Organometal compound, organic light emitting device including organometal compound, and electronic

Abstract

Provided are an organometallic compound, an organic light-emitting device including the organometallic compound, and an electronic device including the organic light-emitting device, in which the organometallic compound is represented by Formula 1, and the groups and variables of Formula 1 are as described herein.

Description

[0001] Cross-reference to related applications

[0002] This application claims priority and benefits to Korean Patent Application No. 10-2024-0147902, filed on October 25, 2024, with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field

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

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

[0005] In this example, the organic light-emitting device includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer includes an emitting layer. A hole transport region may be disposed between the anode and the emitting layer, and an electron transport region may be disposed 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 recombine in the emitting layer to generate excitons. When an exciton transitions from an excited state to the ground state, light is emitted. Summary of the Invention

[0006] Provided are organometallic compounds, organic light-emitting devices including the same, and electronic devices including said organic light-emitting devices.

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

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

[0009] Formula 1

[0010]

[0011] in

[0012] M1 is a transition metal.

[0013] Y2 is either C or N.

[0014] Y3 is either C or N.

[0015] Rings CY1, CY3 to CY5, and CY11 To CY 13 Each independently is C5-C 60 Carbocyclic groups or C1-C 60 Heterocyclic groups, or

[0016] L1 represents a single bond, O, S, Se, or N(R). 61 ), B(R) 61 ), C(R 61 (R) 62 ), or Si(R) 61 (R) 62 ),

[0017] a1 is 1, 2, 3, 4, or 5.

[0018] R 10 R 30 R 40 R 50 R 61 and R 62 Each of the following groups is 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 60Heteroaryl thiols, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -C(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2), or -P(=S)(Q1)(Q2),

[0019] R 20 It is a 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 60Heteroaryl thiols, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -C(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2), or -P(=S)(Q1)(Q2),

[0020] R 10 R 30 R 40 R 50 R 61 and R 62 At least two adjacent groups in the form optionally combine to form a substituted or unsubstituted C5-C 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups,

[0021] b1, b3 to b5, and b11 to b13 are each independently 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

[0022] b2 is 0, 1, or 2.

[0023] 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 60Heteroaryl groups, substituted C1-C 60 At least one substituent of the heteroaryl thio group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heterocyclic group is:

[0024] Deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 alkoxy, or C1-C 60 Alkylthio,

[0025] Each of the following C1-C is replaced: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 alkoxy, or C1-C 60 Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 11 (Q) 12 (Q) 13 -Ge(Q) 11 (Q) 12 (Q) 13 -C(Q) 11 (Q) 12 (Q) 13 -B(Q) 11 (Q) 12-N(Q) 11 (Q) 12 -P(Q) 11 (Q) 12 -C(=O)(Q) 11 -S(=O)(Q) 11 -S(=O)2(Q) 11 -P(=O)(Q) 11 (Q) 12 -P(=S)(Q) 11 (Q) 12 ), or a combination thereof,

[0026] C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups,

[0027] Each of the following C3-C is replaced: 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid groups or their salts, sulfonic acid groups or their salts, phosphate groups or their salts, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C60 alkynyl group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 21 (Q) 22 (Q) 23 -Ge(Q) 21 (Q) 22 (Q) 23 -C(Q) 21 (Q) 22 (Q) 23 -B(Q) 21 (Q) 22 -N(Q) 21 (Q) 22 -P(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)(Q) 21 -S(=O)2(Q) 21 -P(=O)(Q) 21 (Q) 22 -P(=S)(Q) 21 (Q) 22 ), or a combination thereof, or

[0028] -Si(Q 31 (Q) 32 (Q) 33 -Ge(Q) 31 (Q) 32 (Q) 33 -C(Q) 31 (Q) 32 (Q) 33 -B(Q) 31 (Q)32 -N(Q) 31 (Q) 32 -P(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)(Q) 31 -S(=O)2(Q) 31 -P(=O)(Q) 31 (Q) 32 ), or -P(=S)(Q 31 (Q) 32 ),and

[0029] Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 , and Q 31 To Q 33 Each of the following groups is 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 60Heteroaryl thiols, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, or substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups.

[0030] According to another aspect, an organic light-emitting device includes a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer includes at least one organometallic compound represented by Formula 1.

[0031] The organic layer may include an emitter layer. At least one organometallic compound represented by Formula 1 may be included in the emitter layer of the organic layer, and the at least one organometallic compound included in the emitter layer may act as a dopant. Attached Figure Description

[0032] The above and other aspects, features, and advantages of some embodiments of this disclosure will become more apparent from the following description taken in conjunction with the accompanying drawings, wherein:

[0033] Figure 1 It is a schematic cross-sectional view of an organic light-emitting device according to one or more embodiments;

[0034] Figure 2 It is an energy transfer diagram according to one or more embodiments, wherein the emitting layer may include the organometallic compound as an emitter;

[0035] Figure 3 It is an energy transfer diagram according to one or more embodiments, wherein the organometallic compound can be used as a sensitizer, and the emitting layer may further include a fluorescent emitter; and

[0036] Figure 4 It is an energy transfer diagram according to one or more embodiments, wherein the organometallic compound can be used as a sensitizer, and the emitting layer may further include a delayed fluorescent emitter. Detailed Implementation

[0037] Exemplary embodiments will now be described in further detail, examples of which are illustrated in the accompanying drawings, wherein the same reference numerals refer to the same elements throughout the specification. In this respect, these exemplary embodiments may take different forms and should not be construed as limited to the description set forth herein. Therefore, embodiments are described in further detail below and with reference to the accompanying drawings only to illustrate certain features and 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 of” modify the entire list of elements when preceding or following it, without modifying any individual element of the list.

[0038] The terminology used herein is for the purpose of describing one or more exemplary embodiments only and is not intended to be limiting. As used herein, the singular forms “a” and “the” are also intended to include the plural forms unless the context clearly indicates otherwise. The term “or” means “and / or”. It will be further understood that the terms “comprising” or “including” as used in this specification indicate the presence of the stated features, regions, integrals, steps, operations, elements, and / or components, but do not exclude the presence or addition of one or more additional features, regions, integrals, steps, operations, elements, components, and / or sets thereof.

[0039] 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.

[0040] Exemplary embodiments are described herein with reference to cross-sectional views, which are schematic diagrams of idealized embodiments. Thus, deviations from the shapes shown in the figures will be anticipated as a result of, for example, manufacturing techniques and / or tolerances. Therefore, the embodiments described herein should not be construed as limited to the specific shapes of the regions illustrated herein, but rather include deviations in shape caused, for example, by manufacturing processes. For example, regions illustrated or described as flat may typically have rough and / or non-linear characteristics. Furthermore, sharp corners in the figures may be rounded. Therefore, the regions shown in the figures are schematic in nature and their shapes are not intended to illustrate the precise shape of the regions nor to limit the scope of the claims.

[0041] It will be understood that when an element is referred to as being "on" another element, it may be in direct contact with the other element or there may be an intermediate element between them. Conversely, when an element is referred to as being "directly on" another element, there is no intermediate element.

[0042] Unless otherwise defined, all terms used herein (including technical and scientific terms) have the same meaning as commonly understood by one of ordinary skill in the art to which this general inventive concept pertains. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having meanings consistent with their meanings in the context of this disclosure and the relevant field, and will not be interpreted in an idealized or overly formal sense unless expressly defined herein.

[0043] 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%.

[0044] One aspect provides organometallic compounds represented by Formula 1:

[0045] Formula 1

[0046] .

[0047] In Equation 1, M1 is a transition metal.

[0048] In one or more embodiments, M1 in Formula 1 may be 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).

[0049] In one or more embodiments, M1 in Formula 1 may be Pd, Pt, or Au.

[0050] In one or more embodiments, M1 in Formula 1 may be Pt or Pd.

[0051] In one or more embodiments, M1 in Formula 1 may be Pt.

[0052] In Equation 1, Y2 is C or N.

[0053] In one or more embodiments, Y2 may be C.

[0054] In Equation 1, Y3 is C or N.

[0055] In one or more embodiments, Y3 may be N.

[0056] In Equation 1, rings CY1, CY3 to CY5, and CY 11 To CY 13 Each independently is C5-C 60 Carbocyclic groups or C1-C 60 Heterocyclic groups.

[0057] In one or more embodiments, rings CY1, CY3 to CY5, and CY 11 To CY 13Each can be independently (i) a first ring, (ii) a second ring, (iii) a fused ring group in which at least two first rings are fused, (iv) a fused ring group in which at least two second rings are fused, or (v) a fused ring group in which at least one first ring is fused with at least one second ring, wherein

[0058] The first ring can be a cyclopentyl group, a cyclopentadienyl group, a furan group, a thiophene group, a pyrrole group, a thiophene group, an indole group, a benzofuran group, a benzothiophene group, an indole group, or a benzothiophene group. azole group, iso- azole group, diazole group, isodiazole group diazole group, Triazole group, iso 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

[0059] The second ring may be an 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, cyclohexyl group, cyclohexene group, phenyl group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, or triazine group.

[0060] In one or more embodiments, rings CY1, CY3 to CY5, and CY 11 To CY 13 Each group can independently be a phenyl group, naphthyl group, anthracene group, phenanthrene group, benzo[9,10]phenanthrene group, pyrene group, Groups, 1,2,3,4-tetrahydronaphthyl group, benzothiophene group, benzofuran group, indole group, indene group, benzothiophene group, benzoborane heterocyclopentadiene group, benzophosphane heterocyclopentadiene group, benzoselenophene group, benzogermanium heterocyclopentadiene group, dibenzothiophene group, dibenzofuran group, carbazole group, fluorene group, dibenzothiophene group, dibenzoborane heterocyclopentadiene group, dibenzophosphane heterocyclopentadiene group, dibenzoselenophene group, dibenzogermanium heterocyclopentadiene group, dibenzothiophene 5-oxide group, 9H-fluorene-9-one group, dibenzothiophene 5,5-dioxide group, azabenzothiophene group, azabenzofuran group, azaindole group, azaindene group, azabenzothiophene group, azabenzoborane heterocyclopentadiene group, azabenzophosphane heterocyclopentadiene group The following groups are included: azidobenzoselenene group, azidobenzogermanium heterocyclopentadiene group, azidobenzothiophene group, azidobenzofuran group, azidocarbazole group, azidofluorene group, azidobenzothiophene group, azidobenzoborone heterocyclopentadiene group, azidobenzophosphacyclopentadiene group, azidobenzoselenene group, azidobenzogermanium heterocyclopentadiene group, azidobenzothiophene 5-oxide group, azido-9H-fluorene-9-one group, azidobenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazolinine group, phenanthrene group, 5,6,7,8-tetrahydroisoquinoline group, 5,6,7,8-tetrahydroquinoline group, adamantyl group, norbornene group, or norbornene group.

[0061] In one or more embodiments, rings CY1, CY3 to CY5, and CY 11 To CY 13 Each group can be independently a phenyl group, naphthyl group, phenanthrene group, furan group, thiophene group, pyrrole group, cyclopentene group, thiophene group, germanium heterocyclopentadiene group, benzofuran group, benzothiophene group, indole group, indene group, benzothiophene group, benzogermanium heterocyclopentadiene group, dibenzofuran group, dibenzothiophene group, carbazole group, fluorene group, dibenzothiophene group, dibenzogermanium heterocyclopentadiene group, pyridine group, pyrimidine group, pyridazine group, or pyrazine group.

[0062] In Equation 1, L1 represents a single bond, O, S, Se, or N(R). 61 ), B(R) 61 ), C(R 61 (R) 62 ), or Si(R) 61 (R) 62 ).

[0063] In Equation 1, a1 is 1, 2, 3, 4, or 5.

[0064] In Equation 1, R 10 R 30 R 40 R 50 R 61 and R 62 Each of the following groups is independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C1-C 60 Alkylthio, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 arylalkyl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -C(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2), or -P(=S)(Q1)(Q2).

[0065] In one or more embodiments, R 10 R 30 R 40 R 50 R61 and R 62 Each can be independently:

[0066] Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl, C1-C 20 alkoxy, or C1-C 20 Alkylthio;

[0067] 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, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl, deuterated C1-C 20 Alkyl, fluorinated C1-C 20 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl (norbornenyl), 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) 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[2.2.1]heptyl, (C1-C 20 Alkyl)bicyclo[2.2.2]octyl, silylcyclopentyl, phenyl, (C1-C 20 Alkyl)phenyl, biphenyl, terphenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, pyridyl, pyrimidinyl, or combinations thereof;

[0068] Each of the following substituted compounds, either unsubstituted or substituted with: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, silanecyclopentyl, phenyl, (C1-C 20 Alkyl)phenyl, biphenyl, terphenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, 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, -SF5, -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, deuterated C1-C 20 Alkyl, fluorinated C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, 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) norbornenyl, (C1-C 20 alkyl)cyclopentenyl, (C1-C 20alkyl)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[2.2.1]heptyl, (C1-C 20 Alkyl)bicyclo[2.2.2]octyl, silylcyclopentyl, phenyl, (C1-C 20 Alkyl)phenyl, biphenyl, terphenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, 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, benzocarbazoleyl, dibenzocarbazoleyl, imidazopyridyl, imidazopyrimidinyl, azacarbazoleyl, azadibenzofuranyl, azadibenzothiophenyl, or combinations thereof; or

[0069] -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -C(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P( Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2), or -P(=S)(Q1)(Q2).

[0070] In one or more embodiments, R 10 R 30 R 40 R 50 R 61 and R 62 Each can be independently:

[0071] Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, neopentyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, 3-pentyl, 3-methyl-2-butyl, 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, isodeyl, sec-decyl, tert-decyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, 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, or imidazopyrimidinyl;

[0072] Each of the following is replaced by methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, neopentyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, 3-pentyl, 3-methyl-2-butyl, 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, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornenyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, 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, isoindolyl, 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, or imidazopyrimidinyl: deuterium, -F, -Cl, -Br, -I, -SF5, -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 10 Alkyl, C1-C 10 Alkoxy, C1-C 10 Alkylthio, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, 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, isoindolyl, 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, or combinations thereof; or

[0073] -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -C(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P( Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2), or -P(=S)(Q1)(Q2).

[0074] In one or more embodiments, R 10 R 30 R 40 R 50 R 61 and R 62 Each can be independently:

[0075] Hydrogen, Deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, Cl-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 alkoxy, or C1-C 60 Alkylthio; or

[0076] Groups represented by one of formulas 9-1 to 9-61, 9-201 to 9-244, 10-1 to 10-154, or 10-201 to 10-350:

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099] .

[0100] In formulas 9-1 to 9-61, 9-201 to 9-244, 10-1 to 10-154, and 10-201 to 10-350, * indicates a binding site with an adjacent atom, “Ph” represents phenyl, “TMS” represents trimethylsilyl, and “TMG” represents trimethylgermanyl.

[0101] In one or more embodiments, R 10 R 30 R 40 R 50 R 61 and R 62 Each can be independently:

[0102] Hydrogen, deuterium, C1-C 30 Alkyl, C6-C 60 Aryl, or C1-C 60 Mixed aromatics;

[0103] Each of the following C1-C is replaced: 30 Alkyl, C6-C 60 Aryl, or C1-C 60 Heteroaryl groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl, C1-C 10 Alkoxy, C1-C 10 Alkylthio, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norcamphenyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridyl, pyrimidinyl, or combinations thereof;

[0104] -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -C(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P( Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2), or -P(=S)(Q1)(Q2).

[0105] In one or more embodiments, R 10 R 30 R 40 R 50 R 61 and R 62 Each can be independently:

[0106] Hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, neopentyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, 3-pentyl, 3-methyl-2-butyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isonyl, sec-nonyl, tert-nonyl, n-decyl, isodel, sec-decyl, or tert-decyl;

[0107] Each of the following is a deuterium-substituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, neopentyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, 3-pentyl, 3-methyl-2-butyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isonyl, sec-nonyl, tert-nonyl, n-decyl, isodel, sec-decyl, or tert-decyl;

[0108] Phenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, or base;

[0109] Each of the following substituted groups is phenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, or Groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl, C1-C 10 Alkoxy, C1-C 10 Alkylthio, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridyl, pyrimidinyl, or combinations thereof; or

[0110] -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -C(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P( Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2), or -P(=S)(Q1)(Q2).

[0111] In one or more embodiments, R 10 R 30 R 40 R 50 R 61 and R 62 Each can be independently:

[0112] Hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, neopentyl, 3-pentyl, 3-methyl-2-butyl, phenyl, biphenyl, C1-C 20 alkylphenyl, or naphthyl; or

[0113] Each of the following is either unsubstituted or substituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, neopentyl, 3-pentyl, 3-methyl-2-butyl, phenyl, biphenyl, C1-C 20 Alkylphenyl or naphthyl: deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, C1-C 60 Alkyl, 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, C1-C 60 heteroaryl groups or combinations thereof.

[0114] In one or more embodiments, R 10 It may not be deuterium.

[0115] In one or more embodiments, R 10 It can be hydrogen.

[0116] In one or more embodiments, R 10 R 30 R 40 R 50 R61 and R 62 At least one of them may not be hydrogen or deuterium.

[0117] In one or more embodiments, R 10 R 30 R 40 R 50 R 61 and R 62 At least one of them can be:

[0118] Methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, neopentyl, 3-pentyl, 3-methyl-2-butyl, phenyl, biphenyl, C1-C 20 alkylphenyl, or naphthyl; or

[0119] Each of the following is either unsubstituted or substituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, neopentyl, 3-pentyl, 3-methyl-2-butyl, phenyl, biphenyl, C1-C 20 Alkylphenyl or naphthyl: deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, C1-C 60 Alkyl, 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, C1-C 60 heteroaryl groups or combinations thereof.

[0120] In Equation 1, R 20 It is a 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 10Cycloalkenyl, 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 nonaromatic fused polycyclic groups, substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -C(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2), or -P(=S)(Q1)(Q2).

[0121] In one or more embodiments, R 20 Possible forms:

[0122] -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl, C1-C 20 alkoxy, or C1-C 20 Alkylthio;

[0123] 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, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl, deuterated C1-C 20 Alkyl, fluorinated C1-C 20Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl (norbornenyl), 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) 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[2.2.1]heptyl, (C1-C 20 Alkyl)bicyclo[2.2.2]octyl, silylcyclopentyl, phenyl, (C1-C 20 Alkyl)phenyl, biphenyl, terphenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, pyridyl, pyrimidinyl, or combinations thereof;

[0124] Each of the following substituted compounds, either unsubstituted or substituted with: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, silanecyclopentyl, phenyl, (C1-C 20 Alkyl)phenyl, biphenyl, terphenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, 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, -SF5, -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, deuterated C1-C 20 Alkyl, fluorinated C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, 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) 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[2.2.1]heptyl, (C1-C 20 Alkyl)bicyclo[2.2.2]octyl, silylcyclopentyl, phenyl, (C1-C 20 Alkyl)phenyl, biphenyl, terphenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, 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, benzocarbazoleyl, dibenzocarbazoleyl, imidazopyridyl, imidazopyrimidinyl, azacarbazoleyl, azadibenzofuranyl, azadibenzothiophenyl, or combinations thereof; or

[0125] -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -C(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P( Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2), or -P(=S)(Q1)(Q2).

[0126] In one or more embodiments, R 20 Possible forms:

[0127] -F, -Cl, -Br, -I, -SF5, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, neopentyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, 3-pentyl, 3-methyl-2-butyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n- Octyl, Isooctyl, sec-octyl, tert-octyl, n-nonyl, Isonoyl, sec-nonyl, tert-nonyl, n-decyl, Isooctyl, sec-decyl, tert-decyl, Cyclopentyl, Cyclohexyl, Cycloheptyl, Cyclooctyl, Adamantyl, Norbornenyl, Norbornenyl, Cyclopentenyl, Cyclohexenyl, Cycloheptenyl, Phenyl, Naphthyl, Fluorenyl, Phenyl, Anthracite, Fluoranthryl, Benzo[9,10]phenantyl, 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, or imidazopyrimidinyl;

[0128] Each of the following is replaced by methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, neopentyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, 3-pentyl, 3-methyl-2-butyl, 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, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornenyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, 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, isoindolyl, 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, or imidazopyrimidinyl: deuterium, -F, -Cl, -Br, -I, -SF5, -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 10 Alkyl, C1-C 10 Alkoxy, C1-C 10 Alkylthio, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, 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, isoindolyl, 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, or combinations thereof; or

[0129] -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -C(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P( Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2), or -P(=S)(Q1)(Q2).

[0130] In one or more embodiments, R 20 It may be a methyl group, -CD3, -CD2H, -CDH2, or a group represented by one of formulas 9-1 to 9-39 or 9-44 to 9-61:

[0131]

[0132]

[0133] .

[0134] In equations 9-1 to 9-39 and 9-44 to 9-61,

[0135] * indicates a binding site with an adjacent atom.

[0136] In one or more embodiments, R 20 Possible forms:

[0137] C1-C 30 Alkyl, C6-C 60 Aryl, or C1-C 60 Mixed aromatics;

[0138] Each of the following C1-C is replaced: 30 Alkyl, C6-C 60 Aryl, or C1-C 60 Heteroaryl groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl, C1-C 10 Alkoxy, C1-C 10Alkylthio, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norcamphenyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridyl, pyrimidinyl, or combinations thereof;

[0139] -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -C(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P( Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2), or -P(=S)(Q1)(Q2).

[0140] In one or more embodiments, R 20 Possible forms:

[0141] Methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, neopentyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, 3-pentyl, 3-methyl-2-butyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isonyl, sec-nonyl, tert-nonyl, n-decyl, isodel, sec-decyl, or tert-decyl;

[0142] Each of the following is a deuterium-substituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, neopentyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, 3-pentyl, 3-methyl-2-butyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isonyl, sec-nonyl, tert-nonyl, n-decyl, isodel, sec-decyl, or tert-decyl;

[0143] Phenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, or base;

[0144] Each of the following substituted groups is phenyl, naphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, benzo[9,10]phenanthryl, pyrene, or Groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl, C1-C 10 Alkoxy, C1-C 10Alkylthio, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornel, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridyl, pyrimidinyl, or combinations thereof; or

[0145] -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -C(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P( Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2), or -P(=S)(Q1)(Q2).

[0146] In one or more embodiments, R 20 Possible forms:

[0147] Methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, neopentyl, 3-pentyl, 3-methyl-2-butyl, phenyl, biphenyl, C1-C 20 alkylphenyl, or naphthyl; or

[0148] Each of the following is either unsubstituted or substituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, neopentyl, 3-pentyl, 3-methyl-2-butyl, phenyl, biphenyl, C1-C 20 Alkylphenyl or naphthyl: deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, C1-C 60 Alkyl, 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, C1-C 60 heteroaryl groups or combinations thereof.

[0149] In Equation 1, R 10 R 30 R 40 R 50 R 61 and R 62 At least two adjacent groups in the form optionally combine to form a substituted or unsubstituted C5-C 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups.

[0150] In one or more implementations, multiple R 10 Two or more; multiple R 30 Two or more; multiple R 40 Two or more; multiple R 50 Two or more; and / or R 10 R 30 R 40 R 50 R 61 and R 62 Two or more adjacent groups may optionally be linked together 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 30 The carbocyclic group is either unsubstituted or replaced by at least one R 10a Replacement C1-C 30 Heterocyclic groups (e.g., each unsubstituted or with at least one R) 10a Substituted fluorene groups, xanthine groups, acridine groups, etc.). R 10a Can be related to R 10 The description is the same.

[0151] The first linking group can be *-N(R) 71 )-*'、*-B(R 71 )-*'、*-P(R 71 )-*'、*-C(R 71 (R) 72 )-*'、*-Si(R 71 (R) 72 )-*'、*-Ge(R 71 (R) 72 )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R 71 )=*'、*=C(R 71 )-*'、*-C(R 71 )=C(R 72 R = -*', *-C(=S)-*', or *-C≡C-*', where R 71 and R 72 Each can be related to R. 10 The descriptions are identical, and * and *' each represent a binding site with an adjacent atom.

[0152] In Equation 1, b1, b3 to b5, and b11 to b13 are each independently 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

[0153] In one or more embodiments, b1, b3 to b5, and b11 to b13 may each be 1, 2, 3, or 4 independently.

[0154] In Equation 1, b2 is 0, 1, or 2.

[0155] In one or more implementations, b2 may be 0.

[0156] 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 60 At least one substituent of the heteroaryl thio group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heterocyclic group is:

[0157] Deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 alkoxy, or C1-C 60 Alkylthio;

[0158] Each of the following C1-C is replaced: 60Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 alkoxy, or C1-C 60 Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 11 (Q) 12 (Q) 13 -Ge(Q) 11 (Q) 12 (Q) 13 -C(Q) 11 (Q) 12 (Q) 13 -B(Q) 11 (Q) 12 -N(Q) 11 (Q) 12 -P(Q) 11 (Q) 12 -C(=O)(Q) 11 -S(=O)(Q) 11 -S(=O)2(Q) 11 -P(=O)(Q) 11 (Q) 12 -P(=S)(Q) 11 (Q) 12 ), or combinations thereof;

[0159] C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C60 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;

[0160] Each of the following C3-C is replaced: 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid groups or their salts, sulfonic acid groups or their salts, phosphate groups or their salts, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 21 (Q) 22 (Q) 23 -Ge(Q) 21 (Q) 22 (Q) 23 -C(Q) 21 (Q) 22 (Q) 23 -B(Q) 21 (Q) 22 -N(Q) 21 (Q) 22 -P(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)(Q) 21 -S(=O)2(Q) 21 -P(=O)(Q) 21 (Q) 22 -P(=S)(Q) 21 (Q) 22 ), or combinations thereof;

[0161] -Si(Q 31 (Q) 32 (Q) 33 -Ge(Q) 31 (Q) 32 (Q) 33 -C(Q) 31 (Q) 32 (Q) 33 -B(Q) 31 (Q) 32 -N(Q) 31 (Q) 32 -P(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)(Q) 31 -S(=O)2(Q) 31 -P(=O)(Q) 31 (Q) 32 ), or -P(=S)(Q 31 (Q) 32 ),and

[0162] Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 , and Q 31 To Q33 Each of the following groups is independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C1-C 60 Alkylthio, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 arylalkyl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, or substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups.

[0163] In one or more embodiments, Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 , and Q 31 To Q 33 Each can be independently:

[0164] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2;

[0165] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or

[0166] Each of the following is replaced by n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl: deuterium, C1-C 10 Alkyl, phenyl, or combinations thereof.

[0167] In one or more embodiments, the organometallic compound represented by Formula 1 may be a compound represented by Formula 11:

[0168] Formula 11

[0169] .

[0170] In Equation 11,

[0171] M1, Y2, Y3, L1, a1, R 20 b2 and b2 can each be the same as those described in this article.

[0172] X1 can be C(R1) or N, X2 can be C(R2) or N, and X3 can be C(R3) or N.

[0173] X4 can be C(R4) or N, X5 can be C(R5) or N, X6 can be C(R6) or N, and X7 can be C(R7) or N.

[0174] X8 can be C(R8) or N, X9 can be C(R9) or N, X 10 It can be C(R) 10 ) or N, and X 11 It can be C(R) 11 ) or N,

[0175] 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, and X 15 It can be C(R) 15 ) or N,

[0176] X 31 It can be C(R) 31 ) or N, and X 32 It can be C(R) 32 ) or N,

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

[0178] X 51 It can be C(R) 51 ) or N, X 52 It can be C(R) 52 ) or N, X 53 It can be C(R) 53 ) or N, and X 54 It can be C(R) 54 ) or N,

[0179] R1 to R 15 Each can be as follows regarding R 10 As described,

[0180] R 31 and R 32 Each can be as follows regarding R 30 As described,

[0181] R 41 To R 44 Each can be as follows regarding R 40 As described, and

[0182] R 51 To R 54 Each can be as follows regarding R 50 As described.

[0183] In one or more embodiments, the organometallic compound represented by Formula 1 may be a compound represented by any one of Formulas 21 to 27:

[0184] Formula 21

[0185]

[0186] Formula 22

[0187]

[0188] Formula 23

[0189]

[0190] Formula 24

[0191]

[0192] Formula 25

[0193]

[0194] Formula 26

[0195]

[0196] Formula 27

[0197] .

[0198] In equations 21 to 27,

[0199] M1, L1, and a1 can each be the same as those described in this paper.

[0200] R1 to R 15 Each can be as follows regarding R 10 As described,

[0201] R 21 To R 23 Each can be related to R. 20 The descriptions are the same, provided that R is the condition. 21 To R 23 None of them are deuterium.

[0202] R 31 and R 32 Each can be related to R. 30 The same as described.

[0203] R 41 To R 44 Each can be related to R. 40 The same as described, and

[0204] R 51 To R 54 Each can be related to R. 50 The description is the same.

[0205] In one or more embodiments, the organometallic compound represented by Formula 1 may be electrically neutral.

[0206] In one or more embodiments, the organometallic compound represented by Formula 1 may be one of compounds 1 to 180:

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216] .

[0217] Organometallic compounds represented by Formula 1, satisfying the structure of Formula 1, have a structure in which deuterium is substituted at specific positions. Due to such a structure, organometallic compounds represented by Formula 1 can exhibit improved photochemical stability and are suitable for deep blue light emission. Therefore, electronic devices including organometallic compounds represented by Formula 1, such as organic light-emitting devices, can exhibit excellent luminous efficiency, lifetime, and color purity.

[0218] For example, due to the kinetic isotope effect, deuterium substitutes at sites with high electron density and high reactivity in the structure of Formula 1, thereby improving the structural stability of the organometallic compound. Therefore, the efficiency and lifetime of organic light-emitting devices comprising at least one organometallic compound represented by Formula 1 can be improved.

[0219] In one or more embodiments, the half-width at half-maximum (FWHM) of the emission peak of the emission spectrum or electroluminescence spectrum of the organometallic compound represented by Formula 1 may be about 60 nanometers (nm) or less. For example, the FWHM of the emission peak of the emission spectrum or electroluminescence spectrum of the organometallic compound represented by Formula 1 may be about 5 nm to about 50 nm, about 7 nm to about 40 nm, or about 10 nm to about 30 nm.

[0220] The method for synthesizing the organometallic compound represented by Formula 1 is as can be recognized by those skilled in the art and by referring to the synthesis examples described below.

[0221] There are no particular limitations on the method used to confirm the structure of the organometallic compound represented by Formula 1. In one or more embodiments, the structure of the organometallic compound represented by Formula 1 can be determined by known methods (e.g., NMR, LC-MS, etc.).

[0222] electronic devices

[0223] On the other hand, electronic devices are provided, which include at least one organometallic compound represented by Formula 1.

[0224] In one or more embodiments, the electronic device may be an organic light-emitting device (OLED), an organic photodiode (OPD), or an organic solar cell (OSC).

[0225] Organic light-emitting devices

[0226] On the other hand, an organic light-emitting device is provided, which includes at least one organometallic compound represented by Formula 1.

[0227] In one or more embodiments, the organic light-emitting device may include: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer includes an emitting layer, and wherein the organic layer may include at least one organometallic compound represented by Formula 1.

[0228] In one or more embodiments, the emitter layer may include at least one organometallic compound represented by Formula 1.

[0229] In one or more embodiments, the emission layer may include a body and an emitter, and the emitter may include at least one organometallic compound represented by Formula 1.

[0230] In one or more embodiments, the amount of the host in the emitter layer may be greater than the amount of the at least one organometallic compound represented by Formula 1 in the emitter layer, based on weight.

[0231] In one or more embodiments, the emitter layer may further include a sensitizer.

[0232] In one or more embodiments, the sensitizer may include a phosphorescent compound, a delayed fluorescence compound, or a combination thereof.

[0233] The aforementioned subject, emitter, and sensitizer are described in detail herein.

[0234] When an organic light-emitting device includes an emission layer comprising at least one organometallic compound represented by Formula 1, the organic light-emitting device may have a relatively narrow emission peak width (FWHM) of the electroluminescence spectrum, excellent efficiency, and / or long lifetime characteristics.

[0235] In one or more embodiments, the organometallic compound represented by Formula 1 can be used as a dopant (e.g., emitter or sensitizer) in the emission layer, and the emission layer may further include a host (i.e., in the emission layer, the amount of the at least one organometallic compound represented by Formula 1 may be less than the amount of the host based on weight).

[0236] In one or more embodiments, the emitting layer may emit blue light. In one or more embodiments, the emitting layer may emit blue light having a maximum emission wavelength of about 400 nm to about 490 nm. In one or more embodiments, the emitting layer may emit blue light having a maximum emission wavelength of about 430 nm to about 480 nm.

[0237] The statements “(emitting layer) comprises at least one organometallic compound represented by Formula 1” and “(emitting layer) comprises at least one organometallic compound represented by Formula 1” are used interchangeably herein and may include cases in which “(emitting layer) comprises the same organometallic compound represented by Formula 1” and cases in which “(emitting layer) comprises two or more different organometallic compounds represented by Formula 1”.

[0238] For example, the emitting layer may comprise only compound 1 as one of the at least one organometallic compounds represented by formula 1. In this respect, compound 1 may be present in the emitting layer of the organic light-emitting device. In one or more embodiments, the emitting layer may comprise both compound 1 and compound 2 as one of the at least one organometallic compounds represented by formula 1.

[0239] Figure 1 Description

[0240] Figure 1 This is a schematic cross-sectional view of an organic light-emitting device 10 according to one or more embodiments. In the following, regarding... Figure 1 The structure and manufacturing method of an organic light-emitting device 10 according to one or more embodiments are described.

[0241] exist Figure 1 In the organic light-emitting device 10, there is a first electrode 11, a second electrode 19 facing the first electrode 11, and an organic layer 15 disposed between the first electrode 11 and the second electrode 19.

[0242] The organic layer 15 includes an emission layer and may further include a hole transport region disposed between the first electrode 11 and the emission layer, and an electron transport region disposed between the emission layer and the second electrode 19.

[0243] A substrate may be further disposed below the first electrode 11 or on the second electrode 19. The substrate may be a substrate commonly used in organic light-emitting devices, such as a glass substrate or a transparent plastic substrate with excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and / or water resistance.

[0244] First electrode 11

[0245] The first electrode 11 can be formed, for example, by depositing or sputtering a material for forming the first electrode 11 onto a substrate. The first electrode 11 can be an anode. The material used to form the first electrode 11 can be selected from materials with high work function to facilitate hole injection.

[0246] The first electrode 11 can be a reflective electrode, a semi-transparent semi-reflective electrode, or a transmissive electrode. When the first electrode 11 is a transmissive electrode, the material used to form the first electrode 11 can be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or combinations thereof, but the embodiments are not limited thereto. In one or more embodiments, when the first electrode 11 is a semi-transparent semi-reflective electrode or a reflective electrode, at least one of magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or combinations thereof can be used as the material used to form the first electrode 11, but the embodiments are not limited thereto.

[0247] The first electrode 11 may have a single-layer structure or a multi-layer structure including two or more layers.

[0248] Launch layer 15

[0249] The emitter layer 15 may include at least one organometallic compound represented by Formula 1.

[0250] Figure 2 Description

[0251] In one or more embodiments, the emitter layer may include at least one organometallic compound represented by Formula 1 as an emitter.

[0252] In one or more embodiments, the emitter layer may further include a host (hereinafter referred to as 'host A', wherein host A is not the same as the organometallic compound represented by Formula 1). Host A can be understood by referring to the description of the host material provided herein, but embodiments are not limited thereto.

[0253] refer to Figure 2 The energy transfer according to one or more embodiments is described below.

[0254] In the host A of the emitting layer, 25% of the singlet excitons are formed, and the energies of these singlet excitons formed in host A are transferred to the organometallic compound represented by Formula 1 via Forster energy transfer (or Forster resonance energy transfer (FRET)). Furthermore, the energies of 75% of the triplet excitons formed in host A of the emitting layer are transferred to the organometallic compound represented by Formula 1 via Dexter energy transfer. Here, at least a portion of the singlet energy of the organometallic compound represented by Formula 1 is transferred to the triplet energy via intersystem crossing (ISC), and the organometallic compound represented by Formula 1 can therefore emit phosphorescence. In one or more embodiments, at least a portion of the triplet energy of the organometallic compound represented by Formula 1 is transferred to the singlet energy via reverse intersystem crossing (RISC), and the organometallic compound represented by Formula 1 can therefore emit delayed fluorescence (or thermally activated delayed fluorescence (TADF)).

[0255] In one or more embodiments, the ratio of the luminescent component emitted from the organometallic compound represented by Formula 1 to the total luminescent component emitted from the emitting layer may be 80% or greater, for example 90% or greater. In one or more embodiments, the ratio of the luminescent component emitted from the organometallic compound represented by Formula 1 to the total luminescent component emitted from the emitting layer may be 95% or greater.

[0256] Here, the organometallic compound represented by Formula 1 can emit phosphorescence or delayed fluorescence, while the host may not emit light.

[0257] In one or more embodiments, when the emitter layer further comprises a body A in addition to the organometallic compound represented by Formula 1, the amount of the organometallic compound represented by Formula 1 in the emitter layer may be 50 parts by weight or less, for example 30 parts by weight or less, based on 100 parts by weight of the emitter layer, and the amount of body A in the emitter layer may be 50 parts by weight or more, for example 70 parts by weight or more, but the embodiments are not limited thereto.

[0258] Figure 3 Description

[0259] In one or more embodiments, the organometallic compound represented by Formula 1 can be used as a sensitizer, and the emitting layer may further include a fluorescent emitter.

[0260] In one or more embodiments, the emitting layer may further include a host (hereinafter referred to as 'host B', wherein host B is different from the organometallic compound and fluorescent emitter represented by Formula 1) and a fluorescent emitter (hereinafter referred to as 'fluorescent emitter B', wherein fluorescent emitter B is different from host B and the organometallic compound). Host B and fluorescent emitter B can be understood by referring to the host material and fluorescent emitter material described later, but embodiments are not limited thereto.

[0261] In one or more embodiments, the ratio of the luminescent component emitted from the fluorescent emitter B to the total luminescent component emitted from the emitting layer may be 80% or more, for example 90% or more (or for example 95% or more). For example, the fluorescent emitter B may emit fluorescence. Furthermore, the host D and the sensitizer B may each be non-luminescent.

[0262] refer to Figure 3 The energy transfer according to one or more embodiments is described below.

[0263] The energy of 75% of the triplet excitons formed in the host B of the emitter layer can be transferred to the organometallic compound represented by Formula 1 via Dexter energy transfer, and the energy of 25% of the singlet excitons formed in the host B of the emitter layer can be transferred to the singlet and triplet energies of the organometallic compound represented by Formula 1. At least a portion of the energy transferred to the singlet energy of the organometallic compound represented by Formula 1 can be transferred to the triplet energy via ISC. Then, the triplet energy of the organometallic compound represented by Formula 1 can be transferred to the fluorescent emitter B via FRET. Furthermore, at least a portion of the triplet energy of the organometallic compound represented by Formula 1 can first be transferred to the singlet energy via RISC, and then transferred to the fluorescent emitter B.

[0264] Therefore, the energy of all singlet and triplet excitons generated in the emitter layer can be transferred to the emitter, resulting in an organic light-emitting device with improved efficiency. Furthermore, since an organic light-emitting device with significantly reduced energy loss can be obtained, the lifetime characteristics of the organic light-emitting device can be improved.

[0265] In one or more embodiments, the amount of the at least one organometallic compound represented by Formula 1 in the emitter layer can be selected from about 5% to about 50% by weight, for example from about 10% to about 30% by weight, based on the total weight of the emitter layer. When the content is within this range, energy transfer in the emitter layer can occur efficiently. Therefore, the organic light-emitting device can have high efficiency and long lifetime.

[0266] In one or more embodiments, the amount of fluorescent emitter B in the emission layer may be selected from about 0.01% by weight to about 15% by weight, for example from about 0.05% by weight to about 3% by weight, based on the total weight of the emission layer, but the embodiments are not limited thereto.

[0267] Figure 4 Description

[0268] In one or more embodiments, the organometallic compound represented by Formula 1 can be used as a sensitizer, and the emitting layer may further include a delayed fluorescent emitter.

[0269] In one or more embodiments, the emitting layer may further include a host (hereinafter referred to as 'host C', wherein host C is different from the organometallic compound and the delayed fluorescence emitter represented by Formula 1) and a delayed fluorescence emitter (hereinafter referred to as 'delayed fluorescence emitter C', wherein the delayed fluorescence emitter C is different from host C and the organometallic compound represented by Formula 1). Host C and delayed fluorescence emitter C can be understood by referring to the host material and delayed fluorescence emitter material described later, but embodiments are not limited thereto.

[0270] In one or more embodiments, the ratio of the luminescence component emitted from the delayed fluorescent emitter C to the total luminescence component emitted from the emitting layer may be 80% or more, for example 90% or more (or for example 95% or more). For example, the fluorescent emitter C may emit fluorescence. Furthermore, the host D and the sensitizer B may each not emit light.

[0271] refer to Figure 4 The energy transfer according to one or more embodiments is described below.

[0272] The energies of 75% of the triplet excitons formed in the host C of the emitter layer can be transferred to the organometallic compound represented by Formula 1 via Dexter energy transfer, and the energies of 25% of the singlet excitons formed in the host C of the emitter layer can be transferred to the singlet and triplet energies of the organometallic compound represented by Formula 1. At least a portion of the energy transferred to the singlet energy of the organometallic compound represented by Formula 1 can be transferred to the triplet energy via ISC. Then, the triplet energy of the organometallic compound represented by Formula 1 can be transferred to the delayed fluorescent emitter C via FRET. Furthermore, at least a portion of the triplet energy of the organometallic compound represented by Formula 1 can first be transferred to the singlet energy via RISC, and then transferred to the delayed fluorescent emitter C.

[0273] Therefore, the energy of all singlet and triplet excitons generated in the emitter layer can be transferred to the emitter, resulting in an organic light-emitting device with improved efficiency. Furthermore, the lifetime characteristics of the organic light-emitting device can be improved because it exhibits significantly reduced energy loss.

[0274] In one or more embodiments, the amount of the at least one organometallic compound represented by Formula 1 in the emitter layer can be selected from about 5% to about 50% by weight, for example from about 10% to about 30% by weight, based on the total weight of the emitter layer. When the content is within this range, energy transfer in the emitter layer can occur efficiently. Therefore, the organic light-emitting device can have high efficiency and long lifetime.

[0275] In one or more embodiments, the amount of delayed fluorescent emitter C in the emission layer may be selected from about 0.01 wt% to about 15 wt%, for example about 0.05 wt% to about 3 wt%, based on the total weight of the emission layer, but the embodiments are not limited thereto.

[0276] The main body in the emission layer

[0277] In one or more embodiments, the body may not include metal atoms.

[0278] In one or more embodiments, the main body may include at least one of the following compounds: fluorene-containing compounds, carbazole-containing compounds, dibenzofuran-containing compounds, dibenzothiophene-containing compounds, indobenzocarbazole-containing compounds, indobenzocarbazole-containing compounds, benzofuran-carbazole-containing compounds, benzothiophene-carbazole-containing compounds, acridine-containing compounds, dihydroacrylidine-containing compounds, triindobenzobenzene-containing compounds, pyridine-containing compounds, pyrimidine-containing compounds, triazine-containing compounds, silicon-containing compounds, cyano-containing compounds, phosphine oxide-containing compounds, sulfoxide-containing compounds, and sulfonyl-containing compounds.

[0279] For example, the main body may be a compound comprising at least one carbazole ring and at least one cyano group, or a compound containing phosphine oxide.

[0280] In one or more embodiments, the body may be composed of one type of body. When the body is composed of one type of body, the one type of body may be a bipolar body, an electron transport body, or a hole transport body, which will be described below.

[0281] In one or more embodiments, the body may be a mixture of two or more different types of bodies. For example, the body may include a hole transport body, an electron transport body, a bipolar body, or a combination thereof.

[0282] In one or more embodiments, the subject may be a mixture of an electron transport subject and a hole transport subject, a mixture of two different types of electron transport subjects, or a mixture of two different types of hole transport subjects. The electron transport subject and the hole transport subject can be understood by referring to the relevant descriptions presented below.

[0283] In one or more embodiments, the subject may include: an electronic transmission subject including at least one electronic transmission portion; or a hole transmission subject excluding an electronic transmission portion.

[0284] The electron transport moiety used in this article may be a cyano group, a cyclic group containing nitrogen lacking π electrons, or a group represented by one of the ET moieties:

[0285] ET part

[0286] .

[0287] In the above formula, *, *', and *'' each represent a binding site with an adjacent atom.

[0288] In one or more embodiments, the electron transport host in the emitter layer may include at least one cyano group or a cyclic group containing a nitrogen group lacking π electrons.

[0289] In one or more embodiments, the electron transport host in the emitter layer may include at least one cyano group.

[0290] In one or more embodiments, the electron transport host in the emitter layer may include at least one cyano group and at least one cyclic group containing a nitrogen group lacking π electrons.

[0291] In one or more embodiments, in the emitter layer, the hole transport body may include a hole transport portion and may not include an electron transport portion.

[0292] The hole transport component can be a π-electron-rich C3-C 60 Cyclic groups or groups represented by the HT part:

[0293] HT section

[0294] .

[0295] In the above formula, *, *', *'', and *''' each represent a binding site with an adjacent atom.

[0296] In one or more embodiments, the main body may include an electron transport body and a hole transport body, wherein the electron transport body may include at least one cyclic group of nitrogen without π-electron deficiency and at least one electron transport portion, and the hole transport body may include at least one cyclic group of nitrogen without π-electron deficiency and may not include an electron transport portion.

[0297] As used herein, the term "cyclic group containing π-electron-deficient nitrogen" refers to a cyclic group having at least one *-N=*' moiety, and may, for example, be an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, etc. azole group, iso- Azolium group, pyridine group, pyrazine group, pyridazine group, pyrimidine group, indazole group, purine group, quinoline group, isoquinoline group, benzo[a]quinoline group, phthalazine group, naphthidine group, quinoxaline group, quinazoline group, cyclophosphine group, phenanthridine group, acridine group, phenanthrene-rhein group, phenazine group, benzimidazole group, benzisothiazole group, benzo[a] azole group, benzene azole group, triazole group, tetraazole group Diazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group, azacarbazole group; or fused ring group consisting of two or more cyclic groups containing π-electron-deficient nitrogen atoms fused together.

[0298] In one or more embodiments, the cyclic group containing nitrogen without π-electron deficiency may be a phenyl group, a heptadene group, an indene group, a naphthalene group, etc. Group, indole group, acenaphthene group, fluorene group, spirodifluorene group, benzo[9,10]fluorene group, dibenzo[9,10]fluorene group, phenanthracene group, anthracene group, fluoranthracene group, benzo[9,10]phenanthracene group, pyrene group, Group, tetraphenyl group, Groups, Groups, pentaphenyl groups, hexaphenyl groups, pentophenyl groups, rubidium groups, halophenyl groups, ovalphenyl groups, pyrrole groups, isoindole groups, indole groups, furan groups, thiophene groups, benzofuran groups, benzothiophene groups, benzocarbazole groups, dibenzocarbazole groups, dibenzofuran groups, dibenzothiophene groups, dibenzothiophene sulfone groups, carbazole groups, dibenzothiorrole groups, indolecarbazole groups, indolecarbazole groups, benzofuran-carbazole groups, benzothiophene-carbazole groups, triindole-phenyl groups, or fused ring groups containing two or more cyclic groups that do not contain π-electron-deficient nitrogen, but the embodiments are not limited thereto.

[0299] In one or more embodiments, when the body is a mixture of electron transport bodies and hole transport bodies, the weight ratio of the electron transport bodies to the hole transport bodies can be from about 1:9 to about 9:1, for example from about 2:8 to about 8:2, or for example from about 4:6 to about 6:4, or for example 5:5. When the weight ratio of the electron transport bodies to the hole transport bodies meets the ranges described above, a balance between hole and electron transport in the emitter layer can be achieved.

[0300] In one or more embodiments, the bipolar body may include at least one electron transport portion and at least one hole transport portion.

[0301] In one or more embodiments, the main body may include both the first compound and the second compound, wherein:

[0302] i) The first compound can be a hole transport host, and the second compound can be an electron transport host.

[0303] ii) The first compound can be an electron transport host, and the second compound can be a hole transport host.

[0304] iii) Both the first and second compounds can be bipolar hosts.

[0305] iv) The first compound can be a hole transport host, and the second compound can be a bipolar host.

[0306] v) The first compound can be an electron transport host, and the second compound can be a bipolar host.

[0307] vi) The first compound may be a bipolar host, and the second compound may be a hole transport host, or

[0308] vii) The first compound may be a bipolar host, and the second compound may be an electron transport host.

[0309] The main body may include at least one of 1,3,5-tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi), 3-tert-butyl-9,10-bis(naphthyl-2-yl)anthracene (TBADN), 9,10-bis(naphthyl-2-yl)anthracene (ADN) (also known as "DNA"), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 4,4'-bis(9-carbazolyl)-2,2'-dimethyl-biphenyl (CDBP), 1,3,5-tris(carbazolyl-9-yl)benzene (TCP), 1,3-bis(N-carbazolyl)benzene (mCP), compound H50, or compound H51, but the embodiments are not limited thereto:

[0310]

[0311] .

[0312] In one or more embodiments, the body may further include a compound represented by formula 301:

[0313] Formula 301

[0314] .

[0315] In Equation 301, Ar111 and Ar 112 Each can be independently:

[0316] Phenylidene, naphthylene, phenanthrene, or pyrene; or

[0317] The phenylene, naphthylene, phenanthrene, or pyrene group, each substituted with at least one of phenyl, naphthyl, or anthracene.

[0318] Ar in Formula 301 113 To Ar 116 Each can be independently:

[0319] C1-C 10 Alkyl, phenyl, naphthyl, phenanthrene, or pyrene; or

[0320] The phenyl, naphthyl, phenanthryl, or pyrene group, each substituted with at least one of phenyl, naphthyl, or anthracene.

[0321] In Equation 301, g, h, i, and j can each be an integer from 0 to 4, and g, h, i, and j can be, for example, 0, 1, or 2.

[0322] Ar in Formula 301 113 To Ar 116 Each can be independently:

[0323] C1-C substituted with at least one of phenyl, naphthyl, or anthracene 10 alkyl;

[0324] Phenyl, naphthyl, anthraceneyl, pyrene, phenanthryl, or fluoreneyl;

[0325] Each of the following is substituted with at least one of the following: phenyl, naphthyl, anthraceneyl, pyrene, phenanthrene, or fluorenyl: deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, phenyl, naphthyl, anthraceneyl, pyrene, phenanthryl, fluorenyl, or combinations thereof; or

[0326] ,

[0327] However, the implementation methods are not limited to this.

[0328] In one or more embodiments, the body may include a compound represented by formula 302:

[0329] Formula 302

[0330] .

[0331] In Equation 302, Ar 122 To Ar 125 Each can be related to Ar in Equation 301 113 The description is the same.

[0332] In Equation 302, Ar 126 and Ar 127 Each can be independently C1-C 10 Alkyl groups (e.g., methyl, ethyl, propyl, etc.).

[0333] In Equation 302, k and l can each be an integer from 0 to 4 independently. For example, k and l can be 0, 1, or 2.

[0334] In one or more embodiments, the main body may include at least one of compounds H1 to H31:

[0335]

[0336]

[0337]

[0338]

[0339] .

[0340] In one or more embodiments, the host may be composed of a type of compound. For example, the type of compound may optionally be a first material (e.g., a hole transport host) or a second material (e.g., an electron transport host).

[0341] In one or more embodiments, the subject may include two or more types of compounds. For example, the subject may include: two or more different types of hole transport subjects; two or more different types of electron transport subjects; or a combination of one or more types of hole transport subjects and one or more types of electron transport subjects.

[0342] emitters in the emission layer

[0343] The emitter can emit light.

[0344] In one or more embodiments, the emitter may include at least one organometallic compound represented by Formula 1.

[0345] In one or more embodiments, the emitter may be a fluorescent emitter and / or a delayed fluorescent emitter that emits fluorescence and / or delayed fluorescence, respectively. Therefore, the decay time (T) of the emitter... 衰减 (E) can be less than 100 microseconds (μs).

[0346] T 衰减 (E) Time-resolved photoluminescence (TRPL) spectroscopy can be measured from a 40 nm thick film at room temperature, wherein the film passes through 10 -7 The substrate and emitter, including the emitter layer, are vacuum deposited on a quartz substrate at a weight ratio of 90:10 under Töpfer vacuum.

[0347] In one or more embodiments, the emitter may include a carbocyclic group having four or more rings, or a heterocyclic group having four or more rings.

[0348] In one or more embodiments, the emitter may be a metal-free organic compound.

[0349] In one or more embodiments, the emitter may be a compound represented by any one of formulas 51 to 54:

[0350] Formula 51

[0351]

[0352] Formula 52

[0353]

[0354] Formula 53

[0355]

[0356] Formula 54

[0357] .

[0358] In equations 51 to 54,

[0359] X 51 and X 52 Each can be N or B independently.

[0360] Y 51 It can be a single bond, O, S, Se, N(R) 501 ), B(R) 501 ), C(R 501 (R) 502 ), or Si(R) 501 (R) 502 ),

[0361] Y 52It can be a single bond, O, S, Se, N(R) 503 ), B(R) 503 ), C(R 503 (R) 504 ), or Si(R) 503 (R) 504 ),

[0362] Y 53 It can be a single bond, O, S, Se, N(R) 505 ), B(R) 505 ), C(R 505 (R) 506 ), or Si(R) 505 (R) 506 ),

[0363] Y 54 It can be a single bond, O, S, Se, N(R) 507 ), B(R) 507 ), C(R 507 (R) 508 ), or Si(R) 507 (R) 508 ),

[0364] R 51 To R 65 and R 501 To R 508 Each can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, 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-C60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -C(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2), or -P(=S)(Q1)(Q2),

[0365] R 51 To R 65 and R 501 To R 508 Two or more may optionally be combined to form C5-C that is either unsubstituted or substituted by at least one R5. 30 The carbocyclic group is either unsubstituted or substituted with at least one R5 group. 30 Heterocyclic groups,

[0366] 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 may be:

[0367] Deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C1-C 60 Alkylthio;

[0368] Each of the following C1-C is replaced: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 alkoxy, or C1-C 60 Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 11 (Q) 12 (Q) 13 -Ge(Q) 11 (Q) 12 (Q) 13 -C(Q) 11 (Q) 12 (Q) 13 -B(Q) 11 (Q) 12 -N(Q) 11(Q) 12 -P(Q) 11 (Q) 12 -C(=O)(Q) 11 -S(=O)(Q) 11 -S(=O)2(Q) 11 -P(=O)(Q) 11 (Q) 12 -P(=S)(Q) 11 (Q) 12 ), or combinations thereof;

[0369] C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups,

[0370] Each of the following C3-C is replaced: 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid groups or their salts, sulfonic acid groups or their salts, phosphate groups or their salts, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 21 (Q) 22 (Q) 23 -Ge(Q) 21 (Q) 22 (Q) 23 -C(Q) 21 (Q) 22 (Q) 23 -B(Q) 21 (Q) 22 -N(Q) 21 (Q) 22 -P(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)(Q) 21 -S(=O)2(Q) 21 -P(=O)(Q) 21 (Q) 22 -P(=S)(Q) 21 (Q) 22 ), or combinations thereof;

[0371] -Si(Q 31 (Q) 32 (Q) 33 -Ge(Q) 31 (Q) 32 (Q) 33 -C(Q) 31 (Q) 32 (Q) 33 -B(Q) 31 (Q) 32 -N(Q)31 (Q) 32 -P(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)(Q) 31 -S(=O)2(Q) 31 -P(=O)(Q) 31 (Q) 32 ), or -P(=S)(Q 31 (Q) 32 ),and

[0372] Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 , and Q 31 To Q 33 Each group can independently be hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C1-C 60 Alkylthio, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 arylalkyl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, or substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups.

[0373] In one or more embodiments, R5, R 51 To R 65 and R 501 To R 508 Each can be represented as R in Equation 1. 10 As described.

[0374] In one or more embodiments, the emitter may be a fused polycyclic compound or a styrene-based compound.

[0375] In one or more embodiments, the emitter may include one of the following: a naphthalene-containing core, a fluorene-containing core, a spirodifluorene-containing core, a benzo[9,10]fluorene-containing core, a dibenzo[9,10]fluorene-containing core, a phenanthrene-containing core, an anthracene-containing core, a fluoranthene-containing core, a benzo[9,10]phenanthrene-containing core, a pyrene-containing core, or a phenanthrene-containing core. core, containing core, containing The core, a core containing pentabenzene, a core containing indene-anthracene, a core containing tetrabenzene, a core containing bianthracite, or a core represented by one of formulas 501-1 to 501-21:

[0376]

[0377]

[0378]

[0379] .

[0380] In one or more embodiments, the emitter can be represented by formula 501:

[0381] Formula 501

[0382] .

[0383] In Equation 501,

[0384] Ar 51 It can be an unsubstituted or substituted group of the following: naphthyl group, fluorene group, spirodifluorene group, benzo[9,10]fluorene group, dibenzo[9,10]fluorene group, phenanthrene group, anthracene group, fluoranthene group, benzo[9,10]phenanthrene group, pyrene group, Groups, Groups, Group, pentaphenyl group, indene-anthracene group, tetraphenyl group, bianthracite group, or a group represented by any one of formulas 501-1 to 501-21: deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, sulfonic acid group or its salt, C1-C60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 511 (Q) 512 (Q) 513 -Ge(Q) 511 (Q) 512 (Q) 513 -C(Q) 511 (Q) 512 (Q) 513 -B(Q) 511 (Q) 512 -N(Q) 511 (Q) 512 -P(Q) 511 (Q) 512 -C(=O)(Q) 511 -S(=O)(Q) 511 -S(=O)2(Q) 511 -P(=O)(Q) 511 (Q) 512 -P(=S)(Q) 511 (Q) 512 ), or combinations thereof:

[0385]

[0386]

[0387]

[0388] ,

[0389] L 511 To L 514 Each can be independently substituted or unsubstituted C3-C. 10 Cycloalkylene, 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 C1-C 60 Heteroaryl groups, substituted or unsubstituted divalent nonaromatic fused polycyclic groups, or substituted or unsubstituted divalent nonaromatic fused heterocyclic groups.

[0390] a511 to a514 can each be independently 0, 1, 2, or 3.

[0391] R 511 To R 513 Each can be independently substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C3-C 10 cycloalkyl, 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 C1-C 60 heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, or substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups.

[0392] Q 511 To Q 513 They can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C1-C 60 Alkylthio group, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60Alkyl aryl, C7-C 60 Arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthioyl, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy group, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, denoted by deuterium, -F, cyano, C1-C 20 Alkyl, or C6-C 30 At least one substituted C1-C of aryl 60 Alkyl groups, or those with deuterium, -F, cyano, or C1-C groups. 20 Alkyl, or C6-C 30 At least one substituted C6-C of aryl group 60 Aryl, and

[0393] n511 and n512 can each be 0, 1, 2, 3, 4, 5, or 6 independently.

[0394] In one or more embodiments, the sum of n511 and n512 in Formula 501 may be 1 or greater, but the embodiments are not limited thereto.

[0395] In one or more embodiments, in formula 501, R 511 and R 512 Each can be independently:

[0396] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, pyrene alkyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazole group, triazinyl, dibenzofuranyl, or dibenzothiopheneyl; or

[0397] Each of the following is substituted with at least one of the following: phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthraceneyl, pyrene. alkyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, triazinyl, dibenzofuranyl, or dibenzothiopheneyl: deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazyl, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20Alkylthio, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spirodifluorenyl, benzo[a]fluorenyl, dibenzo[a]fluorenyl, phenanthryl, anthracene, pyrene, The compounds are: pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazoleyl, triazinyl, dibenzofuranyl, or dibenzothiopheneyl.

[0398] In one or more embodiments, the emitter may be one of those from group FD1:

[0399] Group FD1

[0400]

[0401]

[0402]

[0403]

[0404]

[0405]

[0406]

[0407]

[0408]

[0409] .

[0410] The maximum emission wavelength of the emitter's emission spectrum can be from about 400 nm to about 650 nm. In one or more embodiments, the maximum emission wavelength of the emitter's emission spectrum can be from about 400 nm to about 550 nm, from about 410 nm to about 495 nm, or from about 450 nm to about 495 nm, but the embodiments are not limited thereto. The emitter can emit blue to green light, such as blue light, but the embodiments are not limited thereto. As used herein, "maximum emission wavelength" refers to the wavelength at which its emission intensity is highest. In other words, "maximum emission wavelength" may be referred to as "peak emission wavelength".

[0411] Based on the total weight of the emitter layer, the emitter layer may have an emitter content in the range of about 0.01% by weight to about 15% by weight, but the implementation is not limited to this.

[0412] In the emitter layer, the content of the main component, the content of the sensitizer, and the content of the emitter are each based on weight, with the content of the main component being the largest and the content of the emitter being the smallest, but the implementation is not limited to this.

[0413] Organic light-emitting devices can meet condition 1:

[0414] Condition 1

[0415] S1(H) > S1(S) ≥ S1(E).

[0416] In condition 1,

[0417] S1(H) represents the lowest excited singlet state energy level of the host.

[0418] S1(S) represents the lowest excited singlet state energy level of the sensitizer, and

[0419] S1(E) represents the lowest excited singlet energy level of the emitter, each in eV.

[0420] S1(H), S1(S), and S1(E) can be calculated from PL spectra obtained from a film with a thickness of 40 nm, which passes through a 10 nm thick spectral density. -7 The substrate, sensitizer, or emitter are vacuum-deposited onto a quartz substrate under a certain vacuum level.

[0421] When condition 1 is met, the emitter can emit light, and the organic light-emitting device can have improved efficiency.

[0422] For example, when condition 1 is met, the emission ratio (proportion) from the emitter in the organic light-emitting device can be 85% or greater. That is, when the aforementioned range is met, only the emitter in the organic light-emitting device can substantially (essentially) emit light, while the exciton complex (host) and sensitizer can substantially (essentially) not emit light.

[0423] When the energy of singlet and / or triplet excitons formed in the host is transferred to the sensitizer, and the triplet excitons in the sensitizer are converted into singlet excitons via RISC, the energy of the singlet excitons is transferred to the emitter via Forster energy transfer (FRET). Since all the energy of the singlet and triplet excitons in the host can be transferred to the emitter, organic light-emitting devices can have significantly improved lifetime and efficiency.

[0424] The host and sensitizer can meet condition 2:

[0425] Condition 2

[0426] T1(H) ≥ T1(S).

[0427] In condition 2,

[0428] T1(H) represents the lowest excited triplet energy level of the host, and

[0429] T1(S) represents the lowest excited triplet energy level of the sensitizer.

[0430] Sensitizer in the emitter layer

[0431] In one or more embodiments, the emission layer may include a body and an emitter, and may further include a sensitizer.

[0432] In one or more embodiments, the sensitizer may include at least one organometallic compound represented by Formula 1.

[0433] In one or more embodiments, the sensitizer may further include a phosphorescent compound.

[0434] In one or more embodiments, the phosphorescent compound may include at least one type of metal.

[0435] In one or more embodiments, the phosphorescent compound may include a type of metal selected from transition metals (M... 11 ) and organic ligands (L 11 ), where L 11 and M 11 It can form one, two, three, or four metallized rings.

[0436] In one or more embodiments, the phosphorescent compound may be represented by formula 101:

[0437] Formula 101

[0438] M 11 (L 11 ) n11 (L 12 ) n12

[0439] In Equation 101,

[0440] M 11 It can be a transition metal.

[0441] L 11 It can be a ligand represented by one of equations 1-1 to 1-4.

[0442] L 12 It can be a monodentate ligand or a bidentate ligand.

[0443] n11 can be 1, and

[0444] n12 can be 0, 1, or 2.

[0445]

[0446] Among them, in equations 1-1 to 1-4,

[0447] A1 to A4 can each be independently substituted or unsubstituted C5-C. 30 Carbocyclic groups, substituted or unsubstituted C1-C 30 Heterocyclic groups or acyclic groups,

[0448] Y 11 To Y 14 Each can independently form a chemical bond, O, S, N (R) 91 ), B(R) 91 ), P(R 91 ), or C(R) 91 (R) 92 ),

[0449] T1 to T4 can each be independently a single bond, a double bond, or *-N(R) bond. 93 )-*'、*-B(R 93 )-*'、*-P(R 93 )-*'、*-C(R 93 (R) 94 )-*'、*-Si(R 93 (R) 94 )-*'、*-Ge(R 93 (R) 94 )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R 93 )=*'、*=C(R 93 )-*'、*-C(R 93 )=C(R 94 )-*', *-C(=S)-*', or *-C≡C-*',

[0450] Replacement C5-C 30 Substituents of carbocyclic groups, C1-C substitutions 30 Substituents of heterocyclic groups, and R 91 To R 94 Each group can independently be 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-C10 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 aromatic fused polycyclic groups, substituted or unsubstituted monovalent aromatic fused heterocyclic groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -C(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2), or -P(=S)(Q1)(Q2), wherein the substituted C5-C 30 Substituents in carbocyclic groups and the C1-C substituents 30 The substituents in the heterocyclic group are not hydrogen.

[0451] *1, *2, *3, and *4 each represent the relationship with M. 11 The binding site, and

[0452] Q1 to Q3 can each be independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C1-C 60 Alkylthio group, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C60 Alkyl aryl, C7-C 60 Arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthioyl, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy group, C1-C 60 Heteroaryl thiols, monovalent aromatic fused polycyclic groups, monovalent aromatic fused heterocyclic groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, derived from deuterium, -F, cyano, C1-C 60 Alkyl, or C6-C 60 At least one substituted C1-C of aryl 60 Alkyl groups, or those derived from deuterium, -F, cyano, C1-C 60 Alkyl, or C6-C 60 At least one substituted C6-C of aryl group 60 Aryl.

[0453] In one or more embodiments, the transition metal may be platinum (Pt), palladium (Pd), gold (Au), iridium (Ir), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).

[0454] In one or more embodiments, the sensitizer may further include a delayed fluorescence compound.

[0455] In one or more embodiments, the delayed fluorescence compound may be represented by formula 101 or 102:

[0456] Formula 101 Formula 102

[0457]

[0458] In equations 101 and 102,

[0459] A 21 It is a receptor group.

[0460] D 21 As a donor group,

[0461] m21 can be 1, 2, or 3, and n21 can be 1, 2, or 3.

[0462] In Equation 101, the sum of n21 and m21 can be 5 or less, and in Equation 102, the sum of n21 and m21 can be 6 or less.

[0463] Each R 201It can independently be hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C1-C 60 Alkylthio, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 arylalkyl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -C(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2), or -P(=S)(Q1)(Q2), wherein multiple R 201 They can be optionally combined to form substituted or unsubstituted C5-C 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups, and

[0464] Q1 to Q3 can each be independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60Alkyne group, C1-C 60 Alkoxy, C1-C 60 Alkylthio group, 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 Arylthioyl, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy group, C1-C 60 Heteroaryl thiols, monovalent aromatic fused polycyclic groups, monovalent aromatic fused heterocyclic groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, derived from deuterium, -F, cyano, C1-C 60 Alkyl, or C6-C 60 At least one substituted C1-C of aryl 60 Alkyl groups, or those derived from deuterium, -F, cyano, C1-C 60 Alkyl, or C6-C 60 At least one substituted C6-C of aryl group 60 Aryl.

[0465] In one or more embodiments, in formulas 101 and 102, D 21 It can be a cyclic group of nitrogen that is either substituted or unsubstituted and does not contain π-electron-deficient nitrogen.

[0466] In one or more embodiments, the cyclic group containing nitrogen without π-electron deficiency may be a phenyl group, a heptadene group, an indene group, a naphthalene group, etc. Group, indole group, acenaphthene group, fluorene group, spirodifluorene group, benzo[9,10]fluorene group, dibenzo[9,10]fluorene group, phenanthracene group, anthracene group, fluoranthracene group, benzo[9,10]phenanthracene group, pyrene group, Group, tetraphenyl group, Groups, Groups, pentaphenyl, hexaphenyl, pentophenyl, rubidium benzoate, halophenyl, ovalphenyl, pyrrole, isoindole, indole, furan, thiophene, benzofuran, benzothiophene, benzocarbazole, dibenzocarbazole, dibenzofuran, dibenzothiophene, dibenzothiophene sulfone, carbazole, dibenzothiorrole, indole-carbazole, benzofuran-carbazole, benzothiophene-carbazole, triindole-phenyl; or fused-ring groups consisting of two or more cyclic groups that do not contain π-electron-deficient nitrogen, but the embodiments are not limited thereto.

[0467] In one or more embodiments, in formulas 101 and 102, A 21 Possible forms:

[0468] -F, cyano, or cyclic groups containing nitrogen lacking π electrons;

[0469] Each of the C1-C groups is substituted by at least one group from -F or cyano. 60 Alkyl groups, cyclic groups containing nitrogen atoms lacking π electrons, or cyclic groups not containing nitrogen atoms lacking π electrons; or

[0470] Deuterium, C1-C 60 At least one substituted cyclic group containing π-electron-deficient nitrogen, of an alkyl group, a cyclic group containing π-electron-deficient nitrogen, or a cyclic group not containing π-electron-deficient nitrogen.

[0471] In one or more embodiments, the cyclic group of nitrogen that does not contain π-electron-deficient nitrogen is the same as that described above.

[0472] As used herein, the term "cyclic group containing π-electron-deficient nitrogen" refers to a cyclic group having at least one *-N=*' moiety, and may be, for example, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, etc. azole group, iso- Azolium group, pyridine group, pyrazine group, pyridazine group, pyrimidine group, indazole group, purine group, quinoline group, isoquinoline group, benzo[a]quinoline group, phthalazine group, naphthidine group, quinoxaline group, quinazoline group, cyclophosphine group, phenanthridine group, acridine group, phenanthrene-rhein group, phenazine group, benzimidazole group, benzisothiazole group, benzo[a] azole group, benzene azole group, triazole group, tetraazole group Diazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group, azacarbazole group, benzimidazole benzimidazole group; or fused ring group in which two or more cyclic groups containing π-electron-deficient nitrogen are fused together.

[0473] In one or more embodiments, the amount of sensitizer in the organic layer (e.g., the emitting layer) may be greater than the amount of emitter in the organic layer (e.g., the emitting layer) based on weight and / or volume. For example, the volume ratio of sensitizer to emitter may be from about 30:0.1 to about 10:3 or from about 10:0.1 to about 20:5. In one or more embodiments, the weight ratio of sensitizer to emitter may be from about 10:0.1 to about 20:5. In one or more embodiments, the weight ratio of body to sensitizer in the organic layer (e.g., the emitting layer) may be from about 60:40 to about 95:5 or from about 70:30 to about 90:10. In one or more embodiments, the weight ratio of body to sensitizer in the organic layer (e.g., the emitting layer) may be from about 60:40 to about 95:5. When amounts within the above ranges are satisfied, the organic light-emitting device may have improved luminous efficiency and / or long lifetime characteristics.

[0474] As described, Figure 1 This is a schematic cross-sectional view of an organic light-emitting device 10 according to one or more embodiments. Referring below, reference will be made to... Figure 1 The structure and manufacturing method of an organic light-emitting device 10 according to one or more embodiments are described. The organic light-emitting device 10 may have a structure in which a first electrode 11, an organic layer 15, and a second electrode 19 are sequentially stacked.

[0475] A substrate may be further disposed below the first electrode 11 or on the second electrode 19. The substrate may be a substrate commonly used in organic light-emitting devices, such as a glass substrate or a transparent plastic substrate with excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.

[0476] The first electrode 11 can be formed, for example, by depositing or sputtering a material for forming the first electrode 11 onto a substrate. The first electrode 11 can be an anode. The material used to form the first electrode 11 can be a material with a high work function to facilitate hole implantation. The first electrode 11 can be a reflective electrode, a semi-transparent semi-reflective electrode, or a transmissive electrode. The material used to form 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 used to form the first electrode 11 can be a metal, such as magnesium (Mg), aluminum (Al), silver (Ag), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag).

[0477] The first electrode 11 may have a single-layer structure or a multi-layer structure including two or more layers. For example, the first electrode 11 may have a three-layer structure of ITO / Ag / ITO, but the structure of the first electrode 11 is not limited to this.

[0478] The organic layer 15 may be disposed on the first electrode 11.

[0479] The organic layer 15 may include a hole transport region, an emitter layer, and an electron transport region.

[0480] The hole transport region can be located between the first electrode 11 and the emitter layer.

[0481] The hole transport region may include a hole injection layer (HIL), a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof.

[0482] The hole transport region may consist of only a hole injection layer or a hole transport layer. The hole transport region may have a hole injection layer / hole transport layer structure, or a hole injection layer / hole transport layer / electron blocking layer structure, wherein the constituent layers are stacked sequentially from the first electrode 11 in the order stated herein.

[0483] When the hole transport region includes a hole injection layer, the hole injection layer can be formed on the first electrode 11 by using various methods such as vacuum deposition, spin coating, tape casting, and / or Langmuir-Broguet (LB) deposition, but the implementation is not limited thereto.

[0484] When a hole injection layer is formed by vacuum deposition, the deposition conditions can vary depending on the compound used to form the hole injection layer, the desired structure of the hole injection layer, and its thermal properties. For example, the deposition temperature can be from about 100°C to about 500°C, and the vacuum level can be about 10. -8 To about 10 -3 The deposition rate can be from about 0.01 Å / s to about 100 Å / s, but the implementation is not limited thereto.

[0485] When a hole injection layer is formed by spin coating, the coating conditions can vary depending on the compound used to form the hole injection layer, the desired structure of the hole injection layer, and its thermal properties. For example, the coating rate can be from about 2,000 rpm to about 5,000 rpm, and the temperature at which the heat treatment is performed after coating to remove the solvent can be from about 80°C to about 200°C, but the implementation is not limited to these.

[0486] In this respect, the conditions for forming the hole transport layer and the electron blocking layer can be understood by referring to the conditions for forming the hole injection layer.

[0487] The hole transport region may include at least one of the following: 4,4',4"-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4"-tri{N-(2-naphthyl)-N-phenylamino}-triphenylamine (2-TNATA), N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine (NPB), β-NPB, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD), spiro-TPD, spiro-NPB, methylated NPB, 4,4'-cyclohexylidene bis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD), α-NPD, 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-sulfonated styrene) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-sulfonated styrene) (PANI / PSS), compounds represented by formula 201, or compounds represented by formula 202, but the embodiments are not limited thereto.

[0488]

[0489]

[0490]

[0491] Formula 201

[0492]

[0493] Formula 202

[0494] .

[0495] In Equation 201, Ar 101 and Ar 102 Each can be independently:

[0496] Phenylidene, cyclopentadienyl, indenyl, naphthyl, and other compounds alkyl, heptadeneyl, acenaphthene, fluoreneyl, phenentheneyl, anthraceneyl, fluoreneyl, benzo[9,10]phenentheneyl, pyreneyl, phenentheneyl alkyl, tetraphenyl, phenyl Base, Asia Benzyl, or pentanediphenyl; or

[0497] Each of the following substituted groups is phenylene, cyclopentadienylene, indenylene, naphthylene, and phenylene oxide. 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, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thio groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, or combinations thereof.

[0498] In Equation 201, xa and xb can each be an integer from 0 to 5, or 0, 1, or 2. For example, xa can be 1 and xb can be 0, but xa and xb are not limited to these values.

[0499] R in Equations 201 and 202 101 To R 108 R 111 To R 119 and R 121 To R 124 Each can be independently:

[0500] Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10Alkyl groups (e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl, etc.), C1-C 10 Alkyl groups (e.g., methoxy, ethoxy, propoxy, butoxy, pentoxy, etc.) or C1-C 10 Alkylthio;

[0501] Each of the following C1-C is replaced: 10 Alkyl, C1-C 10 alkoxy, or C1-C 10 Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, or combinations thereof;

[0502] Phenyl, naphthyl, anthraceneyl, fluorenyl, or pyrene; or

[0503] Each of the following substituted groups is phenyl, naphthyl, anthraceneyl, fluorenyl, or pyrene: deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl, C1-C 10 Alkoxy, C1-C 10 Alkylthio groups, or combinations thereof, but the implementation methods are not limited thereto.

[0504] In Equation 201, R 109 Possible forms:

[0505] phenyl, naphthyl, anthraceneyl, or pyridyl; or

[0506] Each of the following substituted groups is phenyl, naphthyl, anthracene, or pyridyl: deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, phenyl, naphthyl, anthraceneyl, pyridyl, or combinations thereof.

[0507] In one or more embodiments, the compound represented by formula 201 may be represented by formula 201A, but the embodiments are not limited thereto:

[0508] Formula 201A

[0509] .

[0510] In Equation 201A, R 101 R 111 R 112and R 109 Each can be as described in this article regarding Equation 201.

[0511] For example, the compounds represented by formula 201 and the compounds represented by formula 202 may include, but are not limited to, one of compounds HT1 to HT20:

[0512]

[0513]

[0514]

[0515] .

[0516] The thickness of the hole transport region can be from about 100 Å to about 10,000 Å, for example, from about 100 Å to about 1,000 Å. When the hole transport region includes at least one hole injection layer and a hole transport layer, the thickness of the hole injection layer can be from about 100 Å to about 10,000 Å, for example, from about 100 Å to about 1,000 Å, and the thickness of the hole transport layer can be from about 50 Å to about 2,000 Å, for example, from about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transport characteristics can be obtained without a significant increase in driving voltage.

[0517] In addition to the materials described above, the hole transport region may further include a charge-generating material for improving conductivity. The charge-generating material may be uniformly or non-uniformly dispersed in the hole transport region.

[0518] The charge-generating material can be, for example, a p-doper. The p-doper can be, but is not limited to, a quinone derivative, a metal oxide, or a cyano-containing compound. Non-limiting examples of p-dopers include quinone derivatives such as tetracyanoquinone dimethylane (TCNQ) or 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethylane (F4-TCNQ); metal oxides such as tungsten oxide or molybdenum oxide; or cyano-containing compounds such as compound HT-D1 or F12, but the embodiments are not limited thereto.

[0519]

[0520] .

[0521] Hole transport regions may include buffer layers.

[0522] The buffer layer can compensate for the optical resonance distance according to the wavelength of the light emitted from the emission layer 15, and thus the efficiency of the formed organic light-emitting device can be improved.

[0523] In one or more embodiments, when the hole transport region includes an electron blocking layer, the material used to form the electron blocking layer may be selected from, but is not limited to, the materials described above that can be used in the hole transport region and the main materials described above. For example, when the hole transport region includes an electron blocking layer, the material used to form the electron blocking layer may be the mCP described above.

[0524] The emitter layer can 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 generally similar to those used when forming the hole injection layer, although the deposition or coating conditions can vary depending on the material used to form the emitter layer.

[0525] 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, the emitting layer may have a structure in which red emitting layers, green emitting layers, and / or blue emitting layers are stacked, and therefore, various variations such as the emission of white light are possible.

[0526] When the emitter layer comprises a host and a dopant, the amount of dopant is typically from about 0.01 parts by weight to about 15 parts by weight relative to 100 parts by weight of the host, but the implementation is not limited thereto.

[0527] The thickness of the emitting layer can be from about 100 Å to about 1,000 Å, for example from about 200 Å to about 600 Å. When the thickness of the emitting layer is within the above range, excellent light emission characteristics can be obtained without a significant increase in driving voltage.

[0528] Next, the electron transport region can be located on the emitter layer.

[0529] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

[0530] 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, but the structure of the electron transport region is not limited to these. The electron transport layer may have a multilayer structure or a single-layer structure comprising two or more different materials.

[0531] The conditions for forming the hole blocking layer, electron transport layer, and electron injection layer that constitute the electron transport region can be understood by referring to the conditions for forming the hole injection layer.

[0532] When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), or bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), but the embodiments are not limited thereto:

[0533] .

[0534] The thickness of the hole blocking layer can be from about 20 Å to about 1,000 Å, for example from about 30 Å to about 300 Å. When the thickness of the hole blocking layer is within these ranges, excellent hole blocking characteristics can be obtained without a significant increase in driving voltage.

[0535] The electron transport layer may include at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), tris(8-hydroxyquinoline)aluminum (Alq3), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), or 4-(naphthyl-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), but the embodiments are not limited thereto.

[0536] .

[0537] In one or more embodiments, the electronic transport layer may include at least one of ET1 to ET25, but the embodiments are not limited thereto:

[0538]

[0539]

[0540]

[0541] .

[0542] The thickness of the electron transport layer can be from about 100 Å to about 1,000 Å, for example from about 150 Å to about 500 Å. When the thickness of the electron transport layer is within these ranges, satisfactory electron transport characteristics can be obtained without a significant increase in the driving voltage.

[0543] In addition to the materials described above, the electron transport layer may further include a metallic material.

[0544] Metal-containing materials may include Li complexes. Li complexes may include, for example, compounds ET-D1 (lithium 8-hydroxyquinoline, LiQ) or ET-D2, but the embodiments are not limited thereto:

[0545] .

[0546] The electron transport region may also include an electron injection layer that facilitates the injection of electrons from the second electrode 19.

[0547] The electron-injected layer may include LiQ, LiF, NaCl, CsF, Li2O, BaO, or combinations thereof.

[0548] The thickness of the electron injection layer can be from about 1 Å to about 100 Å, for example from about 3 Å to about 90 Å. When the thickness of the electron injection layer is within the range described above, satisfactory electron injection characteristics can be obtained without a significant increase in the driving voltage.

[0549] Second electrode 19

[0550] The second electrode 19 may be disposed 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), silver (Ag), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag) may be used as materials for forming the second electrode 19. In one or more embodiments, various modifications (e.g., using ITO or IZO to form a transmissive second electrode) are possible for fabricating a top-emitting light-emitting device.

[0551] Already referenced Figure 1 Organic light-emitting devices are described, but implementation methods are not limited thereto.

[0552] On the other hand, electronic devices including the organic light-emitting device are provided.

[0553] In addition to the organic light-emitting devices described above, electronic devices may further include thin-film transistors. A thin-film transistor may include a source electrode, a drain electrode, and an active layer, wherein either the source electrode or the drain electrode may be electrically connected to either the first electrode or the second electrode of the organic light-emitting device.

[0554] On the other hand, diagnostic compositions are provided that include at least one organometallic compound represented by Formula 1.

[0555] Organometallic compounds represented by Formula 1 provide high luminescence efficiency, and therefore, diagnostic compositions comprising at least one organometallic compound represented by Formula 1 can have high diagnostic efficiency.

[0556] Diagnostic compositions can be used in a variety of applications, including diagnostic kits, diagnostic reagents, biosensors, biomarkers, etc., but implementation methods are not limited thereto.

[0557] As used in this article, the term "C1-C" 60 "Alkyl" refers to a straight-chain or branched monovalent group of a saturated aliphatic hydrocarbon having 1 to 60 carbon atoms. As used herein, the term "C1-C..." 60 "alkylene" refers to a compound with C1-C2 atoms. 60 Divalent groups with the same structure as alkyl groups.

[0558] In this article, C1-C 60 Alkyl groups can be C1-C 30 Alkyl groups, such as C1-C 20 Alkyl groups, such as C1-C 10 Alkyl or C1-C6 alkyl. These alkyl groups can each be straight-chain or branched. In the case of branched alkyl groups, the lower limit of the carbon number range for each alkyl group becomes 3. C1-C 60 Alkyl, C1-C 30 Alkyl, C1-C 20 Alkyl, and / or C1-C 10 Non-limiting examples of alkyl groups are methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, 2-methylbutyl, sec-pentyl, 3-pentyl, 3-methyl-2-butyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isonyl, sec-nonyl, tert-nonyl, n-decyl, isodel. Sec-decyl or tert-decyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, 2-methylbutyl, sec-pentyl, 3-pentyl, 3-methyl-2-butyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isonyl, sec-nonyl, tert-nonyl, n-decyl, isodel, sec-decyl, tert-decyl, or combinations thereof. For example, formula 9-33 is a branched C6 alkyl group, such as a tert-butyl group substituted with two methyl groups.

[0559] As used in this article, the term "C1-C" 60 "Alkoxy" refers to the compound formed by -OA 101 (where A) 101 It is C1-C 60 Alkyl group represents a monovalent group. C1-C 60 Alkoxy, C1-C 20alkoxy, or C1-C 10 Non-limiting examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, pentoxy, etc.

[0560] As used in this article, the term "C2-C" 60 "Alkenyl" refers to the group formed at C2-C... 60 The alkyl group contains at least one carbon-carbon double bond at its middle or end, and non-limiting examples include vinyl, propenyl, butenyl, etc. As used herein, the term "C2-C" is used... 60 "Alkenyl" refers to a group that has a C2-C bond structure. 60 Divalent groups with the same structure as alkenyl groups.

[0561] As used in this article, the term "C2-C" 60 "Alkyne group" refers to a group formed by the combination of C2-C... 60 A hydrocarbon group formed by substituting at least one carbon-carbon triple bond into the middle or end of an alkyl group, and non-limiting examples include ethynyl, propynyl, etc. As used herein, the term "C2-C" is used in this context. 60 "Immyneyl" refers to a group that has a similar structure to C2-C2. 60 Divalent groups with the same structure as alkynyl groups.

[0562] As used in this article, the term "C3-C" 10 "Cycloalkyl" refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms as cyclic atoms. The term "C3-C" is used herein. 10 "Cycloalkylene" refers to a compound with C3-C66 atoms. 10 Divalent groups with the same structure as cycloalkyl groups.

[0563] As used in this article, “C3-C” 10 Non-limiting examples of "cycloalkyl" 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.

[0564] As used in this article, the term "C1-C" 10 "Heterocyclic alkyl" refers to a monovalent saturated cyclic group having at least one heteroatom selected from B, N, O, P, Si, S, Se, and Ge as a cyclic atom and 1 to 10 carbon atoms as cyclic atoms. The term "C1-C" is used herein. 10 "Heterocyclic alkyl" refers to a compound with C1-C2 atoms. 10 Divalent groups with the same structure as heterocyclic alkyl groups.

[0565] C1-C 10Non-limiting examples of heterocyclic alkyl groups include silylcyclopentyl, silylcyclohexyl, tetrahydrofuranyl, tetrahydro-2H-pyranyl, tetrahydrothiophenyl, etc.

[0566] As used in this article, the term "C3-C" 10 "Cycloalkenyl" refers to a monovalent hydrocarbon cyclic group having 3 to 10 carbon atoms as cyclic atoms and at least one carbon-carbon double bond in its ring and not being aromatic, and non-limiting examples include cyclopentenyl, cyclohexenyl, cycloheptenyl, etc. As used herein, the term "C3-C" is also used. 10 "Biopylidene alkenyl" refers to a group that has a C3-C... 10 A divalent group with the same structure as a cycloalkenyl group.

[0567] As used in this article, the term "C1-C" 10 "Heterocyclic alkenyl" refers to a monovalent cyclic group that has at least one heteroatom selected from B, N, O, P, Si, S, Se, and Ge as a cyclic atom, 2 to 10 carbon atoms as cyclic atoms, and at least one double bond, and is not aromatic. C1-C 10 Non-limiting examples of heterocyclic alkenyl groups include 2,3-dihydrofuranyl, 2,3-dihydrothiophenyl, etc., as used herein with the term "C1-C". 10 "Heterocyclic alkenyl" refers to a group that has a similar structure to C1-C1. 10 Divalent groups with the same structure as heterocyclic alkenyl groups.

[0568] As used in this article, the term "C6-C" 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic ring system with 6 to 60 carbon atoms as cyclic atoms, and as used herein in the term "C6-C". 60 "Arylene" refers to a divalent group in a carbocyclic aromatic ring system with 6 to 60 carbon atoms as cyclic atoms. (C6-C) 60 Non-limiting examples of aryl groups include phenyl, naphthyl, anthraceneyl, phenanthryl, pyrene, Base, etc. When C6-C 60 Aryl and C6-C 60 When each of the aryl groups comprises two or more rings, the rings may be fused together.

[0569] As used in this article, the term "C7-C" 60 "alkylaryl" refers to an alkyl group formed by at least one C1-C2 group. 54 Alkyl-substituted C6-C 59 Aryl. As used in this text, the term "C7-C" 60 "Arylalkyl" refers to an alkyl group consisting of at least one C6-C bond. 59 aryl-substituted C1-C 54 alkyl.

[0570] As used in this article, the term "C1-C" 60 "Heteroaryl" refers to a monovalent group having the following heteroaryl ring system: it has at least one heteroatom selected from B, N, O, P, Si, S, Se, and Ge as a cyclic atom, and 1 to 60 carbon atoms as cyclic atoms. The term "C1-C" is used herein. 60 "Hypo-heteroaryl" refers to a divalent group having the following heteroaromatic ring system: it has at least one heteroatom selected from B, N, O, P, Si, S, Se, and Ge as a cyclic atom, and 1 to 60 carbon atoms as cyclic atoms. C1-C 60 Non-limiting examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, etc. When C1-C... 60 heteroaryl and C1-C 60 When each heteroaryl group comprises two or more rings, the rings can fused together.

[0571] As used in this article, the term "C2-C" 60 "alkyl heteroaryl" refers to an alkyl group formed by at least one C1-C2 group. 59 Alkyl-substituted C1-C 59 heteroaryl. As used in this text, the term "C2-C" is used in conjunction with... 60 "Heteroarylalkyl" refers to an alkyl group consisting of at least one C1-C2 group. 59 heteroaryl-substituted C1-C 59 alkyl.

[0572] As used in this article, the term "C6-C" 60 "Aryloxy group" refers to -OA 102 (where A) 102 It is C6-C 60 Aryl), and as used herein, the term "C6-C" 60 "Arylthio" refers to -SA 103 (where A) 103 It is C6-C 60 Aryl).

[0573] As used in this article, the term "C1-C" 60 "Heteroaryloxy" indicates -OA 104 (where A) 104 It is C1-C 60 (Heteroaryl), and as used herein, the term "C1-C 60 "Heteroarylsulfonyl" indicates -SA 105 (where A) 105 It is C1-C 60 (Miscellaneous aromatic compounds).

[0574] As used herein, the term "monovalent nonaromatic fused polycyclic group" refers to a monovalent group (e.g., having 8 to 60 carbon atoms) that has two or more rings fused together, has only carbon atoms as cyclic atoms, and is not aromatic in terms of its overall molecular structure. Non-limiting examples of monovalent nonaromatic fused polycyclic groups include fluorene groups, etc. As used herein, the term "divalent nonaromatic fused polycyclic group" refers to a divalent group having the same structure as a monovalent nonaromatic fused polycyclic group.

[0575] As used herein, the term "monovalent nonaromatic fused heterocyclic group" refers to a monovalent group (e.g., having 1 to 60 carbon atoms) that has two or more fused rings, has heteroatoms selected from B, N, O, P, Si, S, Se, and Ge as cyclic atoms in addition to carbon atoms, and is not aromatic in relation to its overall molecular structure. Non-limiting examples of monovalent nonaromatic fused heterocyclic groups include carbazole groups, etc. As used herein, the term "divalent nonaromatic fused heterocyclic group" refers to a divalent group having the same structure as a monovalent nonaromatic fused heterocyclic group.

[0576] As used in this article, the term "C5-C" 30 A "carbocyclic group" refers to a saturated or unsaturated cyclic group having only 5 to 30 carbon atoms as cyclic atoms. (C5-C) 30 The carbocyclic group can be a monocyclic or polycyclic group. For example, as used herein, "(unsubstituted or with at least one R)" 1a (Replacement) C5-C 30 Examples of "carbocyclic groups" may include (each unsubstituted or substituted with at least one R) 1a 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, indene group, fluorene group, etc.

[0577] As used in this article, the term "C1-C" 30 A "heterocyclic group" refers to a saturated or unsaturated cyclic group that, in addition to 1 to 30 carbon atoms as cyclic atoms, has at least one heteroatom selected from B, N, O, Si, P, S, Se, and Ge as a cyclic atom. C1-C 30 Heterocyclic groups can be monocyclic or polycyclic. As used herein, “(unsubstituted or with at least one R)” 1a (Replacement) C1-C 30Non-limiting examples of "heterocyclic groups" may include (each unsubstituted or with at least one R) 1a Substituted thiophene group, furan group, pyrrole group, thiophene group, borocyclopentadien group, phosphacyclopentadien group, selenophene group, germanium heterocyclopentadien group, benzothiophene group, benzofuran group, indole group, benzothiophene group, benzoboron heterocyclopentadien group, benzophosphacyclopentadien group, benzoselenophene group, benzogermanium heterocyclopentadien group, dibenzothiophene group, dibenzofuran group, carbazole group, dibenzothiophene group, dibenzoboron heterocyclopentadien group, dibenzophosphacyclopentadien group, dibenzoselenophene group, dibenzogermanium heterocyclopentadien group, dibenzothiophene 5-oxide group, 9H-fluorene-9-one group, dibenzothiophene 5,5-dioxide group, azabenzothiophene group, azabenzofuran group, azaindole group, azaindene group, nitrogen The following groups are listed: benzothiophene group, azibabenzoborane group, azibabenzophosphacyclopentadiene group, azibabenzoselenophene group, azibabenzogeranecyclopentadiene group, azibadibenzothiophene group, azibadibenzofuran group, azibacarbazole group, azibafluorene group, azibadibenzothiophene group, azibadibenzoboranecyclopentadiene group, azibadibenzophosphacyclopentadiene group, azibadibenzoselenophene group, azibadibenzogeranecyclopentadiene group, azibadibenzothiophene 5-oxide group, aziba-9H-fluorene-9-one group, azibadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazolinine group, phenanthrene-rhein group, pyrazole group, imidazole group, triazole group. azole group, iso- azole group, thiazole group, isothiazole group, Diazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzo[] azole group, benzothiazole group, benzo[] Diazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group, 5,6,7,8-tetrahydroquinoline group, etc.

[0578] As used in this article, "TMS" stands for *-Si(CH3)3 and "TMG" stands for *-Ge(CH3)3.

[0579] As used in this article, the term "(C1-C" is similar to the term "(C1-C)" 20 (alkyl)X group (e.g., (C1-C) 20 Alkyl)phenyl) refers to a compound formed by at least one C1-C 20 Alkyl-substituted X group (e.g., phenyl).

[0580] Unless otherwise stated, C5-C is the replacement. 30Carbocyclic 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 60 At least one substituent of the heteroaryl thio group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heterocyclic group may be:

[0581] Deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 alkoxy, or C1-C 60 Alkylthio;

[0582] Each of the following C1-C is replaced: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 alkoxy, or C1-C 60Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 11 (Q) 12 (Q) 13 -Ge(Q) 11 (Q) 12 (Q) 13 -C(Q) 11 (Q) 12 (Q) 13 -B(Q) 11 (Q) 12 -N(Q) 11 (Q) 12 -P(Q) 11 (Q) 12 -C(=O)(Q) 11 -S(=O)(Q) 11 -S(=O)2(Q) 11 -P(=O)(Q) 11 (Q) 12 -P(=S)(Q) 11 (Q) 12 ), or combinations thereof;

[0583] 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-C60 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;

[0584] Each of the following C3-C is replaced: 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid groups or their salts, sulfonic acid groups or their salts, phosphate groups or their salts, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 21 (Q) 22 (Q)23 )、 -Ge(Q 21 )(Q 22 )(Q 23 )、 -C(Q 21 )(Q 22 )(Q 23 )、 -B(Q 21 )(Q 22 )、 -N(Q 21 )(Q 22 )、 -P(Q 21 )(Q 22 )、 -C(=O)(Q 21 )、 -S(=O)(Q 21 )、 -S(=O)2(Q 21 )、 -P(=O)(Q 21 )(Q 22 )、 -P(=S)(Q 21 )(Q 22 )、 or a combination thereof;

[0585] -Si(Q 31 )(Q 32 )(Q 33 )、 -Ge(Q 31 )(Q 32 )(Q 33 )、 -C(Q 31 )(Q 32 )(Q 33 )、 -B(Q 31 s )(Q 32 )、 -N(Q 31 )(Q 32 )、 -P(Q 31 )(Q 32 )、 -C(=O)(Q 31 )、 -S(=O)(Q 31 )、 -S(=O)2(Q 31 )、 -P(=O)(Q 31 )(Q 32 )、 or -P(=S)(Q 31 )(Q 32 ), and

[0586] Q1 to Q3, Q 11 to Q 13 、 Q 21 to Q 23 、 and Q 31 to Q 33Each group can independently be hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C1-C 60 Alkylthio, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 arylalkyl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, or substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups.

[0587] The compounds and organic light-emitting devices according to one or more embodiments will be described in further detail below with reference to synthesis examples and embodiments. However, the following examples are not intended to limit the scope of the embodiments described herein. The phrase "using 'B' instead of 'A'" used in describing the synthesis examples means that the amount of 'A' used is the same as the amount of 'B' used in molar equivalents.

[0588] Example

[0589] Synthesis Example 1: Synthesis of Compound 3

[0590]

[0591] (1) Synthesis of intermediate L2-3

[0592] Under a nitrogen atmosphere, compound L3-3 (4.75 g, 15.0 mmol), 1-bromo-3-iodobenzene-2,4,5,6-d4 (4.73 g, 16.5 mmol), CuI (0.86 g, 4.50 mmol), pyridinecarboxylic acid (1.11 g, 9.0 mmol), and K3PO4 (6.37 g, 30.0 mmol) were mixed with 100 mL of dimethyl sulfoxide (DMSO) and stirred at 80 °C for 12 h. After the reaction was complete, the mixture was cooled to room temperature and subjected to extraction with saturated aqueous NH4Cl solution and ethyl acetate (EA). The extracted organic layer was dried over anhydrous MgSO4 and filtered, and the filtrate was concentrated under reduced pressure. The resulting product was purified by silica gel column chromatography to obtain intermediate L2-3 (5.56 g, 11.70 mmol, 78% yield).

[0593] Liquid chromatography-mass spectrometry (LC-MS) (calculated value 474.12 g / mol, measured value M) +1 = 475 g / mol).

[0594] (2) Synthesis of intermediate L1-3

[0595] Under a nitrogen atmosphere, intermediate L2-3 (5.56 g, 11.70 mmol), compound L4-3 (5.46 g, 11.70 mmol), tris(dibenzylacetone)dipalladium(O)(Pd2(dba)3) (1.07 g, 1.17 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos) (0.96 g, 2.34 mmol), and sodium tert-butoxide (NaOtBu) (1.69 g, 17.55 mmol) were mixed with 117 mL of toluene and stirred at 100 °C for 2 hours. After the reaction was complete, the mixture was cooled to room temperature, and the organic layer obtained by extraction with saturated ammonium chloride aqueous solution and dichloromethane (MC) was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The product was purified by silica gel column chromatography to obtain intermediate L1-3 (8.06 g, 9.36 mmol, 80% yield).

[0596] LC-MS (calculated value 860.44 g / mol, measured value M) +1 = 861 g / mol).

[0597] (3) Synthesis of intermediate L-3

[0598] Under a nitrogen atmosphere, intermediate L1-3 (8.06 g, 9.36 mmol) and 36% HCl (0.96 mL, 11.23 mmol) were mixed with triethyl orthoformate (69.4 mL, 468 mmol), and then stirred at 80 °C for 3 hours. After the reaction was complete, the mixture was cooled to room temperature and concentrated under reduced pressure. The resulting product was purified by silica gel column chromatography to obtain intermediate L-3 (7.89 g, 8.70 mmol, 93% yield).

[0599] LC-MS (calculated value 905.39 g / mol, measured value M) +1 = 906 g / mol).

[0600] (4) Synthesis of compound 3

[0601] Under a nitrogen atmosphere, intermediate L-3 (7.89 g, 8.70 mmol), Pt(acac)2 (3.76 g, 9.57 mmol), and 2,6-dimethylpyridine (3.0 mL, 26.10 mmol) were mixed with 218 mL of propionic acid and stirred at 150 °C for 12 hours. After the reaction was complete, the mixture was cooled to room temperature. The precipitate formed was filtered after adding 200 mL of deionized (DI) water. The filtrate was concentrated and the result was completely dissolved in MC and extracted using a saturated aqueous solution of sodium bicarbonate (NaHCO3) and MC. The resulting organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The product was purified by silica gel column chromatography to obtain compound 3 (4.62 g, 4.35 mmol, 50% yield).

[0602] LC-MS (calculated value 1062.37 g / mol, measured value M) +1 = 1063 g / mol).

[0603] Synthesis Example 2: Synthesis of Compound 4

[0604]

[0605] (1) Synthesis of intermediate L2-4

[0606] Since it is made of the same material as intermediate L2-3 in synthesis example 1, intermediate L2-4 was synthesized using the same method.

[0607] (2) Synthesis of intermediate L1-4

[0608] Intermediate L1-4 was synthesized in the same manner as intermediate L1-3 in Synthesis Example 1, except that compound L4-4 was used instead of compound L4-3.

[0609] (3) Synthesis of intermediate L-4

[0610] Intermediate L-4 was synthesized in the same manner as intermediate L-3 in synthesis example 1, except that intermediate L1-4 was used instead of intermediate L1-3.

[0611] (4) Synthesis of compound 4

[0612] Under a nitrogen atmosphere, intermediate L-4 (7.70 g, 8.0 mmol), Pt(acac)2 (3.46 g, 8.8 mmol), and 2,6-dimethylpyridine (2.77 mL, 24.0 mmol) were mixed with 200 mL of propionic acid and stirred at 150 °C for 12 hours. After the reaction was complete, the mixture was cooled to room temperature. The precipitate formed was filtered after adding 200 mL of DI water. The filtrate was concentrated and the result was completely dissolved in MC and extracted using a saturated sodium bicarbonate aqueous solution and MC. The resulting organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The product was purified by silica gel column chromatography to obtain compound 4 (4.75 g, 4.24 mmol, 53% yield).

[0613] LC-MS (calculated value 1118.43 g / mol, measured value M) +1 = 1119 g / mol).

[0614] Synthesis Example 3: Synthesis of Compound 6

[0615]

[0616] (1) Synthesis of intermediate L2-6

[0617] Since it is made of the same material as intermediate L2-3 in synthesis example 1, intermediate L2-6 was synthesized using the same method.

[0618] (2) Synthesis of intermediate L1-6

[0619] Intermediate L1-6 was synthesized in the same manner as intermediate L1-3 in Synthesis Example 1, except that compound L4-6 was used instead of compound L4-3.

[0620] (3) Synthesis of intermediate L-6

[0621] Intermediate L-6 was synthesized in the same manner as intermediate L-3 in synthesis example 1, except that intermediate L1-6 was used instead of intermediate L1-3.

[0622] (4) Synthesis of compound 6

[0623] Under a nitrogen atmosphere, intermediate L-6 (7.25 g, 8.0 mmol), Pt(acac)2 (3.46 g, 8.8 mmol), and 2,6-dimethylpyridine (2.77 mL, 24.0 mmol) were mixed with 200 mL of propionic acid and stirred at 150 °C for 12 hours. After the reaction was complete, the mixture was cooled to room temperature. The precipitate formed was filtered after adding 200 mL of DI water. The filtrate was concentrated and the result was completely dissolved in MC and extracted using a saturated aqueous sodium bicarbonate solution and MC. The resulting organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The product was purified by silica gel column chromatography to obtain compound 6 (4.51 g, 4.24 mmol, 53% yield).

[0624] LC-MS (calculated value 1062.37 g / mol, measured value M) +1 = 1063 g / mol).

[0625] Synthesis Example 4: Synthesis of Compound 7

[0626]

[0627] (1) Synthesis of intermediate L2-7

[0628] Since it is made of the same material as intermediate L2-3 in synthesis example 1, intermediate L2-7 was synthesized using the same method.

[0629] (2) Synthesis of intermediate L1-7

[0630] Intermediate L1-7 was synthesized in the same manner as intermediate L1-3 in Synthesis Example 1, except that compound L4-7 was used instead of compound L4-3.

[0631] (3) Synthesis of intermediate L-7

[0632] Intermediate L-7 was synthesized in the same manner as intermediate L-3 in synthesis example 1, except that intermediate L1-7 was used instead of intermediate L1-3.

[0633] (4) Synthesis of compound 7

[0634] Under a nitrogen atmosphere, intermediate L-7 (7.70 g, 8.0 mmol), Pt(acac)2 (3.46 g, 8.8 mmol), and 2,6-dimethylpyridine (2.77 mL, 24.0 mmol) were mixed with 200 mL of propionic acid and stirred at 150 °C for 12 hours. After the reaction was complete, the mixture was cooled to room temperature. The precipitate formed was filtered after adding 200 mL of DI water. The filtrate was concentrated and the result was completely dissolved in MC and extracted using a saturated aqueous sodium bicarbonate solution and MC. The resulting organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The product was purified by silica gel column chromatography to obtain compound 7 (4.39 g, 3.92 mmol, 49% yield).

[0635] LC-MS (calculated value 1118.43 g / mol, measured value M) +1 = 1119 g / mol).

[0636] Synthesis Example 5: Synthesis of Compound 8

[0637]

[0638] (1) Synthesis of intermediate L2-8

[0639] Since it is made of the same material as intermediate L2-3 in synthesis example 1, intermediate L2-8 was synthesized using the same method.

[0640] (2) Synthesis of intermediate L1-8

[0641] Intermediate L1-8 was synthesized in the same manner as intermediate L1-3 in Synthesis Example 1, except that compound L4-8 was used instead of compound L4-3.

[0642] (3) Synthesis of intermediate L-8

[0643] Intermediate L-8 was synthesized in the same manner as intermediate L-3 in Synthesis Example 1, except that intermediate L1-8 was used instead of intermediate L1-3.

[0644] (4) Synthesis of compound 8

[0645] Under a nitrogen atmosphere, intermediate L-8 (8.15 g, 8.0 mmol), Pt(acac)2 (3.46 g, 8.8 mmol), and 2,6-dimethylpyridine (2.77 mL, 24.0 mmol) were mixed with 200 mL of propionic acid and stirred at 150 °C for 12 hours. After the reaction was complete, the mixture was cooled to room temperature. The precipitate formed was filtered after adding 200 mL of DI water. The filtrate was concentrated and the result was completely dissolved in MC and extracted using a saturated sodium bicarbonate aqueous solution and MC. The resulting organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The product was purified by silica gel column chromatography to obtain compound 8 (4.89 g, 4.16 mmol, 52% yield).

[0646] LC-MS (calculated value 1174.49 g / mol, measured value M) +1 = 1175 g / mol).

[0647] Synthesis Example 6: Synthesis of Compound 19

[0648]

[0649] (1) Synthesis of intermediate L2-19

[0650] Intermediate L2-19 was synthesized in the same manner as intermediate L2-3 in Synthesis Example 1, except that compound L3-19 was used instead of compound L3-3.

[0651] (2) Synthesis of intermediate L1-19

[0652] Intermediate L1-19 was synthesized in the same manner as intermediate L1-3 in Synthesis Example 1, except that intermediate L2-19 was used instead of intermediate L2-3 and compound L4-19 was used instead of compound L4-3.

[0653] (3) Synthesis of intermediate L-19

[0654] Intermediate L-19 was synthesized in the same manner as intermediate L-3 in synthesis example 1, except that intermediate L1-19 was used instead of intermediate L1-3.

[0655] (4) Synthesis of compound 19

[0656] Under a nitrogen atmosphere, intermediate L-19 (7.83 g, 8.0 mmol), Pt(acac)2 (3.46 g, 8.8 mmol), and 2,6-dimethylpyridine (2.77 mL, 24.0 mmol) were mixed with 200 mL of propionic acid and stirred at 150 °C for 12 hours. After the reaction was complete, the mixture was cooled to room temperature. The precipitate formed was filtered after adding 200 mL of DI water. The filtrate was concentrated and the result was completely dissolved in MC and extracted using a saturated aqueous sodium bicarbonate solution and MC. The resulting organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The product was purified by silica gel column chromatography to obtain compound 19 (4.99 g, 4.40 mmol, 55% yield).

[0657] LC-MS (calculated value 1134.46 g / mol, measured value M) +1 = 1135 g / mol).

[0658] Synthesis Example 7: Synthesis of Compound 65

[0659]

[0660] (1) Synthesis of intermediate L2-65

[0661] Since it is made of the same material as intermediate L2-3 in synthesis example 1, intermediate L2-65 was synthesized using the same method.

[0662] (2) Synthesis of intermediate L1-65

[0663] Intermediate L1-65 was synthesized in the same manner as intermediate L1-3 in Synthesis Example 1, except that compound L4-65 was used instead of compound L4-3.

[0664] (3) Synthesis of intermediate L-65

[0665] Intermediate L-65 was synthesized in the same manner as intermediate L-3 in synthesis example 1, except that intermediate L1-65 was used instead of intermediate L1-3.

[0666] (4) Synthesis of compound 65

[0667] Under a nitrogen atmosphere, intermediate L-65 (7.29 g, 8.0 mmol), Pt(acac)2 (3.46 g, 8.8 mmol), and 2,6-dimethylpyridine (2.77 mL, 24.0 mmol) were mixed with 200 mL of propionic acid and stirred at 150 °C for 12 hours. After the reaction was complete, the mixture was cooled to room temperature. The precipitate formed was filtered after adding 200 mL of DI water. The filtrate was concentrated and the result was completely dissolved in MC and extracted using a saturated aqueous sodium bicarbonate solution and MC. The resulting organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The product was purified by silica gel column chromatography to obtain compound 65 (4.27 g, 4.0 mmol, 50% yield).

[0668] LC-MS (calculated value 1067.40 g / mol, measured value M) +1 = 1068 g / mol).

[0669] Synthesis Example 8: Synthesis of Compound 73

[0670]

[0671] (1) Synthesis of intermediate L2-73

[0672] Since it is made of the same material as intermediate L2-19 in synthesis example 6, intermediate L2-73 was synthesized using the same method.

[0673] (2) Synthesis of intermediate L1-73

[0674] Intermediate L1-73 was synthesized in the same manner as intermediate L1-19 in Synthesis Example 6, except that compound L4-73 was used instead of compound L4-19.

[0675] (3) Synthesis of intermediate L-73

[0676] Intermediate L-73 was synthesized in the same manner as intermediate L-3 in synthesis example 1, except that intermediate L1-73 was used instead of intermediate L1-3.

[0677] (4) Synthesis of compound 73

[0678] Under a nitrogen atmosphere, intermediate L-73 (7.42 g, 8.0 mmol), Pt(acac)2 (3.46 g, 8.8 mmol), and 2,6-dimethylpyridine (2.77 mL, 24.0 mmol) were mixed with 200 mL of propionic acid and stirred at 150 °C for 12 hours. After the reaction was complete, the mixture was cooled to room temperature. The precipitate formed was filtered after adding 200 mL of DI water. The filtrate was concentrated and the result was completely dissolved in MC and extracted using a saturated aqueous sodium bicarbonate solution and MC. The resulting organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The product was purified by silica gel column chromatography to obtain compound 73 (4.60 g, 4.24 mmol, 53% yield).

[0679] LC-MS (calculated value 1083.42 g / mol, measured value M) +1 = 1084 g / mol).

[0680] Example 1

[0681] The ITO glass substrate was cut into 50 mm × 50 mm × 0.5 mm pieces, and then ultrasonically treated with acetone, isopropanol, and DI water for 15 minutes each. It was then cleaned by exposure to UV and ozone for 30 minutes. The resulting ITO glass substrate was then loaded into a vacuum deposition apparatus.

[0682] Subsequently, m-MTDATA was deposited on the ITO electrode (i.e., anode) of the glass substrate at a deposition rate of 1 Å / s to form a hole injection layer with a thickness of 600 Å, and α-NPD was deposited on the hole injection layer at a deposition rate of 1 Å / s to form a hole transport layer with a thickness of 250 Å.

[0683] Compound 3 (as a dopant) and CBP (as the host) were co-deposited on the hole transport layer at deposition rates of 0.1 Å / s and 1 Å / s, respectively, to form an emitter layer with a thickness of 400 Å.

[0684] A hole-blocking layer with a thickness of 50 Å is formed by depositing BAlq on the emitter layer at a deposition rate of 1 Å / s, an electron transport layer with a thickness of 300 Å is formed by depositing Alq3 on the hole-blocking layer, an electron injection layer with a thickness of 10 Å is formed by depositing LiF on the electron transport layer, and Al is vacuum-deposited on the electron injection layer to form a second electrode (i.e., cathode) with a thickness of 1,200 Å, thereby completing the fabrication of an organic light-emitting device with the structure ITO / m-MTDATA (600 Å) / α-NPD (250 Å) / CBP + compound 3 (10 wt%) (400 Å) / BAlq (50 Å) / Alq3 (300 Å) / LiF (10 Å) / Al (1,200 Å).

[0685]

[0686] Examples 2 to 8 and Comparative Examples 1 and 2

[0687] The organic light-emitting device was manufactured in the same manner as in Example 1, except that the compounds shown in Table 1 were used instead of compound 3 as dopants when forming the emission layer.

[0688] Evaluation Example 1: Characterization of Organic Light-Emitting Devices

[0689] Regarding the organic light-emitting devices of Examples 1 to 8 and Comparative Examples 1 and 2, the emission peak wavelength (maximum emission peak wavelength, λ) of the electroluminescence (EL) spectrum was evaluated. max External quantum efficiency (EQE, relative %) at 1000 cd / m² 2 (below), and lifetime characteristics (T) 95 The relative percentages are shown in Table 1. The EL spectra of each organic light-emitting device (at 1000 cd / m²) were evaluated using a luminance meter (Minolta Cs-1000A). 2 The emission peak wavelength (below) was measured. EQE was evaluated using a luminance meter (Minolta Cs-1000A). In Table 1, the EQE of the organic light-emitting devices in the examples and comparative examples is expressed as a relative value (%) relative to Comparative Example 2. Lifetime characteristics (LT) 95 The initial brightness was achieved by measuring the brightness to 100% (at 1000 cd / m²). 2 The time required to evaluate 95% of the results (below) is recorded in Table 1 as a relative value to Comparative Example 2.

[0690] Table 1

[0691]

[0692]

[0693] Referring to Table 1, it is confirmed that the organic light-emitting devices according to one or more embodiments have excellent EQE and long lifetime, and are suitable for deep blue light emission. In particular, compared with those of the organic light-emitting devices of Comparative Examples 1 and 2, the organic light-emitting devices of Examples 1 to 8 have higher or comparable EQE and significantly better lifetime characteristics.

[0694] Example 9

[0695] The organic light-emitting device was fabricated in the same manner as in Example 1, except that, when forming the emission layer, compound 4 (sensitizer), compounds BD1-6 (emitter), and CBP (body) were co-deposited to a thickness of 400 Å in a weight ratio of 10:1.5:88.5.

[0696] Comparative Example 3

[0697] The organic light-emitting device was fabricated in the same manner as in Example 9, except that, when forming the emission layer, compounds BD1-6 (emitter) and CBP (body) were co-deposited at a weight ratio of 10:90 to a thickness of 400 Å, instead of using compound 4.

[0698] Evaluation of Example 2

[0699] Regarding the organic light-emitting devices of Example 9 and Comparative Example 3, the emission peak wavelength and EQE (relative %) of the EL spectrum were evaluated as described above in Evaluation Example 1. 2 (below), and lifespan (T) 95 The y-values ​​of the chromatic coordinates (CIEy) were evaluated, and the results are shown in Table 2. Lifetime (T) 95 The initial brightness was achieved by measuring the brightness to 100% (at 1000 cd / m²). 2 The evaluation time is 95% of the time required for the organic light-emitting devices of Example 9 and Comparative Example 3. In Table 2, the EQE and lifetime of the organic light-emitting devices of Example 9 and Comparative Example 3 are expressed as relative values ​​(%).

[0700] Table 2

[0701]

[0702]

[0703] Referring to Table 2, it is confirmed that, compared with the organic light-emitting devices of Comparative Example 3, the organic light-emitting device of Example 9, which includes compound 4 as a sensitizer, has excellent EQE and excellent lifetime characteristics, and the organic light-emitting device of Example 9 emits blue light with excellent color purity.

[0704] Organometallic compounds represented by Formula 1 exhibit excellent photochemical stability, and organic light-emitting devices using at least one organometallic compound represented by Formula 1 can achieve improved efficiency and lifetime. Therefore, high-quality organic light-emitting devices can be realized by using organometallic compounds represented by Formula 1.

[0705] It should be understood that the embodiments described herein are to be considered in a descriptive sense only and are not intended for limiting purposes. The descriptions of features or aspects in each embodiment should typically be considered applicable to other similar features or aspects in other embodiments. Although one or more embodiments have been described with reference to the accompanying drawings, those skilled in the art will understand that various changes in form and detail may be made therein without departing from the spirit and scope defined by the appended claims.

Claims

1. Organometallic compounds, represented by Formula 1: Formula 1 in, In Equation 1, M1 is a transition metal. Y2 is either C or N. Y3 is either C or N. Rings CY1, CY3 to CY5, and CY 11 To CY 13 Each independently is C5-C 60 Carbocyclic groups or C1-C 60 Heterocyclic groups, L1 represents a single bond, O, S, Se, or N(R). 61 ), B(R) 61 ), C(R 61 (R) 62 ), or Si(R) 61 (R) 62 ), a1 is 1, 2, 3, 4, or 5. R 10 R 30 R 40 R 50 R 61 and R 62 Each of the following groups is independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C1-C 60 Alkylthio, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 arylalkyl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -C(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2), or -P(=S)(Q1)(Q2), R 20 It is a deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C1-C 60 Alkylthio, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 arylalkyl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -C(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P(Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2), or -P(=S)(Q1)(Q2), R 10 R 30 R 40 R 50 R 61 and R 62 At least two adjacent groups in the form optionally combine to form a substituted or unsubstituted C5-C 30 The carbocyclic group is either substituted or unsubstituted C1-C. 30 Heterocyclic groups, b1, b3 to b5, and b11 to b13 are each independently 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. b2 is 0, 1, or 2. 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 60 At least one substituent of the heteroaryl thio group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heterocyclic group is: Deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 alkoxy, or C1-C 60 Alkylthio; Each of the following C1-C is replaced: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 alkoxy, or C1-C 60 Alkylthio groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 11 (Q) 12 (Q) 13 -Ge(Q) 11 (Q) 12 (Q) 13 -C(Q) 11 (Q) 12 (Q) 13 -B(Q) 11 (Q) 12 -N(Q) 11 (Q) 12 -P(Q) 11 (Q) 12 -C(=O)(Q) 11 -S(=O)(Q) 11 -S(=O)2(Q) 11 -P(=O)(Q) 11 (Q) 12 -P(=S)(Q) 11 (Q) 12 ), or combinations thereof; C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups; Each of the following C3-C is replaced: 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid groups or their salts, sulfonic acid groups or their salts, phosphate groups or their salts, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 Arylalkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 Heteroaryl thiols, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -Si(Q) 21 (Q) 22 (Q) 23 -Ge(Q) 21 (Q) 22 (Q) 23 -C(Q) 21 (Q) 22 (Q) 23 -B(Q) 21 (Q) 22 -N(Q) 21 (Q) 22 -P(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)(Q) 21 -S(=O)2(Q) 21 -P(=O)(Q) 21 (Q) 22 -P(=S)(Q) 21 (Q) 22 ), or combinations thereof; or -Si(Q 31 )(Q 32 )(Q 33 )、-Ge(Q 31 )(Q 32 )(Q 33 )、-C(Q 31 )(Q 32 )(Q 33 )、-B(Q 31 )(Q 32 )、-N(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)(Q 31 )、-S(=O)2(Q 31 )、-P(=O)(Q 31 )(Q 32 )、or -P(=S)(Q 31 )(Q 32 ),and Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 , and Q 31 To Q 33 Each of the following groups is independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 alkenyl, substituted or unsubstituted C2-C 60 Alkyne, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C1-C 60 Alkylthio, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 arylalkyl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C1-C 60 Heteroaryl thiols, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, or substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups.

2. The organometallic compound according to claim 1, wherein M1 is 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).

3. The organometallic compound according to claim 1, wherein rings CY1, CY3 to CY5, and CY6 are... 11 To CY 13 Each group can be independently a phenyl group, naphthyl group, phenanthrene group, furan group, thiophene group, pyrrole group, cyclopentene group, thiophene group, germanium heterocyclopentadienyl group, benzofuran group, benzothiophene group, indole group, indene group, benzothiophene group, benzogermanium heterocyclopentadienyl group, dibenzofuran group, dibenzothiophene group, carbazole group, fluorene group, dibenzothiophene group, dibenzogermanium heterocyclopentadienyl group, pyridine group, pyrimidine group, pyridazine group, or pyrazine group.

4. The organometallic compound according to claim 1, wherein... Y2 is C, and Y3 is N.

5. The organometallic compound according to claim 1, wherein R 20 It is a methyl group, -CD3, -CD2H, -CDH2, or a group represented by one of formulas 9-1 to 9-39 or 9-44 to 9-61: in, In equations 9-1 to 9-39 and 9-44 to 9-61, * indicates a binding site with an adjacent atom.

6. The organometallic compound according to claim 1, wherein b2 is 0.

7. The organometallic compound according to claim 1, wherein R 10 R 30 R 40 R 50 R 61 and R 62 Each independently is: Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl, C1-C 20 alkoxy, or C1-C 20 Alkylthio; 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, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl, deuterated C1-C 20 Alkyl, fluorinated C1-C 20 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, 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) 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[2.2.1]heptyl, (C1-C 20 Alkyl)bicyclo[2.2.2]octyl, silylcyclopentyl, phenyl, (C1-C 20 Alkyl)phenyl, biphenyl, terphenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, pyridyl, pyrimidinyl, or combinations thereof; Each of the following substituted compounds, either unsubstituted or substituted with: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, silanecyclopentyl, phenyl, (C1-C 20 Alkyl)phenyl, biphenyl, terphenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, 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, -SF5, -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, deuterated C1-C 20 Alkyl, fluorinated C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, 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) 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[2.2.1]heptyl, (C1-C 20 Alkyl)bicyclo[2.2.2]octyl, silylcyclopentyl, phenyl, (C1-C 20 Alkyl)phenyl, biphenyl, terphenyl, naphthyl, 1,2,3,4-tetrahydronaphthyl, 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 -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -C(Q1)(Q2)(Q3), -B(Q1)(Q2), -N(Q1)(Q2), -P( Q1)(Q2), -C(=O)(Q1), -S(=O)(Q1), -S(=O)2(Q1), -P(=O)(Q1)(Q2), or -P(=S)(Q1)(Q2).

8. The organometallic compound according to claim 1, wherein the organometallic compound is represented by formula 11: Formula 11 in, In Equation 11, M1, Y2, Y3, L1, a1, R 20 b1 and b2 are each as described in claim 1. X1 is C(R1) or N, X2 is C(R2) or N, and X3 is C(R3) or N. X4 is C(R4) or N, X5 is C(R5) or N, X6 is C(R6) or N, and X7 is C(R7) or N. X8 is C(R8) or N, X9 is C(R9) or N, X 10 For C(R) 10 ) or N, and X 11 For C(R) 11 ) or N, X 12 For C(R) 12 ) or N, X 13 For C(R) 13 ) or N, X 14 For C(R) 14 ) or N, and X 15 For C(R) 15 ) or N, X 31 For C(R) 31 ) or N, and X 32 For C(R) 32 ) or N, X 41 For C(R) 41 ) or N, X 42 For C(R) 42 ) or N, X 43 For C(R) 43 ) or N, and X 44 For C(R) 44 ) or N, X 51 For C(R) 51 ) or N, X 52 For C(R) 52 ) or N, X 53 For C(R) 53 ) or N, and X 54 For C(R) 54 ) or N, R1 to R 15 As in claim 1 regarding R 10 As described, R 31 and R 32 As in claim 1 regarding R 30 As described, R 41 To R 44 As in claim 1 regarding R 40 The description, and R 51 To R 54 As in claim 1 regarding R 50 As described.

9. The organometallic compound according to claim 1, wherein the organometallic compound is represented by any one of formulas 21 to 27: Formula 21 Formula 22 Formula 23 Formula 24 Formula 25 Formula 26 Formula 27 in, In equations 21 to 27, M1, L1, and a1 as described in claim 1, R 21 To R 23 As in claim 1 regarding R 20 The described condition is R 21 To R 23 None of them are deuterium. R1 to R 15 As in claim 1 regarding R 10 As described, R 31 and R 32 As in claim 1 regarding R 30 As described, R 41 To R 44 As in claim 1 regarding R 40 The description, and R 51 To R 54 As in claim 1 regarding R 50 As described.

10. The organometallic compound according to claim 1, wherein the organometallic compound is one of compounds 1 to 180: 。 11. Organic light-emitting devices, including: First electrode; Second electrode; as well as An organic layer disposed between the first electrode and the second electrode, wherein The organic layer comprises at least one organometallic compound according to any one of claims 1 to 10.

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

13. The organic light-emitting device of claim 12, wherein the emitting layer emits light having a maximum emission wavelength of 400 nanometers to 490 nanometers.

14. The organic light-emitting device according to claim 12, wherein the emitting layer comprises a body and an emitter, and The emitter includes at least one organometallic compound.

15. The organic light-emitting device according to claim 12, wherein the emitting layer comprises a host, a sensitizer, and an emitter, and The sensitizer includes at least one organometallic compound.

16. The organic light-emitting device according to claim 14 or 15, wherein the host comprises a hole transport host, an electron transport host, a bipolar host, or a combination thereof.

17. The organic light-emitting device according to claim 15, wherein the emitter is a metal-free organic compound.

18. The organic light-emitting device of claim 15, wherein the host and the sensitizer are substantially non-emitting light, and the emitter emits light.

19. The organic light-emitting device of claim 12, wherein the organic layer further comprises a hole transport region disposed between the first electrode and the emitting layer, and an electron transport region disposed between the emitting layer and the second electrode. The hole transport region includes at least one of a hole injection layer, a hole transport layer, or an electron blocking layer. The electron transport region includes at least one of a hole blocking layer, an electron transport layer, or an electron injection layer, and At least one of the hole transport region and the electron transport region optionally includes the at least one organometallic compound.

20. An electronic device, including an organic light-emitting device according to any one of claims 11 to 19.

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