction was complete, the temperature was lowered to room temperature, and ethyl acetate and a saturated aqueous solution of ammonium chloride were added to the reaction mixture to obtain an organic layer. The organic layer was extracted with ethyl acetate, dried over anhydrous MgSO4, and then filtered. The filtrate obtained was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 3.60 g (71% yield) of compound 125G.

[0478] LC-MS: 689.37 [M+H] + .

[0479] Synthesis of Compound 125I

[0480] Compound 125G (3.60 g, 5.23 mmol), compound 5H (2.59 g, 5.49 mmol), Pd2(dba)3 (0.48 g, 0.52 mmol), SPhos (0.43 g, 1.05 mmol), and NaOtBu (0.75 g, 7.84 mmol) were added to a round-bottom flask and combined with toluene (55 mL). The mixture was then stirred under reflux at 110 °C for 15 hours. After the reaction was complete, the temperature was lowered to room temperature, and ethyl acetate and a saturated aqueous solution of ammonium chloride were added to the reaction mixture to obtain an organic layer. The organic layer was extracted with ethyl acetate, dried over anhydrous MgSO4, and then filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 4.80 g (85% yield) of compound 125I.

[0481] LC-MS: 1079.55 [M+H] + .

[0482] Synthesis of Compound 125J

[0483] Compound 125I (4.80 g, 4.45 mmol) was added to a round-bottom flask and mixed with triethyl orthoformate (40 mL), followed by the addition of 35% hydrochloric acid (0.46 mL, 5.34 mmol). The mixture was then stirred at 80 °C for 3 hours. After the reaction was complete, the temperature was lowered to room temperature, and the reaction mixture was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 4.90 g (98% yield) of compound 125J.

[0484] Synthesis of Compound 125

[0485] Compound 125J (4.90 g, 4.35 mmol), K₂PtCl₄ (2.07 g, 4.79 mmol), and NaOAc (1.28 g, 13.1 mmol) were added to a round-bottom flask and combined with dioxane (90 mL). The mixture was then stirred under reflux at 100 °C for 15 hours. After the reaction was complete, the temperature was lowered to room temperature, and ethyl acetate and a saturated aqueous solution of ammonium chloride were added to the reaction mixture to obtain an organic layer. The organic layer was extracted with ethyl acetate, dried over anhydrous MgSO₄, and then filtered. The filtrate was concentrated and purified by silica gel column chromatography to obtain 3.08 g (55% yield) of compound 125.

[0486] LC-MS: 1282.48 [M+H] + .

[0487] Synthesis Example 3 (Compound 140)

[0488]

[0489]

[0490] Synthesis of compound 140C

[0491] Compound 140A (12.0 g, 24.3 mmol), compound 125B (6.73 g, 36.4 mmol), Pd(PPh3)4 (2.80 g, 2.43 mmol), SPhos (1.99 g, 4.86 mmol), and K2CO3 (6.71 g, 48.6 mmol) were added to a round-bottom flask and combined with 1,4-dioxane / H2O (100 mL / 25 mL). The mixture was then stirred under reflux at 110 °C for 15 hours. After the reaction was complete, the temperature was lowered to room temperature, and ethyl acetate and a saturated aqueous solution of ammonium chloride were added to the reaction mixture to obtain an organic layer. The organic layer was extracted with ethyl acetate, dried over anhydrous MgSO4, and then filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 8.60 g (64% yield) of compound 140C.

[0492] LC-MS: 554.05 [M+H] + .

[0493] Synthesis of Compound 140E

[0494] Compound 140C (8.60 g, 15.5 mmol), compound 125D (9.48 g, 23.3 mmol), Pd(PPh3)4 (1.79 g, 1.55 mmol), SPhos (1.27 g, 3.10 mmol), and K2CO3 (4.29 g, 31.0 mmol) were added to a round-bottom flask and combined with 1,4-dioxane / H2O (65 mL / 15 mL). The mixture was then stirred under reflux at 110 °C for 15 hours. After the reaction was complete, the temperature was lowered to room temperature, and ethyl acetate and a saturated aqueous solution of ammonium chloride were added to the reaction mixture to obtain an organic layer. The organic layer was extracted with ethyl acetate, dried over anhydrous MgSO4, and then filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 8.35 g (71% yield) of compound 140E.

[0495] LC-MS: 755.33 [M+H] + .

[0496] Synthesis of compound 140F

[0497] Compound 140E (8.35 g, 11.1 mmol) and K₂CO₃ (4.59 g, 33.2 mmol) were added to a round-bottom flask and combined with DMF (110 mL). The mixture was then stirred at 100 °C for 16 hours. After the reaction was complete, the temperature was lowered to room temperature, and ethyl acetate and a saturated aqueous solution of ammonium chloride were added to the reaction mixture to obtain an organic layer. The organic layer was extracted with ethyl acetate, dried over anhydrous MgSO₄, and then filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 4.70 g (58% yield) of compound 140F.

[0498] LC-MS: 735.32 [M+H] + .

[0499] Synthesis of Compound 140G

[0500] Compound 140F (4.70 g, 6.39 mmol), Pd / C (10 wt% carbon-supported Pd, 0.68 g, 0.64 mmol), and ammonium formate (8.06 g, 128 mmol) were added to a round-bottom flask and combined with ethanol (65 mL). The mixture was then stirred under reflux at 80 °C for 4 h. After the reaction was complete, the temperature was lowered to room temperature, and ethyl acetate and a saturated aqueous solution of ammonium chloride were added to the reaction mixture to obtain an organic layer. The organic layer was extracted with ethyl acetate, dried over anhydrous MgSO4, and then filtered. The filtrate obtained was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 3.82 g (85% yield) of compound 140G.

[0501] LC-MS: 705.36 [M+H] + .

[0502] Synthesis of Compound 140I

[0503] Compound 140G (3.82 g, 5.42 mmol), compound 5H (2.68 g, 5.69 mmol), Pd2(dba)3 (0.50 g, 0.54 mmol), SPhos (0.44 g, 1.08 mmol), and NaOtBu (0.78 g, 8.13 mmol) were added to a round-bottom flask and combined with toluene (55 mL). The mixture was then stirred under reflux at 110 °C for 17 h. After the reaction was complete, the temperature was lowered to room temperature, and ethyl acetate and a saturated aqueous solution of ammonium chloride were added to the reaction mixture to obtain an organic layer. The organic layer was extracted with ethyl acetate, dried over anhydrous MgSO4, and then filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 4.50 g (76% yield) of compound 140I.

[0504] LC-MS: 1095.52 [M+H] + .

[0505] Synthesis of Compound 140J

[0506] Compound 140I (4.50 g, 4.11 mmol) was added to a round-bottom flask and mixed with triethyl orthoformate (35 mL), followed by the addition of 35% hydrochloric acid (0.42 mL, 4.93 mmol). The mixture was then stirred at 80 °C for 3 hours. After the reaction was complete, the temperature was lowered to room temperature, and the reaction mixture was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 4.53 g (97% yield) of compound 140J.

[0507] Synthesis of Compound 140

[0508] Compound 140J (4.53 g, 3.97 mmol), K₂PtCl₄ (1.88 g, 4.36 mmol), and NaOAc (1.17 g, 11.9 mmol) were added to a round-bottom flask and combined with dioxane (80 mL). The mixture was then stirred under reflux at 100 °C for 17 hours. After the reaction was complete, the temperature was lowered to room temperature, and ethyl acetate and a saturated aqueous solution of ammonium chloride were added to the reaction mixture to obtain an organic layer. The organic layer was extracted with ethyl acetate, dried over anhydrous MgSO₄, and then filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 2.66 g (52% yield) of compound 140.

[0509] LC-MS: 1298.47 [M+H] + .

[0510] Synthesis Example 4 (Compound 155)

[0511]

[0512]

[0513] Synthesis of Compound 155E

[0514] Compound 155A (4.20 g, 9.07 mmol), compound 125D (5.54 g, 13.6 mmol), Pd(PPh3)4 (1.05 g, 0.91 mmol), SPhos (0.74 g, 1.81 mmol), and K2CO3 (2.51 g, 18.1 mmol) were added to a round-bottom flask and combined with 1,4-dioxane / H2O (40 mL / 10 mL). The mixture was then stirred under reflux at 110 °C for 19 hours. After the reaction was complete, the temperature was lowered to room temperature, and ethyl acetate and a saturated aqueous solution of ammonium chloride were added to the reaction mixture to obtain an organic layer. The organic layer was extracted with ethyl acetate, dried over anhydrous MgSO4, and then filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 5.00 g (83% yield) of compound 155E.

[0515] LC-MS: 664.32 [M+H] + .

[0516] Synthesis of compound 155F

[0517] Compound 155E (5.00 g, 7.53 mmol) and K₂CO₃ (3.12 g, 22.6 mmol) were added to a round-bottom flask and combined with DMF (75 mL). The mixture was then stirred at 100 °C for 16 hours. After the reaction was complete, the temperature was lowered to room temperature, and ethyl acetate and a saturated aqueous solution of ammonium chloride were added to the reaction mixture to obtain an organic layer. The organic layer was extracted with ethyl acetate, dried over anhydrous MgSO₄, and then filtered. The filtrate obtained was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 2.05 g (42% yield) of compound 155F.

[0518] LC-MS: 644.32 [M+H] + .

[0519] Synthesis of Compound 155G

[0520] Compound 155F (2.05 g, 3.18 mmol), Pd / C (10 wt% carbon-supported Pd, 0.34 g, 0.32 mmol), and ammonium formate (4.02 g, 63.7 mmol) were added to a round-bottom flask and combined with ethanol (32 mL). The mixture was then stirred under reflux at 80 °C for 3 h. After the reaction was complete, the temperature was lowered to room temperature, and ethyl acetate and a saturated aqueous solution of ammonium chloride were added to the reaction mixture to obtain an organic layer. The organic layer was extracted with ethyl acetate, dried over anhydrous MgSO4, and then filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 1.66 g (85% yield) of compound 155G.

[0521] LC-MS: 614.33 [M+H] + .

[0522] Synthesis of compound 155I

[0523] Compound 155G (1.66 g, 2.70 mmol), compound 5H (1.34 g, 2.84 mmol), Pd2(dba)3 (0.25 g, 0.27 mmol), SPhos (0.22 g, 0.54 mmol), and NaOtBu (0.39 g, 4.06 mmol) were added to a round-bottom flask and combined with toluene (30 mL). The mixture was then stirred under reflux at 110 °C for 15 h. After the reaction was complete, the temperature was lowered to room temperature, and ethyl acetate and a saturated aqueous solution of ammonium chloride were added to the reaction mixture to obtain an organic layer. The organic layer was extracted with ethyl acetate, dried over anhydrous MgSO4, and then filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 1.80 g (66% yield) of compound 155I.

[0524] LC-MS: 1004.51 [M+H] + .

[0525] Synthesis of compound 155J

[0526] Compound 155I (1.80 g, 1.79 mmol) was added to a round-bottom flask and mixed with triethyl orthoformate (15 mL), followed by the addition of 35% hydrochloric acid (0.18 mL, 2.15 mmol). The mixture was then stirred at 80 °C for 3 hours. After the reaction was complete, the temperature was lowered to room temperature, and the reaction mixture was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 1.65 g (88% yield) of compound 155J.

[0527] Synthesis of Compound 155

[0528] Compound 155J (1.65 g, 1.57 mmol), K₂PtCl₄ (0.75 g, 1.73 mmol), and NaOAc (0.46 g, 4.71 mmol) were added to a round-bottom flask and combined with dioxane (30 mL). The mixture was then stirred under reflux at 100 °C for 18 hours. After the reaction was complete, the temperature was lowered to room temperature, and ethyl acetate and a saturated aqueous solution of ammonium chloride were added to the reaction mixture to obtain an organic layer. The organic layer was extracted with ethyl acetate, dried over anhydrous MgSO₄, and then filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 1.10 g (58% yield) of compound 155.

[0529] LC-MS: 1207.45 [M+H] + .

[0530] Synthesis Example 5 (Compound 190)

[0531]

[0532] Synthesis of compound 190E

[0533] Compound 190A (5.00 g, 11.3 mmol), compound 125D (6.88 g, 16.9 mmol), Pd(PPh3)4 (1.30 g, 1.13 mmol), SPhos (0.92 g, 2.25 mmol), and K2CO3 (3.11 g, 22.5 mmol) were added to a round-bottom flask and combined with 1,4-dioxane / H2O (40 mL / 10 mL). The mixture was then stirred under reflux at 110 °C for 5 hours. After the reaction was complete, the temperature was lowered to room temperature, and ethyl acetate and a saturated aqueous solution of ammonium chloride were added to the reaction mixture to obtain an organic layer. The organic layer was extracted with ethyl acetate, dried over anhydrous MgSO4, and then filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 7.15 g (99% yield) of compound 190E.

[0534] LC-MS: 645.32 [M+H] + .

[0535] Synthesis of compound 190F

[0536] Compound 190E (1.63 g, 2.53 mmol) and K₂CO₃ (1.05 g, 7.58 mmol) were added to a round-bottom flask and combined with DMF (25 mL). The mixture was then stirred at 100 °C for 16 hours. After the reaction was complete, the temperature was lowered to room temperature, and ethyl acetate and a saturated aqueous solution of ammonium chloride were added to the reaction mixture to obtain an organic layer. The organic layer was extracted with ethyl acetate, dried over anhydrous MgSO₄, and then filtered. The filtrate was concentrated and purified by silica gel column chromatography to obtain 1.03 g (65% yield) of compound 190F.

[0537] LC-MS: 625.32 [M+H] + .

[0538] Synthesis of Compound 190G

[0539] Compound 190F (1.03 g, 1.65 mmol), Pd / C (10 wt% carbon-supported Pd, 0.18 g, 0.16 mmol), and ammonium formate (2.08 g, 33.0 mmol) were added to a round-bottom flask and combined with ethanol (20 mL). The mixture was then stirred under reflux at 80 °C for 3 h. After the reaction was complete, the temperature was lowered to room temperature, and ethyl acetate and a saturated aqueous solution of ammonium chloride were added to the reaction mixture to obtain an organic layer. The organic layer was extracted with ethyl acetate, dried over anhydrous MgSO4, and then filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 0.93 g (95% yield) of compound 190G.

[0540] LC-MS: 595.35 [M+H] + .

[0541] Synthesis of compound 190I

[0542] Compound 190G (0.93 g, 1.56 mmol), compound 5H (0.77 g, 1.64 mmol), Pd2(dba)3 (0.14 g, 0.16 mmol), SPhos (0.13 g, 0.31 mmol), and NaOtBu (0.23 g, 2.35 mmol) were added to a round-bottom flask and combined with toluene (20 mL). The mixture was then stirred under reflux at 110 °C for 5 hours. After the reaction was complete, the temperature was lowered to room temperature, and ethyl acetate and a saturated aqueous solution of ammonium chloride were added to the reaction mixture to obtain an organic layer. The organic layer was extracted with ethyl acetate, dried over anhydrous MgSO4, and then filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 1.42 g (92% yield) of compound 190I.

[0543] LC-MS: 985.53 [M+H] + .

[0544] Synthesis of compound 190J

[0545] Compound 190I (1.42 g, 1.44 mmol) was added to a round-bottom flask and mixed with triethyl orthoformate (12 mL), followed by the addition of 35% hydrochloric acid (0.15 mL, 1.73 mmol). The mixture was then stirred at 80 °C for 2 hours. After the reaction was complete, the temperature was lowered to room temperature, and the reaction mixture was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 1.45 g (98% yield) of compound 190J.

[0546] Synthesis of Compound 190

[0547] Compound 190J (1.45 g, 1.41 mmol), K₂PtCl₄ (0.67 g, 1.55 mmol), and NaOAc (0.41 g, 4.22 mmol) were added to a round-bottom flask and combined with dioxane (30 mL). The mixture was then stirred under reflux at 100 °C for 13 hours. After the reaction was complete, the temperature was lowered to room temperature, and ethyl acetate and a saturated aqueous solution of ammonium chloride were added to the reaction mixture to obtain an organic layer. The organic layer was extracted with ethyl acetate, dried over anhydrous MgSO₄, and then filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 1.05 g (63% yield) of compound 190.

[0548] LC-MS: 1188.47 [M+H] + .

[0549] Synthesis Example 6 (Compound 395)

[0550]

[0551]

[0552] Synthesis of compound 395E

[0553] Compound 395A (7.00 g, 16.7 mmol), compound 125D (10.2 g, 25.1 mmol), Pd(PPh3)4 (1.93 g, 1.67 mmol), SPhos (1.37 g, 3.34 mmol), and K2CO3 (4.62 g, 33.4 mmol) were added to a round-bottom flask and combined with 1,4-dioxane / H2O (75 mL / 20 mL). The mixture was then stirred under reflux at 110 °C for 18 hours. After the reaction was complete, the temperature was lowered to room temperature, and ethyl acetate and a saturated aqueous solution of ammonium chloride were added to the reaction mixture to obtain an organic layer. The organic layer was extracted with ethyl acetate, dried over anhydrous MgSO4, and then filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 6.20 g (56% yield) of compound 395E.

[0554] LC-MS: 664.32 [M+H] + .

[0555] Synthesis of compound 395F

[0556] Compound 395E (6.20 g, 9.34 mmol) and K₂CO₃ (3.87 g, 28.0 mmol) were added to a round-bottom flask and combined with DMF (95 mL). The mixture was then stirred at 100 °C for 16 hours. After the reaction was complete, the temperature was lowered to room temperature, and ethyl acetate and a saturated aqueous solution of ammonium chloride were added to the reaction mixture to obtain an organic layer. The organic layer was extracted with ethyl acetate, dried over anhydrous MgSO₄, and then filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 2.35 g (39% yield) of compound 395F.

[0557] LC-MS: 644.32 [M+H] + .

[0558] Synthesis of Compound 395G

[0559] Compound 395F (2.35 g, 3.65 mmol), Pd / C (10 wt% carbon-supported Pd, 0.39 g, 0.37 mmol), and ammonium formate (4.60 g, 73.0 mmol) were added to a round-bottom flask, combined with ethanol (40 mL), and stirred under reflux at 80 °C for 3 h. After the reaction was complete, the temperature was lowered to room temperature, and ethyl acetate and a saturated aqueous solution of ammonium chloride were added to the reaction mixture to obtain an organic layer. The organic layer was extracted with ethyl acetate, dried over anhydrous MgSO4, and then filtered. The filtrate obtained was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 1.83 g (82% yield) of compound 395G.

[0560] LC-MS: 614.33 [M+H] + .

[0561] Synthesis of compound 395I

[0562] Compound 395G (1.83 g, 2.98 mmol), compound 5H (1.48 g, 3.13 mmol), Pd2(dba)3 (0.27 g, 0.30 mmol), SPhos (0.24 g, 0.60 mmol), and NaOtBu (0.43 g, 4.47 mmol) were added to a round-bottom flask and combined with toluene (30 mL). The mixture was then stirred under reflux at 110 °C for 15 hours. After the reaction was complete, the temperature was lowered to room temperature, and ethyl acetate and a saturated aqueous solution of ammonium chloride were added to the reaction mixture to obtain an organic layer. The organic layer was extracted with ethyl acetate, dried over anhydrous MgSO4, and then filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 1.92 g (64% yield) of compound 395I.

[0563] LC-MS: 1004.51 [M+H] + .

[0564] Synthesis of compound 395J

[0565] Compound 395I (1.92 g, 1.91 mmol) was added to a round-bottom flask and mixed with triethyl orthoformate (20 mL), followed by the addition of 35% hydrochloric acid (0.20 mL, 2.29 mmol). The mixture was then stirred at 80 °C for 3 hours. After the reaction was complete, the temperature was lowered to room temperature, and the reaction mixture was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 1.73 g (86% yield) of compound 395J.

[0566] Synthesis of Compound 395

[0567] Compound 395J (1.73 g, 1.65 mmol), K₂PtCl₄ (0.78 g, 1.81 mmol), and NaOAc (0.48 g, 4.94 mmol) were added to a round-bottom flask and combined with dioxane (35 mL). The mixture was then stirred under reflux at 100 °C for 18 hours. After the reaction was complete, the temperature was lowered to room temperature, and ethyl acetate and a saturated aqueous solution of ammonium chloride were added to the reaction mixture to obtain an organic layer. The organic layer was extracted with ethyl acetate, dried over anhydrous MgSO₄, and then filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 1.15 g (58% yield) of compound 395.

[0568] LC-MS: 1207.45 [M+H] + .

[0569] Evaluation of Example 1

[0570] Compound 5 was mixed with a CH2Cl2 solution of PMMA at 0.5 wt% relative to PMMA, and the resulting product was coated onto a quartz substrate using a spin coater, heat-treated in an oven at 80°C, and then cooled to room temperature to obtain a film.

[0571] The photoluminescence quantum yield (PLQY) of compound 5 in the film was evaluated using a Hamamatsu Photonics absolute PL quantum yield measurement system (Hamamatsu Photonics, Ltd., Shizuoka, Japan) equipped with a xenon lamp source, monochromator, photon multichannel analyzer, and integrating sphere, and using PLQY measurement software. The same procedure was repeated for each of the remaining compounds shown in Table 2. The results are shown in Table 2. In Table 2, the PLQY of compounds 5, 125, 140, 155, 190, 395, C2, C3, and C4 are expressed as relative values ​​(%) of the PLQY of compound C1.

[0572] Table 2

[0573]

[0574]

[0575]

[0576] Table 2 confirms that compounds 5, 125, 140, 155, 190, and 395 exhibit superior PLQY properties compared to compounds C1, C2, C3, and C4.

[0577] Example 1

[0578] The glass substrate on which the 1,500 Å thick ITO electrode is formed is cut into 50 mm × 50 mm × 0.5 mm dimensions, ultrasonically treated for 15 minutes each in acetone, isopropanol, and deionized (DI) water, and then cleaned by exposure to UV and ozone for 30 minutes.

[0579] Next, m-MTDATA is deposited on the ITO electrode (anode) on the glass substrate to form a hole injection layer with a thickness of 600 Å, and α-NPD is deposited on the hole injection layer to form a hole transport layer with a thickness of 250 Å.

[0580] Compound 5 (emitter) and CBP (body) were co-deposited on the hole transport layer at a weight ratio of 10:90 to form an emitter layer with a thickness of 400 Å.

[0581] A 50 Å thick hole-blocking layer is formed by depositing BAlq on the emitting layer, an 300 Å thick electron transport layer is formed by depositing Alq3 on the hole-blocking layer, and an 10 Å thick electron injection layer is formed by depositing LiF on the electron transport layer. Then, Al is vacuum-deposited on the electron injection layer to form a second electrode (cathode) with a thickness of 1,200 Å, thereby completing the fabrication of a light-emitting device with the structure ITO / m-MTDATA (600 Å) / α-NPD (250 Å) / CBP + compound 5 (10 wt%) (400 Å) / BAlq (50 Å) / Alq3 (300 Å) / LiF (10 Å) / Al (1,200 Å).

[0582]

[0583] Examples 2 to 5 and Comparative Examples C1 and C2

[0584] The light-emitting device was manufactured in the same manner as in Example 1, except that, when forming the emitting layer, the compounds shown in Table 3 were used instead of compound 5 as the emitter.

[0585] Evaluation of Example 2

[0586] For each of the light-emitting devices fabricated in Examples 1 to 5 and Comparative Examples C1 and C2, the driving voltage (relative %), external quantum efficiency (EQE, relative %), CIE color coordinates (x, y), and FWHM (nm) of the emission peak of the EL spectrum were evaluated, and the results are shown in Table 3.

[0587] The driving voltage and EQE were evaluated using a current-voltmeter (Keithley 2400) and a luminance meter (Minolta Cs-1000A). For each of the light-emitting devices, the EL spectrum (at 1,000 cd / m²) was measured using the luminance meter (Minolta Cs-1000A). 2 The FWHM (nm) of the emission peak of the CIE color coordinates (x, y) and EL spectrum was evaluated. In Table 3, the driving voltage (relative %) and EQE (relative %) of the light-emitting devices of Examples 1 to 5 and Comparative Example C2 are expressed as relative values ​​(%) of the driving voltage and EQE relative to the light-emitting device of Comparative Example C1.

[0588] Table 3

[0589]

[0590]

[0591]

[0592] As confirmed by Table 3, compared with the light-emitting devices of Comparative Examples C1 and C2, the light-emitting devices of Examples 1 to 5 emit blue light with excellent color purity and a relatively narrow FWHM, and have excellent driving voltage and excellent EQE.

[0593] Example 6 and Comparative Examples C3 and C4

[0594] The light-emitting device was manufactured in the same manner as in Example 1, except that, when forming the emitting layer, the compounds shown in Table 4 were used instead of compound 5 as the emitter.

[0595] Evaluation of Example 3

[0596] For each of the light-emitting devices manufactured in Example 6 and Comparative Examples C3 and C4, the driving voltage, EQE, and CIE color coordinates were evaluated in the same manner as in Example 2, and the results are shown in Table 4. Data for Comparative Examples C1 and C2 have also been added to Table 4, and the driving voltage and EQE of the light-emitting devices of Example 6 and Comparative Examples C2 to C4 in Table 4 are expressed as relative values ​​(%) of the driving voltage and EQE of the light-emitting device relative to Comparative Example C1.

[0597] Table 4

[0598]

[0599]

[0600]

[0601] As confirmed by Table 4, compared with the light-emitting devices of Comparative Examples C1 to C4, the light-emitting device of Example 6 emits blue light with excellent color purity, and has excellent driving voltage and excellent EQE.

[0602] Example 7

[0603] The light-emitting device was manufactured in the same manner as in Example 1, except that, when forming the emission layer, compound 155 (sensitizer), compound FD14 (emitter), and CBP (body) were co-deposited to a thickness of 400 Å in a weight ratio of 10:1.5:88.5.

[0604] Comparative Example X

[0605] The light-emitting device was manufactured in the same manner as in Example 1, except that, when forming the emission layer, compound FD14 (emitter) and CBP (body) were co-deposited at a weight ratio of 10:90 to a thickness of 400 Å.

[0606] Evaluation of Example 4

[0607] For each of the light-emitting devices manufactured in Example 7 and Comparative Example X, the maximum emission wavelength (λ) of the EL spectrum was evaluated in the same manner as in Example 2. max The y-values ​​of the color coordinates (CIEy), EQE (relative %), and driving voltage (relative %) are calculated, and the results are shown in Table 5. In Table 5, the EQE and driving voltage of the light-emitting device of Example 7 are each expressed as relative values ​​(%) compared to Comparative Example X.

[0608] Table 5

[0609]

[0610]

[0611] As confirmed by Table 5, compared with the light-emitting device of Comparative Example X, the light-emitting device of Example 7, which includes compound 155 as a sensitizer, has excellent EQE and excellent driving voltage characteristics, and emits blue light with excellent color purity.

[0612] According to one or more embodiments, the organometallic compound represented by Formula 1 can possess excellent thermal stability and excellent electrical properties, and can emit blue light with high color purity and / or a relatively narrow field of view (FWHM). Therefore, electronic devices, such as light-emitting devices, comprising at least one organometallic compound represented by Formula 1 can emit blue light with high color purity and can have improved driving voltage and improved EQE. By using said light-emitting device, high-quality electronic devices can be manufactured.

[0613] It should be understood that the exemplary embodiments described herein are to be considered in a descriptive sense only and are not intended for limiting purposes. The descriptions of features or aspects in the various exemplary embodiments should be typically considered applicable to other similar features or aspects in other exemplary embodiments. Although one or more exemplary embodiments have been described with reference to the accompanying drawings, those skilled in the art will understand that various changes in form and detail may be made therein without departing from the spirit and scope defined by the appended claims.

Claims

1. Organometallic compounds, represented by Formula 1: Formula 1 in, In Equation 1, M is either Pt or Pd. X1 is C, X2 to X4 are each independently C or N. CY2 ring, CY ring 31 CY 32 CY4 and CY5 are independently C5-C 30 Carbocyclic groups or C1-C 30 Heterocyclic groups, X 11 For N or C(R) 11 ), X 12 For N or C(R) 12 ), and X 13 For N or C(R) 13 ), X 51 For N or C(R) 51 ), X 52 For N or C(R) 52 ), X 53 For N or C(R) 53 ), and X 54 For N or C(R) 54 ), X 61 For N or C(R) 61 ), X 62 For N or C(R) 62 ), X 63 For N or C(R) 63 ), and X 64 For N or C(R) 64 ), X 71 For N or C(R) 71 ), X 72 For N or C(R) 72 ), X 73 For N or C(R) 73 ), and X 74 For N or C(R) 74 ), L1 is O, S, Se, N (R 101 ), C(R 101 (R) 102 ), or Si(R) 101 (R) 102 ), L2, L3, and L4 are each independently a single bond, O, S, Se, N(R'), C(R')(R"), or Si(R')(R"). At least one of L2, L3, and L4 is O, S, Se, N(R'), C(R')(R"), or Si(R')(R"), R2, R3, R4, R 11 To R 13 R 51 To R 54 R 61 To R 64 R 71 To R 74 R 101 R 102 R' and R" are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C1-C 60 Alkylthio, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 arylalkyl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -N(Q4)(Q5), -B(Q6)(Q7), -P(Q8)(Q9), or -P(=O)(Q8)(Q9), a2 to a4 are each an independent integer from 0 to 20. R 11 To R 13 Two or more may be optionally connected to each other to form an unreplaced or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups, Two or more of R2s are optionally connected to each other to form a group that is not replaced or is occupied by at least one R. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups, Two or more of a plurality of R3s are optionally connected to each other to form an unsubstituted or at least one R 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups, Two or more of a plurality of R4s are optionally connected to each other to form an unsubstituted or at least one R 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups, R 51 To R 54 Two or more may be optionally connected to each other to form an unreplaced or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups, R 61 To R 64 Two or more may be optionally connected to each other to form an unreplaced or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups, R 71 To R 74 Two or more may be optionally connected to each other to form an unreplaced or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups, R 101 and R 102 Optionally connected to each other to form an unreplaced or at least R 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups, R' and R" are optionally connected to each other to form an unsubstituted or at least one R 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups, R 10a For example, regarding R 11 As described, Replacement C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C1-C 60 Alkylthio, substituted C3-C 10 cycloalkyl, substituted C1-C 10 Heterocyclic alkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocyclic alkenyl, substituted C6-C 60 Aryl, substituted C7-C 60 Alkyl aryl, substituted C7-C 60 Arylalkyl, substituted C6-C 60 aryloxy groups, substituted C6-C 60 Arylthioyl, substituted C1-C 60 heteroaryl, substituted C2-C 60 Alkyl heteroaryl, substituted C2-C 60 Heteroarylalkyl, substituted C1-C 60 Heteroaryl groups, substituted C1-C 60 At least one substituent of the heteroaryl thio group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heterocyclic group is: Deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 alkoxy, or C1-C 60 Alkylthio; Each of the following C1-C is replaced: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 alkoxy, or C1-C 60 Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 11 (Q) 12 (Q) 13 -Ge(Q) 11 (Q) 12 (Q) 13 -N(Q) 14 (Q) 15 -B(Q) 16 (Q) 17 -P(Q) 18 (Q) 19 -P(=O)(Q) 18 (Q) 19 ), or combinations thereof; Each of the following C3-Cs was not replaced or was replaced as follows 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid groups or their salts, sulfonic acid groups or their salts, phosphate groups or their salts, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 21 (Q) 22 (Q) 23 -Ge(Q) 21 (Q) 22 (Q) 23 -N(Q) 24 (Q) 25 -B(Q) 26 (Q) 27 -P(Q) 28 (Q) 29 -P(=O)(Q) 28 (Q) 29 ), or combinations thereof; -Si(Q 31 )(Q 32 )(Q 33 )、-Ge(Q 31 )(Q 32 )(Q 33 )、-N(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 )、-P(Q 38 )(Q 39 )、 or -P(=O)(Q 38 )(Q 39 ); or Its combination, and Q1 to Q9, Q 11 To Q 19 Q 21 To Q 29 , and Q 31 To Q 39 Each independently is: Hydrogen, deuterium, or -F; or Each of the following C1-Cs was not replaced or was replaced as follows 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 Arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups: deuterium, -F, cyano, C1-C 60 Alkyl, C6-C 60 Aryl groups, or combinations thereof.

2. The organometallic compound according to claim 1, wherein... X2 and X3 are each C, and X4 is N.

3. The organometallic compound according to claim 1, wherein... CY2 ring, CY ring 31 , and CY 32 Each of these groups independently comprises a phenyl group, a naphthyl group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a triazine group, a quinoline group, an isoquinoline group, a benzo[a]quinoline group, or a benzo[a]isoquinoline group, and Cyclic CY4 can be a pyridine group, pyrimidine group, pyridazine group, pyrazine group, triazine group, quinoline group, isoquinoline group, benzo[a]quinoline group, or benzo[a]isoquinoline group.

4. The organometallic compound according to claim 1, wherein at least one of L2, L3, and L4 is N(R').

5. The organometallic compound according to claim 1, wherein at least one of L2, L3, and L4 is O, S, or Se.

6. The organometallic compound according to claim 1, wherein at least one of L2, L3, and L4 is C(R')(R") or Si(R')(R").

7. The organometallic compound according to claim 1, wherein... i) L2 and L3 are each single bonds; and L4 is O, S, Se, N(R'), C(R')(R"), or Si(R')(R"). ii) L2 and L4 are each single bonds; and L3 is O, S, Se, N(R'), C(R')(R"), or Si(R')(R"), or iii) L3 and L4 are each single bonds; and L2 is O, S, Se, N(R'), C(R')(R"), or Si(R')(R").

8. The organometallic compound according to claim 1, wherein R2, R3, R4, R 11 To R 13 R 51 To R 54 R 61 To R 64 R 71 To R 74 R 101 R 102 R' and R" are each independently: Hydrogen, deuterium, -F, or cyano; Each of them was not replaced or replaced by deuterium, -F, cyano, C1-C 20 C1-C substituted with alkyl, phenyl, carbazole, or combinations thereof 20 Alkyl or C1-C 20 Alkoxy; Each of the following C3-Cs was not replaced or was replaced as follows 10 Cycloalkyl, phenyl, naphthyl, pyridyl, furanyl, thiophene, benzofuranyl, benzothiophene, carbazole, dibenzofuranyl, or dibenzothiophene: deuterium, -F, cyano, C1-C 20 Alkyl, C1-C 20 Alkoxy, deuterated C1-C 20 Alkyl, fluorinated C1-C 20 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 Cycloalkyl, fluorinated C3-C 10 cycloalkyl, (C1-C 20 Alkyl)C3-C 10 Cycloalkyl, phenyl, deuterated phenyl, fluorophenyl, (C1-C 20 Alkyl)phenyl, naphthyl, pyridyl, furanyl, thiophene, benzofuranyl, benzothiophene, carbazole, dibenzofuranyl, dibenzothiophene, -Si(Q) 31 (Q) 32 (Q) 33 -Ge(Q) 31 (Q) 32 (Q) 33 ), or a combination thereof; or -Si(Q1)(Q2)(Q3) or -Ge(Q1)(Q2)(Q3).

9. The organometallic compound of claim 1, wherein the organometallic compound comprises deuterium, unsubstituted or substituted tert-butyl, or combinations thereof.

10. The organometallic compound according to claim 1, wherein the organometallic compound is represented by formula 1-1: Formula 1-1 in, In Equation 1-1, M, X1 to X4, X 11 To X 13 X 51 To X 54 X 61 To X 64 X 71 To X 74 L1 to L4 are each as described in claim 1. X 21 For N or C(R) 21 ), X 22 For N or C(R) 22 ), and X 23 For N or C(R) 23 ), R 21 To R 23 Each as described in claim 1 with respect to R2, X 31 For N or C(R) 31 ), X 32 For N or C(R) 32 ), X 33 For N or C(R) 33 ), X 34 For N or C(R) 34 ), X 35 For N or C(R) 35 ), and X 36 For N or C(R) 36 ), R 31 To R 36 Each as described in claim 1 with respect to R3, X 41 For N or C(R) 41 ), X 42 For N or C(R) 42 ), X 43 For N or C(R) 43 ), and X 44 For N or C(R) 44 ), R 41 To R 44 Each as described in claim 1 with respect to R4, R 11 To R 13 Two or more may be optionally connected to each other to form an unreplaced or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups, R 21 To R 23 Two or more may be optionally connected to each other to form an unreplaced or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups, R 31 To R 36 Two or more may be optionally connected to each other to form an unreplaced or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups, R 41 To R 44 Two or more may be optionally connected to each other to form an unreplaced or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups, and R 10a As in claim 1 regarding R 11 As described.

11. Light-emitting devices, including: First electrode; Second electrode; as well as An intermediate layer disposed between the first electrode and the second electrode. The intermediate layer includes an emission layer. The intermediate layer comprises at least one organometallic compound according to any one of claims 1 to 10.

12. The light-emitting device according to claim 11, wherein the emitting layer comprises the at least one organometallic compound.

13. The light-emitting device according to claim 12, wherein the light emitted from the emitting layer is blue light.

14. The light-emitting device of claim 12, wherein the CIEy value of the light emitted from the emitting layer is from 0.040 to 0.

170.

15. The light-emitting device of claim 12, wherein the maximum emission wavelength of the light emitted from the emitting layer is 440 nm to 470 nm.

16. The light-emitting device according to claim 12, wherein the at least one organometallic compound is an emitter.

17. The light-emitting device according to claim 12, wherein... The at least one organometallic compound is a sensitizer. The emission layer further includes an emitter, and The emitter is different from the at least one organometallic compound.

18. The light-emitting device according to claim 17, wherein the emitter is a transient fluorescent compound or a delayed fluorescent compound.

19. The light-emitting device according to claim 17, wherein the emitter is a multiple resonant thermally activated delayed fluorescence compound.

20. An electronic device, comprising a light-emitting device according to any one of claims 11 to 19.

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