Organometallic compounds, organic light-emitting devices including the same, and diagnostic compositions including the same.

Abstract

This invention relates to organometallic compounds represented by Formula 1, organic light-emitting devices comprising the same, and diagnostic compositions comprising the same, wherein, in Formula 1, Y2, ring CY2, R1-R8, R 20 A1-A7 and d2 can each be independently identical to those described in the specification. Equation 1

Description

[0001] Cross-reference to related applications

[0002] This application claims priority and benefits, and all benefits arising therefrom, to Korean Patent Application No. 10-2019-0037212 filed on March 29, 2019 and Korean Patent Application No. 10-2019-0136671 filed on October 30, 2019, the entire contents of which are incorporated herein by reference. Technical Field

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

[0004] Organic light-emitting devices (OLEDs) are self-emitting devices that produce full-color images. In addition, OLEDs have a wide viewing angle and exhibit excellent driving voltage and response speed characteristics.

[0005] An OLED comprises an anode, a cathode, and an organic layer between the anode and cathode, including an emitter layer. A hole transport region is located between the anode and the emitter layer, and an electron transport region is located between the emitter layer and the cathode. Holes supplied from the anode can move towards the emitter layer through the hole transport region, and electrons supplied from the cathode can move towards the emitter layer through the electron transport region. Holes and electrons recombine in the emitter layer to generate excitons. These excitons transition from an excited state to the ground state, thereby producing light.

[0006] In addition, luminescent compounds, such as phosphorescent compounds, can also be used to monitor, sense, or detect biological materials, including a variety of cells and proteins. Summary of the Invention

[0007] Provided are organometallic compounds, organic light-emitting devices comprising said organometallic compounds, and diagnostic compositions comprising said organometallic compounds.

[0008] Additional aspects will be set forth in part in the following description, and in part will be apparent from the description, or may be learned through practice of the presented embodiments.

[0009] According to one embodiment, the organometallic compound can be represented by Formula 1:

[0010] Formula 1

[0011]

[0012] In Equation 1,

[0013] Y2 can be C,

[0014] Cyclic CY2 can be C5-C 30 Carbocyclic groups or C1-C 30 Heterocyclic groups,

[0015] R1-R8, R 20 A7 can be 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 C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C2-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9),

[0016] d2 can be an integer from 0 to 10, and when d2 is 2 or greater, two or more R 20 They can be the same or different from each other.

[0017] R1-R8, R 20 At least one of the following, or any combination thereof, includes at least one fluorine group (-F).

[0018] A1-A6 can each be independently 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 C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C2-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, or substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups,

[0019] Two or more of R1-R8 are optionally connected to form an unsubstituted or at least one R 1a Replacement C5-C 30 The carbocyclic group is either unsubstituted or has at least one R group. 1a Replacement C1-C 30 Heterocyclic groups,

[0020] The quantity d2 of R 20 Two or more may be optionally connected to form an unsubstituted or R-shaped structure. 1a Replacement C5-C 30 The carbocyclic group is either unsubstituted or has at least one R group. 1a Replacement C1-C 30 Heterocyclic groups,

[0021] Two or more of A1-A7 are optionally connected to form an unsubstituted or R-shaped structure. 1a Replacement C5-C 30 The carbocyclic group is either unsubstituted or has at least one R group. 1a Replacement C1-C 30 Heterocyclic groups,

[0022] R 1a Same as described regarding A7, and

[0023] Replacement C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C3-C 10 cycloalkyl, substituted C2-C 10 Heterocyclic alkyl, substituted C3-C 10 Cycloalkenyl, substituted C2-C 10 Heterocyclic alkenyl, substituted C6-C 60 Aryl, substituted C6-C 60 aryloxy groups, substituted C6-C 60Arylthioyl, substituted C1-C 60 The substituents of heteroaryl groups, substituted monovalent non-aromatic fused polycyclic groups, and substituted monovalent non-aromatic fused heterocyclic groups are:

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

[0025] Each of the following C1-C is replaced: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, or C1-C 60 Alkoxy 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, C2-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C2-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -N(Q 11 (Q) 12 ), -Si(Q 13 (Q) 14 (Q) 15 -Ge(Q) 13 (Q) 14 (Q) 15 -B(Q) 16 (Q) 17 -P(=O)(Q) 18 (Q) 19 -P(Q) 18 (Q) 19 ), or any combination thereof;

[0026] Each of the following C3-Cs that are not substituted or are substituted: 10 cycloalkyl, C2-C10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C2-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid groups or their salts, sulfonic acid groups or their salts, phosphate groups or their salts, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C2-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C2-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -N(Q 21 (Q) 22 ), -Si(Q 23 (Q) 24 (Q) 25 -Ge(Q) 23 (Q) 24 (Q) 25 -B(Q) 26 (Q) 27 -P(=O)(Q) 28 (Q) 29 -P(Q) 28 (Q) 29 ), or any combination thereof;

[0027] -N(Q 31 (Q) 32 ), -Si(Q 33 (Q) 34 (Q) 35 -Ge(Q) 33 (Q) 34 (Q) 35 -B(Q) 36 (Q) 37 -P(=O)(Q)38 (Q) 39 ), or -P(Q 38 (Q) 39 );or

[0028] Any combination of them,

[0029] Among them, Q1-Q9, Q 11 -Q 19 Q 21 -Q 29 , and Q 31 -Q 39 Each of these groups is independently hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; amidine; hydrazine; hydrazone; carboxylic acid group or its salt; sulfonic acid group or its salt; phosphate group or its salt; unsubstituted or deuterated, C1-C 60 Alkyl, C6-C 60 C1-C substituted with aryl or any combination thereof 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkyne group; C1-C 60 Alkoxy group; C3-C 10 cycloalkyl; C2-C 10 Heterocyclic alkyl; C3-C 10 Cycloalkenyl; C2-C 10 Heterocyclic alkenyl; unsubstituted or deuterated, C1-C 60 Alkyl, C6-C 60 C6-C substituted with aryl or any combination thereof 60 Aryl; C6-C 60 Aryloxy group; C6-C 60 Arylthio; C1-C 60 Heteroaryl; monovalent non-aromatic fused polycyclic group; or monovalent non-aromatic fused heterocyclic group.

[0030] On the other hand, an organic light-emitting device is provided comprising: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode and including an emission layer, wherein the organic layer comprises at least one organometallic compound represented by Formula 1.

[0031] In the organic layer, the organometallic compound included in the emitter layer can act as a dopant.

[0032] According to another aspect, the diagnostic composition may include at least one organometallic compound represented by Formula 1. Attached Figure Description

[0033] These and / or other aspects will become clearer and more readily understood from the following description of embodiments considered in conjunction with the accompanying drawings, wherein:

[0034] Figure 1 This is a schematic cross-sectional view of an organic light-emitting device according to an embodiment. Detailed Implementation

[0035] The embodiments will now be described in detail, examples of which are illustrated in the accompanying drawings, wherein the same reference numerals always refer to the same elements. In this respect, the embodiments may take different forms and should not be construed as limited to the description set forth herein. Therefore, the embodiments are described below only by reference to the accompanying drawings to illustrate aspects. As used herein, the term "and / or" includes any and all combinations of one or more of the associated enumerated items. Expressions such as "at least one of..." modify the entire list of elements when preceding or following it, without modifying any individual element of the list.

[0036] It will be understood that when an element is referred to as being "on" another element, it may be directly on said other element or there may be intermediate elements therein. Conversely, when an element is referred to as being "directly on" another element, there are no intermediate elements.

[0037] 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 parts, these elements, components, regions, layers, and / or parts should not be limited by these terms. These terms are used only to distinguish one element, component, region, layer, or part from another. Therefore, without departing from the teachings herein, the “first element,” “component,” “region,” “layer,” or “part” discussed below may be referred to as a second element, component, region, layer, or part.

[0038] The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting. As used herein, “a,” “the,” and “at least one” do not indicate a limitation of quantity and are intended to cover both the singular and the plural unless the context clearly indicates otherwise. For example, “(a) element” has the same meaning as “at least one element” unless the context clearly indicates otherwise.

[0039] "Or" means "and / or". As used herein, the term "and / or" includes any and all combinations of one or more of the associated listed items. It will be further understood that the terms "comprising" and / or "including", when used in this specification, indicate the presence of the stated features, areas, integrals, steps, operations, elements, and / or components, but do not preclude the presence or addition of one or more additional features, areas, integrals, steps, operations, elements, components, and / or collections thereof.

[0040] Furthermore, relative terms such as “lower” or “bottom” and “upper” or “top” may be used herein to describe the relationship between one element and another element as shown in the figures. It will be understood that, in addition to the orientations shown in the figures, relative terms are also intended to include different orientations of the device. For example, if a device in one of the figures is flipped, an element described as being “below” the other element will be oriented “upper” the other element. Thus, depending on the specific orientation of the figure, the exemplary term “lower” can include both “lower” and “upper” orientations. Similarly, if a device in one of the figures is flipped, an element described as being “below” or “under” the other element will be oriented “above” the other element. Thus, the exemplary terms “below” or “under” can include both “above” and “below” orientations.

[0041] 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 of the stated value, or within ±30%, 20%, 10%, or 5% of the stated value.

[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 disclosure pertains. It will be further understood that terms, such as those defined in common dictionaries, should be interpreted as having the same meaning as they have in the context of this disclosure and the relevant field, and will not be interpreted in an idealized or overly formal sense unless clearly defined herein.

[0043] Exemplary embodiments are described herein with reference to cross-sectional views that are schematic illustrations of idealized implementations. Therefore, deviations from the shapes illustrated will be anticipated as a result of, for example, manufacturing techniques and / or tolerances. Consequently, 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 illustrations may be rounded. Therefore, the regions illustrated in the figures are schematic in nature and their shapes are not intended to illustrate the precise shapes of the regions nor to limit the scope of the claims.

[0044] According to one aspect, organometallic compounds can be represented by Formula 1:

[0045] Formula 1

[0046]

[0047] In Equation 1, Y2 can be C.

[0048] In Equation 1, ring CY2 can be C5-C. 30 Carbocyclic groups or C1-C 30 Heterocyclic groups.

[0049] For example, the ring CY2 in Formula 1 can be i) a first ring, ii) a second ring, iii) a fused cyclic group in which two or more first rings are fused together, iv) a fused cyclic group in which two or more second rings are fused together, or v) a fused cyclic group in which at least one first ring is fused with at least one second ring.

[0050] The first ring is 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

[0051] 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]heptyl group (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.

[0052] In one or more embodiments, the cyclo(CY2) in Formula 1 may be a cyclopentyl group, a cyclohexyl group, a cyclohexene group, a phenyl group, a naphthyl group, an anthracene group, a phenanthrene group, a benzo[9,10]phenanthrene group, a pyrene group, etc. Groups, 1,2,3,4-tetrahydronaphthalene group, thiophene group, furan group, pyrrole group, cyclopentadienyl group, thiophene group, borocyclopentadienyl group, phosphacyclopentadienyl group, selenophene group, germanium heterocyclopentadienyl group, benzothiophene group, benzofuran group, indole group, indene group, benzothiophene group, benzoboron heterocyclopentadienyl group, benzophosphacyclopentadienyl group, benzoselenophene group, benzogermanium heterocycle Pentadiene group, dibenzothiophene group, dibenzofuran group, carbazole group, fluorene group, dibenzothiophene group, dibenzoborone heterocyclopentadiene group, dibenzophosphonone heterocyclopentadiene group, dibenzoselenophene group, dibenzogermanium heterocyclopentadiene group, dibenzothiophene 5-oxide group, 9H-fluorene-9-one group, dibenzothiophene 5,5-dioxide group, azibabenzothiophene group, azibabenzofuran group, Azaindole group, azaindenyl group, azabenzothiophene group, azabenzoborone heterocyclopentadienyl group, azabenzophosphacyclopentadienyl group, azabenzoselenophene group, azabenzogermanium heterocyclopentadienyl group, azadibenzothiophene group, azadibenzofuran group, azacarbazole group, azafluorene group, azadibenzothiophene group, azadibenzoborone heterocyclopentadienyl group, azadibenzophosphacyclopentadienyl group Azadibenzoselenophene group, azadibenzogermanium heterocyclopentadiene group, azadibenzothiophene 5-oxide group, aza-9H-fluorene-9-one group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, phenanthrene-rhein group, pyrazole group, imidazole group, triazole group azole group, iso- azole group, thiazole group, isothiazole group, Diazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzo[] azole group, benzothiazole group, benzo[] The diazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group, 5,6,7,8-tetrahydroquinoline group, adamantyl group, norbornene group, or norbornene group.

[0053] In one or more embodiments, cycloCY2 may be a phenyl group, a naphthyl group, a 1,2,3,4-tetrahydronaphthyl group, a thiophene group, a furan group, a pyrrole group, a cyclopentadiene group, a thiophene group, a benzothiophene group, a benzofuran group, an indole group, an indole group, a benzothiophene group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a fluorene group, or a dibenzothiophene group.

[0054] In Equation 1, R1-R8, R 20A7 can be 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 C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C2-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9). Q1-Q9 can be understood separately by referring to the descriptions of Q1-Q9 provided herein.

[0055] In some implementations, R in Equation 1 20 It may contain neither fluorine (-F) nor cyanine groups. For example, R 20 It can be a group that does not contain either a fluorine group (-F) or a cyano group.

[0056] In some implementations, in Equation 1, R1-R8, R 20 A7 and A7 can be independently defined as follows:

[0057] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, -SF5, C1-C 20 Alkyl, or C1-C 20 Alkoxy;

[0058] Each of the following C1-C is replaced: 20 Alkyl or C1-C 20Alkoxy groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl groups, deuterium-containing 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 any combination thereof;

[0059] Each of the following unsubstituted or substituted compounds: 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, cyclolinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, isobenzothiazolyl, benzo[] azole, isobenzo Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, imidazopyrimidinyl, azacarbazoyl, azadibenzofuranyl, or azadibenzothiophenyl: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazyl, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl groups, deuterium-containing C1-C 20 Alkyl, fluorinated C1-C 20 Alkyl, C1-C 20 Alkoxy, 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, cyclolinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, isobenzothiazolyl, benzo[] azole, isobenzo Azolyl, triazolyl, tetrazolyl, Diazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazole, dibenzocarbazole, imidazopyridyl, imidazopyrimidinyl, azacarbazole, azadibenzofuranyl, azadibenzothiophenyl, or any combination thereof; or

[0060] -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q 9) or -P(Q8)(Q9),

[0061] Q1-Q9 can be independently defined as follows:

[0062] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H or -CD2CDH2; or

[0063] Each of the following unsubstituted or substituted groups: n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, phenyl, biphenyl, or naphthyl: deuterium, C1-C 20 Alkyl, phenyl, or any combination thereof. Here, R in Formula 1 20 It may contain neither fluorine (-F) nor cyanide.

[0064] In one or more embodiments, R1-R8, R in Formula 1 20 A7 and A7 can each be independently hydrogen, deuterium, -F, substituted or unsubstituted C1-C. 20 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Heterocyclic alkyl groups, -Si(Q3)(Q4)(Q5), or -Ge(Q3)(Q4)(Q5). Here, R... 20 It may contain neither fluorine nor cyanide groups.

[0065] In one or more embodiments, R1-R8 and A7 in Equation 1 can each be independently:

[0066] Hydrogen, deuterium, or -F;

[0067] Each of the unsubstituted or substituted C1-C as follows 20 Alkyl, C3-C 10 cycloalkyl, or C2-C 10 Heterocyclic alkyl groups: deuterium, -F, C1-C 20 Alkyl, C3-C 10 cycloalkyl, C2-C 10 Heterocyclic alkyl groups, or any combination thereof; or

[0068] -Si(Q3)(Q4)(Q5), or -Ge(Q3)(Q4)(Q5).

[0069] In one or more embodiments, R in Formula 1 20 Possible forms:

[0070] Hydrogen or deuterium;

[0071] Each of the unsubstituted or substituted C1-C as follows 20 Alkyl, C3-C 10 cycloalkyl, or C2-C 10 Heterocyclic alkyl groups: deuterium, C1-C 20 Alkyl, C3-C 10 cycloalkyl, C2-C 10 Heterocyclic alkyl groups, or any combination thereof; or

[0072] -Si(Q3)(Q4)(Q5), or -Ge(Q3)(Q4)(Q5).

[0073] In Equation 1, the notation d2 represents R. 20 The number of R, and can be an integer from 0 to 10. When d2 is 2 or greater, two or more R 20 They can be the same or different from each other. For example, d2 can be an integer from 0 to 6.

[0074] In an exemplary embodiment, R1-R8, R in Equation 1 20 At least one of the following, or any combination thereof, may include at least one fluorine group (-F).

[0075] In an exemplary embodiment, at least one of R1-R8 of Formula 1 (e.g., at least one of R2-R8, or at least one of R3-R6) may include at least one fluorine group (-F).

[0076] In an exemplary embodiment, at least one of R1-R8 of Formula 1 (e.g., at least one of R2-R8, or at least one of R3-R6) may be a group comprising at least one fluorine group (-F).

[0077] In one or more embodiments, at least one of R1-R8 in Equation 1 can be independently:

[0078] Fluoroyl (-F); or

[0079] Each of the unsubstituted or fluorinated C1-Cs as follows 20 Alkyl, fluorinated C3-C 10 Cycloalkyl or fluorinated C2-C 10 Heterocyclic alkyl groups: deuterium, C1-C 20 Alkyl, C3-C 10 cycloalkyl, C2-C 10 Heterocyclic alkyl groups, or any combination thereof.

[0080] In Equation 1, A1-A6 can each be independently 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 C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C2-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted monovalent nonaromatic fused polycyclic group, or substituted or unsubstituted monovalent nonaromatic fused heterocyclic group.

[0081] For example, A1-A6 in Equation 1 can each be independently defined as follows:

[0082] C1-C 20 Alkyl or C1-C 20 Alkoxy;

[0083] Each of the following C1-C is replaced: 20 Alkyl or C1-C 20Alkoxy groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl groups, deuterium-containing 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 any combination thereof; or

[0084] Each of the following unsubstituted or substituted compounds: 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, 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, cyclolinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, isobenzothiazolyl, benzo[] azole, isobenzo Azolyl, triazolyl, tetrazolyl, Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, imidazopyrimidinyl, azacarbazoyl, azadibenzofuranyl, or azadibenzothiophenyl: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amido, hydrazyl, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl groups, deuterium-containing C1-C 20 Alkyl, fluorinated C1-C 20 Alkyl, C1-C 20 Alkoxy, 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, cyclolinyl, carbazole, phenanthrolinel, benzimidazolyl, benzofuranyl, benzothiophene, isobenzothiazolyl, benzo[] azole, isobenzo Azolyl, triazolyl, tetrazolyl, Diazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazoyl, dibenzocarbazoyl, imidazopyridyl, imidazopyrimidinyl, azacarbazoyl, azadibenzofuranyl, azadibenzothiophenyl, or any combination thereof.

[0085] In one or more embodiments, A1-A6 in Formula 1 can each be independently substituted or unsubstituted C1-C. 60 Alkyl, substituted or unsubstituted C3-C 10 cycloalkyl, or substituted or unsubstituted C2-C 10 Heterocyclic alkyl groups.

[0086] In one or more embodiments, A1-A6 in Formula 1 may each be independently an unsubstituted or substituted C1-C as follows. 20 Alkyl, C3-C 10 cycloalkyl, or C2-C 10 Heterocyclic alkyl groups: deuterium, -F, C1-C 20 Alkyl, C3-C 10 cycloalkyl, C2-C 10 Heterocyclic alkyl groups, or any combination thereof.

[0087] In an exemplary embodiment, R1-R8, R in Equation 1 20A7 can be independently represented by hydrogen, deuterium, -F, -CH3, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, a group represented by any one of formulas 9-1 to 9-39, a group represented by any one of formulas 9-1 to 9-39 in which at least one hydrogen is replaced by deuterium, a group represented by any one of formulas 9-1 to 9-39 in which at least one hydrogen is replaced by -F, a group represented by any one of formulas 9-201 to 9-233, and a group in which at least one hydrogen is replaced by deuterium. A group represented by any one of formulas 9-201 to 9-233 in which at least one hydrogen is replaced by deuterium; a group represented by any one of formulas 9-201 to 9-233 in which at least one hydrogen is replaced by -F; a group represented by any one of formulas 10-1 to 10-126 in which at least one hydrogen is replaced by deuterium; a group represented by any one of formulas 10-1 to 10-126 in which at least one hydrogen is replaced by -F; a group represented by any one of formulas 10-201 to 10-343 in which at least one hydrogen is replaced by -F; A group represented by a symbol, a group represented by one of formulas 10-201 to 10-343 wherein at least one hydrogen is replaced by deuterium, a group represented by one of formulas 10-201 to 10-343 wherein at least one hydrogen is replaced by -F, -Si(Q3)(Q4)(Q5), or -Ge(Q3)(Q4)(Q5) (where Q3-Q5 are the same as those described in this specification), and at least one of R1-R8 (e.g., at least one of R2-R8, or R3-R6). At least one of them may be -F, -CF3, -CF2H, -CFH2, a group represented by one of formulas 9-1 to 9-39 in which at least one hydrogen is replaced by -F, a group represented by one of formulas 9-201 to 9-233 in which at least one hydrogen is replaced by -F, a group represented by one of formulas 10-1 to 10-126 in which at least one hydrogen is replaced by -F, or a group represented by one of formulas 10-201 to 10-343 in which at least one hydrogen is replaced by -F.

[0088] In one or more embodiments, R in Formula 1 20It may be hydrogen, deuterium, -CH3, -CD3, -CD2H, -CDH2, a group represented by any one of formulas 9-1 to 9-39, a group represented by any one of formulas 9-1 to 9-39 wherein at least one hydrogen is replaced by deuterium, a group represented by any one of formulas 9-201 to 9-233 wherein at least one hydrogen is replaced by deuterium, a group represented by any one of formulas 10-1 to 10-126, a group represented by any one of formulas 10-1 to 10-126 wherein at least one hydrogen is replaced by deuterium, a group represented by any one of formulas 10-201 to 10-343, a group represented by any one of formulas 10-201 to 10-343 wherein at least one hydrogen is replaced by deuterium, -Si(Q3)(Q4)(Q5), or -Ge(Q3)(Q4)(Q5) (where Q3-Q5 are the same as those described in this specification).

[0089] In one or more embodiments, A1-A6 in Formula 1 may each independently be -CH3, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, a group represented by any one of Formulas 9-1 to 9-39, a group represented by any one of Formulas 9-1 to 9-39 wherein at least one hydrogen is replaced by deuterium, a group represented by any one of Formulas 9-1 to 9-39 wherein at least one hydrogen is replaced by -F, a group represented by any one of Formulas 9-201 to 9-233, a group represented by any one of Formulas 9-201 to 9-233 wherein at least one hydrogen is replaced by deuterium, or a group represented by any one of Formulas 9-201 to 9-233 wherein at least one hydrogen is replaced by -F. A group represented by one of formulas 9-201 to 9-233 with -F substitution, a group represented by one of formulas 10-1 to 10-126, a group represented by one of formulas 10-1 to 10-126 in which at least one hydrogen is substituted by deuterium, a group represented by one of formulas 10-1 to 10-126 in which at least one hydrogen is substituted by -F substitution, a group represented by one of formulas 10-201 to 10-343, a group represented by one of formulas 10-201 to 10-343 in which at least one hydrogen is substituted by deuterium substitution, or a group represented by one of formulas 10-201 to 10-343 in which at least one hydrogen is substituted by -F substitution:

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098] In formulas 9-1 to 9-39, 9-201 to 9-233, 10-1 to 10-126, and 10-201 to 10-343, * indicates a binding site with an adjacent atom, Ph is phenyl, TMS is trimethylsilyl, and TMG is trimethylgermanyl.

[0099] "A group represented by one of formulas 9-1 to 9-39 in which at least one hydrogen is replaced by deuterium" and "a group represented by one of formulas 9-201 to 9-233 in which at least one hydrogen is replaced by deuterium" can each be, for example, a group represented by one of formulas 9-501 to 9-514 and 9-601 to 9-635:

[0100]

[0101]

[0102] "A group represented by one of formulas 9-1 to 9-39 in which at least one hydrogen is replaced by -F" and "a group represented by one of formulas 9-201 to 9-233 in which at least one hydrogen is replaced by -F" can each be, for example, a group represented by one of formulas 9-701 to 9-710:

[0103]

[0104] "A group represented by one of formulas 10-1 to 10-126 in which at least one hydrogen is replaced by deuterium" and "a group represented by one of formulas 10-201 to 10-343 in which at least one hydrogen is replaced by deuterium" can each be, for example, a group represented by one of formulas 10-501 to 10-553:

[0105]

[0106]

[0107] "A group represented by one of formulas 10-1 to 10-126 in which at least one hydrogen is replaced by -F" and "a group represented by one of formulas 10-201 to 10-343 in which at least one hydrogen is replaced by -F" can each be, for example, a group represented by one of formulas 10-601 to 10-615:

[0108]

[0109] In one or more embodiments, at least one of R2-R8 of Formula 1 (e.g., one or both of R2-R8) may include at least one fluorine group (-F).

[0110] In one or more embodiments, in Formula 1,

[0111] 1) R2 may include at least one fluorine group (-F);

[0112] 2) R3 may include at least one fluorine group (-F);

[0113] 3) R4 may include at least one fluorine group (-F);

[0114] 4) R5 may include at least one fluorine group (-F);

[0115] 5) R6 may include at least one fluorine group (-F);

[0116] 6) R7 may include at least one fluorine group (-F);

[0117] 7) R8 may include at least one fluorine group (-F);

[0118] 8) R4 and R5 may each include at least one fluorine group (-F);

[0119] 9) R4 and R6 may each include at least one fluorine group (-F);

[0120] 10) R5 and R6 may each include at least one fluorine group (-F).

[0121] 11) R3 and R4 may each include at least one fluorine group (-F); or

[0122] 12) R3 and R6 may each include at least one fluorine group (-F).

[0123] In one or more embodiments, regarding formula 1,

[0124] One or both of R1-R8 may independently include at least one fluorine group (-F), and

[0125] At least one of R1-R8 may not contain a fluorine group (-F) and may not be hydrogen.

[0126] In one or more embodiments, R5 in Formula 1 may not be hydrogen.

[0127] In one or more embodiments, R in Formula 1 20 It can be either the unsubstituted C1-C or the C1-C substituted by the following: 20 Alkyl, C3-C 10 cycloalkyl, or C2-C 10 Heterocyclic alkyl groups: deuterium, C1-C 20 Alkyl, C3-C 10 cycloalkyl, C2-C 10Heterocyclic alkyl groups, or any combination thereof.

[0128] In one or more embodiments, R in Formula 1 20 It can be unsubstituted or substituted C1-C as follows 20 Alkyl groups: deuterium, C1-C 20 Alkyl groups, or any combination thereof.

[0129] In one or more embodiments, d2 in Equation 1 may be 2.

[0130] In one or more embodiments, R in Formula 1 20 It can be unsubstituted or substituted C1-C as follows 20 Alkyl groups: deuterium, C1-C 20 Alkyl groups, or any combination thereof, and d2 may be 2.

[0131] In one or more embodiments, the organometallic compound represented by Formula 1 may have at least one deuterium.

[0132] In one or more embodiments, at least one of R1-R8 of Formula 1 may have at least one deuterium.

[0133] In one or more embodiments, the number of R d2 20 At least one of them may have at least one deuterium.

[0134] In one or more embodiments, the number d2 of R 20 At least one of them may be a deuterium-containing C1-C that is either unsubstituted or substituted as follows. 20 Alkyl groups, deuterium-containing C3-C 10 cycloalkyl, or deuterium-containing C2-C 10 Heterocyclic alkyl groups: C1-C 20 Alkyl, C3-C 10 cycloalkyl, C2-C 10 Heterocyclic alkyl groups, or any combination thereof.

[0135] In Equation 1, 1) two or more of R1-R8 may optionally be connected to each other to form an unsubstituted or at least one R 1a Replacement C5-C 30 The carbocyclic group is either unsubstituted or has at least one R group. 1a Replacement C1-C 30 Heterocyclic groups, 2) number d2 of R 20 Two or more may optionally be connected to each other to form an unsubstituted or R-shaped structure. 1a Replacement C5-C 30 The carbocyclic group is either unsubstituted or has at least one R group. 1a Replacement C1-C30 Heterocyclic groups, and 3) two or more of A1-A7 may optionally be linked together to form an unsubstituted or R-shaped group. 1a Replacement C5-C 30 The carbocyclic group is either unsubstituted or has at least one R group. 1a Replacement C1-C 30 Heterocyclic groups. Here, referring to the description in A7, R can be understood. 1a .

[0136] As used in this article, the term "C5-C" 30 A "carbocyclic group" refers to a saturated or unsaturated cyclic group with only 5-30 carbon atoms as cyclic atoms. (C5-C) 30 The carbon ring group can be a monocyclic group or a polycyclic group.

[0137] The phrase "(unreplaced or replaced by at least one R)" 1a (Replacement) C5-C 30 "Carbocyclic groups" may include, for example, unsubstituted groups or groups modified by at least one R group. 1a Substituted adamantyl groups, norbornene groups, bicyclo[1.1.1]pentyl groups, bicyclo[2.1.1]hexyl groups, bicyclo[2.2.1]heptyl groups (norbornene groups), bicyclo[2.2.2]octyl groups, cyclopentyl groups, cyclohexyl groups, cyclohexene groups, phenyl groups, naphthyl groups, anthracene groups, phenanthrene groups, benzo[9,10]phenanthrene groups, pyrene groups, Groups, cyclopentadienyl groups, 1,2,3,4-tetrahydronaphthalene groups, fluorene groups.

[0138] 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 1-30 carbon atoms, has at least one heteroatom selected from N, O, Si, P, Se, B, Ge, or S as a cyclic atom. (C1-C) 30 Heterocyclic groups can be monocyclic or polycyclic.

[0139] The phrase "(unreplaced or replaced by at least one R)" 1a (replaced) C1-C 30 "Heterocyclic groups" may include, for example, those that are unsubstituted or substituted by at least one R 1aSubstituted thiophene groups, furan groups, pyrrole groups, thiophene groups, borocyclopentadien groups, phosphacyclopentadien groups, selenophene groups, germanium heterocyclopentadien groups, benzothiophene groups, benzofuran groups, indole groups, indene groups, benzothiophene groups, benzoboron heterocyclopentadien groups, benzophosphacyclopentadien groups, benzoselenophene groups, benzogermanium heterocyclopentadien groups, dibenzothiophene groups, dibenzofuran groups, carbazole groups, dibenzothiophene groups, dibenzoboron heterocyclopentadien groups, dibenzophosphacyclopentadien groups, dibenzoselenophene groups, dibenzogermanium heterocyclopentadien groups, dibenzothiophene 5-oxide groups, 9H-fluorene-9-one groups, dibenzothiophene 5,5-dioxide groups, azabenzothiophene groups, azabenzofuran groups, azaindole groups, azaindene groups Azabenzothiophene group, azabenzoboron heterocyclopentadienyl group, azabenzophosphacyclopentadienyl group, azabenzoselenophene group, azabenzogermanium heterocyclopentadienyl group, azadibenzothiophene group, azadibenzofuran group, azacarbazole group, azafluorene group, azadibenzothiophene group, azadibenzoboron heterocyclopentadienyl group, azadibenzophosphacyclopentadienyl group, azadibenzoselenophene group, azadibenzogermanium heterocyclopentadienyl group, azadibenzothiophene 5-oxide group, aza-9H-fluorene-9-one group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazolinine group, phenanthrene-rhein group, pyrazole group, imidazole group, triazole group azole group, iso- azole group, thiazole group, isothiazole group, Diazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzo[] azole group, benzothiazole group, benzo[] The diazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group, and 5,6,7,8-tetrahydroquinoline group.

[0140] As used in this article, the term "C1-C" 60 "alkyl" refers to a straight-chain or branched monovalent group of a saturated aliphatic hydrocarbon having 1-60 carbon atoms, and non-limiting examples include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl. The term "C1-C" is used herein. 60 "alkylene" refers to a compound with C1-C2 atoms. 60 Alkyl groups are divalent groups with the same structure.

[0141] C1-C 60 Alkyl, C1-C 20 Alkyl, and / or C1-C 10Examples of alkyl groups are methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodel, sec-decyl methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodel, sec-decyl, tert-decyl, or any combination thereof. For example, formula 9-33 can be a branched C6 alkyl group and can be a tert-butyl group substituted with two methyl groups.

[0142] The term "C1-C" used in this article 60 "Alkoxy" refers to the compound formed by -OA 101 (where A) 101 For C1-C 60 Alkyl groups are monovalent groups.

[0143] C1-C 60 Alkoxy, C1-C 20 alkoxy, or C1-C 10 Examples of alkoxy groups are methoxy, ethoxy, propoxy, isopropoxy, butoxy, or pentoxy.

[0144] As used in this article, the term "C3-C" 10 "Cycloalkyl" refers to a monocyclic saturated hydrocarbon group having 3-10 carbon atoms, and examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. As used herein, the term "C3-C" is also relevant. 10 "Cycloalkylene" refers to a compound with C3-C66 atoms. 10 Cycloalkyl groups are divalent groups with the same structure.

[0145] C3-C 10 Examples of cycloalkyl groups are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, bicyclo[1.1.1]pentyl (bicyclo[1.1.1]pentyl), bicyclo[2.1.1]hexyl (bicyclo[2.1.1]hexyl), bicyclo[2.2.1]heptyl (bicyclo[2.2.1]heptyl) (norbornel), and bicyclo[2.2.2]octyl.

[0146] As used in this article, the term "C2-C" 10"Heterocyclic alkyl" refers to a monovalent saturated monocyclic group having at least one heteroatom selected from N, O, P, Si, Se, B, Ge, or S as the cyclic atom and 2-10 carbon atoms, and non-limiting examples include tetrahydrofuranyl and tetrahydrothiophenyl. The term "C2-C" is used as is herein. 10 "Heterocyclic alkyl" refers to a compound with C2-C ... 10 Divalent groups with the same structure as heterocyclic alkyl groups.

[0147] C2-C 10 Examples of heterocyclic alkyl groups are silylcyclopentyl, silylcyclohexyl, tetrahydrofuranyl, tetrahydro-2H-pyranyl, and tetrahydrothiophenyl.

[0148] As used in this article, the term "deuterium-containing C1-C" 60 Alkyl groups (or C1-C deuterium-containing groups) 20 Alkyl groups, deuterium-containing C2-C 20 "alkyl, etc." refers to C1-C alkyl groups substituted with at least one deuterium. 60 Alkyl groups (or C1-C groups substituted with at least one deuterium) 20 Alkyl group, C2-C substituted with at least one deuterium 20 Alkyl groups, etc. For example, the term "deuterium-containing C1 alkyl (that is, deuterium-containing methyl)" as used herein includes -CD3, -CD2H, and -CDH2.

[0149] As used in this article, "deuterium-containing C3-C" 10 "Cycloalkyl" refers to a C3-C alkyl group that has been substituted with at least one deuterium. 10 Cycloalkyl. For example, formula 10-501 provides "deuterium-containing C3-C..." 10 Examples of "cycloalkyl".

[0150] As used in this article, the term "fluorinated C1-C" 60 Alkyl (or fluorinated C1-C) 20 Alkyl groups, etc., and fluorinated C3-C... 10 "Cycloalkyl" or "fluorinated C2-C" 10 "Heterocyclic alkyl" refers to C1-C1 alkyl groups substituted with at least one fluorine group (-F). 60 Alkyl (or C1-C) 20 Alkyl groups, etc., C3-C substituted with at least one fluorine group (-F) 10 Cycloalkyl groups, and C2-C groups substituted with at least one fluorine group (-F). 10 Heterocyclic alkyl groups. For example, the term "fluorinated C1 alkyl (that is, fluorinated methyl)" includes -CF3, -CF2H, and -CFH2. "Fluorinated C1-C..." 60 Alkyl (or fluorinated C1-C) 20Alkyl groups, etc., and fluorinated C3-C... 10 "Cycloalkyl" or "fluorinated C2-C" 10 Heterocyclic alkyl groups can be i) fully fluorinated C1-C 60 Alkyl (or fully fluorinated C1-C) 20 Alkyl groups, etc., and fully fluorinated C3-C 10 cycloalkyl or fully fluorinated C2-C 10 Heterocyclic alkyl groups in which all hydrogens are replaced by fluorine groups, or ii) partially fluorinated C1-C 60 Alkyl (or partially fluorinated C1-C) 20 Alkyl groups, etc., and partially fluorinated C3-C 10 Cycloalkyl or partially fluorinated C2-C 10 Heterocyclic alkyl groups, in which some of the hydrogen atoms in each group are replaced by fluorine groups.

[0151] As used in this article, the term "(C1-C" is similar to the term "(C1-C)" 20 "alkyl)'X' group" refers to a group consisting of at least one C1-C1 group. 20 Alkyl-substituted 'X' groups. For example, as used herein, the term "(C1-C1)" 20 Alkyl)C3-C 10 "Cycloalkyl" refers to a compound formed by at least one C1-C2 group. 20 Alkyl-substituted C3-C 10 Cycloalkyl, and as used herein, the term "(C1-C1)" 20 "alkyl)phenyl" refers to a compound formed by at least one C1-C2 bond. 20 Alkyl-substituted phenyl groups.

[0152] As used in this article, the term "C2-C" 60 "Alkenyl" refers to the group formed by the carbon atoms in the C2-C2 group. 60 A hydrocarbon group formed by substituting at least one carbon-carbon double bond into the middle or end of an alkyl group, and examples include vinyl, propenyl, and butenyl groups. As used herein, the term "C2-C" is used in this context. 60 "Alkenyl" refers to a group with a C2-C ratio. 60 Alkenyl groups are divalent groups with the same structure.

[0153] As used in this article, the term "C2-C" 60 "Alkyne" refers to the group formed by the combination of C2-C... 60 A hydrocarbon group formed by substituting at least one carbon-carbon triple bond into the middle or end of an alkyl group, and examples include ethynyl and propynyl. As used herein, the term "C2-C" is used in this context. 60 "Alynyl group" refers to a group with a C2-C group. 60 A divalent group with the same structure as an alkynyl group.

[0154] As used in this article, the term "C3-C" 10 "Cycloalkenyl" refers to a monovalent monocyclic group having 3-10 carbon atoms and at least one carbon-carbon double bond in its ring and not being aromatic, and non-limiting examples include cyclopentenyl, cyclohexenyl, and cycloheptenyl. The term "C3-C" is used as is herein. 10 "Cyclopentene" refers to a group with a C3-C6 bond structure. 10 A divalent group with the same structure as a cycloalkenyl group.

[0155] As used in this article, the term "C2-C" 10 "Heterocyclic alkenyl" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, P, Si, Se, B, Ge, or S as the cyclic atom, 2-10 carbon atoms, and at least one double bond in its ring. C2-C 10 Examples of heterocyclic alkenyl groups are 2,3-dihydrofuranyl and 2,3-dihydrothiophenyl. As used herein, the term "C2-C" is used in conjunction with these examples. 10 "Heterocyclic alkenyl" refers to a group with a C2-C... 10 Divalent groups with the same structure as heterocyclic alkenyl groups.

[0156] As used in this article, the term "C6-C" 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic system with 6-60 carbon atoms, and as used herein, "C6-C". 60 "Arylene" refers to a divalent group that has a carbocyclic aromatic system with 6-60 carbon atoms. (C6-C) 60 Non-limiting examples of aryl groups include phenyl, naphthyl, anthraceneyl, phenanthryl, pyrene, and Base. When C6-C 60 Aryl and C6-C 60 When each of the aryl groups comprises two or more rings, the rings may be fused together.

[0157] The term "C7-C" used in this article 60 "Alkyl" refers to an aryl group formed by at least one C1-C2 group. 60 Alkyl-substituted C6-C 60 Aryl.

[0158] As used in this article, the term "C1-C" 60 "Heteroaryl" refers to a monovalent group having a cyclic aromatic system having at least one heteroatom selected from N, O, P, Si, Se, B, Ge, or S as the cyclic atom and 1-60 carbon atoms. The term "C1-C" is used herein. 60"Hypo-aryl" refers to a divalent group having a cyclic aromatic system with at least one heteroatom selected from N, O, P, Si, Se, B, Ge, or S as the cyclic atom and 1-60 carbon atoms. C1-C 60 Examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. When C1-C... 60 heteroaryl and C1-C 60 When each heteroaryl group comprises two or more rings, the rings can fused together.

[0159] The term "C2-C" used in this article 60 "alkyl heteroaryl" refers to an alkyl group formed by at least one C1-C2 group. 60 Alkyl-substituted C1-C 60 Mixed aromatic compounds.

[0160] As used in this article, the term "C6-C" 60 "Aryloxy group" represents -OA 102 (where A) 102 For C6-C 60 Aryl), and as used herein by the term "C6-C" 60 "Arylthio" indicates -SA 103 (where A) 103 For C6-C 60 Aryl).

[0161] As used herein, the term "monovalent nonaromatic fused polycyclic group" refers to a monovalent group (e.g., having 8-60 carbon atoms) that has two or more rings fused together, has only carbon atoms as cyclic atoms, and is not aromatic in its overall molecular structure. Examples of such monovalent nonaromatic fused polycyclic groups include the fluorene group. As used herein, the term "divalent nonaromatic fused polycyclic group" refers to a divalent group having the same structure as the monovalent nonaromatic fused polycyclic group.

[0162] As used herein, the term "monovalent nonaromatic fused heterocyclic group" refers to a monovalent group (e.g., having 2-60 carbon atoms) that has two or more rings fused together, has heteroatoms selected from N, O, P, Si, Se, B, Ge, or S as cyclic atoms in addition to carbon atoms, and is not aromatic in its overall molecular structure. Non-limiting examples of such monovalent nonaromatic fused heterocyclic groups include the carbazole group. As used herein, the term "divalent nonaromatic fused heterocyclic group" refers to a divalent group having the same structure as the monovalent nonaromatic fused heterocyclic group.

[0163] Replacement C5-C 30 Carbocyclic groups, substituted C1-C30 Heterocyclic groups, substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkyne group, substituted C1-C 60 Alkoxy, substituted C3-C 10 cycloalkyl, substituted C2-C 10 Heterocyclic alkyl, substituted C3-C 10 Cycloalkenyl, substituted C2-C 10 Heterocyclic alkenyl, substituted C6-C 60 Aryl, substituted C7-C 60 Alkyl, substituted C6-C 60 aryloxy groups, substituted C6-C 60 Arylthioyl, substituted C1-C 60 heteroaryl, substituted C2-C 60 The substituents of alkyl heteroaryl groups, substituted monovalent non-aromatic fused polycyclic groups, and substituted monovalent non-aromatic fused heterocyclic groups can be:

[0164] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, or C1-C 60 Alkoxy;

[0165] Each of the unsubstituted or substituted C1-C as follows 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, or C1-C 60 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C3-C 10 cycloalkyl, C2-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C2-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C60 Alkyl heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heterocyclic group, -N(Q 11 (Q) 12 ), -Si(Q 13 (Q) 14 (Q) 15 -Ge(Q) 13 (Q) 14 (Q) 15 -B(Q) 16 (Q) 17 -P(=O)(Q) 18 (Q) 19 -P(Q) 18 (Q) 19 ), or any combination thereof;

[0166] Each of the following C3-Cs that are not substituted or are substituted: 10 cycloalkyl, C2-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C2-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heterocyclic groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, carboxylic acid 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, C3-C 10 cycloalkyl, C2-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C2-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C7-C 60 Alkyl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 heteroaryl, C2-C 60 Alkyl heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heterocyclic group, -N(Q 21(Q) 22 ), -Si(Q 23 (Q) 24 (Q) 25 -Ge(Q) 23 (Q) 24 (Q) 25 -B(Q) 26 (Q) 27 -P(=O)(Q) 28 (Q) 29 -P(Q) 28 (Q) 29 ), or any combination thereof;

[0167] -N(Q 31 (Q) 32 ), -Si(Q 33 (Q) 34 (Q) 35 -Ge(Q) 33 (Q) 34 (Q) 35 -B(Q) 36 (Q) 37 -P(=O)(Q) 38 (Q) 39 ), or -P(Q 38 (Q) 39 );or

[0168] Any combination thereof.

[0169] In this specification, Q1-Q9, Q 11 -Q 19 Q 21 -Q 29 , and Q 31 -Q 39 Each can be independently hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; amidine; hydrazine; hydrazone; carboxylic acid group or its salt; sulfonic acid group or its salt; phosphate group or its salt; unsubstituted or deuterated, C1-C 60 Alkyl, C6-C 60 C1-C substituted with aryl or any combination thereof 60 Alkyl; C2-C 60 Alkenyl; C2-C 60 Alkyne group; C1-C 60 Alkoxy group; C3-C 10 cycloalkyl; C2-C 10 Heterocyclic alkyl; C3-C 10 Cycloalkenyl; C2-C 10 Heterocyclic alkenyl; unsubstituted or deuterated, C1-C 60 Alkyl, C6-C60 C6-C substituted with aryl or any combination thereof 60 Aryl; C6-C 60 Aryloxy group; C6-C 60 Arylthio; C1-C 60 Heteroaryl; monovalent non-aromatic fused polycyclic group; or monovalent non-aromatic fused heterocyclic group.

[0170] For example, in this specification, Q1-Q9, Q 11 -Q 19 Q 21 -Q 29 , and Q 31 -Q 39 Each can be independently:

[0171] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; or

[0172] Each of the following unsubstituted or substituted groups: n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, phenyl, biphenyl, or naphthyl: deuterium, C1-C 10 Alkyl, phenyl, or any combination thereof.

[0173] The terms "azaindole group, azabenzoboranecyclopentadienyl group, azabenzophosphacyclopentadienyl group, azaindene group, azabenzothiophene group, azabenzogermanium cyclopentadienyl group, azabenzothiophene group, azabenzoselenene group, azabenzofuran group, azacarbazole group, azadibenzoboranecyclopentadienyl group, azadibenzophosphacyclopentadienyl group, azafluorene group, azadibenzothiophene group, azadibenzogermanium cyclopentadienyl group, azadibenzothiophene group, azadibenzoselenene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluorene-9-one group, and azadibenzothiophene 5,5-dioxide group" are also mentioned. "These refer to heterocyclic groups that have the same skeleton as "indole group, benzoborane heterocyclopentadienyl group, benzophosphonane heterocyclopentadienyl group, indene group, benzothiophene group, benzogermanium heterocyclopentadienyl group, benzothiophene group, benzoselenene group, benzofuran group, carbazole group, dibenzoborane heterocyclopentadienyl group, dibenzophosphonane heterocyclopentadienyl group, fluorene group, dibenzothiophene group, dibenzogermanium heterocyclopentadienyl group, dibenzothiophene group, dibenzoselenene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluorene-9-one group, and dibenzothiophene 5,5-dioxide group", wherein at least one carbon atom constituting the cyclic group is replaced by nitrogen.

[0174] In one or more embodiments, the formula in Equation 1 is... The group represented can be one of the groups represented by formulas CY1 to CY108:

[0175]

[0176]

[0177]

[0178]

[0179]

[0180] In equations CY1 to CY108,

[0181] T2-T8 can each be independently:

[0182] Fluoroyl (-F); or

[0183] Each of the unreplaced or replaced by deuterium, C1-C 20 Alkyl, C3-C 10 cycloalkyl, C2-C 10 Fluorinated C1-C atoms substituted with heterocyclic alkyl groups or any combination thereof 20 Alkyl, fluorinated C3-C10 Cycloalkyl or fluorinated C2-C 10 Heterocyclic alkyl groups;

[0184] R2-R8 and R 1a Each is the same as described above, and R2-R8 are not hydrogen.

[0185] * indicates the binding site with Ir in Equation 1.

[0186] *" indicates the binding site with adjacent atoms in Formula 1.

[0187] For example, R2-R8 in equations CY1 to CY108 can each be independently defined as follows:

[0188] Deuterium; or

[0189] Each of the unreplaced or replaced by deuterium, C1-C 20 Alkyl, C3-C 10 cycloalkyl, C2-C 10 Heterocyclic alkyl groups, or any combination thereof, substituted C1-C 20 Alkyl, C3-C 10 cycloalkyl, or C2-C 10 Heterocyclic alkyl groups.

[0190] In one or more embodiments, the formula in Equation 1 is... The group represented can be one of the groups represented by formulas A(1) to A(7):

[0191]

[0192] In equations A(1) to A(7),

[0193] Y2 is C,

[0194] X 21 For O, S, N(R) 25 ), C(R 25 (R) 26 ), or Si(R) 25 (R) 26 ),

[0195] R9-R 12 and R 21 -R 26 Each and about R 20 The descriptions are the same.

[0196] *' indicates the binding site with Ir in Equation 1, and

[0197] *" indicates the binding site with adjacent atoms in Formula 1.

[0198] For example, R9 and R in equation A(1) 11 Each can independently be either unsubstituted or replaced by deuterium, C1-C 20 Alkyl, C3-C 10 cycloalkyl, C2-C 10 Heterocyclic alkyl groups, or any combination thereof, substituted C1-C 20 Alkyl, C3-C 10 cycloalkyl, or C2-C 10 Heterocyclic alkyl groups.

[0199] In one or more embodiments, R9 and R in formula A(1) 11 Each can be independently an unsubstituted or substituted C1-C as follows 20 Alkyl groups: deuterium, C1-C 20 Alkyl groups, or any combination thereof.

[0200] In one or more embodiments, R in formula A(1) 10 and R 12 They can be hydrogen or deuterium independently.

[0201] In one or more embodiments, R9 and R in formula A(1) 11 They can be the same as each other.

[0202] In one or more embodiments, R9 and R in formula A(1) 11 But they are different from each other.

[0203] In one or more embodiments, R9 and R in formula A(1) 11 They can be different from each other, and include R 11 The number of carbons in it can be greater than the number of carbons included in R9.

[0204] In one or more embodiments, i) R9-R in equation A(1) 12 At least one of, ii) R in equations A(2) and A(3) 11 R 12 R 21 -R 26 One of them, or any combination thereof, iii) R9, R in equations A(4) and A(5) 12 R 21 -R 26 One of them, or any combination thereof, and iv) R9, R in equations A(6) and A(7) 10 R 21 -R 26 One of them, or any combination thereof, can be independently a deuterated C1-C that is either unsubstituted or substituted as follows. 20 Alkyl groups, deuterium-containing C3-C10 cycloalkyl, or deuterium-containing C2-C 10 Heterocyclic alkyl groups: C1-C 20 Alkyl, C3-C 10 cycloalkyl, C2-C 10 Heterocyclic alkyl groups, or any combination thereof.

[0205] In one or more embodiments, R9 and R in formula A(1) 11 At least one of (e.g., R9 and R in equation A(1)) 11 Each can be independently a deuterated C1-C that is either unsubstituted or substituted as follows. 20 Alkyl groups, deuterium-containing C3-C 10 cycloalkyl, or deuterium-containing C2-C 10 Heterocyclic alkyl groups: C1-C 20 Alkyl, C3-C 10 cycloalkyl, C2-C 10 Heterocyclic alkyl groups, or any combination thereof.

[0206] In one or more embodiments, the formula in Equation 1 is... The group represented can be a group represented by formula A(1) or A(5).

[0207] In one or more embodiments, at least one of A1-A6 in Formula 1 may be independently substituted or unsubstituted C2-C. 60 Alkyl, substituted or unsubstituted C3-C 10 cycloalkyl, or substituted or unsubstituted C2-C 10 Heterocyclic alkyl groups.

[0208] In one or more embodiments, at least one of A1-A3 and at least one of A4-A6 in Formula 1 may each be independently substituted or unsubstituted C2-C. 60 Alkyl, substituted or unsubstituted C3-C 10 cycloalkyl, or substituted or unsubstituted C2-C 10 Heterocyclic alkyl groups.

[0209] In one or more embodiments, the number of carbons in the groups represented by *-C(A1)(A2)(A3) in Formula 1 may be 5 or more, and / or the number of carbons in the groups represented by *-C(A4)(A5)(A6) in Formula 1 may be 5 or more.

[0210] In one or more embodiments, the A1, A2, and A3 groups represented by *-C(A1)(A2)(A3) in Formula 1 may be linked together to form an unsubstituted or at least R group. 1a Replacement C5-C 30The carbocyclic group is either unsubstituted or has at least one R group. 1a Replacement C1-C 30 Heterocyclic groups. That is, the groups represented by *-C(A1)(A2)(A3) in Formula 1 can be unsubstituted or substituted with at least one R. 1a Replacement C5-C 30 The carbocyclic group is either unsubstituted or has at least one R group. 1a Replacement C1-C 30 Heterocyclic groups (e.g., each unsubstituted or 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]heptyl group (norbornene group), bicyclo[2.2.2]octyl group, cyclopentyl group, cyclohexyl group, or cyclohexene group).

[0211] In one or more embodiments, the A4, A5, and A6 groups represented by *-C(A4)(A5)(A6) in Formula 1 may be linked together to form an unsubstituted or at least R group. 1a Replacement C5-C 30 The carbocyclic group is either unsubstituted or has at least one R group. 1a Replacement C1-C 30 Heterocyclic groups. That is, the groups represented by *-C(A4)(A5)(A6) in Formula 1 can be unsubstituted or substituted with at least one R. 1a Replacement C5-C 30 The carbocyclic group is either unsubstituted or has at least one R group. 1a Replacement C1-C 30 Heterocyclic groups (e.g., each unsubstituted or 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]heptyl group (norbornene group), bicyclo[2.2.2]octyl group, cyclopentyl group, cyclohexyl group, or cyclohexene group).

[0212] In one or more embodiments, A1, A2, and A3 in Formula 1 may each be independently a substituted or unsubstituted C1 alkyl group (substituted or unsubstituted methyl group).

[0213] In one or more embodiments, A1, A2, and A3 in Formula 1 may each be independently unsubstituted or substituted with C1 alkyl groups as follows: deuterium, -F, C3-C. 10 cycloalkyl, C2-C 10 Heterocyclic alkyl groups, or any combination thereof.

[0214] For example, the organometallic compound may be at least one of compounds 1 to 16 below, but the embodiments of this disclosure are not limited thereto.

[0215]

[0216] In the organometallic compounds represented by Formula 1, 1) cyclo CY1 (see Formula 1'), as shown in Formula 1, is a fused cyclic group in which two phenyl groups are fused with a pyridine group, and 2) R1-R8, R 20 At least one of the following, or any combination thereof, includes at least one fluorine group (-F). Therefore, the transition dipole moment of the organometallic compound can be increased, and the conjugation length of the organometallic compound is relatively increased, as is its structural stiffness, leading to a reduction in nonradiative transitions. Therefore, electronic devices including the organometallic compound represented by Formula 1, such as organic light-emitting devices, can have high external quantum efficiency (EQE) and thus high luminous efficiency.

[0217] Formula 1'

[0218]

[0219] In one or more embodiments, A1-A6 in Formula 1 can each be independently 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 C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Heterocyclic alkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C2-C 10 Heterocyclic alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 The polycyclic aromatic hydrocarbon group can be a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or a substituted or unsubstituted monovalent non-aromatic fused heterocyclic hydrocarbon group. That is, each of A1-A6 in Formula 1 may have one or more carbons.

[0220] Despite not wishing to be bound by any particular theory, the α-proton possesses approximately 10 times the chemical reactivity of the β-proton. 5The chemical reactivity is significantly increased. That is, during the synthesis and / or storage of the compound, α-protons can cause side reactions due to the formation of various forms of intermediates. However, the carbons bonded to each Al-A6 in Formula 1 as described above may not contain α-protons, and in this respect, the organometallic compound represented by Formula 1 can have a stable chemical structure, with minimal side reactions occurring before / after synthesis, and simultaneously, the intermolecular interactions of the organometallic compound can be minimized during the operation of electronic devices (e.g., organic light-emitting devices) including the organometallic compound.

[0221] Furthermore, Formula 1 contains ligand 2, which is large and possesses a strong electron-donating ability, thus enhancing the interaction between ligand 1 and ligand 2 in Formula 1. Therefore, the organometallic compound represented by Formula 1 can have improved structural stiffness, a reduced half-width (FWHM) in its photoluminescence or electroluminescence spectrum, and a reduced electronic vibrational dynamics. Consequently, the nonradiative decay of the organometallic compound represented by Formula 1 can be reduced, and electronic devices including the organometallic compound represented by Formula 1, such as organic light-emitting devices, can exhibit high luminous efficiency and long lifetime.

[0222] The highest occupied molecular orbital (HOMO) level, lowest unoccupied molecular orbital (LUMO) level, and T1 level of the organometallic compounds represented by Equation 1, denoted by Gaussian09, were evaluated using molecular structure optimization at the B3LYP level based on density functional theory (DFT). The results are shown in Table 1.

[0223] Table 1

[0224] Compound numbering HOMO(eV) LUMO(eV) <![CDATA[T1(eV)]]> 1 -4.798 -1.951 1.988 2 -4.792 -1.948 1.987 3 -4.791 -1.946 1.985 4 -4.678 -1.732 2.049 5 -4.682 -1.785 2.019 6 -4.677 -1.781 2.021 7 -4.610 -1.688 2.038 8 -4.804 -1.987 1.975 9 -4.764 -1.895 1.995 10 -4.798 -1.951 1.988 11 -4.736 -1.875 2.001 12 -4.673 -1.856 2.002 13 -4.647 -1.771 2.007 14 -4.678 -1.712 2.069 15 -4.594 -1.732 1.951 16 -4.674 -1.775 2.019

[0225] In one or more embodiments, when R in the organometallic compound represented by Formula 1 20 When neither fluorine (-F) nor cyano is included, the organometallic compound represented by Formula 1 can emit light with high color purity (e.g., light with a relatively narrow half-width (FWHM) in a photoluminescence or electroluminescence spectrum).

[0226] In one or more embodiments, the field-whole-hundred-meter (FWHM) of the emission peak of the photoluminescence or electroluminescence spectrum of the organometallic compound may be 64 nm or less. For example, the FWHM of the emission peak of the photoluminescence or electroluminescence spectrum of the organometallic compound may be about 45 nm to about 64 nm, about 45 nm to about 59 nm, about 49 nm to about 55 nm, or about 50 nm to about 55 nm.

[0227] In one or more embodiments, the maximum emission wavelength (emission peak wavelength, λ) of the emission peak of the photoluminescence or electroluminescence spectrum of the organometallic compound is... 最大 The wavelength can be from about 615 nm to about 640 nm. In one or more embodiments, the maximum emission wavelength (emission peak wavelength, λ) of the photoluminescence or electroluminescence spectrum of the organometallic compound is... 最大 It can be approximately 615nm to approximately 630nm or approximately 620nm to approximately 630nm.

[0228] In one or more embodiments, the highest occupied molecular orbital (HOMO) energy level of the organometallic compound represented by Formula 1 can be in the range of -5.300 eV to -5.050 eV, for example -5.200 eV to -5.100 eV. The HOMO energy level can be evaluated by cyclic voltammetry. For example, the HOMO energy level can be evaluated according to the method described in Table 2 below.

[0229] In one or more embodiments, the lowest unoccupied molecular orbital (LUMO) energy level of the organometallic compound represented by Formula 1 may be in the range of -2.900 eV to -2.300 eV, for example -2.700 eV to -2.300 eV. The LUMO energy level can be evaluated using UV absorption spectroscopy. For example, the LUMO energy level can be evaluated according to the methods described in Table 2 below.

[0230] In one or more embodiments, the photoluminescence quantum yield of the organometallic compound represented by Formula 1 in film form can be from about 91% to about 100%. For example, the PLQY of the organometallic compound in film form can be from about 92% to about 100%, from about 93% to about 100%, from about 94% to about 100%, from about 95% to about 100%, from about 96% to about 100%, from about 97% to about 100%, from about 98% to about 100%, or from about 99% to about 100%, or about 100%. For example, the PLQY in film form can be evaluated according to Evaluation 2 described below.

[0231] In one or more embodiments, the decay time of the organometallic compound represented by Formula 1 may be 0.9 μs or less, for example, in the range of 0.6 μs to 0.8 μs. The decay time can be evaluated by the time-resolved photoluminescence (TRPL) of the organometallic compound represented by Formula 1. For example, the decay time can be evaluated according to Evaluation 3 described below.

[0232] In one or more embodiments, the horizontal orientation ratio of the transition dipole moment of the organometallic compound represented by Formula 1 may be from about 90% to about 100%.

[0233] For example, the horizontal orientation ratio of the transition dipole moment of the organometallic compound may be, for example, about 90% to about 100%, about 91% to about 100%, about 92% to about 100%, about 93% to about 100%, about 94% to about 100%, about 95% to about 100%, about 96% to about 100%, about 97% to about 100%, about 98% to about 100%, about 99% to about 100%, or about 100%.

[0234] The horizontal orientation ratio of the transition dipole moment can be evaluated using an angle-dependent photoluminescence (PL) measurement device. The angle-dependent PL measurement device can be understood by referring to, for example, the description of the angle-dependent PL measurement device disclosed in Korean Application No. 2013-0150834. Korean Application No. 2013-0150834 is incorporated herein by reference.

[0235] As described above, due to the high horizontal orientation ratio of the transition dipole moments of the organometallic compounds, when driving an organic light-emitting device comprising the organometallic compound, an electric field can be emitted substantially parallel to the film comprising the organometallic compound, and therefore, optical losses caused by waveguide modes and / or surface plasmon polariton modes can be reduced. An external extraction efficiency (i.e., the efficiency of extracting light from the outside of an electronic device (e.g., an organic light-emitting device) comprising a film including the organometallic compound (e.g., the emitting layer described herein) can exist through such a mechanism. Therefore, electronic devices comprising the organometallic compound, such as organic light-emitting devices, can have high luminous efficiency.

[0236] By referring to the synthesis examples provided below, those skilled in the art will understand the method for synthesizing the organometallic compound represented by Formula 1.

[0237] The organometallic compound represented by Formula 1 is suitable for use in the organic layer of an organic light-emitting device, for example, as a dopant in the emitting layer of the organic layer. Therefore, another aspect provides an organic light-emitting device comprising: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode and including an emitting layer, wherein the organic layer comprises at least one organometallic compound represented by Formula 1.

[0238] Since the organic light-emitting device comprises an organic layer containing the organometallic compound represented by Formula 1, it can achieve excellent characteristics in terms of driving voltage, external quantum efficiency, roll-off ratio, lifetime, and a relatively narrow FWHM of the electroluminescence (EL) emission peak.

[0239] An organometallic compound of Formula 1 can be used between electrode pairs in an organic light-emitting device. For example, the organometallic compound represented by Formula 1 can be included in the emitting layer. In this respect, the organometallic compound can act as a dopant, and the emitting layer can further include a host (that is, the amount of the organometallic compound represented by Formula 1 in the emitting layer is less than the amount of the host).

[0240] In one or more embodiments, the emitting layer can emit red light.

[0241] The expression “(organic layer) comprises at least one organometallic compound” as used herein may include cases where “(organic layer) comprises the same organometallic compound represented by Formula 1” and cases where “(organic layer) comprises two or more different organometallic compounds represented by Formula 1”.

[0242] For example, the organic layer may include only compound 1 as the organometallic compound. In this respect, compound 1 may be present in the emitting layer of the organic light-emitting device. In one or more embodiments, the organic layer may include both compound 1 and compound 2 as the organometallic compound. In this respect, compound 1 and compound 2 may be present in the same layer (e.g., both compound 1 and compound 2 may be present in the emitting layer).

[0243] The first electrode may be the anode of the hole injection electrode and the second electrode may be the cathode of the electron injection electrode, or the first electrode may be the cathode of the electron injection electrode and the second electrode may be the anode of the hole injection electrode.

[0244] In one or more embodiments, in the organic light-emitting device, the first electrode is an anode and the second electrode is a cathode, and the organic layer further includes a hole transport region between the first electrode and the emitting layer and an electron transport region between the emitting layer and the second electrode, wherein the hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, and the electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0245] As used herein, the term "organic layer" refers to a single layer and / or multiple layers between the first electrode and the second electrode of the organic light-emitting device. In addition to organic compounds, the "organic layer" may include organometallic complexes containing metals.

[0246] Figure 1 This is a schematic diagram of the organic light-emitting device 10 according to an embodiment. In the following text, it will be referred to in conjunction with... Figure 1The structure of an organic light-emitting device according to an embodiment and a method for manufacturing an organic light-emitting device according to an embodiment are described. The organic light-emitting device 10 includes a first electrode 11, an organic layer 15, and a second electrode 19 stacked in sequence.

[0247] The substrate may be additionally located below the first electrode 11 or above the second electrode 19. Any substrate used in conventional organic light-emitting devices may be used as the substrate, and the substrate may be a glass substrate or a transparent plastic substrate, each of which has excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.

[0248] In one or more embodiments, the first electrode 11 can be formed by depositing or sputtering a material for forming the first electrode 11 onto the substrate. The first electrode 11 can be an anode. The material for forming the first electrode 11 can include a material having a high work function to facilitate hole injection. The first electrode 11 can be a reflective electrode, a semi-transparent electrode, or a transmissive electrode. The material for forming the first electrode 11 can be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), or zinc oxide (ZnO). In one or more embodiments, the material for forming the first electrode 11 can be a metal such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag).

[0249] The first electrode 11 may have a single-layer structure or a multi-layer structure comprising two or more layers. For example, the first electrode 11 may have a three-layer structure of ITO / Ag / ITO.

[0250] The organic layer 15 is located on the first electrode 11.

[0251] The organic layer 15 may include a hole transport region, an emitter layer, and an electron transport region.

[0252] The hole transport region may be located between the first electrode 11 and the emitter layer.

[0253] The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof.

[0254] The hole transport region may include a hole injection layer only or a hole transport layer. In one or more embodiments, the hole transport region may have a hole injection layer / hole transport layer structure or a hole injection layer / hole transport layer / electron blocking layer structure, which are stacked sequentially from the first electrode 11 in the order stated above.

[0255] When the hole transport region includes a hole injection layer (HIL), the hole injection layer can be formed on the first electrode 11 by using one or more suitable methods such as vacuum deposition, spin coating, casting, and / or Langmuir-Broguet (LB) deposition.

[0256] When a hole injection layer is formed by vacuum deposition, the deposition conditions can be varied depending on the material used to form the hole injection layer, as well as the structure and thermal properties of the hole injection layer. For example, deposition conditions may include a deposition temperature of about 100°C to about 500°C, and about 10 -8 To about 10 -3 The vacuum pressure of Tor, and about to approximately The deposition rate. However, deposition conditions are not limited to this.

[0257] When spin coating is used to form the hole injection layer, the coating conditions can be varied depending on the material used to form the hole injection layer, as well as the structure and thermal properties of the hole injection layer. For example, the coating speed can be from about 2,000 rpm to about 5,000 rpm, and the temperature at which heat treatment is performed after coating to remove the solvent can be from about 80°C to about 200°C. However, the coating conditions are not limited to these.

[0258] By referring to the conditions for forming the hole injection layer, the conditions for forming the hole transport layer and the electron blocking layer can be understood.

[0259] The hole transport region may include m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-sulfonated styrene) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-sulfonated styrene) (PANI / PSS), compounds represented by formula 201, compounds represented by formula 202, or any combination thereof:

[0260]

[0261] Formula 201

[0262]

[0263] Formula 202

[0264]

[0265] Ar in Equation 201 101and Ar 102 Each can be independently unsubstituted or substituted with the following: phenylene, cyclopentadienylene, indenylene, naphthylene, azuleylene, heptadienylene, acenaphtheylene, fluoreneylene, phenenylene, anthraceneylene, fluorenylene, benzo[9,10]phenenylene, pyreneylene, etc. alkyl, tetraphenylene, terephthalyl, perylene, or pentaphenylene: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl group, C1-C 60 Alkoxy, C3-C 10 cycloalkyl, C3-C 10 Cycloalkenyl, C2-C 10 Heterocyclic alkyl, C2-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, or any combination thereof.

[0266] In Equation 201, the notations xa and xb can each be independent integers 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.

[0267] R in equations 201 and 202 101 -R 108 R 111 -R 119 and R 121 -R 124 Each can be independently:

[0268] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl (e.g., methyl, ethyl, propyl, butyl, pentyl, or hexyl), or C1-C 10 Alkyl groups (e.g., methoxy, ethoxy, propoxy, butoxy, or pentoxy);

[0269] Each of the unsubstituted or substituted C1-C as follows 10 Alkyl or C1-C 10Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, or any combination thereof; or

[0270] Each of the following unsubstituted or substituted groups—phenyl, naphthyl, anthraceneyl, fluorenyl, or pyrene—is a deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl, C1-C 10 Alkoxy groups, or any combination thereof.

[0271] R in Equation 201 109 It may be an unsubstituted or substituted phenyl, naphthyl, anthracene, or pyridyl group, respectively, or substituted with the following: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amido, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl, C1-C 20 Alkoxy, phenyl, naphthyl, anthraceneyl, pyridyl, or any combination thereof.

[0272] In one or more embodiments, the compound represented by formula 201 may be represented by formula 201A:

[0273] Formula 201A

[0274]

[0275] By referring to the description provided in this article, R in Equation 201A can be understood. 101 R 111 R 112 and R 109 .

[0276] For example, the hole transport region may include one of compounds HT1 to HT21 or any combination thereof:

[0277]

[0278]

[0279]

[0280] The thickness of the hole transport region can be approximately to approximately For example, about to approximately Within the range. When the hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, the thickness of the hole injection layer can be approximately to approximately For example, about to approximately Within a certain range, and the thickness of the hole transport layer can be approximately [missing information]. to approximately For example, about to approximately Within these ranges, satisfactory hole transport characteristics can be obtained without a significant increase in driving voltage when the hole transport region, hole injection layer, and thickness of the hole transport layer are within these ranges.

[0281] In addition to these materials, the hole transport region may further include a charge-generating material for improving conductivity. The charge-generating material may be uniformly or non-uniformly dispersed in the hole transport region.

[0282] The charge-generating material may be, for example, a p-doper. The p-doper may be a quinone derivative, a metal oxide, a cyano-containing compound, or any combination thereof, but the embodiments of this disclosure are not limited thereto. Examples of the p-doper are quinone derivatives such as tetracyanoquinone dimethylane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethylane (F4-TCNQ), or F6-TCNNQ; metal oxides such as tungsten oxide or molybdenum oxide; cyano-containing compounds such as the following compound HT-D1; or any combination thereof.

[0283]

[0284] The hole transport region may include a buffer layer.

[0285] Furthermore, the buffer layer can compensate for the optical resonance distance according to the wavelength of the light emitted from the emission layer, and thus the efficiency of the formed organic light-emitting device can be improved.

[0286] Furthermore, when the hole transport region includes an electron blocking layer, the material used for the electron blocking layer can be the material described above for the hole transport region, the material used for the body (described later), or any combination thereof. For example, when the hole transport region includes an electron blocking layer, the material used for the electron blocking layer can be mCP, compound H21 (described later), or any combination thereof.

[0287] Then, an emitter layer (EML) 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 similar to those used when forming the hole injection layer, although the deposition or coating conditions can be varied depending on the material used to form the emitter layer.

[0288] The emitter layer may include a host and a dopant, and the dopant may include an organometallic compound represented by Formula 1 as described herein.

[0289] The subject may include TPBi, TBADN, ADN (also known as "DNA"), CBP, CDBP, TCP, mCP, compound H50, compound H51, compound H52, or any combination thereof.

[0290]

[0291] When the organic light-emitting device is a full-color organic light-emitting device, the emitting layer can be patterned as a red emitting layer, a green emitting layer, and / or a blue emitting layer. In one or more embodiments, due to the stacked structure including red, green, and / or blue emitting layers, the emitting layer can emit white light.

[0292] When the emitter layer comprises a host and a dopant, the amount of the dopant may be in the range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host, but embodiments of the present disclosure are not limited thereto.

[0293] The thickness of the emission layer can be approximately to approximately For example, about to approximately Within this range, excellent light emission characteristics can be obtained without a significant increase in driving voltage when the thickness of the emitting layer is within this range.

[0294] Then, the electron transport region can be located on the emission layer.

[0295] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0296] 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.

[0297] By referring to the conditions for forming the hole injection layer, the conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer constituting the electron transport region can be understood.

[0298] When the electron transport region includes a hole blocking layer, the hole blocking layer may include at least one of, for example, BCP, Bphen, and BAlq:

[0299]

[0300] In one or more embodiments, the hole blocking layer may include the body, a material for forming an electron transport layer (described later), a material for forming an electron injection layer (described later), or any combination thereof.

[0301] The thickness of the hole-blocking layer can be approximately to approximately For example, about to approximately Within these ranges, when the thickness of the hole blocking layer is within these ranges, the hole blocking layer can have excellent hole blocking characteristics without a significant increase in driving voltage.

[0302] The electron transport layer may include BCP, Bphen, TPBi, Alq3, BAlq, TAZ, NTAZ, or any combination thereof:

[0303]

[0304] In one or more embodiments, the electron transport layer may include one of compounds ET1 to ET25 or any combination thereof:

[0305]

[0306]

[0307]

[0308] The thickness of the electron transport layer can be approximately to approximately For example, about to approximately Within the range described above, when the thickness of the electron transport layer is within the range described above, the electron transport layer can have satisfactory electron transport characteristics without a significant increase in driving voltage.

[0309] Furthermore, in addition to the materials described above, the electron transport layer may further include a metallic material.

[0310] The metal-containing material may include Li complexes. The Li complexes may include, for example, compounds ET-D1, ET-D2, or combinations thereof.

[0311]

[0312] The electron transport region may include an electron injection layer (EIL) that facilitates the inflow of electrons from the second electrode 19 therein.

[0313] The electron injection layer may include LiF, NaCl, CsF, Li2O, BaO, or any combination thereof.

[0314] The thickness of the electron injection layer can be approximately to approximately For example, about to approximately Within the range described above, when the thickness of the electron injection layer is within the range described above, the electron injection layer can have satisfactory electron injection characteristics without a significant increase in driving voltage.

[0315] The second electrode 19 may be located on the organic layer 15. The second electrode 19 may be a cathode. The material used to form the second electrode 19 may be a metal, alloy, conductive compound, or any combination thereof with a relatively low work function. For example, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag) may be used as materials for forming the second electrode 19. For the fabrication of a top-emitting light-emitting device, a transmissive electrode formed using ITO or IZO may be used as the second electrode 19.

[0316] As mentioned above, [the text has already been referenced]. Figure 1 Organic light-emitting devices have been described, but embodiments of the present disclosure are not limited thereto.

[0317] In the following, the compounds and organic light-emitting devices according to the embodiments are described in detail with reference to the synthesis examples and examples. However, the organic light-emitting devices are not limited thereto. The phrase "using B instead of A" used in describing the synthesis examples means that, in molar equivalents, the amount of A used is the same as the amount of B used.

[0318] Example

[0319] Synthesis Example 1 (Compound 1)

[0320]

[0321] Synthesis of compound L1(1)

[0322] 4-Chloro-8-methyl-9-(trifluoromethyl)benzo[f]isoquinoline (24.53 g, 82.95 mmol), (3,5-dimethylphenyl)boronic acid (14.93 g, 99.54 mmol), Pd(PPh3)4 (4.80 g, 4.15 mmol), K2CO3 (34.38 g, 248.85 mmol), tetrahydrofuran (THF) (200 mL), and distilled water (50 mL) were mixed together, and the mixture was stirred under reflux for 18 hours. The reaction temperature was then lowered to room temperature, and the mixture was extracted using dichloromethane (MC). The resulting organic layer was dried by adding anhydrous magnesium sulfate (MgSO4) to remove moisture, and then filtered. The solvent was removed from the filtrate under reduced pressure, and the residue was purified by column chromatography at ethyl acetate (EA):hexane = 1:5, thereby yielding 24.37 g (80%) of compound L1 (1).

[0323] MALDI-TOFMS (m / z): C 23 H 18 F3N(M+)365.37

[0324] Synthesis of compound L1(2)

[0325] Compound L1(1) (24.37 g, 66.70 mmol), iridium chloride (11.75 g, 33.32 mmol), ethoxyethanol (300 mL), and distilled water (100 mL) were mixed together, and the mixture was stirred under reflux for 24 hours. The reaction temperature was lowered to room temperature, and the resulting solid was separated by filtration, then thoroughly washed with water, methanol, and hexane in the order stated, and the resulting solid was dried in a vacuum oven to obtain compound L1(2) (19.00 g, 69%).

[0326] Synthesis of Compound 1

[0327] Compound L1(2) (19.00 g, 11.48 mmol), 3,7-diethyl-3,7-dimethylnonane-4,6-dione (13.80 g, 57.40 mmol), Na2CO3 (12.17 g, 114.80 mmol), and ethoxyethanol (300 mL) were mixed together and stirred for 24 hours. The resulting mixture was filtered, and the filtered solid was thoroughly washed with methanol and hexane and purified by column chromatography at a dichloromethane:n-hexane ratio of 1:1 (v / v) to obtain compound 1 (13.00 g, 55%). Compound 1 was confirmed by mass spectrometry and high-performance liquid chromatography (HPLC).

[0328] For C 61 H 60 HRMS (MALDI) calculated for F6IrN2O2: m / z 1159.42, measured value: 1159.37

[0329] Synthesis Example 2 (Compound 2)

[0330]

[0331] Compound 2 (11 g, 60%) was obtained in the same manner as in the synthesis of compound 1 in Synthetic Example 1, except that 3,3,7,7-tetramethylnonane-4,6-dione was used instead of 3,7-diethyl-3,7-dimethylnonane-4,6-dione. Compound 2 was confirmed by mass spectrometry and HPLC.

[0332] For C 59 H 56 HRMS (MALDI) calculated for F6IrN2O2: m / z 1131.39, measured value: 1131.32

[0333] Synthesis Example 3 (Compound 3)

[0334]

[0335] Compound 3 (5 g, 50%) was obtained in the same manner as in the synthesis of compound 1 in Synthetic Example 1, except that 2,2,6,6-tetramethylheptane-3,5-dione was used instead of 3,7-diethyl-3,7-dimethylnonane-4,6-dione. Compound 3 was confirmed by mass spectrometry and HPLC.

[0336] For C 57 H 52 HRMS (MALDI) calculated for F6IrN2O2: m / z 1160.35, measured value: 1160.37

[0337] Synthesis Example 4 (Compound 4)

[0338]

[0339] Synthesis of compound L4(1)

[0340] 4-Chloro-8-fluorobenzo[f]isoquinoline (19.22 g, 82.95 mmol), (3,5-dimethylphenyl)boronic acid (14.93 g, 99.54 mmol), Pd(PPh3)4 (4.80 g, 4.15 mmol), K2CO3 (34.38 g, 248.85 mmol), THF (200 mL), and distilled water (50 mL) were mixed together and the mixture was stirred under reflux for 18 hours. The reaction temperature was then lowered to room temperature and extracted using MC. The resulting organic layer was dried by adding MgSO4 to remove moisture and then filtered. The solvent was removed from the filtrate under reduced pressure, and the residue was purified by column chromatography at EA:hexane = 1:5, thereby yielding 20.1 g (80%) of compound L4 (1).

[0341] MALDI-TOFMS (m / z): C 21 H 16 FN(M+)301.36

[0342] Synthesis of compound L4(2)

[0343] Compound L4(1) (20.10 g, 66.70 mmol), iridium chloride (11.75 g, 33.32 mmol), ethoxyethanol (300 mL), and distilled water (100 mL) were mixed together, and the mixture was stirred under reflux for 24 hours. The reaction temperature was lowered to room temperature, and the resulting solid was separated by filtration, then thoroughly washed with water, methanol, and hexane in the order stated, and the resulting solid was dried in a vacuum oven to obtain compound L4(2) (19.00 g, 69%).

[0344] Synthesis of Compound 4

[0345] Compound L4(2) (19.00 g, 11.48 mmol), 2,2,6,6-tetramethylheptane-3,5-dione (10.56 g, 57.40 mmol), Na2CO3 (12.17 g, 114.80 mmol), and ethoxyethanol (300 mL) were mixed together, and the mixture was stirred for 24 hours to allow the reaction to proceed. The resulting mixture was filtered, and the filtered solid was thoroughly washed with methanol and hexane, and purified by column chromatography at a dichloromethane:n-hexane ratio of 1:1 (v / v) to obtain compound 4 (13.00 g, 55%). Compound 4 was confirmed by mass spectrometry and HPLC.

[0346] For C 53 H 48HRMS (MALDI) calculated for F₂IrN₂O₂: m / z 975.19, measured value: 975.20

[0347] Synthesis Example 5 (Compound 5)

[0348]

[0349] Synthesis of compound L5(1)

[0350] 4-Chloro-7,9-difluorobenzo[f]isoquinoline (20.71 g, 82.95 mmol), (3,5-dimethylphenyl)boronic acid (14.93 g, 99.54 mmol), Pd(PPh3)4 (4.80 g, 4.15 mmol), K2CO3 (34.38 g, 248.85 mmol), THF (200 mL), and distilled water (50 mL) were mixed together and the mixture was stirred under reflux for 18 hours. The reaction temperature was then lowered to room temperature and extracted using MC. The resulting organic layer was dried by adding MgSO4 to remove moisture and then filtered. The solvent was removed from the filtrate under reduced pressure, and the residue was purified by column chromatography at EA:hexane = 1:5, thereby yielding 21.30 g (80%) of compound L5 (1).

[0351] MALDI-TOFMS (m / z): C 21 H 15 F2N(M+)319.35

[0352] Synthesis of compound L5(2)

[0353] Compound L5(1) (21.30 g, 66.70 mmol), iridium chloride (11.75 g, 33.32 mmol), ethoxyethanol (300 mL), and distilled water (100 mL) were mixed together, and the mixture was stirred under reflux for 24 hours. The reaction temperature was lowered to room temperature, and the resulting solid was separated by filtration, then thoroughly washed with water, methanol, and hexane in the order stated, and the resulting solid was dried in a vacuum oven to obtain compound L5(2) (19.00 g, 69%).

[0354] Synthesis of Compound 5

[0355] Compound L5(2) (19.00 g, 11.48 mmol), 3,7-diethyl-3,7-dimethylnonane-4,6-dione (13.80 g, 57.40 mmol), Na2CO3 (12.17 g, 114.80 mmol), and ethoxyethanol (300 mL) were mixed together and stirred for 24 hours. The resulting mixture was filtered, and the filtered solid was thoroughly washed with methanol and hexane and purified by column chromatography at a dichloromethane:n-hexane ratio of 1:1 (v / v) to obtain compound 5 (13.00 g, 55%). Compound 5 was confirmed by mass spectrometry and HPLC.

[0356] For C 57 H 54 HRMS (MALDI) calculated for F4IrN2O2: m / z 1067.38, measured value: 1067.28

[0357] Synthesis Example 6 (Compound 6)

[0358]

[0359] Synthesis of compound L6(1)

[0360] 4-Chloro-9-fluorobenzo[f]isoquinoline (19.21 g, 82.95 mmol), (3,5-dimethylphenyl)boronic acid (14.93 g, 99.54 mmol), Pd(PPh3)4 (4.80 g, 4.15 mmol), K2CO3 (34.38 g, 248.85 mmol), THF (200 mL), and distilled water (50 mL) were mixed together and the mixture was stirred under reflux for 18 hours. The reaction temperature was then lowered to room temperature and extracted using MC. The extracted organic layer was dried by adding MgSO4 to remove moisture and then filtered. The solvent was removed from the filtrate under reduced pressure, and the residue was purified by column chromatography at EA:hexane = 1:5, thereby giving 20.10 g (80%) of compound L6 (1).

[0361] MALDI-TOFMS (m / z): C 21 H 16 FN(M+)301.36

[0362] Synthesis of compound L6(2)

[0363] Compound L6(1) (20.10 g, 66.70 mmol), iridium chloride (11.75 g, 33.32 mmol), ethoxyethanol (300 mL), and distilled water (100 mL) were mixed together, and the mixture was stirred under reflux for 24 hours. The reaction temperature was lowered to room temperature, and the resulting solid was separated by filtration, then thoroughly washed with water, methanol, and hexane in the order stated, and the resulting solid was dried in a vacuum oven to obtain compound L6(2) (19.00 g, 69%).

[0364] Synthesis of Compound 6

[0365] Compound L6(2) (19.00 g, 11.48 mmol), 3,3,7,7-tetramethylnonane-4,6-dione (13.80 g, 57.40 mmol), Na2CO3 (12.17 g, 114.80 mmol), and ethoxyethanol (300 mL) were mixed together and stirred for 24 hours. The resulting mixture was filtered, and the filtered solid was thoroughly washed with methanol and hexane and purified by column chromatography at a dichloromethane:n-hexane ratio of 1:1 (v / v) to obtain compound 6 (13.00 g, 55%). Compound 6 was confirmed by mass spectrometry and HPLC.

[0366] For C 55 H 52 HRMS (MALDI) calculated for F₂IrN₂O₂: m / z 1003.36, measured value: 1003.25

[0367] Synthesis Example 7 (Compound 10)

[0368]

[0369] Synthesis of compound L10(1)

[0370] 4-Chloro-9-(trifluoromethyl)benzo[f]isoquinoline (23.36 g, 82.95 mmol), (3,5-dimethylphenyl)boronic acid (14.93 g, 99.54 mmol), Pd(PPh3)4 (4.80 g, 4.15 mmol), K2CO3 (34.38 g, 248.85 mmol), THF (200 mL), and distilled water (50 mL) were mixed together and the mixture was stirred under reflux for 18 hours. The reaction temperature was then lowered to room temperature and extracted using MC. The resulting organic layer was dried by adding MgSO4 to remove moisture and then filtered. The solvent was removed from the filtrate under reduced pressure, and the residue was purified by column chromatography at EA:hexane = 1:5, thereby yielding 23.43 g (80%) of compound L10 (1).

[0371] MALDI-TOFMS (m / z): C 22 H 16 FN(M+)351.36

[0372] Synthesis of compound L10(2)

[0373] Compound L10(1) (23.43 g, 66.70 mmol), iridium chloride (11.75 g, 33.32 mmol), ethoxyethanol (300 mL), and distilled water (100 mL) were mixed together, and the mixture was stirred under reflux for 24 hours. The reaction temperature was lowered to room temperature, and the resulting solid was separated by filtration, then thoroughly washed with water, methanol, and hexane in the order stated, and the resulting solid was dried in a vacuum oven to obtain compound L10(2) (19.00 g, 69%).

[0374] Synthesis of Compound 10

[0375] Compound L10(2) (19.00 g, 11.48 mmol), 1-((3R,5R,7R)-adamantane-1-yl)-4,4-dimethylpentane-1,3-dione (15.06 g, 57.40 mmol), Na2CO3 (12.17 g, 114.80 mmol), and ethoxyethanol (300 mL) were mixed together and stirred for 24 hours. The resulting mixture was filtered, and the filtered solid was thoroughly washed with methanol and hexane and purified by column chromatography at a dichloromethane:n-hexane ratio of 1:1 (v / v) to obtain compound 10 (13.00 g, 55%). Compound 10 was confirmed by mass spectrometry and HPLC.

[0376] For C61 H 54 HRMS (MALDI) calculated for F6IrN2O2: m / z 1153.37, measured value: 1153.32

[0377] Synthesis Example 8 (Compound 13)

[0378]

[0379] Synthesis of compound L13(1)

[0380] 4-Chloro-6-fluorobenzo[f]isoquinoline (19.21 g, 82.95 mmol), (3,5-dimethylphenyl)boronic acid (14.93 g, 99.54 mmol), Pd(PPh3)4 (4.80 g, 4.15 mmol), K2CO3 (34.38 g, 248.85 mmol), THF (200 mL), and distilled water (50 mL) were mixed together and the mixture was stirred under reflux for 18 hours. The reaction temperature was then lowered to room temperature and extracted using MC. The resulting organic layer was dried by adding MgSO4 to remove moisture and then filtered. The solvent was removed from the filtrate under reduced pressure, and the residue was purified by column chromatography at EA:hexane = 1:5, thereby yielding 20.10 g (80%) of compound L13 (1).

[0381] MALDI-TOFMS (m / z): C 21 H 16 FN(M+)301.36

[0382] Synthesis of compound L13(2)

[0383] Compound L13(1) (20.10 g, 66.70 mmol), iridium chloride (11.75 g, 33.32 mmol), ethoxyethanol (300 mL), and distilled water (100 mL) were mixed together, and the mixture was stirred under reflux for 24 hours. The reaction temperature was lowered to room temperature, and the resulting solid was separated by filtration, then thoroughly washed with water, methanol, and hexane in the order stated, and the resulting solid was dried in a vacuum oven to obtain compound L13(2) (19.00 g, 69%).

[0384] Synthesis of Compound 13

[0385] Compound L13(2) (19.00 g, 11.48 mmol), 2,2,6,6-tetramethylheptane-3,5-dione (10.56 g, 57.40 mmol), Na2CO3 (12.17 g, 114.80 mmol), and ethoxyethanol (300 mL) were mixed together and stirred for 24 hours. The resulting mixture was filtered, and the filtered solid was thoroughly washed with methanol and hexane and purified by column chromatography at a dichloromethane:n-hexane ratio of 1:1 (v / v) to obtain compound 13 (13.00 g, 55%). Compound 13 was confirmed by mass spectrometry and HPLC.

[0386] For C 53 H 48 HRMS (MALDI) calculated for F₂IrN₂O₂: m / z 975.19, measured value: 975.20

[0387] Synthesis of Example 9 (Compound 16)

[0388]

[0389] Synthesis of compound L16(1)

[0390] 4-Chloro-7-fluorobenzo[f]isoquinoline (19.21 g, 82.95 mmol), (3,5-dimethylphenyl)boronic acid (14.93 g, 99.54 mmol), Pd(PPh3)4 (4.80 g, 4.15 mmol), K2CO3 (34.38 g, 248.85 mmol), THF (200 mL), and distilled water (50 mL) were mixed together and the mixture was stirred under reflux for 18 hours. The reaction temperature was then lowered to room temperature and extracted using MC. The resulting organic layer was dried by adding MgSO4 to remove moisture and then filtered. The solvent was removed from the filtrate under reduced pressure, and the residue was purified by column chromatography at EA:hexane = 1:5, thereby yielding 20.10 g (80%) of compound L16 (1).

[0391] MALDI-TOFMS (m / z): C 21 H 16 FN(M+)301.36

[0392] Synthesis of compound L16(2)

[0393] Compound L16(1) (20.10 g, 66.70 mmol), iridium chloride (11.75 g, 33.32 mmol), ethoxyethanol (300 mL), and distilled water (100 mL) were mixed together, and the mixture was stirred under reflux for 24 hours. The reaction temperature was lowered to room temperature, and the resulting solid was separated by filtration, then thoroughly washed with water, methanol, and hexane in the order stated, and the resulting solid was dried in a vacuum oven to obtain compound L16(2) (19.00 g, 69%).

[0394] Synthesis of Compound 16

[0395] Compound L16(2) (19.00 g, 11.48 mmol), 2,2,6,6-tetramethylheptane-3,5-dione (10.56 g, 57.40 mmol), Na2CO3 (12.17 g, 114.80 mmol), and ethoxyethanol (300 mL) were mixed together and stirred for 24 hours. The resulting mixture was filtered, and the filtered solid was thoroughly washed with methanol and hexane and purified by column chromatography at a dichloromethane:n-hexane ratio of 1:1 (v / v) to obtain compound 16 (13.00 g, 55%). Compound 16 was confirmed by mass spectrometry and HPLC.

[0396] For C 53 H 48 HRMS (MALDI) calculated for F₂IrN₂O₂: m / z 975.19, measured value: 975.20

[0397] Evaluation Example 1: Evaluation of HOMO and LUMO energy levels

[0398] The HOMO and LUMO levels of compounds 1-6, 10, 13, 16, AD, and E1-E3 were evaluated according to the methods in Table 2. The results are shown in Table 3.

[0399] Table 2

[0400]

[0401]

[0402] Table 3

[0403] Compound numbering HOMO(eV) LUMO(eV) 1 -5.140 -2.572 2 -5.150 -2.571 3 -5.130 -2.571 4 -5.110 -2.460 5 -5.160 -2.600 6 -5.120 -2.500 10 -5.150 -2.571 13 -5.110 -2.521 16 -5.119 -2.530 A -5.010 -2.351 B -5.000 -2.328 C -5.373 -2.487 D -5.908 -3.014 E1 -5.216 -2.722 E2 -5.237 -2.673 E3 -5.166 -2.571

[0404]

[0405]

[0406] Evaluation Example 2: Evaluation of Photoluminescent Quantum Yield (PLQY)

[0407] Compound H52 and compound 1 were mixed at 10 -7 A 40 nm thick film was prepared by co-deposition under vacuum pressure and at a weight ratio of 98:2.

[0408] The PLQY of compound 1 in film form was evaluated using the Hamamatsu Photonics absolute PL quantum yield measurement system equipped with a xenon light source, monochromator, photon multichannel analyzer, and integrating sphere, and using PLQY measurement software (Hamamatsu Photonics, Ltd., Shizuoka, Japan). The results are shown in Table 4.

[0409] The PLQY of compounds 2-6, 10, 13, 16, AD and E1-E3 was measured, and the results are shown in Table 4.

[0410] Table 4

[0411]

[0412]

[0413] As shown in Table 4, compounds 1-6, 10, 13 and 16 were found to have superior PLQY (in membrane form) compared to compounds AD and E1-E3.

[0414]

[0415] Evaluation Example 3: Measurement of Decay Time

[0416] Prepare a quartz substrate that has been washed with chloroform and pure water. Then, place the materials shown in Table 5 in a 10-meter range. -7 Vacuum (co)deposition under vacuum pressure was used to prepare films 1-6, 10, 13, 16, AD and E1-E3, each with a thickness of 50 nanometers (nm).

[0417] Using a time-resolved photoluminescence (TRPL) measurement system, FluoTime 300 (available from PicoQuant), and a pump source, PLS340 (available from PicoQuant, excitation wavelength = 340 nm, spectral width = 20 nm), the PL spectra of each of the prepared films 1-6, 10, 13, 16, AD, and E1-E3 were evaluated at room temperature. The wavelength of the main peak in each PL spectrum was then determined, and the number of photons emitted at the main peak wavelength of each film was repeatedly measured over time using time-correlated single-photon counting (TCSPC) under a photon pulse (pulse width = 500 picoseconds, ps) applied to the film through the PLS340, thereby obtaining a TRPL curve suitable for adequate fitting. For films 1-6, 10, 13, 16, AD, and E1-E3, based on the obtained results, two or more exponential decay functions were proposed for fitting, thereby obtaining the T... 衰减 (Ex), i.e., the decay time. The results are shown in Table 5. The function used for fitting is as described in Equation 1, and the decay time T is the maximum value among the respective values ​​of the exponential decay function used for fitting. 衰减 Let T be the value of T. 衰减 (Ex), i.e., decay time. Here, the same measurement is repeated again in darkness (i.e., where the pump signal incident on each of the membranes is blocked) during the same measurement time used to obtain the TRPL curve, thereby obtaining a baseline or a background signal curve that can be used as a baseline for fitting:

[0418] Equation 1

[0419]

[0420] Table 5

[0421]

[0422] As shown in Table 5, compounds 1-6, 10, 13 and 16 were found to have superior decay times compared to compounds AD and E1-E3.

[0423] Example 1

[0424] The ITO patterned glass substrate, used as the anode, was cut into 50mm x 50mm x 0.5mm pieces, ultrasonically cleaned with isopropanol and pure water for 5 minutes each, then irradiated with ultraviolet light for 30 minutes and cleaned by exposure to ozone. The resulting substrate was then mounted on a vacuum deposition apparatus.

[0425] HT3 and F6-TCNNQ were vacuum co-deposited on an ITO anode at a weight ratio of 98:2 to form a structure with... A thick hole injection layer is formed by vacuum deposition of HT3 onto the hole injection layer to create a layer with [missing information]. A hole transport layer of thickness is formed, and then HT21 is vacuum deposited on the hole transport layer to form a hole transport layer with a thickness of [missing information]. A thick electron blocking layer.

[0426] Then, H52 (the host) and Compound 1 (the dopant) were co-deposited on the electron blocking layer at a weight ratio of 98:2 to form a structure with... Thick emission layer.

[0427] Then, ET3 and ET-D1 were co-deposited on the emitter layer at a volume ratio of 50:50 to form a structure with... A thick electron transport layer is formed, and ET-D1 is vacuum-deposited onto the electron transport layer to form a layer with... A thick electron-injected layer is formed, and Al is vacuum-deposited onto the electron-injected layer to form a layer with [missing information]. A cathode of a certain thickness is thus formed, thereby achieving an ITO-based cathode. / HT3+F6-TCNNQ (2% by weight) / HT3 / HT21 / H52+ compound 1 (2 wt%) / ET3+ET-D1(50%) / ET-D1 / Al Fabrication of organic light-emitting devices with specific structures.

[0428]

[0429] Examples 2-9 and Comparative Examples AD and E1-E3

[0430] The organic light-emitting device was fabricated in essentially the same manner as in Example 1, except that the compounds shown in Table 6 were used instead of compound 1 as dopants in the formation of the emitting layer.

[0431] Evaluation Example 4: Evaluation of the characteristics of organic light-emitting devices

[0432] The driving voltage, current density, maximum external quantum efficiency (Max EQE), roll-off ratio, FWHM of the emission peak in the EL spectrum, color coordinates, and / or lifetime (LT) of the organic light-emitting devices fabricated in Examples 1-9 and Comparative Examples AD and E1-E3 were evaluated. 97 The results are shown in Tables 6 and 7. A Keithley 2400 ammeter / voltmeter and a luminance meter (Minolta Cs-1000A) were used in the evaluation. Lifetime (LT) 97The roll-off ratio () refers to the time required for the initial luminance of an organic light-emitting device (OLED) to decrease from 3,500 nits to 97%, expressed as a relative value (%). The roll-off ratio is calculated using Equation 20:

[0433] Equation 20

[0434] Roll-off ratio = {1 - (efficiency (at 3,500 nits) / maximum luminous efficacy)} × 100%

[0435] Table 6

[0436]

[0437] Table 7

[0438]

[0439]

[0440] Referring to Tables 6 and 7, it was found that compared with Comparative Examples AD and E1-E3, the organic light-emitting devices of Examples 1-9 have excellent driving voltage, excellent external quantum efficiency, excellent roll-off ratio, and excellent lifetime characteristics, while emitting red light with a relatively narrow FWHM.

[0441] As clearly described above, the organometallic compounds can possess excellent electrical properties and stability. Therefore, electronic devices including these organometallic compounds, such as organic light-emitting devices, can exhibit improved driving voltage, improved external quantum emission efficiency, improved roll-off ratio, improved lifetime, and a relatively narrow emission peak FWHM in the EL spectrum. Furthermore, diagnostic compositions including these organometallic compounds can possess high diagnostic efficiency because these organometallic compounds are excellent in terms of phosphorescence emission properties.

[0442] It should be understood that the embodiments described herein should be considered only in a descriptive sense and are not intended for limiting purposes. The description of features or aspects within each embodiment should typically be considered applicable to other similar features or aspects in other embodiments.

[0443] 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, Depend on The group represented is the group represented by formula A(1): In equation A(1), Y2 is C, R9-R 12 Each is independently hydrogen, deuterium, -F, and either unsubstituted or deuterated, -F, or C1-C. 20 Alkyl, C3-C 10 Cycloalkyl, or any combination thereof, substituted C1-C 20 Alkyl or C3-C 10 Cycloalkyl, -Si(Q3)(Q4)(Q5), or -Ge(Q3)(Q4)(Q5), *' indicates the binding site with Ir in Equation 1, and * indicates a binding site with an adjacent atom in Equation 1. R1-R8 and A7 are each independently hydrogen, deuterium, -F, unsubstituted or deuterated, -F, C1-C. 20 Alkyl, C3-C 10 Cycloalkyl, or any combination thereof, substituted C1-C 20 Alkyl or C3-C 10 Cycloalkyl, -Si(Q3)(Q4)(Q5), or -Ge(Q3)(Q4)(Q5), R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 and R 12 At least one of them includes at least one fluorine group (-F), A1-A6 are each independently unsubstituted or replaced by deuterium, -F, C1-C. 20 Alkyl, C3-C 10 Cycloalkyl, or any combination thereof, substituted C1-C 20 Alkyl or C3-C 10 cycloalkyl, and Where Q3-Q5 are each independently -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; or Each of the following unsubstituted or substituted groups: n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, phenyl, biphenyl, or naphthyl: deuterium, C1-C 10 Alkyl, phenyl, or any combination thereof, The condition is that the organometallic compound is not one of the following compounds:

2. The organometallic compound of claim 1, wherein... At least one of R1-R8 is: Fluorine (-F); or Each of the unreplaced or replaced by deuterium, C1-C 20 Alkyl, C3-C 10 Fluorinated C1-C atoms substituted with cycloalkyl groups or any combination thereof 20 Alkyl or fluorinated C3-C 10 Cycloalkyl.

3. The organometallic compound of claim 1, wherein... At least one of R2-R8 includes at least one fluorine group.

4. The organometallic compound of claim 1, wherein... In Equation 1, by The group represented is one of the groups represented by formulas CY1 to CY84: in, In formulas CY1 to CY84, T2-T8 are each independent of: Fluorine (-F); or Each of the unreplaced or replaced by deuterium, C1-C 20 Alkyl, C3-C 10 Fluorinated C1-C atoms substituted with cycloalkyl groups or any combination thereof 20 Alkyl or fluorinated C3-C 10 cycloalkyl; R2-R8 are each identical to those described in claim 1, and R2-R8 are not hydrogen. * indicates the binding site with Ir in Equation 1, and *" indicates the binding site with adjacent atoms in Formula 1.

5. The organometallic compound of claim 4, wherein... In equations CY1 to CY84, R2-R8 are each independently: Deuterium; or Each of the unreplaced or replaced by deuterium, C1-C 20 Alkyl, C3-C 10 Cycloalkyl, or any combination thereof, substituted C1-C 20 Alkyl or C3-C 10 Cycloalkyl.

6. The organometallic compound of claim 1, wherein... In equation A(1), R9 and R 11 Each independently constitutes its own unreplaced or deuterated, C1-C 20 Alkyl, C3-C 10 Cycloalkyl, or any combination thereof, substituted C1-C 20 Alkyl or C3-C 10 Cycloalkyl.

7. The organometallic compound of claim 1, wherein... At least one of A1-A6 is independently a substituted or unsubstituted C2-C. 20 Alkyl, or substituted or unsubstituted C3-C 10 Cycloalkyl.

8. The organometallic compound of claim 1, wherein... The groups represented by *-C(A1)(A2)(A3) in Formula 1 contain 5 or more carbon atoms, and The number of carbons in the groups represented by *-C(A4)(A5)(A6) in Formula 1 is 5 or more.

9. The organometallic compound of claim 1, wherein... The organometallic compound is at least one of the following compounds: 1, 4, 6 to 9, and 11 to 15:

10. Organic light-emitting devices, including: First electrode; Second electrode; as well as An organic layer comprising an emission layer is disposed between the first electrode and the second electrode. The organic layer comprises at least one organometallic compound as described in any one of claims 1-9.

11. The organic light-emitting device of claim 10, wherein... The first electrode is the anode. The second electrode is a cathode. The organic layer further includes a hole transport region between the first electrode and the emitter layer, and an electron transport region between the emitter layer and the second electrode. The hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof. The electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

12. The organic light-emitting device of claim 10, wherein... The organometallic compound is included in the emitter layer.

13. A diagnostic composition comprising at least one organometallic compound as claimed in any one of claims 1-9.

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