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

Abstract

The present invention relates to an organometallic compound, an organic light emitting device including the same, and an electronic device including the organic light emitting device. The organometallic compound represented by Formula 1, wherein M is beryllium (Be), magnesium (Mg), aluminum (Al), calcium (Ca), titanium (Ti), manganese (Mn), cobalt (Co), copper (Cu), zinc (Zn), gallium (Ga), germanium (Ge), zirconium (Zr), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), rhenium (Re), platinum (Pt), or gold (Au); and wherein ring CY1 to ring CY5, X1 to X4, X 51 , Y1 to Y5, R1 to R4, L1 to L4, L 13 , L 14 , T1, T2, Z 13 , Z 14 , b1 to b4, b7, b13, b14, c1 to c4, c7, c13, c14, n13, and n14 are as defined herein. Formula 1

Description

[0001] Cross-reference to related applications

[0002] This application claims priority and benefits, and all benefits arising therefrom, to Korean Patent Application No. 10-2021-0003568 filed with the Korean Intellectual Property Office on January 11, 2021, the entire contents of which are incorporated herein by reference. Technical Field

[0003] One or more embodiments described herein relate to organometallic compounds, organic light-emitting devices including the same, and electronic devices including said organic light-emitting devices. Background Technology

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

[0005] In this example, the organic light-emitting device includes an anode, a cathode, and an organic layer located between the anode and the cathode, wherein the organic layer includes an emitting layer. A hole transport region may be located between the anode and the emitting layer, and an electron transport region may be located between the emitting layer and the cathode. Holes supplied from the anode can move towards the emitting layer through the hole transport region, and electrons supplied from the cathode can move towards the emitting layer through the electron transport region. Holes and electrons can then recombine in the emitting layer to generate excitons. These excitons transition from an excited state to a ground state, thereby producing light, such as visible light. Summary of the Invention

[0006] One or more embodiments described herein relate to organometallic compounds, organic light-emitting devices including the same, and electronic devices including said organic light-emitting devices.

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

[0008] According to one or more embodiments, an organometallic compound represented by Formula 1 is provided.

[0009] Formula 1

[0010]

[0011] In Equation 1,

[0012] M represents beryllium (Be), magnesium (Mg), aluminum (Al), calcium (Ca), titanium (Ti), manganese (Mn), cobalt (Co), copper (Cu), zinc (Zn), gallium (Ga), germanium (Ge), zirconium (Zr), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), rhenium (Re), platinum (Pt), or gold (Au).

[0013] X1 can be a single bond, O, S, N(R'), P(R'), B(R'), C(R')(R”), or Si(R')(R”), and when X1 is a single bond, Y1 is directly bonded to M.

[0014] X2-X4 can each be independently C or N.

[0015] The bond between X1 or Y1 and M is a covalent bond.

[0016] One of the bonds between X2 and M, between X3 and M, and between X4 and M is a covalent bond, and the rest of the bonds between X2 and M, between X3 and M, and between X4 and M are coordinate bonds.

[0017] Y1 and Y3-Y5 are each independently C or N.

[0018] X2 and Y3, X2 and Y4, Y4 and Y5, X 51 And Y3, and X 51 Y and Y5 are each connected by chemical bonds.

[0019] Rings CY1 to CY4 can each be independently C5-C. 30 Carbocyclic groups or C1-C 30 Heterocyclic groups, provided that ring CY1, ring CY3, and ring CY4 are not benzimidazole groups.

[0020] Ring CY5 can be a 5-membered ring fused with ring CY2.

[0021] The cyclic metallized groups formed by rings CY5, CY2, CY3, and M are 6-membered rings.

[0022] X 51 For O, S, N-[(L7) b7 -(R7) c7 ], C(R7)(R8), Si(R7)(R8), Ge(R7)(R8), C(=O), N, C(R7), Si(R7), or Ge(R7),

[0023] R7 and R8 may optionally be linked via a single bond, a double bond, or a first linking group to form an unsubstituted or linked group with at least one R 10a Replacement C5-C 30The carbocyclic group, or the unsubstituted group or the group with at least one R 10a Replacement C1-C 30 Heterocyclic groups,

[0024] T1 and T2 are independently single bonds, double bonds, *-N(R9)-*', *-B(R9)-*', *-P(R9)-*', and *-C(R9)-*', respectively. 9a (R) 9b )-*'、*-Si(R 9a (R) 9b )-*'、*-Ge(R 9a (R) 9b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R9)=*', *=C(R9)-*', *-C(R 9a )=C(R 9b )-*', *-C(=S)-*', or *-C≡C-*', where * and *' each represent a bond with an adjacent atom.

[0025] Z 13 and Z 14 Each is an independent group represented by formula 2.

[0026] n13 and n14 can each be an integer between 0 and 20, and the sum of n13 and n14 can be 1 or greater.

[0027] L1-L4, L7, L 13 and L 14 Each is independently a single bond, unsubstituted, or bound by at least one R. 10a Replacement C5-C 30 The carbocyclic group, or the unsubstituted group or the group with at least one R 10a Replacement C1-C 30 Heterocyclic groups,

[0028] b1-b4, b7, b13, and b14 are each independent integers from 1 to 5.

[0029] R1-R4, R7-R9, R 9a R 9b 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 60Alkyne, 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, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9),

[0030] c1-c4, c7, c13, and c14 are each independent integers from 1 to 5.

[0031] a1-a4 are each an independent integer between 0 and 20.

[0032] Two or more of the plurality of R1s are optionally connected to form a group that is not replaced or is occupied by at least one R. 10a Replacement C5-C 30 The carbocyclic group, or the unsubstituted group or the group with at least one R 10a Replacement C1-C 30 Heterocyclic groups,

[0033] Two or more of R2s are optionally connected to form a group that is not replaced or is occupied by at least one R. 10a Replacement C5-C 30 The carbocyclic group, or the unsubstituted group or the group with at least one R 10a Replacement C1-C 30 Heterocyclic groups,

[0034] Two or more of the plurality of R3s are optionally connected to form an unsubstituted or at least one R 10a Replacement C5-C 30 The carbocyclic group, or the unsubstituted group or the group with at least one R 10a Replacement C1-C 30 Heterocyclic groups,

[0035] Two or more of a plurality of R4s are optionally connected to form an unsubstituted or at least one R 10a Replacement C5-C 30 The carbocyclic group, or the unsubstituted group or the group with at least one R 10a Replacement C1-C 30 Heterocyclic groups,

[0036] R1-R4, R7-R9, R 9a R 9b Two or more groups of R' and R" are optionally linked to form an unsubstituted or R" group. 10a Replacement C5-C 30 The carbocyclic group, or the unsubstituted group or the group with at least one R 10a Replacement C1-C 30 Heterocyclic groups,

[0037] R 10a As defined regarding R1,

[0038] Formula 2

[0039]

[0040] In Equation 2,

[0041] CY 10 Unsaturated C5-C 30 Carbocyclic groups or unsaturated C1-C 30 Heterocyclic groups,

[0042] R 10 As defined regarding R1,

[0043] a10 is an integer between 0 and 20.

[0044] Z 10 It is an -F or fluorinated group.

[0045] n10 is an integer between 1 and 20.

[0046] Replacement C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60Alkoxy, 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 The substituents of heteroaryl thio groups, substituted monovalent non-aromatic fused polycyclic groups, and substituted monovalent non-aromatic fused heterocyclic groups are:

[0047] Deuterium, -F, -Cl, -Br, -I, -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 Alkyne group, C1-C 60 alkoxy, or C1-C 60 Alkylthio;

[0048] Each of the following C1-C is replaced: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 alkoxy, or C1-C 60 Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -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, C6-C 60 Aryloxy group, C6-C60 Arylthio, C1-C 60 heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -N(Q) 11 (Q) 12 ), -Si(Q 13 (Q) 14 (Q) 15 -Ge(Q) 13 (Q) 14 (Q) 15 -B(Q) 16 (Q) 17 -P(=O)(Q) 18 (Q) 19 -P(Q) 18 (Q) 19 ), or combinations thereof;

[0049] 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, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 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, -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 Alkyne 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, -N(Q) 21 (Q) 22 ), -Si(Q 23 (Q) 24 (Q) 25 -Ge(Q) 23 (Q) 24 (Q) 25 -B(Q) 26 (Q) 27 -P(=O)(Q) 28 (Q) 29 -P(Q) 28 (Q) 29 ), or combinations thereof;

[0050] -N(Q 31 (Q) 32 ), -Si(Q 33 (Q) 34 (Q) 35 -Ge(Q) 33 (Q) 34 (Q) 35 -B(Q) 36 (Q) 37 -P(=O)(Q) 38 (Q) 39 ), or -P(Q 38 (Q) 39 );or

[0051] Its combination,

[0052] Among them, Q1-Q9, Q 11 -Q 19 Q 21 -Q 29 , and Q 31 -Q 39 Each of these can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; amidine; hydrazine; hydrazone; carboxylic acid group or its salt; sulfonic acid group or its salt; phosphate group or its salt; unsubstituted or deuterated, C1-C 60 Alkyl, C6-C 60 aryl, or combined substituted C1-C 60 Alkyl; C2-C60 Alkenyl; C2-C 60 Alkyne group; C1-C 60 Alkoxy group; C1-C 60 Alkylthio group; C3-C 10 cycloalkyl; C1-C 10 Heterocyclic alkyl; C3-C 10 Cycloalkenyl; C1-C 10 Heterocyclic alkenyl groups; unsubstituted or deuterated, C1-C 60 Alkyl, C6-C 60 aryl, or combined substituted C6-C 60 Aryl; C6-C 60 Aryloxy group; C6-C 60 Arylthio; C1-C 60 heteroaryl; C1-C 60 Heteroaryloxy group; C1-C 60 Heteroaryl thio group; monovalent non-aromatic fused polycyclic group; or monovalent non-aromatic fused heterocyclic group.

[0053] According to one or more embodiments, an organic light-emitting device is provided, comprising a first electrode, a second electrode, and an organic layer located between the first electrode and the second electrode, wherein the organic layer comprises an emitting layer, and wherein the organic layer comprises at least one organometallic compound represented by Formula 1.

[0054] The organometallic compound may be included in the emitter layer of the organic layer, and the organometallic compound included in the emitter layer may act as a dopant.

[0055] According to one or more embodiments, the electronic device may include the organic light-emitting device. Attached Figure Description

[0056] The above and other aspects, features, and advantages of some embodiments of this disclosure will become clearer from the following description taken in conjunction with the accompanying drawings, wherein

[0057] Figure 1 This shows a schematic cross-sectional view of an organic light-emitting device according to one or more embodiments. Detailed Implementation

[0058] The embodiments will now be described in detail, examples of which are shown in the accompanying drawings, wherein the same reference numerals throughout the description refer to the same elements. In this respect, the embodiments may take different forms and should not be construed as limited to the description set forth herein. Therefore, the embodiments are described below only by reference to the accompanying drawings to illustrate aspects. 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” modify the entire list of elements and not individual elements of the list when appearing before or after the list of elements.

[0059] 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 intended to include the plural forms as well, 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.

[0060] 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.

[0061] Exemplary embodiments are described herein with reference to cross-sectional views that serve as schematic representations 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 illustrated in the figures are schematic in nature, and their shapes are not intended to illustrate the precise shapes of the regions nor to limit the scope of the claims.

[0062] It will be understood that when an element is referred to as being "on" another element, it may be in direct contact with said 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.

[0063] Unless otherwise defined, all terms used herein (including technical and scientific terms) shall have the same meaning as commonly understood by one of ordinary skill in the art to which this general inventive concept pertains. It will be further understood that terms, such as those defined in commonly used dictionaries, shall be interpreted as having a meaning consistent with their meaning in the context of the relevant field and in the present disclosure, and shall not be interpreted in an idealized or overly formal sense unless clearly defined herein.

[0064] 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%.

[0065] According to one aspect, one or more embodiments describe organometallic compounds represented by Formula 1:

[0066] Formula 1

[0067]

[0068] In Formula 1, M represents beryllium (Be), magnesium (Mg), aluminum (Al), calcium (Ca), titanium (Ti), manganese (Mn), cobalt (Co), copper (Cu), zinc (Zn), gallium (Ga), germanium (Ge), zirconium (Zr), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), rhenium (Re), platinum (Pt), or gold (Au).

[0069] For example, M can be Pt, Pd, or Au.

[0070] In Equation 1, X1 can be a single bond (e.g., a covalent bond), O, S, N(R'), P(R'), B(R'), C(R')(R"), or Si(R')(R"). R' and R" are each as defined above. When X1 is a single bond, Y1 and M are directly connected to each other.

[0071] In one or more embodiments, X1 in Formula 1 may be O or S.

[0072] In Equation 1, X2-X4 are each independently C or N.

[0073] For example, two of X2-X4 can be N, and one can be C.

[0074] In one or more embodiments, in Equation 1, X2 and X4 can be N, and X3 can be C.

[0075] In Formula 1, the bond between X1 or Y1 and M is a covalent bond. One of the bonds between X2 and M, X3 and M, and X4 and M is a covalent bond, and the remaining bonds between X2 and M, X3 and M, and X4 and M are coordinate bonds. Therefore, the organometallic compound represented by Formula 1 is electrically neutral.

[0076] In one or more embodiments, in Formula 1, the bond between X1 or Y1 and M and the bond between X3 and M can each be a covalent bond, and the bond between X2 and M and the bond between X4 and M can be a coordinate bond.

[0077] In one or more embodiments, in Formula 1,

[0078] i) X2 and X4 can each be N, X3 can be C, the bond between X2 and M and the bond between X4 and M can each be a coordinate bond, and the bond between X3 and M can be a covalent bond.

[0079] ii) X2 and X3 can each be N, X4 can be C, the bond between X2 and M and the bond between X3 and M can each be a coordinate bond, and the bond between X4 and M can be a covalent bond, or

[0080] iii) X3 and X4 can be N, X2 can be C, the bond between X3 and M and the bond between X4 and M can be a coordinate bond, and the bond between X2 and M can be a covalent bond.

[0081] In Equation 1, Y1 and Y3-Y5 are each independently C or N.

[0082] For example, in one or more embodiments, in Formula 1, Y1 and Y3-Y5 can each be C.

[0083] In Equation 1, X2 and Y3, X2 and Y4, Y4 and Y5, X 51 And Y3, and X 51 Y5 and Y2 are each connected by chemical bonds. Therefore, ring CY5 in Formula 1 can be a 5-membered ring fused with ring CY2.

[0084] In Equation 1, rings CY1 to CY4 are each independently C5-C. 30 Carbocyclic groups or C1-C 30Heterocyclic groups are allowed, provided that rings CY1, CY3, and CY4 are not each a benzimidazole group. Additionally, in Formula 1, ring CY2 is not a benzimidazole group. In other words, in Formula 1, rings CY1 through CY4 are not each a benzimidazole group.

[0085] In one or more embodiments, in Formula 1, rings CY1 to CY4 can each independently be i) a first ring, ii) a second ring, iii) a fused ring in which two or more first rings are fused together, iv) a fused ring in which two or more second rings are fused together, or v) a fused ring in which one or more first rings and one or more second rings are fused together.

[0086] The first ring may be a cyclopentyl group, a cyclopentadienyl group, a furan group, a thiophene group, a pyrrole group, or a thiophene group. azole group, iso- azole group, diazole group, isodiazole group diazole group, Triazole group, isotriazole group Triazole group, thiazole group, isothiazole group, thiadiazole group, isothiazole group, thiatriazole group, isothiazole group, pyrazole group, imidazole group, triazole group, tetraazole group, azathiophene group, diazathiophene group, or triazathiophene group, and

[0087] The second ring may be an adamantyl group, a norbornel group, a cyclohexyl group, a cyclohexene group, a phenyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

[0088] In one or more embodiments, in Formula 1, rings CY1 to CY4 may each independently be a phenyl group, a naphthyl group, an anthracene group, a phenanthrene group, a benzo[9,10]phenanthrene group, a pyrene group, etc. Groups, 1,2,3,4-tetrahydronaphthyl group, furan group, thiophene group, pyrrole group, cyclopentadienyl group, thiophene group, benzofuran group, benzothiophene group, indole group, indene group, benzothiophene group, dibenzofuran group, dibenzothiophene group, carbazole group, fluorene group, dibenzothiophene group, azathiophene group, azabenzofuran group, azabenzothiophene group, azabenzylfuran group, azabenzylthiophene group, azacarbazole group, azafluorene group, azabenzylthiophene group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, phenanthrene-rhein group, pyrazole group, imidazole group, triazole group azole group, iso- azole group, thiazole group, isothiazole group, The diazole group, thiadiazole group, 5,6,7,8-tetrahydroisoquinoline group, 5,6,7,8-tetrahydroquinoline group, phenyl group fused with norbornene, or pyridine group fused with norbornene.

[0089] The ring metallized by rings CY5, CY2, CY3, and M in Formula 1 is a 6-membered ring.

[0090] In Equation 1, X 51 For O, S, N-[(L7) b7 -(R7) c7 ], C(R7)(R8), Si(R7)(R8), Ge(R7)(R8), C(=O), N, C(R7), Si(R7), or Ge(R7). R7 and R8 are optionally linked via single bonds, double bonds, or a first linking group to form an unsubstituted or linked group with at least one R 10a Replacement C5-C 30 The carbocyclic group, or the unsubstituted group or the group with at least one R 10a Replacement C1-C 30 Heterocyclic groups. L7, b7, R7, R8, and c7 are as defined herein.

[0091] The first linking group may be *-O-*', *-S-*', *-C(R5)(R6)-*', *-C(R5)=*', *=C(R6)-*', *-C(R5)=C(R6)-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-N(R5)-*', *-Si(R5)(R6)-*', *-P(R5)-*', or a combination thereof, wherein R5 and R6 are each as defined with respect to R1, and * and *' each represent a binding site with an adjacent atom.

[0092] For example, in one or more embodiments, X in Formula 1 51 It can be O, S, N-[(L7)] b7 -(R7) c7 ], C(R7)(R8), Si(R7)(R8), Ge(R7)(R8), or C(=O).

[0093] In one or more embodiments, X in Formula 1 51 It can be N-[(L7)] b7 -(R7) c7 ].

[0094] In one or more embodiments, in Formula 1, X 51 It can be N-[(L7)] b7 -(R7) c7L7 may not be a single bond, c7 may be greater than or equal to 2, and one of two or more R7 bonds may be a substituted or unsubstituted C4-C bond. 20 Alkyl (e.g., tert-butyl, etc.), and one of the remaining R7s may be a substituted or unsubstituted phenyl (e.g., phenyl, deuterated phenyl, (C1-C... 20 Alkyl) phenyl, etc.) or substituted or unsubstituted biphenyl (e.g., biphenyl, deuterated biphenyl, or (C1-C1) biphenyl). 20 (alkyl) biphenyl, etc.

[0095] In one or more embodiments, in Formula 1,

[0096] i) Y3-Y5 can each be C, in X 51 The bond between Y3 and X 51 The keys between Y5 and X can each be single keys, and X 51 It can be O, S, N-[(L7)] b7 -(R7) c7 ], C(R7)(R8), Si(R7)(R8), Ge(R7)(R8), or C(=O),

[0097] ii) Y3 and Y4 can each be C, Y5 can be N, in X 51 The bond between Y and Y3 can be a double bond, in X 51 The key between Y5 and X can be a single key, and X 51 It can be N, C(R7), Si(R7), or Ge(R7).

[0098] iii) Y3 and Y5 can each be C, Y4 can be N, in X 51 The bond between Y and Y3 can be a single bond, in X 51 The key between Y5 and X can be a double key, and X 51 It can be N, C(R7), Si(R7), or Ge(R7),

[0099] iv) Y3 can be N, Y4 and Y5 can each be C, in X 51 The bond between Y and Y3 can be a single bond, in X 51 The key between Y5 and X can be a double key, and X 51 It can be N, C(R7), Si(R7), or Ge(R7), or

[0100] v)Y3-Y5 can be C, in X 51 The bond between Y and Y3 can be a double bond, in X 51 The key between Y5 and X can be a single key, and X 51 It can be N, C(R7), Si(R7), or Ge(R7).

[0101] In one or more embodiments, in Equation 1, Y3-Y5 can be C; in X 51 The bond between Y3 and X 51 Each key between Y5 and X can be a single key; and X 51 It can be O, S, N-[(L7)] b7 -(R7) c7 ], C(R7)(R8), Si(R7)(R8), Ge(R7)(R8), or C(=O).

[0102] In Equation 1, T1 and T2 are independently a single bond, a double bond, *-N(R9)-*', *-B(R9)-*', *-P(R9)-*', and *-C(R9)-*', respectively. 9a (R) 9b )-*'、*-Si(R 9a (R) 9b )-*'、*-Ge(R 9a (R) 9b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R9)=*', *=C(R9)-*', *-C(R 9a )=C(R 9b )-*', *-C(=S)-*', or *-C≡C-*', where * and *' each represent a bond with an adjacent atom. R 9a and R 9b Optionally linked via single bonds, double bonds, or a second linker to form an unsubstituted or linked group with 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. The second linking group is as defined with respect to the first linking group.

[0103] In one or more embodiments, T1 and T2 in Formula 1 may be single bonds.

[0104] In Equation 1, Z 13 and Z 14 Each is an independent group represented by formula 2:

[0105] Formula 2

[0106]

[0107] The ring CY in Formula 2 10 Unsaturated C5-C 30 Carbocyclic groups or unsaturated C1-C 30Heterocyclic groups.

[0108] In one or more embodiments, the ring CY in Formula 2 10 It can be a phenyl group, naphthyl group, fluorene group, phenanthrene group, anthracene group, fluoranthene group, benzo[9,10]phenanthrene group, pyrene group, Groups, pyrrole groups, thiophene groups, furan groups, imidazole groups, pyrazole groups, thiazole groups, isothiazole groups, azole group, iso- Azolium group, pyridine group, pyrazine group, pyrimidine group, pyridazine group, isoindole group, indole group, indazole group, purine group, quinoline group, isoquinoline group, benzo[a]quinoline group, quinoxaline group, quinazoline group, cyclophosphine group, carbazole group, phenanthroline group, benzimidazole group, benzo[a]furan group, benzo[a]thiophene group, benzo[a]isothiazolium group, benzo[a] azole group, benzene azole group, triazole group, tetraazole group Diazole group, triazine group, dibenzofuran group, dibenzothiophene group, benzocarbazole group, dibenzocarbazole group, imidazopyridine group, imidazopyrimidine group, azacarbazole group, azadibenzofuran group, or azadibenzothiophene group.

[0109] In one or more embodiments, the ring CY in Formula 2 10 It can be a phenyl group, a naphthyl group, a dibenzofuran group, or a dibenzothiophene group.

[0110] R in Equation 2 10 As defined with respect to R1.

[0111] For example, in Equation 2, R 10 Possible forms:

[0112] Deuterium, -CN, -Si(Q3)(Q4)(Q5), or -Ge(Q3)(Q4)(Q5); or

[0113] Each of the following C1-Cs was not replaced or was replaced as follows 20 Alkyl or C3-C 10 Cycloalkyl groups: deuterium, -CN, C1-C 20 Alkyl, deuterated C1-C 20 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, (C1-C 20 Alkyl)C3-C 10 Cycloalkyl groups, or combinations thereof.

[0114] In Equation 2, a10 represents R 10The quantity is an integer between 0 and 20. When a10 is 2 or greater, two or more R... 10 They can be the same or different from each other. For example, a10 can be an integer from 0 to 5.

[0115] Z in Equation 2 10 It is a fluorinated group (-F) or a fluorinated group. As used herein, "fluorinated group" refers to a group that is substituted by at least one fluorinated group (-F).

[0116] For example, in Equation 2, Z 10 Can be

[0117] -F; or

[0118] Fluorinated C1-C molecules that are either unsubstituted or substituted as follows 20 Alkyl, fluorophenyl, or fluorobiphenyl: deuterium, C1-C 20 Alkyl, deuterated C1-C 20 Alkyl, phenyl, deuterated phenyl, (C1-C 20 Alkyl)phenyl, biphenyl, deuterated biphenyl, (C1-C) 20 Alkyl)biphenyl, or combinations thereof.

[0119] In Equation 2, n10 represents Z 10 The number is an integer from 1 to 20. Therefore, the group represented by Equation 2 may include at least one Z as defined herein. 10 When n10 is 2 or greater, two or more Z 10 They can be the same or different from each other. For example, n10 can be an integer from 1 to 5.

[0120] In one or more embodiments, the group represented by Formula 2 may be a group represented by one of Formulas 2-1 to 2-42:

[0121]

[0122]

[0123] In equations 2-1 to 2-42,

[0124] R 1001 -R 1005 Each as related to R 10 The defined condition is R 1001 -R 1005 Each is not hydrogen.

[0125] Z 1001 -Z 1003 Each as related to Z 10 Defined, and

[0126] * indicates a binding site with an adjacent atom.

[0127] In Equation 1, n13 and n14 are each independent integers from 0 to 20, and the sum of n13 and n14 is 1 or greater. Therefore, Equation 1 can include Z as defined herein. 13 and Z 14 At least one of them.

[0128] In one or more embodiments, in Equation 1, n13 and n14 can each be an integer from 0 to 5 independently, and the sum of n13 and n14 can be from 1 to 5.

[0129] In one or more embodiments, the organometallic compound represented by Formula 1 can satisfy at least one of conditions 3 and 4:

[0130] Condition 3

[0131] In Equation 1, n13 is 1 or 2

[0132] Condition 4

[0133] In Equation 1, n14 is 1 or 2

[0134] In Equation 1, L1-L4, L7, L 13 and L 14 Each is independently a single bond, unsubstituted, or bound by at least one R. 10a Replacement C5-C 30 The carbocyclic group, or the unsubstituted group or the group with at least one R 10a Replacement C1-C 30 Heterocyclic groups.

[0135] For example, L1-L4, L7, L in Equation 1 13 and L 14 Each can be independently:

[0136] Single key; or

[0137] Each was not replaced or was replaced by at least one R 10a Substituted phenyl groups, naphthyl groups, anthracene groups, phenanthrene groups, benzo[9,10]phenanthrene groups, pyrene groups, Groups, cyclopentadienyl group, furan group, thiophene group, thiophene group, indene group, fluorene group, indole group, carbazole group, benzofuran group, dibenzofuran group, benzothiophene group, dibenzothiophene group, benzothiophene group, dibenzothiophene group, azafluorene group, azacarbazole group, azadibenzofuran group, azadibenzothiophene group, azadibenzothiophene group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, phenanthrene group, pyrrole 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 or benzothiadiazole group.

[0138] In one or more embodiments, L1-L4, L7, L... in Formula 1 13 and L 14 Each can be independently:

[0139] Single key; or

[0140] Not replaced or replaced by at least one R 10a Substituted phenyl groups.

[0141] In Equation 1, b1-b4, b7, b13, and b14 respectively represent L1-L4, L7, and L... 13 and L 14 The number of L1s, each an independent integer from 1 to 5. When b1 is 2 or greater, two or more L1s are the same or different from each other; when b2 is 2 or greater, two or more L2s are the same or different from each other; when b3 is 2 or greater, two or more L3s are the same or different from each other; when b4 is 2 or greater, two or more L4s are the same or different from each other; when b7 is 2 or greater, two or more L7s are the same or different from each other; when b13 is 2 or greater, two or more L1s are the same or different from each other. 13 Whether they are the same or different from each other, and when b14 is 2 or greater, two or more L 14 They are the same or different from each other.

[0142] In one or more embodiments, b1-b4, b7, b13, and b14 in Formula 1 can each be 1, 2, or 3 independently.

[0143] In Equation 1, R1-R4, R7-R9, R 9a R 9bR' 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 The groups are heteroaryl thio groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9). Q1-Q9 are each as defined herein.

[0144] For example, R1-R4, R7-R9, R 9a R 9b R' and R" can each be independently defined as:

[0145] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, -SF5, C1-C 20 Alkyl, C1-C 20 alkoxy, or C1-C 20 Alkylthio;

[0146] Each of the following C1-C is replaced: 20 Alkyl, C1-C 20 alkoxy, or C1-C 20 Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -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 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, (C1-C 20 alkyl)cyclopentyl, (C1-C 20 alkyl)cyclohexyl, (C1-C 20 alkyl)cycloheptyl, (C1-C 20 alkyl)cyclooctyl, (C1-C 20 Alkyl) adamantyl, (C1-C 20 Alkyl)norbornel, (C1-C 20 alkyl) norbornenyl, (C1-C 20 alkyl)cyclopentenyl, (C1-C 20 alkyl)cyclohexenyl, (C1-C 20 alkyl)cycloheptenyl, (C1-C 20 Alkyl)bicyclo[1.1.1]pentyl, (C1-C 20 Alkyl)bicyclo[2.1.1]hexyl, (C1-C 20 Alkyl)bicyclo[2.2.2]octyl, phenyl, (C1-C 20 Alkyl)phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidinyl, or combinations thereof;

[0147] Each of the following substituted compounds, either unsubstituted or substituted with: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, phenyl, (C1-C 20 Alkyl)phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cyclophosphinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, benzoisothiazolyl, benzo[] azole group, benzo[a] Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, imidazopyrimidinyl, azacarbazoyl, azadibenzofuranyl, or azadibenzothiophenyl: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, 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, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, (C1-C 20 alkyl)cyclopentyl, (C1-C 20 alkyl)cyclohexyl, (C1-C 20 alkyl)cycloheptyl, (C1-C 20 alkyl)cyclooctyl, (C1-C 20 Alkyl) adamantyl, (C1-C 20 Alkyl)norbornel, (C1-C 20 alkyl) norbornenyl, (C1-C 20 alkyl)cyclopentenyl, (C1-C 20 alkyl)cyclohexenyl, (C1-C 20 alkyl)cycloheptenyl, (C1-C 20 Alkyl)bicyclo[1.1.1]pentyl, (C1-C 20 Alkyl)bicyclo[2.1.1]hexyl, (C1-C 20 Alkyl)bicyclo[2.2.2]octyl, phenyl, (C1-C 20 Alkyl)phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, alkyl, pyrroleyl, thiophenyl, furanyl, imidazoleyl, pyrazolyl, thiazolyl, isothiazolyl, azole group, iso Azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cyclophosphinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, benzoisothiazolyl, benzo[] azole group, benzo[a] Azolyl, triazolyl, tetrazolyl, Diazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazole, dibenzocarbazole, imidazopyridyl, imidazopyrimidinyl, azacarbazole, azadibenzofuranyl, azadibenzothiophenyl, or combinations thereof; or

[0148] -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9),

[0149] Q1-Q9 can be independently defined as follows:

[0150] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; or

[0151] Each of the following is either unsubstituted or substituted with: n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, phenyl, biphenyl, or naphthyl: deuterium, C1-C 10 Alkyl, phenyl, or combinations thereof.

[0152] In Equation 1, c1-c4, c7, c13, and c14 represent R1-R4, R7, and Z, respectively. 13 and Z 14 The number of each R1 and each R2 is an integer from 1 to 5, and each R1 is an integer from 1 to 5. When c1 is 2 or greater, two or more R1s are the same or different from each other; when c2 is 2 or greater, two or more R2s are the same or different from each other; when c3 is 2 or greater, two or more R3s are the same or different from each other; when c4 is 2 or greater, two or more R4s are the same or different from each other; when c7 is 2 or greater, two or more R7s are the same or different from each other; when c13 is 2 or greater, two or more R7s are the same or different from each other. 13 Whether they are the same or different, and when c14 is 2 or greater, two or more Z 14 They are the same or different from each other.

[0153] In one or more embodiments, c1-c4, c7, c13 and c14 in Formula 1 can each be 1 or 2 independently.

[0154] In Equation 1, a1-a4 each represent *-[(L1)] b1 -(R1) c1 ]、*-[(L2) b2 -(R2) c2 ]、*-[(L3) b3 -(R3) c3 ]、and *-[(L4) b4 -(R4) c4 The number of *-[(L1)], each an independent integer from 0 to 20. When a1 is 2 or greater, two or more *-[(L1)] b1 -(R1) c1 They are the same or different from each other, and when a2 is 2 or greater, there are two or more *-[(L2)]. b2 -(R2) c2 They are the same or different from each other, and when a3 is 2 or greater, there are two or more *-[(L3)]. b3 -(R3) c3 They are the same or different from each other, and when a4 is 2 or greater, two or more *-[(L4)] b4 -(R4) c4 They are the same or different from each other.

[0155] In one or more embodiments, R1-R4, R7-R9, R in Formula 1 9a R 9bR' and R" can each independently be hydrogen, deuterium, -F, cyano, nitro, -SF5, -CH3, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, -OCH3, -OCDH2, -OCD2H, -OCD3, -SCH3, -SCDH2, -SCD2H, -SCD3, a group represented by any one of formulas 9-1 to 9-39, a group represented by any one of formulas 9-1 to 9-39 wherein at least one hydrogen is replaced by deuterium, a group represented by any one of formulas 9-1 to 9-39 wherein at least one hydrogen is replaced by -F, a group represented by any one of formulas 9-201 to 9-233, a group represented by any one of formulas 9-201 to 9-233 wherein at least one hydrogen is replaced by deuterium, and a group represented by any one of formulas 9-201 to 9-233 wherein at least one hydrogen is replaced by deuterium. A group represented by any one of formulas 9-201 to 9-233 in which hydrogen is replaced by -F, a group represented by any one of formulas 10-1 to 10-132, a group represented by any one of formulas 10-1 to 10-132 in which at least one hydrogen is replaced by deuterium, a group represented by any one of formulas 10-1 to 10-132 in which at least one hydrogen is replaced by -F, a group represented by any one of formulas 10-201 to 10-353, a group represented by any one of formulas 10-201 to 10-353 in which at least one hydrogen is replaced by deuterium, a group represented by any one of formulas 10-201 to 10-353 in which at least one hydrogen is replaced by -F, -Si(Q3)(Q4)(Q5), or -Ge(Q3)(Q4)(Q5) (Q3-Q5 are each the same as described herein).

[0156] In one or more embodiments, Z in Equation 2 10 It may be -F, -CF3, -CF2H, -CFH2, a group represented by one of formulas 9-1 to 9-39 in which at least one hydrogen is replaced by -F, a group represented by one of formulas 9-201 to 9-233 in which at least one hydrogen is replaced by -F, a group represented by one of formulas 10-1 to 10-132 in which at least one hydrogen is replaced by -F, or a group represented by one of formulas 10-201 to 10-353 in which at least one hydrogen is replaced by -F.

[0157] In one or more embodiments, the group represented by Formula 2 may be a group represented by one of Formulas 10-12 to 10-132 in which at least one hydrogen is replaced by -F, or a group represented by one of Formulas 10-201 to 10-353 in which at least one hydrogen is replaced by -F:

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167] In formulas 9-1 to 9-39, 9-201 to 9-233, 10-1 to 10-132, and 10-201 to 10-353, * indicates a binding site with an adjacent atom, Ph is phenyl, TMS is trimethylsilyl, TMG is trimethylgermanyl, and OMe is methoxy.

[0168] As used herein, "a group represented by one of formulas 9-1 to 9-39 in which at least one hydrogen is replaced by deuterium" and "a group represented by one of formulas 9-201 to 9-233 in which at least one hydrogen is replaced by deuterium" can be, for example, a group represented by one of formulas 9-501 to 9-514 and 9-601 to 9-635:

[0169]

[0170]

[0171] As used herein, "a group represented by one of formulas 9-1 to 9-39 in which at least one hydrogen is replaced by -F" and "a group represented by one of formulas 9-201 to 9-233 in which at least one hydrogen is replaced by -F" can be, for example, a group represented by one of formulas 9-701 to 9-710:

[0172]

[0173] As used herein, "a group represented by one of formulas 10-1 to 10-132 in which at least one hydrogen is replaced by deuterium" and "a group represented by one of formulas 10-201 to 10-353 in which at least one hydrogen is replaced by deuterium" can be, for example, a group represented by one of formulas 10-501 to 10-553:

[0174]

[0175]

[0176] As used herein, "a group represented by one of formulas 10-1 to 10-132 in which at least one hydrogen is replaced by -F" and "a group represented by one of formulas 10-201 to 10-353 in which at least one hydrogen is replaced by -F" can be, for example, a group represented by one of formulas 10-601 to 10-620:

[0177]

[0178] In Equation 1, i) two or more of the plurality of R1s are optionally connected 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, ii) two or more of the plurality of R2s optionally linked 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, iii) two or more of the plurality of R3s are optionally linked 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 (iv) Two or more of the heterocyclic groups R4 are optionally linked to form an unsubstituted or at least one R4 group. 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, v)R1-R4, R7-R9, R 9a R 9b Two or more of R' and R" are optionally connected 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.

[0179] R 10a As defined with respect to R1.

[0180] In one or more embodiments, the formula 1 is derived from... The group represented can be one of the groups represented by formulas CY1-1 to CY1-40:

[0181]

[0182]

[0183] In equations CY1-1 to CY1-40,

[0184] Y1 is as defined in this article.

[0185] X 19 For C(R) 19a (R) 19b ), N[(L 19 ) b19 -(R 19 ) c19 ], O, S, or Si(R 19a (R) 19b ),

[0186] L 19 As defined in L1;

[0187] b19 and c19 are as defined with respect to b1 and c1, respectively.

[0188] R 19 R 19a and R 19b Each as defined with respect to R1, and

[0189] *' indicates the binding site with X1 or M in Equation 1, and

[0190] * indicates the binding site with ring CY5 in Formula 1.

[0191] In one or more embodiments, the formula 1 is derived from... The group represented can be one of the groups represented by formulas CY1(1) to CY1(22):

[0192]

[0193] In equations CY1(1) to CY1(22),

[0194] Y1 is as defined in this article.

[0195] R 11 -R 14 Each as defined with respect to R1, with the condition being R 11 -R 14 Each is not hydrogen.

[0196] X 19 It can be C(R) 19a (R) 19b ), N[(L 19 ) b19 -(R19 ) c19 ], O, S, or Si(R 19a (R) 19b ),

[0197] L 19 It can be the same as that defined with respect to L1;

[0198] b19 and c19 are as defined with respect to b1 and c1, respectively.

[0199] R 19 R 19a and R 19b Each as defined with respect to R1,

[0200] *' indicates the binding site with X1 or M in Equation 1, and

[0201] * indicates the binding site with ring CY5 in Formula 1.

[0202] For example, R in equations CY1(1) to CY1(22) 11 -R 14 It can be substituted or unsubstituted C4-C 20 alkyl.

[0203] In one or more embodiments, the formula 1 is derived from... The group represented can be one of the groups represented by formulas CY2-1 to CY2-20:

[0204]

[0205] Among them, in formulas CY2-1 to CY2-20,

[0206] X2 and X 51 Each as defined in this article,

[0207] * indicates the binding site with ring CY1 in Formula 1.

[0208] *' indicates the binding site with M in Equation 1, and

[0209] *" indicates the binding site with T1 in Equation 1.

[0210] In one or more embodiments, the formula 1 is derived from... The group represented can be one of the groups represented by formulas CY2(1) to CY2(20):

[0211]

[0212] In equations CY2(1) to CY2(20),

[0213] X2 and X51 Each as defined in this article,

[0214] R 21 -R 23 Each as defined with respect to R2, with the condition R 21 -R 23 Each may not be hydrogen.

[0215] * indicates the binding site with ring CY1 in Formula 1.

[0216] *' indicates the binding site with M in Equation 1, and

[0217] *" indicates the binding site with T1 in Equation 1.

[0218] In one or more embodiments,

[0219] Equation 1 The group represented can be a group represented by one of the formulas CY3-1 to CY3-14, and

[0220] Equation 1 The group represented can be one of the groups represented by formulas CY4-1 to CY4-26.

[0221] In one or more embodiments,

[0222] Equation 1 The group represented may be a group represented by one of the formulas CY3-1 to CY3-14, or

[0223] Equation 1 The group represented can be one of the groups represented by formulas CY4-1 to CY4-26.

[0224]

[0225] In equations CY3-1 to 3-14,

[0226] X3 is as defined in this article.

[0227] X 39 It can be C(R) 39a (R) 39b ), N[(L 39 ) b39 -(R 39 ) c39 ], O, S, or Si(R 39a (R) 39b ),

[0228] L 39 As defined regarding L3,

[0229] b39 and c39 are as defined with respect to b3 and c3, respectively.

[0230] R 39 R 39a and R 39b Each as defined in relation to R3,

[0231] * indicates the binding site with T2 in Equation 1.

[0232] *' indicates the binding site with M in Equation 1.

[0233] *" indicates the binding site with T1 in Equation 1.

[0234]

[0235] In equations CY4-1 to 4-26,

[0236] X4 is as defined in this article.

[0237] X 49 It can be C(R) 49a (R) 49b ), N[(L 49 ) b49 -(R 49 ) c49 ], O, S, or Si(R 49a (R) 49b ),

[0238] L 49 As defined regarding L4,

[0239] b49 and c49 are as defined with respect to b4 and c4, respectively.

[0240] R 49 R 49a and R 49b Each as defined for R4,

[0241] * indicates the binding position with T2 in Equation 1, and

[0242] *' indicates the binding site with M in Equation 1.

[0243] In one or more embodiments,

[0244] Equation 1 The group represented can be one of the groups represented by formulas CY3(1) to CY3(12) or CY3(1)F to CY3(12)F, and

[0245] Equation 1 The group represented can be one of the groups represented by formula CY4(1) to CY4(16) or CY4(1)F to CY4(32)F.

[0246] In one or more embodiments,

[0247] Equation 1 The group represented may be a group represented by one of the formulas CY3(1) to CY3(12) or CY3(1)F to CY3(12)F, or

[0248] Equation 1 The group represented can be one of the groups represented by formula CY4(1) to CY4(16) or CY4(1)F to CY4(32)F.

[0249]

[0250] In equations CY3(1) to CY3(12) and CY3(1)F to CY3(12)F,

[0251] X3 and Z 13 Each as defined in this article,

[0252] R 31 -R 33 Each as defined with respect to R3, with the condition that R 31 -R 33 Each may not be hydrogen.

[0253] X 39 It can be C(R) 39a (R) 39b ), N[(L 39 ) b39 -(R 39 ) c39 ], O, S, or Si(R 39a (R) 39b ),

[0254] L 39 As defined regarding L3,

[0255] b39 and c39 are as defined with respect to b3 and c3, respectively.

[0256] R 39 R 39a and R 39b Each as defined in relation to R3,

[0257] * indicates the binding site with T2 in Equation 1.

[0258] *' indicates the binding site with M in Equation 1, and

[0259] *" indicates the binding site with T1 in Equation 1.

[0260]

[0261]

[0262] In equations CY4(1) to CY4(16) and CY4(1)F to CY4(32)F,

[0263] X4, L 14 and Z 14 Each as defined in this article,

[0264] L 41 -L 44 Each as defined for L4,

[0265] R 41 -R 44 Each as defined with respect to R4, with the condition that R 41 -R 44 Each may not be hydrogen.

[0266] * indicates the binding site with T2 in Equation 1, and

[0267] *' indicates the binding site with M in Equation 1.

[0268] In one or more embodiments, the organometallic compound represented by Formula 1 may satisfy at least one of conditions 3-1 and 4-1:

[0269] Condition 3-1

[0270] Equation 1 The group represented is one of the groups represented by formulas CY3(1)F to CY3(12)F.

[0271] Condition 4-1

[0272] Equation 1 The group represented is one of the groups represented by formulas CY4(1)F to CY4(32)F.

[0273] Organometallic compounds represented by Formula 1 can be represented by Formula 1A:

[0274] Formula 1A

[0275]

[0276] In Equation 1A,

[0277] M, X1-X4, Y1, and X 51 Each as defined in this article,

[0278] X 11 It can be C(R) 11 ) or N, X 12 It can be C(R) 12 ) or N, X 13 It can be C(R) 13 ) or N, X 14 It can be C(R) 14 ) or N, R 11 -R 14 Each as defined with respect to R1,

[0279] X 21 It can be C(R) 21 ) or N, X 22 It can be C(R) 22 ) or N, X 23 It can be C(R) 23 ) or N, R 21 -R 23 Each as defined with respect to R2,

[0280] X 31 It can be C(R) 31 ), C(Z) 13 ) or N, X 32 It can be C(R) 32 ), C(Z) 13 ) or N, X 33 It can be C(R) 33 ), C(Z) 13 ) or N, R 31 -R 33 Each as defined for R3, Z 13 As defined in this article,

[0281] X 41 It can be C-[(L 41 )-(R 41 )]、C-[(L 14 )-(Z 14 )]、or N, X 42 It can be C-[(L 42 )-(R 42 )]、C-[(L 14 )-(Z 14 )]、or N, X 43 It can be C-[(L 43 )-(R 43 )]、C-[(L 14 )-(Z 14 )]、or N, X 44 It can be C-[(L 44 )-(R 44 )]、C-[(L 14 )-(Z14 )]、or N, L 41 -L 44 As defined for L4, R 41 -R 44 Each as defined with respect to R4, and L 14 and Z 14 Each as defined in this article,

[0282] R 11 -R 14 Two or more may be optionally connected to form an unsubstituted or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group, or the unsubstituted group or the group with at least one R 10a Replacement C1-C 30 Heterocyclic groups,

[0283] R 21 -R 23 Two or more may be optionally connected to form an unsubstituted or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group, or the unsubstituted group or the group with at least one R 10a Replacement C1-C 30 Heterocyclic groups,

[0284] R 31 -R 33 Two or more may be optionally connected to form an unsubstituted or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group, or the unsubstituted group or the group with at least one R 10a Replacement C1-C 30 Heterocyclic groups, and

[0285] R 41 -R 44 Two or more may be optionally connected to form an unsubstituted or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group, or the unsubstituted group or the group with at least one R 10a Replacement C1-C 30 Heterocyclic groups.

[0286] R 10a As defined with respect to R1.

[0287] The organometallic compound represented by formula 1A can satisfy at least one of conditions (1) to (7):

[0288] Condition (1)

[0289] X31 For C(Z) 13 )

[0290] Condition (2)

[0291] X 32 For C(Z) 13 )

[0292] Condition (3)

[0293] X 33 For C(Z) 13 )

[0294] Condition (4)

[0295] X 41 For C-[(L 14 )-(Z 14 )]

[0296] Condition (5)

[0297] X 42 For C-[(L 14 )-(Z 14 )]

[0298] Condition (6)

[0299] X 43 For C-[(L 14 )-(Z 14 )]

[0300] Condition (7)

[0301] X 44 For C-[(L 14 )-(Z 14 )]

[0302] In one or more embodiments, X in Formula 1A 51 It can be O, S, N-[(L7)] b7 -(R7) c7 ], C(R7)(R8), Si(R7)(R8), Ge(R7)(R8), or C(=O).

[0303] In one or more embodiments, X in Formula 1A 51 It can be N-[(L7)] b7 -(R7) c7 ].

[0304] In one or more embodiments, in Formula 1A, X 51 It can be N-[(L7)] b7 -(R7) c7L7 may not be a single bond, c7 may be greater than or equal to 2, and one of two or more R7 bonds may be a substituted or unsubstituted C4-C bond. 20 Alkyl (e.g., tert-butyl, etc.), and one of the remaining R7s may be a substituted or unsubstituted phenyl (e.g., phenyl, deuterated phenyl, (C1-C... 20 Alkyl) phenyl, etc.) or substituted or unsubstituted biphenyl (e.g., biphenyl, deuterated biphenyl, or (C1-C1) biphenyl). 20 (alkyl) biphenyl, etc.

[0305] In one or more embodiments, in Formula 1A, X 11 It can be C(R) 11 ), X 13 It can be C(R) 13 ), and R 11 and R 13 Each can be independently substituted or unsubstituted C4-C. 20 alkyl.

[0306] In one or more embodiments, the organometallic compound represented by formula 1A may satisfy at least one of conditions (1) to (3).

[0307] In one or more embodiments, the organometallic compound represented by formula 1A may satisfy at least one of conditions (4) to (7).

[0308] The additional description of Equation 1A is the same as the description of Equation 1.

[0309] In one or more embodiments, the formula 1A is derived from... The group represented can be one of the groups represented by formula CY1(1) to CY1(22).

[0310] In one or more embodiments, the formula 1A is derived from... The group represented can be one of the groups represented by formula CY2(1) to CY2(20).

[0311] In one or more embodiments, the formula 1A is derived from... The group represented can be one of the groups represented by formulas CY3(1) to CY3(12) or CY3(1)F to CY3(12)F.

[0312] In one or more embodiments, the formula 1A is derived from... The group represented can be one of the groups represented by formula CY4(1) to CY4(16) or CY4(1)F to CY4(32)F.

[0313] In one or more embodiments, Formula 1 and Formula 1A may each include at least one deuterium.

[0314] In one or more embodiments, L1, L2, R1, R2, and X in Formula 1 51 Each may not include a fluorine group (-F).

[0315] In one or more embodiments, R in Formula 1A 11 -R 14 R 21 -R 23 and X 51 Each may not include a fluorine group (-F).

[0316] In one or more embodiments, the organometallic compound may be one of compounds 1 to 3:

[0317]

[0318] In Equation 1, Z 13 and Z 14 Each can be an independent group represented by Formula 2, and n13 and n14 can each be an integer from 0 to 20, and the sum of n13 and n14 can be 1 or greater. Therefore, at least one of the rings CY3 and CY4 in the organometallic compound represented by Formula 1 can include a group represented by Formula 2. Furthermore, the group represented by Formula 2 can include rings CY3 and CY4 as defined in this specification. 10 Therefore, since the organometallic compounds represented by Formula 1 can simultaneously maintain excellent electrical properties and have low Ts temperatures or low sublimation temperatures, electronic devices using these organometallic compounds, such as organic light-emitting devices, can simultaneously possess excellent emission efficiency and lifetime characteristics.

[0319] Furthermore, rings CY1, CY3, and CY4 in Formula 1 may not each be a benzimidazole group. Therefore, due to the improved steric hindrance of the ligands surrounding the central metal M, electronic devices including the aforementioned organometallic compounds, such as organic light-emitting devices, can exhibit improved lifetime characteristics and sharp electroluminescence peaks.

[0320] For example, density functional theory (DFT) methods in the Gaussian 09 program (with structural optimization at the B3LYP, 6-31G(d,p) level) were used to calculate the highest occupied molecular orbital (HOMO) level, lowest unoccupied molecular orbital (LUMO) level, band gap (eV), lowest excited singlet (S1) level, and lowest excited triplet (T1) level for compounds 1 to 3. The evaluation results are shown in Table 1 below.

[0321] Table 1

[0322]

[0323] Table 1 confirms that the organometallic compounds represented by Formula 1 possess electrical properties suitable for use as dopants in electronic devices such as organic light-emitting devices.

[0324] The method for synthesizing the organometallic compounds represented by Formula 1 can be understood by those skilled in the art by referring to the synthesis examples provided below.

[0325] Therefore, organometallic compounds represented by Formula 1 are suitable for use as materials for organic layers in organic light-emitting devices, for example, as dopants in the emitting layer of said organic layer. Thus, on the other hand, an organic light-emitting device is provided, comprising: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode, including an emitting layer, wherein said organic layer comprises at least one organometallic compound represented by Formula 1.

[0326] Because it includes an organic layer comprising an organometallic compound represented by Formula 1, the organic light-emitting device can have a low driving voltage, high external quantum efficiency, low roll-off ratio, and long lifetime.

[0327] The organometallic compound of Formula 1 can be used between electrode pairs in an organic light-emitting device. For example, the organometallic compound represented by Formula 1 can be included in the emitting layer. In this respect, the organometallic compound can act as a dopant, and the emitting layer can further include a host (i.e., the amount of the organometallic compound represented by Formula 1 is less than the amount of the host). The emitting layer can emit, for example, green or blue light.

[0328] As used herein, the expression “(organic layer) comprises at least one organometallic compound” may include cases where “(organic layer) comprises the same organometallic compound represented by Formula 1” and cases where “(organic layer) comprises two or more different organometallic compounds represented by Formula 1”.

[0329] For example, the organic layer may include only compound 1 as the organometallic compound. In this embodiment, compound 1 may be included in the emitting layer of the organic light-emitting device. In one or more embodiments, the organic layer may include both compound 1 and compound 2 as the organometallic compound. In this respect, compound 1 and compound 2 may be in the same layer (e.g., both compound 1 and compound 2 may be in the emitting layer).

[0330] 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.

[0331] In one or more embodiments, in the organic light-emitting device, the first electrode is an anode and the second electrode is a cathode, and the organic layer may further include a hole transport region located between the first electrode and the emitting layer and an electron transport region located between the emitting layer and the second electrode, and 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.

[0332] As used herein, "organic layer" refers to a single layer or multiple layers between the first electrode and the second electrode of the organic light-emitting device. In addition to organic compounds, "organic layer" may include organometallic complexes containing metals.

[0333] Figure 1 This is a schematic cross-sectional view of an organic light-emitting device 10 according to one or more embodiments. Hereinafter, regarding... Figure 1 The present disclosure describes the structure of an organic light-emitting device according to one or more embodiments and a method of manufacturing an organic light-emitting device according to one or more embodiments. The organic light-emitting device 10 includes a first electrode 11, an organic layer 15, and a second electrode 19 sequentially stacked.

[0334] A substrate may be additionally placed below the first electrode 11 or above the second electrode 19. Any substrate available in the art for use in organic light-emitting devices may be used as the substrate, and the substrate may be a glass substrate or a transparent plastic substrate, each possessing excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.

[0335] In one or more embodiments, the first electrode 11 can be formed 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 having a high work function to facilitate hole injection. The first electrode 11 can be a reflective electrode, a semi-transparent 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), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag).

[0336] 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.

[0337] The organic layer 15 is located on the first electrode 11.

[0338] The organic layer 15 may include a hole transport region, an emitter layer, and an electron transport region.

[0339] The hole transport region may be located between the first electrode 11 and the emitter layer.

[0340] 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.

[0341] 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, for each structure, the layers are stacked sequentially from the first electrode 11 in the order stated herein.

[0342] 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, and / or Langmuir-Broguet (LB) deposition.

[0343] When a hole injection layer is formed by vacuum deposition, the deposition conditions can vary depending on the material used to form the hole injection layer, as well as the structure and thermal properties of the hole injection layer. For example, deposition conditions may include a deposition temperature of about 100°C to about 500°C, and a deposition temperature of about 10... -8 To-10 -3 The vacuum pressure of Tor and the treaty -about The deposition rate.

[0344] When spin coating is used to form the hole injection layer, the coating conditions can be varied depending on the material used to form the hole injection layer, as well as the structure and thermal properties of the hole injection layer. For example, the coating speed can be from about 2,000 rpm to about 5,000 rpm, and the temperature at which heat treatment is performed after coating to remove the solvent can be from about 80°C to about 200°C.

[0345] The conditions for forming the hole transport layer and the electron blocking layer can be the same as the conditions for forming the hole injection layer.

[0346] The hole transport region may include 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(naphth-1-yl)-N,N′-diphenyl-benzidine (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′- Cyclohexylbis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4′-bis[N,N′-(3-tolyl)amino]-3,3′-dimethylbiphenyl (HMTPD), 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 below, compounds represented by formula 202 below, or combinations thereof:

[0347]

[0348] Formula 201

[0349]

[0350] Formula 202

[0351]

[0352] Ar in Equation 201 101 and Ar 102 Each can be independently represented as either unsubstituted or substituted with the following: phenylene, cyclopentadienylene, indenylene, naphthylene, or phenylene. Alkyl, heptadeneyl, acenaphthene, fluoreneyl, phenentheneyl, anthraceneyl, fluoreneyl, benzo[9,10]phenentheneyl, pyreneyl, phenentheneyl alkyl, tetraphenyl, phenyl Base, Asia alkyl, or pentanephenyl: deuterium, -F, -Cl, -Br, -I, 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 60Alkoxy, C3-C 10 cycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, 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.

[0353] 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, in one or more embodiments, xa can be 1 and xb can be 0.

[0354] R in Equations 201 and 202 101 -R 108 R 111 -R 119 and R 121 -R 124 Each can be independently:

[0355] Hydrogen, deuterium, -F, -Cl, -Br, -I, 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 (e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl, etc.), or C1-C 10 Alkyl groups (e.g., methoxy, ethoxy, propoxy, butoxy, pentoxy, etc.);

[0356] Each of the following C1-Cs was not replaced or was replaced as follows 10 Alkyl or C1-C 10 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, or combinations thereof; or

[0357] Each of the following groups—either unsubstituted or substituted with: deuterium, -F, -Cl, -Br, -I, 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 or C1-C 10 Alkoxy groups, or combinations thereof.

[0358] 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, 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, phenyl, naphthyl, anthraceneyl, pyridyl, or combinations thereof.

[0359] In one embodiment, the compound represented by formula 201 can be represented by formula 201A:

[0360] Formula 201A

[0361]

[0362] R in Equation 201A 101 R 111 R 112 and R 109 This can be understood by referring to the descriptions provided in this article.

[0363] For example, the hole transport region may include one or a combination of compounds HT1 to HT20:

[0364]

[0365]

[0366]

[0367] The thickness of the hole transport region can be approximately to approximately For example, about to approximately Within the range. When the hole transport region includes at least one hole injection layer and a hole transport layer, the thickness of the hole injection layer can be approximately to approximately For example, about to approximately Within a certain range, and the thickness of the hole transport layer can be approximately [missing information]. to approximately For example, about to approximately Within these ranges, satisfactory hole transport characteristics can be obtained without a significant increase in driving voltage when the hole transport region, hole injection layer, and thickness of the hole transport layer are within these ranges.

[0368] In addition to these materials, 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.

[0369] The charge-generating material may be, for example, a p-doper. The p-doper may include quinone derivatives, metal oxides, cyano-containing compounds, or combinations thereof. For example, the p-doper may be: 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 and molybdenum oxide; cyano-containing compounds such as compound HT-D1; or combinations thereof.

[0370]

[0371] The hole transport region may include a buffer layer.

[0372] Furthermore, the buffer layer can compensate for the optical resonance distance according to the wavelength of the light emitted from the emission layer, and thus the efficiency of the formed organic light-emitting device can be improved.

[0373] Furthermore, when the hole transport region includes an electron blocking layer, the material used to form the electron blocking layer may include the material used in the hole transport region as described above, the body material described below, or a combination thereof. For example, when the hole transport region includes an electron blocking layer, mCP described below can be used as the material used to form the electron blocking layer.

[0374] The emitter layer can then be formed on the hole transport region by vacuum deposition, spin coating, casting, LB deposition, etc. 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 be varied depending on the material used to form the emitter layer.

[0375] The emitter layer may include a host and a dopant, and the dopant may include an organometallic compound represented by Formula 1 as described herein.

[0376] The main body may include 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBi), 3-tert-butyl-9,10-di-2-naphthylanthracene (TBADN), 9,10-di(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′-dimethylbiphenyl (CDBP), 1,3,5-tris(carbazolyl-9-yl)benzene (TCP), 1,3-bis(carbazolyl-9-yl)benzene (mCP), compound H50, compound H51, compound H52, or combinations thereof:

[0377]

[0378] 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.

[0379] When the emitter layer comprises a host and a dopant, the amount of the dopant may be in the range of about 0.01 parts by weight to about 15 parts by weight, based on 100 parts by weight of the host.

[0380] The thickness of the emission layer can be approximately -about For example, about -about Within these ranges, excellent light emission characteristics can be obtained without a significant increase in driving voltage when the thickness of the emitting layer is within these ranges.

[0381] Then, the electron transport region can be located on the emission layer.

[0382] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

[0383] For example, 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. The electron transport layer may have a multilayer structure or a single-layer structure comprising two or more different materials.

[0384] The conditions for forming the hole blocking layer, electron transport layer, and electron injection layer constituting the electron transport region can be understood through the conditions for forming the hole injection layer.

[0385] When the electron transport region includes a hole-blocking layer, the hole-blocking layer may include, for example, 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:

[0386]

[0387] The thickness of the hole-blocking layer can be approximately to approximately For example, about to approximately Within these ranges, excellent hole blocking characteristics can be obtained without a significant increase in driving voltage when the thickness of the hole blocking layer is within these ranges.

[0388] The electron transport layer may include BCP, Bphen, TPBi, Alq3, Balq, TAZ, NTAZ, or combinations thereof:

[0389]

[0390] In one or more embodiments, the electron transport layer may include one or a combination of compounds ET1 to ET25:

[0391]

[0392]

[0393] The thickness of the electron transport layer can be approximately to approximately For example, about to approximately Within the range described above, when the thickness of the electron transport layer is within the range described above, the electron transport layer can have satisfactory electron transport characteristics without a significant increase in driving voltage.

[0394] In addition to the materials described above, the electron transport layer may include a material containing metal.

[0395] The metal-containing material may include Li complexes. The Li complexes may include, for example, compounds ET-D1 or ET-D2.

[0396]

[0397] The electron transport region may include an electron injection layer that facilitates the inflow of electrons from the second electrode 19 therein.

[0398] The electron injection layer may include LiF, NaCl, CsF, Li2O, BaO, or combinations thereof.

[0399] The thickness of the electron injection layer can be approximately to approximately For example, about to approximately Within the range described above, when the thickness of the electron injection layer is within the range described above, the electron injection layer can have satisfactory electron injection characteristics without a significant increase in driving voltage.

[0400] The second electrode 19 may be located on the organic 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 having a relatively low work function. For example, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag) may be used as the material for forming the second electrode 19. In one or more embodiments, for the fabrication of a top-emitting light-emitting device, a transmissive electrode formed using ITO or IZO may be used as the second electrode 19.

[0401] The above text has already referred to Figure 1 Organic light-emitting devices have been described, but embodiments of the present disclosure are not limited thereto.

[0402] According to another aspect, the organic light-emitting device can be included in an electronic device. Therefore, an electronic device including the organic light-emitting device is provided. The electronic device may include, for example, a display, a lighting device, a sensor, etc.

[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 provide high emission efficiency. Therefore, diagnostic compositions comprising said organometallic compounds can have high diagnostic efficiency.

[0405] The diagnostic composition can be used in a variety of applications, including diagnostic kits, diagnostic reagents, biosensors, and biomarkers.

[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 1-60 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] C1-C 60 Alkyl, C1-C20 Alkyl, and / or C1-C 10 Examples of alkyl groups are 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 tert-decyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodel, sec-decyl, tert-decyl, or combinations thereof. For example, formulas 9-33 are branched C6 alkyl groups, such as tert-butyl substituted with two methyl groups.

[0408] The term "C1-C" used in this article 60 "Alkoxy" refers to the compound formed by -OA 101 (where A) 101 For C1-C 60 Alkyl groups are monovalent groups, and examples of them are methoxy, ethoxy, propoxy, butoxy, and pentoxy.

[0409] As used in this article, the term "C2-C" 60 "Alkenyl" refers to the group formed by the carbon atoms in the C2-C2 group. 60 A hydrocarbon group formed by substituting at least one carbon-carbon double bond into the middle or end of an alkyl group, and examples include vinyl, propenyl, and butenyl groups. As used herein, the term "C2-C" is used... 60 "Alkenyl" refers to a group with a C2-C ratio. 60 Divalent groups with the same structure as alkenyl groups.

[0410] As used in this article, the term "C2-C" 60 "Alkyne" refers to the 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 examples include ethynyl and propynyl. As used herein, the term "C2-C" is used in this context. 60 "Alynyl group" refers to a group with a C2-C group. 60 Divalent groups with the same structure as alkynyl groups.

[0411] As used in this article, the term "C3-C" 10 "Cycloalkyl" refers to a monovalent saturated hydrocarbon cyclic group having 3-10 carbon atoms, and C3-C4. 10Cycloalkylene compounds are those with C3-C6 ... 10 Divalent groups with the same structure as cycloalkyl groups.

[0412] C3-C 10 Examples of cycloalkyl groups may 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.

[0413] As used in this article, the term "C1-C" 10 "Heterocyclic alkyl" refers to a saturated monocyclic group comprising at least one heteroatom selected from N, O, P, Si, S, B, Ge, and Se as the cyclic atom and 1-10 carbon 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.

[0414] C1-C 10 Examples of heterocyclic alkyl groups include silylcyclopentyl, silylcyclohexyl, tetrahydrofuranyl, tetrahydro-2H-pyranyl, and tetrahydrothiophenyl.

[0415] As used in this article, the term "C3-C" 10 "Cycloalkenyl" refers to a monovalent monocyclic group having 3-10 carbon atoms and at least one carbon-carbon double bond in its ring and not being aromatic, and non-limiting examples include cyclopentenyl, cyclohexenyl, and cycloheptenyl. The term "C3-C" is used as is herein. 10 "Cyclopentene" refers to a group with a C3-C6 bond structure. 10 A divalent group with the same structure as a cycloalkenyl group.

[0416] As used in this article, the term "C1-C" 10 "Heterocyclic alkenyl" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, P, Si, S, B, Ge, and Se as the cyclizing atom, 1-10 carbon atoms, and at least one double bond in its ring. C1-C 10 Examples of heterocyclic alkenyl groups are 2,3-dihydrofuranyl and 2,3-dihydrothiophenyl. As used herein, the term "C1-C..." 10 "Heterocyclic alkenyl" refers to a group that has a C1-C2 bond structure. 10 Divalent groups with the same structure as heterocyclic alkenyl groups.

[0417] As used in this article, the term "C6-C" 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic system with 6-60 carbon atoms, and as used herein, "C6-C".60 "Arylene" refers to a divalent group that has a carbocyclic aromatic system with 6-60 carbon atoms. (C6-C) 60 Examples of aryl groups include phenyl, naphthyl, anthraceneyl, phenanthryl, pyrene, and... Base. 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.

[0418] The term "C7-C" used in this article 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-C2 group. 59 Aryl-substituted C1-C 54 alkyl.

[0419] As used in this article, the term "C1-C" 60 "Heteroaryl" refers to a monovalent group having a cyclic aromatic system having at least one heteroatom selected from N, O, P, Si, S, B, Ge, and Se as the cyclic atom and 1-60 carbon atoms, and as used herein by the term "C1-C". 60 "Hypo-heteroaryl" refers to a divalent group having a cyclic aromatic system having at least one heteroatom selected from N, O, P, Si, S, B, Ge, and Se as the cyclic atom and 1-60 carbon atoms. C1-C 60 Examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. When C1-C... 60 heteroaryl and C1-C 60 When each heteroaryl group comprises two or more rings, the rings can fused together.

[0420] 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 herein, the term "C2-C" is used in this text. 60 "Heteroarylalkyl" refers to an alkyl group consisting of at least one C1-C2 group. 59 heteroaryl-substituted C1-C 59 alkyl.

[0421] As used in this article, the term "C6-C" 60 "Aryloxy group" represents -OA 102 (where A) 102Indicates C6-C 60 Aryl), C6-C 60 Arylthioyl group represents -SA 103 (where A) 103 Indicates C6-C 60 (aryl), and C1-C 60 Alkyl thio group represents -SA 104 (where A) 104 Indicates C1-C 60 alkyl).

[0422] As used in this article, the term "C1-C" 60 "Heteroaryloxy" representation -OA 102a (where A) 102a Indicates C1-C 60 (Heteroaryl) groups, and C1-C 60 heteroaryl thiol representation -SA 103a (where A) 103a Indicates C1-C 60 (A heteroaryl) group.

[0423] As used herein, the term "monovalent nonaromatic fused polycyclic group" refers to a monovalent group (e.g., having 8-60 carbon atoms) that has two or more rings fused together, has only carbon atoms as cyclic atoms, and is not aromatic in its overall molecular structure. Examples of monovalent nonaromatic fused polycyclic groups include the fluorene group. 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.

[0424] As used herein, the term "monovalent nonaromatic fused heterocyclic group" refers to a monovalent group (e.g., having 2-60 carbon atoms) that has two or more fused rings, has heteroatoms selected from N, O, P, Si, S, B, Ge, and Se as cyclic atoms in addition to carbon atoms, and is not aromatic in its overall molecular structure. Examples of monovalent nonaromatic fused heterocyclic groups include the carbazole group. 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.

[0425] As used in this article, the term "C5-C" 30 A "carbocyclic group" refers to a saturated or unsaturated cyclic group with only 5-30 carbon atoms as cyclic atoms. (C5-C) 30 The carbocyclic group can be a monocyclic or polycyclic group. "(Unsubstituted or with at least one R)" 10a (Replacement) C5-C 30 Examples of "carbocyclic groups" are (each unsubstituted or substituted by 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, 1,2,3,4-tetrahydronaphthalene group, cyclopentadienyl group, and fluorene group.

[0426] As used in this article, the term "C1-C" 30 A "heterocyclic group" refers to a saturated or unsaturated cyclic group that has at least one heteroatom selected from N, O, P, Si, Se, Ge, B, and S as a cyclic atom in addition to 1-30 carbon atoms. (C1-C) 30 Heterocyclic groups can be monocyclic or polycyclic. "(Unsubstituted or substituted with at least one R)" 10a (replaced) C1-C 30 "Heterocyclic group" can be, for example, (each unsubstituted or by at least one R as defined herein) 10a Substituted thiophene group, furan group, pyrrole group, thiophene group, borocyclopentadiene, phosphacyclopentadiene, selenophene group, germanium heterocyclopentadiene, benzothiophene group, benzofuran group, indole group, benzothiophene group, benzoboron heterocyclopentadiene, benzophosphacyclopentadiene, benzoselenophene group, benzogermanium heterocyclopentadiene, dibenzothiophene group, dibenzofuran group, carbazole group, dibenzothiophene group, dibenzoboron heterocyclopentadiene, dibenzophosphacyclopentadiene, dibenzoselenophene group, dibenzogermanium heterocyclopentadiene, dibenzothiophene 5-oxide group, 9H-fluorene-9-one group, dibenzothiophene 5,5-dioxide group, azabenzothiophene group, azabenzofuran group, azaindole group, azaindene group, azabenzothiophene group, azabenzothiophene group Thiophene group, azabenzoborane, azabenzophosphacyclopentadiene, azabenzoselenophene group, azabenzogermanium cyclopentadiene, azadibenzothiophene group, azadibenzofuran group, azacarbazole group, azafluorene group, azadibenzothiophene group, azadibenzoborane, azadibenzophosphacyclopentadiene, azadibenzoselenophene group, azadibenzogermanium cyclopentadiene, azadibenzothiophene 5-oxide group, aza-9H-fluorene-9-one group, azadibenzothiophene 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[] The diazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group, or 5,6,7,8-tetrahydroquinoline group.

[0427] As used in this article, the term "fluorinated C1-C" 60 Alkyl (or fluorinated C1-C) 20 Alkyl groups, etc.; Fluorinated C3-C 10 "cycloalkyl", "fluorinated C1-C" 10 "Heterocyclic alkyl" and "fluorophenyl" respectively represent C1-C1 alkyl groups substituted with at least one fluorine group (-F). 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 "fluoroC1 alkyl (i.e., fluoromethyl)" includes -CF3, -CF2H, and -CFH2. "Fluoro-C1-C..." 60 Alkyl (or fluorinated C1-C) 20 Alkyl groups, etc.; Fluorinated C3-C 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., and fully fluorinated C3-C groups 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 fluorinated groups; or ii) partially fluorinated C1-C 60 Alkyl (or partially fluorinated C1-C) 20 Alkyl groups, etc., and partially fluorinated C3-C groups 10 Cycloalkyl, partially fluorinated C1-C 10 Heterocyclic alkyl groups or partially fluorinated phenyl groups, wherein not all hydrogen atoms in each group are replaced by fluorinated groups.

[0428] As used in this article, the term "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" respectively represent C1-C alkyl groups substituted with at least one deuterium. 60 Alkyl (or C1-C) 20Alkyl groups, etc., C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl groups and phenyl groups. For example, "deuterated C1 alkyl (i.e., deuterated methyl)" may include -CD3, -CD2H, and -CDH2, and "deuterated C3-C 10 Examples of "cycloalkyl" are, for example, formula 10-501, etc. "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., and 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... 60 Alkyl (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.

[0429] As used in this article, the term "(C1-C" is similar to the term "(C1-C)" 20 "alkyl)'X' group" refers to a group consisting of at least one C1-C1 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 by 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.

[0430] The terms "azaindole group, azabenzoboranecyclopentadiene, azabenzophosphacyclopentadiene, azaindene group, azabenzothiophene group, azabenzogermanium cyclopentadiene, azabenzothiophene group, azabenzoselenene group, azabenzofuran group, azacarbazole group, azadibenzoboranecyclopentadiene, azadibenzophosphacyclopentadiene, azafluorene group, azadibenzothiophene group, azadibenzogermanium cyclopentadiene, azadibenzothiophene group, azadibenzoselenene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluorene-9-one group, and azadibenzothiophene 5,5-dioxide group" are also mentioned. "These refer to heterocyclic groups having the same skeleton as "indole group, benzoborane heterocyclopentadiene, benzophoshexacyclopentadiene, indene group, benzothiophene group, benzogermanium heterocyclopentadiene, benzothiophene group, benzoselenene group, benzofuran group, carbazole group, dibenzoborane heterocyclopentadiene, dibenzophoshexacyclopentadiene, fluorene group, dibenzothiophene group, dibenzogermanium heterocyclopentadiene, 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 selected from cyclic carbons is replaced by nitrogen.

[0431] Replacement C5-C 30 Carbocyclic groups, substituted C1-C 30 Heterocyclic groups, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 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 can each independently be:

[0432] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, 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;

[0433] The C1-C that was removed and 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, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, 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, -N(Q) 11 (Q) 12 ), -Si(Q 13 (Q) 14 (Q) 15 -Ge(Q) 13 (Q) 14 (Q) 15 -B(Q) 16 (Q) 17 -P(=O)(Q) 18 (Q) 19 -P(Q)18 (Q) 19 ), or combinations thereof;

[0434] 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, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, 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 Alkyne 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, -N(Q) 21 (Q) 22 ), -Si(Q 23 (Q) 24 (Q) 25 -Ge(Q) 23 (Q) 24(Q) 25 -B(Q) 26 (Q) 27 -P(=O)(Q) 28 (Q) 29 -P(Q) 28 (Q) 29 ), or combinations thereof;

[0435] -N(Q 31 (Q) 32 ), -Si(Q 33 (Q) 34 (Q) 35 -Ge(Q) 33 (Q) 34 (Q) 35 -B(Q) 36 (Q) 37 -P(=O)(Q) 38 (Q) 39 ), or -P(Q 38 (Q) 39 );or

[0436] Its combination,

[0437] Among them, Q1-Q9 and Q are used in this article. 11 -Q 19 Q 21 -Q 29 and Q 31 -Q 39 Each of these can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; amidine; hydrazine; hydrazone; carboxylic acid group or its salt; sulfonic acid group or its salt; phosphate group or its salt; unsubstituted or deuterated, C1-C 60 Alkyl, C6-C 60 aryl, or combined substituted C1-C 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkyne group; C1-C 60 Alkoxy group; C1-C 60 Alkylthio group; C3-C 10 cycloalkyl; C1-C 10 Heterocyclic alkyl; C3-C 10 Cycloalkenyl; C1-C 10 Heterocyclic alkenyl groups; unsubstituted or deuterated, C1-C 60 Alkyl, C6-C 60 aryl, or combined substituted C6-C 60 Aryl; C6-C 60 Aryloxy group; C6-C 60Arylthio; C1-C 60 heteroaryl; C1-C 60 Heteroaryloxy group; C1-C 60 Heteroaryl thio group; monovalent non-aromatic fused polycyclic group; or monovalent non-aromatic fused heterocyclic group.

[0438] For example, Q1-Q9, Q as used in this article 11 -Q 19 Q 21 -Q 29 and Q 31 -Q 39 Each can be independently:

[0439] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; or

[0440] Each of the following is either unsubstituted or substituted with: n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, phenyl, biphenyl, or naphthyl: deuterium, C1-C 10 Alkyl, phenyl, or combinations thereof.

[0441] The compounds and organic light-emitting devices according to one or more exemplary embodiments are described in further detail below with reference to synthesis examples and embodiments. However, the organic light-emitting devices 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.

[0442] Example

[0443] Synthesis Example 1 (Compound 1)

[0444]

[0445] Synthesis of compound 1-C(2,4-di-tert-butyl-6-(4-(3-(tert-butyl)-5-(4-(2-fluoro-4-(methyl-d3)phenyl)pyridin-2-yl)phenyl)-1-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-1H-benzis[d]imidazol-2-yl)phenol)

[0446] 1.5 g (0.002 mol, 1.0 equiv.) of compound 1-A (2-(4-bromo-1-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-1H-benzo[d]imidazol-2-yl)-4,6-di-tert-butylphenol) and 1.22 g (0.003 mol, 1.1 equiv.) of compound 1-B (2-(3-(tert-butyl)-5-(4,4,5,5-tetramethyl-1, 3,2-Dioxacyclopentaborane-2-yl)phenyl)-4-(2-fluoro-4-(methyl-d3)phenyl)pyridine, 0.20 g (0.001 mol, 0.07 equivalent) of tetra(triphenylphosphine)palladium(O), and 1.0 g (0.007 mol, 3 equivalent) of potassium carbonate were mixed with 40 mL of a solvent in which tetrahydrofuran (THF) and deionized water (DI water) were mixed in a 3:1 volume ratio. The resulting mixture was then heated under reflux for 12 hours. The obtained crude product mixture was allowed to cool to room temperature, and the precipitate was then removed to obtain a filtrate. The filtrate was washed with ethyl acetate (EA) and DI water and subjected to column chromatography (using a solvent gradient of 5-10 v / v EA and 90-95 v / v hexane) to complete the production of 1.8 g (86% yield) of ligand C. The obtained compounds were identified by high-resolution mass spectrometry (HRMS) (using matrix-assisted laser desorption / ionization (MALDI)) and high-performance liquid chromatography (HPLC).

[0447] HRMS (MALDI): For C 59 H 59 Calculated value of D3FN3O: Mass-to-charge ratio (m / z) 850.5065; Measured value: 850.5067

[0448] Synthesis of Compound 1

[0449] 1.8 g (2.03 mmol) of compound 1-C and 1.01 g (2.43 mmol, 1.2 equivalents) of K₂PtCl₄ were mixed with a solvent mixture containing 30 mL of acetic acid (AcOH) and 10 mL of DI water. The resulting mixture was then heated under reflux for 16 hours. The obtained crude product mixture was allowed to cool to room temperature, and the precipitate was removed to obtain a filtrate. The filtrate was dissolved in dichloromethane (MC) and washed with DI water, and subjected to column chromatography (using a solvent gradient of 10–35 vol% MC and 65–90 vol% hexane) to complete the preparation of 1.2 g (57% yield) of compound 1. The obtained compound was confirmed by HRMS and HPLC analysis.

[0450] HRMS (MALDI): For C59 H 57 Calculated value of D3FN3OPt: m / z 1043.4556, measured value: 1043.4555

[0451] Synthesis Example 2 (Compound 2)

[0452]

[0453] Synthesis of compound 2-C(2,4-di-tert-butyl-6-(4-(3-(tert-butyl)-5-(4-(4-fluorophenyl)pyridin-2-yl)phenyl)-1-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-1H-benzis[d]imidazol-2-yl)phenol)

[0454] Compound 2-C was obtained in a similar manner to that used to obtain compound 1-C in Synthetic Example 1, except that compound 2-B (2-(3-(tert-butyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)-4-(4-fluorophenyl)pyridine) was used instead of compound 1-B. The obtained compound was confirmed by HRMS and HPLC analysis.

[0455] HRMS (MALDI): For C 58 H 60 Calculated value of FN3O: m / z 833.4720, measured value: 833.4722

[0456] Synthesis of Compound 2

[0457] Compound 2 was obtained in a similar manner to that used to obtain compound 1 in Synthetic Example 1, except that 1.7 g (1.92 mmol) of compound 2-C was used instead of compound 1-C. The obtained compound was confirmed by HRMS and HPLC analysis.

[0458] HRMS (MALDI): For C 58 H 58 Calculated value of FN3OPt: m / z 1026.4212, measured value: 1026.4213

[0459] Synthesis Example 3 (Compound 3)

[0460]

[0461] Synthesis of compound 3-C(2,4-di-tert-butyl-6-(1-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-4-(4'-fluoro-5-(4-phenylpyridin-2-yl)-[1,1'-biphenyl]-3-yl)-1H-benzis[d]imidazol-2-yl)phenol)

[0462] Compound 3-C was obtained in a similar manner to that used to obtain compound 1-C in Synthetic Example 1, except that compound 3-B (2-(4'-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaneborane-2-yl)-[1,1'-biphenyl]-3-yl)-4-phenylpyridine) was used instead of compound 1-B. The obtained compound was confirmed by HRMS and HPLC analysis.

[0463] HRMS (MALDI): For C 60 H 56 Calculated value of FN3O: m / z 853.4407, measured value: 853.4408

[0464] Synthesis of Compound 3

[0465] Compound 3 was obtained in a manner similar to that used to obtain compound 1 in Synthetic Example 1, except that 2.4 g (2.81 mmol) of compound 3-C was used instead of compound 1-C. The obtained compound was confirmed by HRMS and HPLC analysis.

[0466] HRMS (MALDI): For C 60 H 54 Calculated value of FN3OPt: m / z 1046.3899, measured value: 1046.3896

[0467] Evaluation Example 1: Evaluation of Thermal Properties

[0468] Thermal analysis was performed under a nitrogen atmosphere. The temperature ranges were as follows: for thermogravimetric analysis (TGA), from room temperature to 800 °C (10 °C / min), or for differential scanning calorimetry (DSC), from room temperature to 400 °C (10 °C / min). Disk types were used as follows: for TGA, a Pt disk was placed in a disposable Al disk, or for DSC, a disposable Al disk was used. Thermal analysis of compounds 1 to 2 and A to C was performed using TGA and DSC to obtain their glass transition temperatures (T0). g (℃), and the results are shown in Table 2.

[0469] Table 2

[0470] 1 269 2 267 A 289 B 339 C 342

[0471]

[0472] Table 2 shows that compounds 1 and 2 have a higher T value than compounds A to C. g Low T g Therefore, compared with the thermal stability of compounds A to C, compounds 1 and 2 each have excellent thermal stability, and the amount of impurities generated after sublimation purification of compounds 1 and 2 is less than that generated after sublimation purification of compounds A to C, and they can have high purity.

[0473] Evaluation Example 2: Evaluation of Photoluminescence Quantum Efficiency (PLQY)

[0474] A PMMA solution in CH2Cl2, CBP, and compound 1 (5 parts by weight / 100 parts by weight of CBP) were mixed and then the resulting mixture was coated onto a quartz substrate using a spin coater. The coated substrate was then heated in an oven at 80°C and subsequently allowed to cool to room temperature to obtain a film.

[0475] The PLQY of the film obtained from compound 1 was evaluated using a Hamamatsu Photonics absolute photoluminescence (PL) quantum yield measurement system equipped with a xenon lamp source, monochromator, quantum multichannel analyzer, and integrating sphere, and the data were analyzed using PLQY measurement software (Hamamatsu Photonics, Ltd., Shizuoka, Japan). The procedure was repeated for compounds 2 and 3. The PLQY results of the films obtained from compounds 1 to 3 are shown in Table 3.

[0476] Table 3

[0477] 1 0.985 2 0.996 3 0.929

[0478] Referring to Table 3, it is confirmed that the films obtained from compounds 1 to 3 have excellent PLQY.

[0479] Evaluation Example 3: Decay Time Measurement

[0480] The quartz substrate was prepared by washing with chloroform and deionized water, and then (at 10...) -7 Films 1 to 3, each having a thickness of 50 nm, were prepared by vacuum (co)deposition of predetermined materials as shown in Table 4 under static vacuum.

[0481] Table 4

[0482] Membrane 1 CBP / Compound 1 (at a weight ratio of 9:1) Membrane 2 CBP / Compound 2 (at a weight ratio of 9:1) Membrane 3 CBP / Compound 3 (at a weight ratio of 9:1)

[0483] The photoluminescence (PL) spectra of films 1 to 3 were measured at room temperature using a FluoTime 300 spectrometer (TRPL measurement system manufactured by PicoQuant Inc.). Excitation light was provided using a PLS340 light source (excitation wavelength = 340 nm, spectral width = 20 nm) (PicoQuant Inc.) as the pump source. The dominant peak of each spectrum was then determined, and the number of photons emitted at said wavelength by each photon pulse (pulse = 500 picoseconds) applied to films 1 to 3 via the PLS340 was measured multiple times according to time-correlated single-photon counting (TCSPC) to obtain sufficient TRPL curves for fitting. The obtained results were fitted with two or more exponential decay functions to obtain the TT curves. 衰减 (Ex), that is, the decay times (decay times) of membranes 1 to 3 respectively. The results obtained are shown in Table 5. The function used for fitting is shown in Equation 1, and T is obtained from the respective exponential decay functions used for fitting. 衰减 Among the values, use the maximum T. 衰减 As T 衰减 (Ex). At this point, the same measurements are performed in the dark state (where the pump signal entering the membrane is blocked) for the same period of time as used to obtain the TRPL curve to obtain the baseline spectrum or the background signal curve used as the baseline spectrum for fitting.

[0484] Equation 1

[0485]

[0486] Table 5

[0487] Membrane 1 (Compound 3) 2.201 Membrane 2 (Compound 2) 2.332 Membrane 3 (Compound 3) 2.572

[0488] Referring to Table 5, compounds 1 to 3 are confirmed to have excellent decay times.

[0489] Example 1

[0490] The ITO glass substrate was cut into 50 mm × 50 mm × 0.5 mm sizes, and then ultrasonically treated with acetone, isopropanol and DI water for 15 minutes each, and then exposed to ozone generated by ultraviolet light (UV light) for 30 minutes.

[0491] Then, m-MTDATA with The deposition rate is used to deposit the ITO electrode (anode) on the ITO glass substrate to form a structure with... A hole injection layer of a certain thickness is formed, and then NPB is applied. The deposition rate is deposited on the hole injection layer to form a layer with A hole transport layer of a certain thickness.

[0492] Compound 1 (doper) and CBP (host) were respectively used as... deposition rate and The deposition rate is co-deposited on the hole transport layer to form a layer with... The emission layer has a thickness of [missing information]. The emission layer comprises compound 1 in an amount of 10% by weight, based on the total weight of the emission layer.

[0493] BAlq with The deposition rate is deposited on the emission layer to form a layer with A hole-blocking layer of a certain thickness is formed, and Alq3 is deposited on the hole-blocking layer to form a hole-blocking layer with a thickness of [missing information]. An electron transport layer of a certain thickness is formed, and then LiF is deposited on the electron transport layer to form an electron transport layer with a thickness of [missing information]. An electron injection layer of a certain thickness is formed, and then Al is vacuum deposited on the electron injection layer to form a layer with... The second electrode (cathode) has a thickness of [thickness value missing], thereby completing the [structure / m-MTDATA] [structure missing]. Fabrication of organic light-emitting devices with a specific structure.

[0494]

[0495] Examples 2 to 3 and Comparative Examples A to C

[0496] The organic light-emitting device was fabricated in a similar manner to that used to prepare Example 1, except that, when forming the emission layer, the compounds shown in Table 4 were used instead of compound 1 as dopants.

[0497] Evaluation Example 4: Evaluation of the characteristics of organic light-emitting devices

[0498] The driving voltage (V), luminous quantum efficiency (%), roll-off ratio (%), and lifetime (LT) of the organic light-emitting devices fabricated according to Examples 1 to 3 and Comparative Examples A to C were evaluated. 95 The results are shown in Table 6. This evaluation was conducted using a current-voltmeter (Keithley 2400) and a light meter (Minolta Cs-1000A), and the lifetime (LT) was... 95 (at 6,000 cd / m 2 (Below) The evaluation is as follows: the amount of time elapsed before the brightness decreases to 95% of the initial brightness, as a relative value (%). The roll-off ratio is calculated using Equation 2:

[0499] Equation 2

[0500] Roll-off ratio = {1 - (efficiency (at 9,000 cd / m)}2 (Lower) / (Maximum launch efficiency) × 100%

[0501] Table 6

[0502]

[0503]

[0504]

[0505] Table 6 confirms that, compared with the organic light-emitting devices of Comparative Examples A to C in terms of luminous quantum efficiency, roll-off ratio, and lifetime characteristics, the organic light-emitting devices of Examples 1 to 3 have superior luminous quantum efficiency, superior roll-off ratio, and superior lifetime characteristics.

[0506] Organometallic compounds according to one or more embodiments possess excellent electrical properties and / or thermal stability. Therefore, organic light-emitting devices using these organometallic compounds can exhibit improved characteristics in terms of driving voltage, external quantum efficiency (EQE), roll-off ratio, and lifetime. Thus, the use of organometallic compounds according to one or more embodiments as described herein allows for the manufacture of high-quality organic light-emitting devices and electronic devices incorporating them.

[0507] It should be understood that one or more exemplary embodiments described herein are to be considered only in the descriptive sense and are not intended for limiting purposes. The descriptions of features or aspects in the various exemplary embodiments should typically be 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 1A: Formula 1 in, In Equation 1A, M stands for platinum (Pt). X1 is either O or S. X2 and X4 are N, and X3 is C. The bond between X1 and M is a covalent bond. The bond between X3 and M is a covalent bond, while the bonds between X2 and M and between X4 and M are coordinate bonds. Y1 is C, X 51 For N-[(L7)] b7 -(R7) c7 ], X 11 For C(R) 11 ), X 12 For C(R) 12 ), X 13 For C(R) 13 ), X 14 For C(R) 14 ), R 11 -R 14 Each as defined with respect to R1, X 21 For C(R) 21 ), X 22 For C(R) 22 ), X 23 For C(R) 23 ), R 21 -R 23 Each as defined with respect to R2, X 31 For C(R) 31 ), X 32 For C(R) 32 ) or C(Z 13 ), X 33 For C(R) 33 ), R 31 -R 33 Each is the same as described regarding R3. X 41 For C-[(L 41 )-(R 41 )], X 42 For C-[(L 42 )-(R 42 )] or C-[(L 14 )-(Z 14 )], X 43 For C-[(L 43 )-(R 43 )], X 44 For C-[(L 44 )-(R 44 )], R 41 -R 44 Each as defined for R4, Z 13 and Z 14 Each is an independent group represented by formula 2. L 41 L 43 and L 44 It is a single key. L7 and L 42 For not being replaced or by at least one R 10a Substituted phenyl groups, L 14 It is a single key. b7 is 1. R1-R4 and R7 are each independent of: Hydrogen, -F, or C1-C 20 alkyl; C1-C replaced as follows 20 Alkyl groups: -F, -CF3, -CF2H, -CFH2, or combinations thereof; or Phenyl groups that are not substituted or are substituted with the following: -F, -CF3, -CF2H, -CFH2, C1-C 20 Alkyl groups or combinations thereof, c7 is an integer between 2 and 5. One of two or more R7s is a C4-C that is either unsubstituted or substituted with -F, -CF3, -CF2H, -CFH2, or a combination thereof. 20 Alkyl group, and one of the remaining R7 groups is unsubstituted or substituted with -F, -CF3, -CF2H, -CFH2, C1-C. 20 Alkyl groups, or combinations thereof, substituted phenyl groups R 10a As defined regarding R1, Formula 2 In Equation 2, CY 10 It is a phenyl group. R 10 As defined regarding R1, a10 is an integer between 0 and 5. Z 10 for: -F; or Unsubstituted fluorinated C1-C 20 alkyl, n10 is an integer between 1 and 5. When a10 is 2 or greater, two or more R 10 Whether they are the same or different, When n10 is 2 or greater, there are two or more Z 10 They are the same or different from each other, and Indicates the binding site with adjacent atoms. At least one of conditions (2) and (5) is satisfied: Condition (2) X 32 For C(Z) 13 ) Condition (5) X 42 For C-[(L 14 )-(Z 14 )).

2. The organometallic compound of claim 1, wherein the group represented by formula 2 is a group represented by any one of formulas 2-1 to 2-42: in, In equations 2-1 to 2-42, R 1001 -R 1005 Each as described in claim 1 regarding R 10 The defined condition is R 1001 -R 1005 Each is not hydrogen. Z 1001 -Z 1003 Each as described in claim 1 regarding Z 10 Defined, and Indicates the binding site with adjacent atoms.

3. The organometallic compound of claim 1, wherein the organometallic compound satisfies condition (2).

4. The organometallic compound of claim 1, wherein the organometallic compound satisfies condition (5).

5. Organic light-emitting devices, including: First electrode; Second electrode; as well as An organic layer located between the first electrode and the second electrode; The organic layer mentioned above includes an emission layer, and The organic layer thereof comprises at least one organometallic compound as described in any one of claims 1-4.

6. The organic light-emitting device as claimed in claim 5, wherein... The first electrode is the anode. The second electrode is a cathode. The organic layer further includes a hole transport region located between the first electrode and the emitter layer, and an electron transport region located between the emitter layer and the second electrode. The hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof, and The electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

7. The organic light-emitting device of claim 5, wherein the emitting layer comprises the organometallic compound.

8. The organic light-emitting device as claimed in claim 7, wherein... The emission layer further includes a body, and The amount of the host in the emitter layer is greater than the amount of the organometallic compound in the emitter layer.

9. An electronic device comprising an organic light-emitting device as claimed in any one of claims 5-8.

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