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

Abstract

Provided are an organometallic compound, an organic light-emitting device including the same, and an electronic device including the organic light-emitting device, wherein the organometallic compound is represented by Formula 1, and in Formula 1, Y2, Ring CY1, Ring CY2, T1, T2, A1-A7, a1, and a2 are as defined in the specification. <Formula 1>#imgabs0#.

Description

[0001] Cross - reference to related applications

[0002] This application claims the benefit of Korean Patent Application Nos. 10 - 2019 - 0037213, filed on March 29, 2019, and 10 - 2020 - 0035405, filed on March 24, 2020, with the Korean Intellectual Property Office, the entire disclosures of which are incorporated herein by reference. Technical field

[0003] One or more embodiments relate to an organometallic compound, an organic light - emitting device including the organometallic compound, and an electronic device including the organic light - emitting device. Background art

[0004] An organic light - emitting device is a self - emitting device having good characteristics in terms of viewing angle, response time, brightness, driving voltage, and response speed and generating a full - color image.

[0005] In an example, an organic light - emitting device includes an anode, a cathode, and an organic layer between the anode and the cathode, where the organic layer includes an emission layer. A hole - transport region may be between the anode and the emission layer, and an electron - transport region may be between the emission layer and the cathode. Holes provided from the anode may move toward the emission layer through the hole - transport region, and electrons provided from the cathode may move toward the emission layer through the electron - transport region. The holes and electrons recombine in the emission layer to generate excitons. These excitons transition from an excited state to a ground state, thereby generating light. Summary of the invention

[0006] Aspects of the present disclosure provide an organometallic compound, an organic light - emitting device including the organometallic compound, and an electronic device including the organic light - emitting device.

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

[0008] One aspect of the present disclosure provides an organometallic compound represented by Formula 1:

[0009] <Formula 1>

[0010]

[0011] Wherein, in Formula 1,

[0012] Y2 is C or N,

[0013] Ring CY1 is a C5 - C polycyclic group in which three or more monocyclic groups are fused to each other, where in Formula 1, 30 by The group represented is not the group represented by and ＊ is a binding site to iridium (Ir) in Formula 1, and ＊ " is a binding site to ring CY2 in Formula 1,

[0014] Ring CY2 is a C5-C 30 carbocyclic group or a C1-C 30 heterocyclic group,

[0015] T1, T2, and A1 - A7 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, a carboxylic acid group or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, a substituted or unsubstituted C1-C 60 alkyl group, a substituted or unsubstituted C2-C 60 alkenyl group, a substituted or unsubstituted C2-C 60 alkynyl group, a substituted or unsubstituted C1-C 60 alkoxy group, a substituted or unsubstituted C1-C 60 alkylthio group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 heterocycloalkyl group, a substituted or unsubstituted C3-C 10 cycloalkenyl group, a substituted or unsubstituted C1-C 10 heterocycloalkenyl group, a substituted or unsubstituted C6-C 60 aryl group, a substituted or unsubstituted C6-C 60 aryloxy group, a substituted or unsubstituted C6-C 60 arylthio group, a substituted or unsubstituted C1-C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9),

[0016] a1 and a2 are each independently an integer from 0 to 20; when a1 is 2 or greater, two or more of T1 are the same or different from each other; when a2 is 2 or greater, two or more of T2 are the same or different from each other; and the sum of a1 and a2 is 1 or greater,

[0017] At least one of T1 in the amount of a1, at least one of T2 in the amount of a2, or any combination thereof includes at least one fluorine group (-F),

[0018] Two or more of T1 in the amount of a1 are optionally connected to each other to form an unsubstituted or at least one R 1a substituted C5-C 30 carbocyclic group, or an unsubstituted or at least one R 1a substituted C1-C 30 heterocyclic group,

[0019] Two or more of T2 in the amount of a2 are optionally connected to each other to form an unsubstituted or at least one R 1a substituted C5-C 30 carbocyclic group, or an unsubstituted or at least one R 1a substituted C1-C 30 heterocyclic group,

[0020] T1 and T2 are optionally connected to each other to form an unsubstituted or at least one R 1a substituted C5-C 30 carbocyclic group, or an unsubstituted or at least one R 1a substituted C1-C 30 heterocyclic group,

[0021] Two or more of A1 - A7 are optionally connected to each other to form an unsubstituted or at least one R 1a substituted C5-C 30 carbocyclic group, or an unsubstituted or at least one R 1a substituted C1-C 30 heterocyclic group,

[0022] R 1a is the same as defined for A7,

[0023] substituted C1-C 60 alkyl, substituted C2-C 60 alkenyl, substituted C2-C 60 alkynyl, substituted C1-C 60 alkoxy, substituted C1-C 60 alkylthio, substituted C3-C 10 cycloalkyl, substituted C1-C 10 heterocycloalkyl, substituted C3-C 10 cycloalkenyl, substituted C1-C 10 heterocycloalkenyl, substituted C6-C 60 aryl, substituted C6-C 60 aryloxy, substituted C6-C 60 arylthio, substituted C1-C 60 One or more substituents of heteroaryl, substituted monovalent non-aromatic fused polycyclic groups, and substituted monovalent non-aromatic fused heteropolycyclic groups are each independently:

[0024] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazono, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, or C1-C 60 alkoxy;

[0025] C1-C each substituted by the following 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, or C1-C 60 alkoxy: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amidino, hydrazino, hydrazono, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C6-C 60 aryloxy, C6-C 60 arylthio, C1-C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic 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;

[0026] C3-C each unsubstituted or substituted by the following 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, amidino, hydrazino, hydrazono, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic 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;

[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 thereof,

[0029] Q1-Q9, Q 11 -Q 19 , Q 21 -Q 29 and Q 31 -Q 39 each independently is:

[0030] Hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl group; cyano group; nitro group; amidino group; hydrazino group; hydrazono group; carboxylic acid group or its salt; sulfonic acid group or its salt; phosphoric acid group or its salt; unsubstituted or substituted by deuterium, C1-C 60 alkyl, C6-C 60 aryl, or C1-C substituted by any combination thereof 60 alkyl; C2-C 60 alkenyl; C2-C 60 alkynyl; C1-C 60 alkoxy; C3-C 10 cycloalkyl; C1-C 10 heterocycloalkyl; C3-C 10 cycloalkenyl; C1-C 10 heterocycloalkenyl; unsubstituted or substituted by deuterium, C1-C 60 alkyl, C6-C 60 aryl, or C6-C substituted by any combination thereof 60 aryl; C6-C 60 aryloxy; C6-C 60 arylthio; C1-C 60 heteroaryl; monovalent non-aromatic fused polycyclic group; or monovalent non-aromatic fused heteropolycyclic group.

[0031] Another aspect of the present disclosure provides an organic light-emitting device, which includes: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode and including an emission layer, and the organic layer includes at least one organometallic compound represented by Formula 1.

[0032] Another aspect of the present disclosure provides an electronic device including the above organic light-emitting device.

[0033] In one or more embodiments, the organometallic compound may be in the emission layer of the organic layer, and the organometallic compound in the emission layer may act as a dopant.

[0034] Another aspect of the present disclosure provides a diagnostic composition including at least one organometallic compound represented by Formula 1. BRIEF DESCRIPTION OF THE DRAWINGS

[0035] The following description of the embodiments, considered in conjunction with the accompanying drawings, will make these and / or other aspects clear and easier to understand, where:

[0036] Figure 1 is a schematic cross-sectional view of an organic light-emitting device according to an embodiment. Detailed Embodiment

[0037] Embodiments will now be described in detail, examples of which are illustrated in the accompanying drawings, where like reference numerals always refer to like elements. In this regard, the present embodiments may have different forms and should not be construed as limited to the description set forth herein. Accordingly, the embodiments are described below only by reference to the accompanying drawings to illustrate aspects of the present description. As used herein, the term "and / or" includes any and all combinations of one or more of the associated listed items. Expressions such as "at least one (kind) of" when before or after a list of elements modify the entire list of elements and not individual elements of the list.

[0038] One aspect of the present disclosure provides an organometallic compound represented by Formula 1:

[0039] <Formula 1>

[0040]

[0041] In Formula 1, Y2 may be C or N. For example, Y2 may be C.

[0042] In Formula 1, the ring CY1 may be a C5-C polycyclic group in which three or more (e.g., three, four, five, or six) monocyclic groups are fused to each other, where the group represented by 30 in Formula 1 may not be the group represented by and represents the binding site to iridium (Ir) in Formula 1, and ＊ is the binding site to the ring CY2 in Formula 1. ＊ "

[0043] For example, the monocyclic group may be a cyclopentyl group, a cyclopentenyl group, a cyclopentadienyl group, a furan group, a thiophene group, a pyrrole group, a silole group, an oxazole group, an iso oxazole group, a dioxazole group, an iso dioxazole group, a triazole group, an iso Triazole group, thiazole group, isothiazole group, thiadiazole group, isothiadiazole group, thiatriazole group, isothiatriazole group, pyrazole group, imidazole group, triazole group, tetrazole group, azathiophene group, diazathiophene group, triazathiophene group, adamantyl group, norbornyl group, norbornene group, cyclohexyl group, cyclohexene group, phenyl group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, oxazine group, thiazine group, dihydropyrazine group, dihydropyridine group, or dihydroazathiophene group, and the three or more monocyclic groups may be the same or different.

[0044] In one or more embodiments, the monocyclic group may include: a phenyl group; and at least one of a pyridine group, a pyrimidine group, a pyrazine group, and a pyridazine group.

[0045] In one or more embodiments, the monocyclic group may include: a phenyl group; and at least one of a pyridine group, a pyrimidine group, a pyrazine group, and a pyridazine group, and optionally further includes a cyclopentyl group, a cyclopentene group, a cyclohexyl group, a cyclohexene group, an adamantyl group, a norbornyl group, a norbornene group, or any combination thereof.

[0046] In one or more embodiments, in Formula 1, ring CY1 may include one or two nitrogens.

[0047] In Formula 1, ring CY2 may be a C5-C 30 carbocyclic group or a C1-C 30 heterocyclic group.

[0048] For example, in Formula 1, ring CY2 may be a phenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a benzo[9,10]phenanthryl group, a pyrenyl group, group, cyclopentadienyl group, 1,2,3,4-tetrahydronaphthyl group, thiophene group, furan group, indole group, benzoborole group, benzophosphole group, indene group, benzosilole group, benzogermole group, benzothiophene group, benzoselenophene group, benzofuran group, carbazole group, dibenzoborole group, dibenzophosphole group, fluorene group, dibenzosilole group, dibenzogermole group, dibenzothiophene group, dibenzoselenophene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, azaindole group, azabenzoborole group, azabenzophosphole group, azaindene group, azabenzosilole group, azabenzogermole group, azabenzothiophene group, azabenzoselenophene group, azabenzofuran group, azacarbazole group, azadibenzoborole group, azadibenzophosphole group, azafluorene group, azadibenzosilole group, azadibenzogermole group, azadibenzothiophene group, azadibenzoselenophene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluoren-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, phenanthroline group, pyrrole group, pyrazole group, imidazole group, triazole group, azole group, iso azole group, thiazole group, isothiazole group, diazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzo azole group, benzothiazole group, benzo diazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group, 5,6,7,8-tetrahydroquinoline group, phen azine group, phenothiazine group, dihydrophenazine group, dihydroacridine group, azaphen azine group, azaphenothiazine group, azadihydrophenazine group, or azadihydroacridine group.

[0049] In one or more embodiments, in Formula 1, ring CY2 can be a benzene group, naphthalene group, 1,2,3,4-tetrahydronaphthyl group, thiophene group, furan group, pyrrole group, cyclopentadienyl group, silole group, benzothiophene group, benzofuran group, indole group, indene group, benzosilole group, dibenzothiophene group, dibenzofuran group, carbazole group, fluorene group, or dibenzosilole group.

[0050] In one or more embodiments, in Formula 1, ring CY2 can be a benzene group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a fluorene group, or a dibenzosilole group.

[0051] In Formula 1, T1, T2, and A1 - A7 can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, a carboxylic acid group or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, a substituted or unsubstituted C1 - C 60 alkyl group, a substituted or unsubstituted C2 - C 60 alkenyl group, a substituted or unsubstituted C2 - C 60 alkynyl group, a substituted or unsubstituted C1 - C 60 alkoxy group, a substituted or unsubstituted C1 - C 60 alkylthio group, a substituted or unsubstituted C3 - C 10 cycloalkyl group, a substituted or unsubstituted C1 - C 10 heterocycloalkyl group, a substituted or unsubstituted C3 - C 10 cycloalkenyl group, a substituted or unsubstituted C1 - C 10 heterocycloalkenyl group, a substituted or unsubstituted C6 - C 60 aryl group, a substituted or unsubstituted C6 - C 60 aryloxy group, a substituted or unsubstituted C6 - C 60 arylthio group, a substituted or unsubstituted C1 - C 60 heteroaryl group, a substituted or unsubstituted monovalent non - aromatic fused polycyclic group, a substituted or unsubstituted monovalent non - aromatic fused heteropolycyclic group, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9). Herein, Q1 - Q9 are to be understood with reference to their description in this specification.

[0052] For example, in Formula 1, T1, T2, and A1 - A7 can each independently be:

[0053] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, a carboxylic acid group or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, -SF5, a C1 - C 20 alkyl group, a C2 - C 20 alkenyl group, a C1 - C 20 alkoxy group, or a C1 - C 20 alkylthio group;

[0054] A C1 - C 20 alkyl group, a C2 - C 20Alkenyl, C1-C 20 Alkoxy, or C1-C 20 Alkylthio: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, (C1-C 20 Alkyl)cyclopentyl, (C1-C 20 Alkyl)cyclohexyl, (C1-C 20 Alkyl)cycloheptyl, (C1-C 20 Alkyl)cyclooctyl, (C1-C 20 Alkyl)adamantyl, (C1-C 20 Alkyl)norbornyl, (C1-C 20 Alkyl)norbornenyl, (C1-C 20 Alkyl)cyclopentenyl, (C1-C 20 Alkyl)cyclohexenyl, (C1-C 20 Alkyl)cycloheptenyl, (C1-C 20 Alkyl)bicyclo[1.1.1]pentyl, (C1-C 20 Alkyl)bicyclo[2.1.1]hexyl, (C1-C 20 Alkyl)bicyclo[2.2.2]octyl, phenyl, (C1-C 20 Alkyl)phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidinyl, or any combination thereof;

[0055] Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, phenyl, (C1-C 20 Alkyl)phenyl, biphenyl, terphenyl, naphthyl, fluorene, phenanthrene, anthracene, fluoranthene, benzo[9,10]phenanthrene, pyrene, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, azolyl, iso azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo azolyl, isobenzo azolyl, triazolyl, tetrazolyl, diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, or azadibenzothiophenyl: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 20 alkyl, deuterated C2-C 20 alkyl, C1-C 20 alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, (C1-C 20 alkyl)cyclopentyl, (C1-C 20 alkyl)cyclohexyl, (C1-C 20 alkyl)cycloheptyl, (C1-C 20 alkyl)cyclooctyl, (C1-C 20 alkyl)adamantyl, (C1-C 20 alkyl)norbornyl, (C1-C 20 alkyl)norbornenyl, (C1-C 20 alkyl)cyclopentenyl, (C1-C 20 alkyl)cyclohexenyl, (C1-C 20 alkyl)cycloheptenyl, (C1-C 20 alkyl)bicyclo[1.1.1]pentyl, (C1-C 20 alkyl)bicyclo[2.1.1]hexyl, (C1-C 20 alkyl)bicyclo[2.2.2]octyl, phenyl, (C1-C 20 alkyl)phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, yl, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, azolyl, iso azolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo azolyl, isobenzo azolyl, triazolyl, tetrazolyl, diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, or any combination thereof; or

[0056] -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9); and

[0057] Q1 - Q9 may each independently be:

[0058] deuterium, -F, -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, -CD2CDH2, -CF3, -CF2H, -CFH2, -CH2CF3, -CH2CF2H, -CH2CFH2, -CHFCH3, -CHFCF2H, -CHFCFH2, -CHFCF3, -CF2CF3, -CF2CF2H, or -CF2CFH2; or

[0059] 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, each unsubstituted or substituted with: deuterium, -F, C1 - C 10 alkyl, phenyl, or any combination thereof.

[0060] In one or more embodiments, in Formula 1, T1, T2, and A1 - A7 may each independently be hydrogen, deuterium, -F, -CH3, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, C2 - C 10 alkenyl, C1 - C 10 alkoxy, C1 - C 10An alkylthio group, one of the groups represented by Formulas 9-1 to 9-39, one of the groups represented by Formulas 9-1 to 9-39 in which at least one hydrogen is replaced by deuterium, one of the groups represented by Formulas 9-1 to 9-39 in which at least one hydrogen is replaced by -F, one of the groups represented by Formulas 9-201 to 9-237, one of the groups represented by Formulas 9-201 to 9-237 in which at least one hydrogen is replaced by deuterium, one of the groups represented by Formulas 9-201 to 9-237 in which at least one hydrogen is replaced by -F, one of the groups represented by Formulas 10-1 to 10-129, one of the groups represented by Formulas 10-1 to 10-129 in which at least one hydrogen is replaced by deuterium, one of the groups represented by Formulas 10-1 to 10-129 in which at least one hydrogen is replaced by -F, one of the groups represented by Formulas 10-201 to 10-350, one of the groups represented by Formulas 10-201 to 10-350 in which at least one hydrogen is replaced by deuterium, one of the groups represented by Formulas 10-201 to 10-350 in which at least one hydrogen is replaced by -F, -Si(Q3)(Q4)(Q5), or -Ge(Q3)(Q4)(Q5) (where Q3 - Q5 will be understood with reference to its description in this specification).

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070] In Formulas 9-1 to 9-39, 9-201 to 9-237, 10-1 to 10-129, and 10-201 to 10-350, ＊ represents the binding site to an adjacent atom, Ph represents a phenyl group, TMS represents a trimethylsilyl group, and TMG represents a trimethylgermyl group.

[0071] Groups represented by Formulas 9-1 to 9-39 in which at least one hydrogen is replaced by deuterium, and groups represented by Formulas 9-201 to 9-237 in which at least one hydrogen is replaced by deuterium may be, for example, groups represented by Formulas 9-501 to 9-514 and 9-601 to 9-636.

[0072]

[0073]

[0074] Groups represented by Formulas 9-1 to 9-39 in which at least one hydrogen is replaced by -F, and groups represented by Formulas 9-201 to 9-236 in which at least one hydrogen is replaced by -F may be, for example, groups represented by Formulas 9-701 to 9-710.

[0075]

[0076] Groups represented by Formulas 10-1 to 10-129 in which at least one hydrogen is replaced by deuterium, and groups represented by Formulas 10-201 to 10-350 in which at least one hydrogen is replaced by deuterium may be, for example, groups represented by Formulas 10-501 to 10-553.

[0077]

[0078]

[0079] Groups represented by Formulas 10-1 to 10-129 in which at least one hydrogen is replaced by -F, and groups represented by Formulas 10-201 to 10-350 in which at least one hydrogen is replaced by -F may be, for example, groups represented by Formulas 10-601 to 10-617.

[0080]

[0081] In Formula 1, a1 and a2 respectively represent the number of T1 and the number of T2, and may each independently be an integer from 0 to 20, for example, an integer from 0 to 8. When a1 is 2 or greater, two or more T1s may be the same as or different from each other. When a2 is 2 or greater, two or more T2s may be the same as or different from each other. In Formula 1, the sum of a1 and a2 may be 1 or greater. For example, in Formula 1, a1 may be an integer from 1 to 20, for example, an integer from 1 to 8.

[0082] In Formula 1, at least one of the T1s in the amount of a1, at least one of the T2s in the amount of a2, or any combination thereof may include at least one fluorine group (-F).

[0083] In one or more embodiments, in Formula 1, T1, T2, and A1 - A7 can each independently be hydrogen, deuterium, -F, a substituted or unsubstituted C1 - C 20 alkyl, a substituted or unsubstituted C3 - C 10 cycloalkyl, a substituted or unsubstituted C1 - C 10 heterocycloalkyl, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, -Si(Q3)(Q4)(Q5), or -Ge(Q3)(Q4)(Q5).

[0084] In one or more embodiments, in Formula 1, T1 and A1 - A7 can each independently be:

[0085] hydrogen, deuterium, -F, C1 - C 20 alkyl, C3 - C 10 cycloalkyl, C1 - C 10 heterocycloalkyl, phenyl, biphenyl, or terphenyl;

[0086] fluorinated C1 - C 20 alkyl, fluorinated C3 - C 10 cycloalkyl, fluorinated C1 - C 10 heterocycloalkyl, fluorinated phenyl, fluorinated biphenyl, or fluorinated terphenyl: deuterium, C1 - C 20 alkyl, C3 - C 10 cycloalkyl, C1 - C 10 heterocycloalkyl, phenyl, biphenyl, terphenyl, or any combination thereof;

[0087] deuterated C1 - C 20 alkyl, deuterated C3 - C 10 cycloalkyl, deuterated C1 - C 10 heterocycloalkyl, deuterated phenyl, deuterated biphenyl, or deuterated terphenyl: -F, C1 - C 20 alkyl, C3 - C 10 cycloalkyl, C1 - C 10 heterocycloalkyl, phenyl, biphenyl, terphenyl, or any combination thereof; or

[0088] -Si(Q3)(Q4)(Q5), or -Ge(Q3)(Q4)(Q5).

[0089] In one or more embodiments, in Formula 1, a1 can be an integer from 1 - 20, and at least one of T1 in the amount of a1 can include at least one -F.

[0090] In one or more embodiments, in Formula 1, a1 can be an integer from 1 - 20, and at least one of T1 in the amount of a1 can each independently be:

[0091] -F; or

[0092] each unsubstituted or substituted with the following fluorinated C1-C 20 alkyl, fluorinated C3-C 10 cycloalkyl, fluorinated C1-C 10 heterocycloalkyl, fluorinated phenyl, fluorinated biphenyl, or fluorinated terphenyl: deuterium, C1-C 20 alkyl, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, phenyl, biphenyl, terphenyl, or any combination thereof.

[0093] In one or more embodiments, in Formula 1, T2 may not include -F and cyano.

[0094] In one or more embodiments, in Formula 1, T2 and A1-A7 may each independently be:

[0095] hydrogen, deuterium, C1-C 20 alkyl, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, phenyl, biphenyl, or terphenyl;

[0096] each unsubstituted or substituted with the following deuterated C1-C 20 alkyl, deuterated C3-C 10 cycloalkyl, deuterated C1-C 10 heterocycloalkyl, deuterated phenyl, deuterated biphenyl, or deuterated terphenyl: C1-C 20 alkyl, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, phenyl, biphenyl, terphenyl, or any combination thereof; or

[0097] -Si(Q3)(Q4)(Q5), or -Ge(Q3)(Q4)(Q5).

[0098] In Formula 1, 1) two or more of the T1 groups in number a1 may optionally be connected to each other to form an unsubstituted or at least one R 1a substituted C5-C 30 carbocyclic group, or an unsubstituted or at least one R 1a substituted C1-C 30 heterocyclic group, 2) two or more of the T2 groups in number a2 may optionally be connected to each other to form an unsubstituted or at least one R 1a substituted C5-C 30 carbocyclic group, or an unsubstituted or at least one R 1a substituted C1-C30 heterocyclic group, 3) T1 and T2 may optionally be connected to each other to form an unsubstituted or at least one R 1a substituted C5-C 30 carbocyclic group, or an unsubstituted or at least one R 1a substituted C1-C 30 heterocyclic group, 4) two or more of A1 - A7 may optionally be connected to each other to form an unsubstituted or at least one R 1a substituted C5-C 30 carbocyclic group, or an unsubstituted or at least one R 1a substituted C1-C 30 heterocyclic group. Here, R 1a will be understood with reference to the description of A7 provided above.

[0099] In one or more embodiments, in Formula 1, the group represented by may be one of the groups represented by Formulae CY1-1 to CY1-27.

[0100]

[0101]

[0102] In Formulae CY1-1 to CY1-27,

[0103] X1 - X8 may each independently be C or N, excluding the case where all of X1 - X8 are N, and the ring CY 11 may be a cyclopentyl group, a cyclopentenyl group, a cyclohexyl group, a cyclohexenyl group, an adamantyl group, a norbornyl group, a norbornenyl group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a naphthalene group, a quinoline group, an isoquinoline group, or a quinoxaline group,

[0104] ＊ represents the binding site to Ir in Formula 1, and

[0105] ＊ " represents the binding site to the ring CY2 in Formula 1.

[0106] In one or more embodiments, in Formula 1, the group represented by may be one of the groups represented by Formulae CY1(1) to CY1(6).

[0107]

[0108] In Formulae CY1(1) to CY1(6),

[0109] T 11 -T18 It is to be understood with reference to the description of T1 in this text, provided that T 11 -T 18 at least one of which may include a fluorine group (-F),

[0110] ＊ represents a binding site to Ir in Formula 1, and

[0111] ＊ " represents a binding site to ring CY2 in Formula 1.

[0112] For example, T in Formulas CY1(1) to CY1(6) 11 -T 18 one, two, or three of which may include at least one -F, and

[0113] the remaining Ts in Formulas CY1(1) to CY1(6) that do not include -F 11 -T 18 may each independently be:

[0114] hydrogen, deuterium, C1-C 20 alkyl, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, phenyl, biphenyl, or terphenyl;

[0115] each unsubstituted or substituted with deuterated C1-C 20 alkyl, deuterated C3-C 10 cycloalkyl, deuterated C1-C 10 heterocycloalkyl, deuterated phenyl, deuterated biphenyl, or deuterated terphenyl: C1-C 20 alkyl, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, phenyl, biphenyl, terphenyl, or any combination thereof; or

[0116] -Si(Q3)(Q4)(Q5), or -Ge(Q3)(Q4)(Q5).

[0117] In one or more embodiments, T in Formulas CY1(1) to CY1(6) 11 -T 18 one, two, or three of which may each independently be:

[0118] -F; or

[0119] each unsubstituted or substituted with fluorinated C1-C 20 alkyl, fluorinated C3-C 10 cycloalkyl, fluorinated C1-C 10Heterocycloalkyl, fluorinated phenyl, fluorinated biphenyl, or fluorinated terphenyl: deuterium, C1-C 20 alkyl, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, phenyl, biphenyl, terphenyl, or any combination thereof.

[0120] In one or more embodiments, in Formula 1, the group represented by may be one of the groups represented by Formula CY1(1)-1 to CY1(1)-64, Formula CY1(4)-1 to CY1(4)-16, and Formula CY1(6)-1 to CY1(6)-16.

[0121]

[0122]

[0123]

[0124]

[0125]

[0126] In Formula CY1(1)-1 to CY1(1)-64, Formula CY1(4)-1 to CY1(4)-16, and Formula CY1(6)-1 to CY1(6)-16,

[0127] T 11 -T 18 will be understood with reference to the description of T1 herein, provided that T 11 -T 18 are each not hydrogen,

[0128] T 101 -T 108 may each include at least one fluorine group (-F),

[0129] ＊ represents the binding site to Ir in Formula 1, and

[0130] ＊ " represents the binding site to ring CY2 in Formula 1.

[0131] For example, in Formula CY1(1)-1 to CY1(1)-64, Formula CY1(4)-1 to CY1(4)-16, and Formula CY1(6)-1 to CY1(6)-16, T 11 -T 18 may each independently be:

[0132] deuterium, C1-C 20 alkyl, C3-C10 Cycloalkyl, C1-C 10 heterocycloalkyl, phenyl, biphenyl, or terphenyl;

[0133] Each unsubstituted or substituted by deuterated C1-C 20 alkyl, deuterated C3-C 10 cycloalkyl, deuterated C1-C 10 heterocycloalkyl, deuterated phenyl, deuterated biphenyl, or deuterated terphenyl: C1-C 20 alkyl, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, phenyl, biphenyl, terphenyl, or any combination thereof; or

[0134] -Si(Q3)(Q4)(Q5), or -Ge(Q3)(Q4)(Q5).

[0135] In one or more embodiments, in Formulas CY1(1)-1 to CY1(1)-64, Formulas CY1(4)-1 to CY1(4)-16, and Formulas CY1(6)-1 to CY1(6)-16, T 101 -T 108 may each independently be:

[0136] -F; or

[0137] Each unsubstituted or substituted by fluorinated C1-C 20 alkyl, fluorinated C3-C 10 cycloalkyl, fluorinated C1-C 10 heterocycloalkyl, fluorinated phenyl, fluorinated biphenyl, or fluorinated terphenyl: deuterium, C1-C 20 alkyl, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, phenyl, biphenyl, terphenyl, or any combination thereof.

[0138] In one or more embodiments, in Formula 1, the group represented by may be one of the groups represented by Formulas CY2-1 to CY2-31.

[0139]

[0140]

[0141] In Formulas CY2-1 to CY2-31,

[0142] Y2 and T2 are to be understood with reference to their description in this specification,

[0143] X 22 may be C(T28 )(T 29 )、N(T 28 )、O、S、 or Si(T 28 )(T 29 ),

[0144] T 22 -T 29 will be understood with reference to the description of T2 in this specification,

[0145] a26 can be an integer from 0 to 6,

[0146] a25 can be an integer from 0 to 5,

[0147] a24 can be an integer from 0 to 4,

[0148] a23 can be an integer from 0 to 3,

[0149] a22 can be an integer from 0 to 2,

[0150] ＊ " represents the binding site to the ring CY1 in Formula 1, and

[0151] ＊ ' represents the binding site to Ir in Formula 1.

[0152] In one or more embodiments, in Formula 1, the group represented by can be one of the groups represented by Formula CY2(1) to CY2(68).

[0153]

[0154]

[0155]

[0156] In Formulas CY2(1) to CY2(68),

[0157] Y2 will be understood with reference to the description provided in this specification,

[0158] X 22 can be C(T 28 )(T 29 )、N(T 28 )、O、S、 or Si(T 28 )(T 29 ),

[0159] T 21 -T 25 、T 28 and T 29Reference will be made to the description of T2 in this specification, provided that T 21 -T 24 is not hydrogen respectively,

[0160] ＊ " represents the binding site to the ring CY1 in Formula 1, and

[0161] ＊ ' represents the binding site to Ir in Formula 1.

[0162] In one or more embodiments, in Formula 1, T2 may not be hydrogen, and a2 may be 1, 2, or 3.

[0163] In one or more embodiments, in Formula 1, the group represented by may be the group represented by Formula CY2(10).

[0164] For example, in Formula CY2(10), T 22 and T 24 may each independently be a C1-C 20 alkyl, C3-C 10 cycloalkyl, phenyl, biphenyl, or terphenyl, which is unsubstituted or substituted by: deuterium, C1-C 20 alkyl, C3-C 10 cycloalkyl, phenyl, biphenyl, terphenyl, or any combination thereof.

[0165] In one or more embodiments, in Formula CY2(10), T 22 and T 24 may be the same as each other.

[0166] In one or more embodiments, in Formula CY2(10), T 22 and T 24 may be different from each other.

[0167] In one or more embodiments, in Formula CY2(10), the number of carbons in T 22 may be greater than the number of carbons in T 24 In one or more embodiments, in Formula 1,

[0168] a1 may not be 0,

[0169] and at least one of the T1s with the quantity a1 may be:

[0170] a fluorine group (-F); or

[0171] each unsubstituted or substituted by the following fluorinated C1-C

[0172] alkyl, fluorinated C3-C 20 alkyl,10 Cycloalkyl, fluorinated C1-C 10 Heterocycloalkyl, fluorinated phenyl, fluorinated biphenyl, or fluorinated terphenyl: deuterium, C1-C 20 Alkyl, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, phenyl, biphenyl, terphenyl, or any combination thereof, and

[0173] The organometallic compound represented by Formula 1 may further satisfy at least one of <Condition A> to <Condition G>:

[0174] <Condition A>

[0175] All remaining T1 are hydrogen;

[0176] <Condition B>

[0177] At least one of the remaining T1 in Formula 1 is C1-C 20 Alkyl, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, phenyl, biphenyl, or terphenyl;

[0178] <Condition C>

[0179] At least one of the remaining T1 in Formula 1 is:

[0180] Deuterium, or

[0181] Each deuterated C1-C that is unsubstituted or substituted with the following 20 Alkyl, deuterated C3-C 10 Cycloalkyl, deuterated C1-C 10 Heterocycloalkyl, deuterated phenyl, deuterated biphenyl, or deuterated terphenyl: -F, C1-C 20 Alkyl, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, phenyl, biphenyl, terphenyl, or any combination thereof;

[0182] <Condition D>

[0183] At least one of the remaining T1 in Formula 1 is -Si(Q3)(Q4)(Q5);

[0184] <Condition E>

[0185] At least one of the remaining T1 in Formula 1 is -Ge(Q3)(Q4)(Q5);

[0186] <Condition F>

[0187] In Formula 1, a2 is not 0, and at least one of the T2 with the number a2 is C1-C20 alkyl, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, phenyl, biphenyl, or terphenyl; and

[0188] <Condition G>

[0189] In Formula 1, a2 is not 0, and at least one of T2 with a quantity of a2 is:

[0190] deuterium, or

[0191] each deuterated C1-C optionally unsubstituted or substituted with the following 20 alkyl, deuterated C3-C 10 cycloalkyl, deuterated C1-C 10 heterocycloalkyl, deuterated phenyl, deuterated biphenyl, or deuterated terphenyl: C1-C 20 alkyl, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, phenyl, biphenyl, terphenyl, or any combination thereof.

[0192] In one or more embodiments, the organometallic compound represented by Formula 1 may satisfy at least one of <Condition 1> to <Condition 3>:

[0193] <Condition 1>

[0194] In Formula 1, A1 - A6 are each independently a substituted or unsubstituted C1-C 60 alkyl, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C2-C 10 heterocycloalkyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C2-C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group;

[0195] <Condition 2>

[0196] In Formula 1, at least one of A1 - A6 (e.g., at least one of A1 - A3, and at least one of A4 - A6) is each independently a substituted or unsubstituted C2-C 60 alkyl, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C2-C 10 heterocycloalkyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C2-C 60A heteroaryl, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group; and

[0197] <Condition 3>

[0198] In Formula 1, A7 is deuterium, a substituted or unsubstituted C1-C 60 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C2-C 10 heterocycloalkyl group, a substituted or unsubstituted C6-C 60 aryl group, a substituted or unsubstituted C2-C 60 heteroaryl, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group.

[0199] In one or more embodiments, the organometallic compound represented by Formula 1 can satisfy at least one of <Condition 1> and <Condition 2> described above.

[0200] In one or more embodiments, in Formula 1, a2 can be 2, and T2 can be a substituted or unsubstituted C1-C 60 alkyl group.

[0201] In one or more embodiments, the organometallic compound represented by Formula 1 can satisfy at least one of <Condition 4> and <Condition 5>:

[0202] <Condition 4>

[0203] In Formula 1, two or more of A1-A3 of the group represented by ＊ -C(A1)(A2)(A3) are connected to the C in the group represented by ＊ -C(A1)(A2)(A3) to form an unsubstituted or at least one R 1a substituted C5-C 30 carbocyclic group, or an unsubstituted or at least one R 1a substituted C1-C 30 heterocyclic group, such that the group represented by ＊ -C(A1)(A2)(A3) is an unsubstituted or at least one R 1a substituted C5-C 30 carbocyclic group, or an unsubstituted or at least one R 1a substituted C1-C 30 heterocyclic group; and

[0204] <Condition 5>

[0205] In Formula 1, by ＊-C(A4)(A5)(A6) represents a group in which two or more of A4 - A6 are connected to the C in the group represented by ＊ -C(A4)(A5)(A6) to form an unsubstituted or at least one R 1a substituted C5 - C 30 carbocyclic group, or an unsubstituted or at least one R 1a substituted C1 - C 30 heterocyclic group, such that the group represented by ＊ -C(A4)(A5)(A6) is an unsubstituted or at least one R 1a substituted C5 - C 30 carbocyclic group, or an unsubstituted or at least one R 1a substituted C1 - C 30 heterocyclic group.

[0206] In one or more embodiments, in Formula 1, the group represented by ＊ -C(A1)(A2)(A3) and the group represented by ＊ -C(A4)(A5)(A6) may be the same as each other.

[0207] In one or more embodiments, in Formula 1, the group represented by ＊ -C(A1)(A2)(A3) and the group represented by ＊ -C(A4)(A5)(A6) may be different from each other.

[0208] In one or more embodiments, in Formula 1, the number of carbons in the group represented by ＊ -C(A1)(A2)(A3) may be 4 or greater, 5 or greater, or 6 or greater.

[0209] In one or more embodiments, in Formula 1, the number of carbons in the group represented by ＊ -C(A4)(A5)(A6) may be 4 or greater, 5 or greater, or 6 or greater.

[0210] In one or more embodiments, in Formula 1, the following cases are excluded: 1) A7 is hydrogen, and 2) both the group represented by *-C(A1)(A2)(A3) and the group represented by *-C(A4)(A5)(A6) are methyl.

[0211] In one or more embodiments, in Formula 1, the following cases are excluded: 1) A7 is hydrogen; and 2) A1 - A6 are all methyl.

[0212] In one or more embodiments, in Formula 1, at least one deuterium may be included.

[0213] In one or more embodiments, in Formula 1, a2 may not be 0, and at least one of T2 having a quantity of a2 may include at least one deuterium.

[0214] In one or more embodiments, the organometallic compound represented by Formula 1 may emit red or green light, for example, red or green light having a maximum emission wavelength of about 500 nm or greater, such as in the range of about 500 nm or greater and about 650 nm or less.

[0215] The organometallic compound represented by Formula 1 may be one of Compounds 1 to 90 below.

[0216]

[0217]

[0218]

[0219]

[0220]

[0221] Since in Formula 1, at least one of T1 having a quantity of a1, at least one of T2 having a quantity of a2, or any combination thereof includes at least one fluorine group (-F), an electronic device including the organometallic compound represented by Formula 1, such as an organic light-emitting device, may have high emission efficiency.

[0222] In one or more embodiments, the organometallic compound represented by Formula 1 may satisfy <Condition 1> described above, and thus result in reduced intermolecular interactions in the organometallic compound. Although not limited by a specific theory, an α-proton may have about 10 5 times higher chemical reactivity than a β-proton to generate various forms of intermediates during compound synthesis and / or storage, thereby causing side reactions. However, since A1 - A6 in Formula 1 is defined to satisfy <Condition 1>, the carbon bonded to A1 - A6 of Formula 1 may not include an α-proton, and the organometallic compound represented by Formula 1 that satisfies <Condition 1> may have a stable chemical structure in which side reactions before / after synthesis are minimized (reduced), and at the same time may have reduced intermolecular interactions during the operation of an electronic device (e.g., an organic light-emitting device) employing the organometallic compound.

[0223] In one or more embodiments, when the organometallic compound represented by Formula 1 satisfies at least one of <Condition 2> to <Condition 5>, the organometallic compound represented by Formula 1 may have a relatively large steric hindrance, thereby reducing triplet-triplet annihilation. Therefore, an electronic device using the organometallic compound represented by Formula 1 and satisfying at least one of <Condition 2> to <Condition 5>, such as an organic light-emitting device, may have an improved internal quantum luminescence efficiency.

[0224] In one or more embodiments, when the organometallic compound represented by Formula 1 satisfies at least one of <Condition 1> to <Condition 5>, and / or when in Formula 1, a2 is 2 and T2 is a substituted or unsubstituted C1-C 60 alkyl group, due to the enhanced interaction between ligand 2 and ligand 1 (see Formula 1' below), the organometallic compound represented by Formula 1 may have improved rigidity. Therefore, in the photoluminescence (PL) or electroluminescence (EL) spectrum of the organometallic compound represented by Formula 1, the full width at half maximum (FWHM) of the emission peak may decrease, and the vibrational state (vibronic state) of the molecules of the organometallic compound represented by Formula 1 may decrease, resulting in a reduction of non-radiative decay. Therefore, an electronic device including the organometallic compound represented by Formula 1, such as an organic light-emitting device, may emit light with high color purity (e.g., high color purity red light), and at the same time have high emission efficiency and improved lifetime.

[0225] <Formula 1'>

[0226]

[0227] Therefore, an electronic device using the organometallic compound represented by Formula 1, such as an organic light-emitting device, may have high emission efficiency and long lifetime.

[0228] The highest occupied molecular orbital (HOMO) energy level, the lowest unoccupied molecular orbital (LUMO) energy level, the singlet (S1) energy level, and the triplet (T1) energy level of some compounds of the organometallic compound represented by Formula 1 were evaluated by density functional theory (DFT) of the Gaussian program with B3LYP-based molecular structure optimization, and the results are shown in Table 1.

[0229] [Table 1]

[0230]

[0231]

[0232] Referring to Table 1, it was confirmed that the organometallic compound represented by Formula 1 has electrical properties suitable for use in electronic devices, such as a dopant for an organic light-emitting device.

[0233] Referring to the synthesis examples described below, those of ordinary skill in the art can understand the method for synthesizing the organometallic compound represented by Formula 1.

[0234] Therefore, the organometallic compound represented by Formula 1 is suitable for use in an organic layer of an organic light-emitting device, for example, as a dopant in an emission layer of the organic layer. Accordingly, another aspect of the present disclosure provides an organic light-emitting device including: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode and including an emission layer, the organic layer including at least one organometallic compound represented by Formula 1.

[0235] Due to including the organic layer containing the above-described organometallic compound represented by Formula 1, the organic light-emitting device can have excellent driving voltage, excellent external quantum efficiency, excellent roll-off ratio, relatively small FWHM of the emission peak in the EL spectrum, and improved lifetime characteristics.

[0236] The organometallic compound represented by Formula 1 can be used between electrode pairs of an organic light-emitting device. For example, the organometallic compound represented by Formula 1 can be included in the emission layer. In this regard, the organometallic compound can act as a dopant, and the emission layer can further include a host (that is, the amount of the organometallic compound represented by Formula 1 is less than the amount of the host). The emission layer can emit, for example, red light or green light, for example, red light or green light having a maximum emission wavelength of about 500 nm or greater, for example, 500 nm or greater and 650 nm or less.

[0237] In one or more embodiments, the emission layer can emit red light.

[0238] As used herein, the expression “(the organic layer) includes at least one organometallic compound represented by Formula 1” can be interpreted as the organic layer includes one organometallic compound belonging to the category of Formula 1, or the organic layer includes two or more different organometallic compounds belonging to the category of Formula 1.

[0239] For example, the organic layer can include only Compound 1 as the organometallic compound. In this regard, Compound 1 can be only in the emission layer of the organic light-emitting device. In one or more embodiments, the organic layer can include Compound 1 and Compound 2 as the organometallic compounds. In this regard, Compound 1 and Compound 2 can be in the same layer (for example, both Compound 1 and Compound 2 can be in the emission layer).

[0240] The first electrode may be an anode serving as a hole injection electrode, and the second electrode may be a cathode serving as an electron injection electrode. In other embodiments, the first electrode may be a cathode serving as an electron injection electrode, and the second electrode may be an anode serving as a hole injection electrode.

[0241] For example, in the organic light emitting device, the first electrode may be an anode, the second electrode may be a cathode, the organic layer may further include a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode, 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, and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0242] As used herein, the term "organic layer" refers to a single layer and / or multiple layers disposed between a first electrode and a second electrode of an organic light emitting device. In addition to organic compounds, the "organic layer" may further include an organometallic complex containing a metal.

[0243] Figure 1 FIG. 10 is a schematic cross-sectional view of an organic light emitting device 10 according to an embodiment. Hereinafter, reference will be made to Figure 1 the structure of an organic light emitting device according to an embodiment and a method of manufacturing an organic light emitting device according to an embodiment. The organic light emitting device 10 may have a structure in which a first electrode 11, an organic layer 15, and a second electrode 19 are sequentially stacked.

[0244] A substrate may be additionally provided under the first electrode 11 or above the second electrode 19. For use as the substrate, any substrate used in a typical organic light emitting device may be used. The substrate may be a glass substrate or a transparent plastic substrate each having excellent mechanical strength, thermal stability, transparency, surface smoothness, handleability, and water resistance.

[0245] The first electrode 11 may be formed by depositing or sputtering a material for forming the first electrode 11 on the substrate. The first electrode 11 may be an anode. The material for forming the first electrode 11 may include a material having a high work function to facilitate hole injection. The first electrode 11 may be a reflective electrode, a semi-reflective electrode, or a transmissive electrode. The material for forming the first electrode may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), and zinc oxide (ZnO). In one or more embodiments, the material for forming the first electrode 11 may be a metal such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag).

[0246] The first electrode 11 may have a single-layer structure or a multi-layer structure including two or more layers. For example, the first electrode 11 may have a three-layer structure of ITO / Ag / ITO.

[0247] The organic layer 15 may be disposed on the first electrode 11.

[0248] The organic layer 15 may include a hole transport region, an emission layer, and an electron transport region.

[0249] The hole transport region may be disposed between the first electrode 11 and the emission layer.

[0250] 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.

[0251] The hole transport region may include only a hole injection layer 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 sequentially stacked in the stated order starting from the first electrode 11.

[0252] When the hole transport region includes a hole injection layer (HIL), the hole injection layer may be formed on the first electrode 11 by using one or more suitable methods such as vacuum deposition, spin coating, casting, and / or Langmuir-Blodgett (LB) deposition.

[0253] When the hole injection layer is formed by vacuum deposition, the deposition conditions may vary depending on the material used to form the hole injection layer, as well as the structure and thermal properties of the hole injection layer. For example, the deposition conditions may include a deposition temperature of about 100°C - about 500°C, a vacuum pressure of about 10 - 8 - about 10 - 3 torr, and a deposition rate of about / sec - about / sec. However, the deposition conditions are not limited thereto.

[0254] When the hole injection layer is formed by spin coating, the coating conditions may vary depending on the material used to form the hole injection layer, as well as the structure and thermal properties of the hole injection layer. For example, the coating speed may be about 2,000 rpm - about 5,000 rpm, and the temperature for heat treatment to remove the solvent after coating may be about 80°C - about 200°C. However, the coating conditions are not limited thereto.

[0255] 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.

[0256] 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-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:

[0257]

[0258] <Formula 201>

[0259]

[0260] <Formula 202>

[0261]

[0262] In Formula 201, Ar 101 and Ar 102 may each independently be a phenylene, a s-indacenyl, an indenyl, a naphthylene, an azulenyl, a heptalenyl, an acenaphthylenyl, a fluorenyl, an aceanthrenyl, a phenanthrenyl, an anthracenyl, a fluoranthenyl, a benzo[9,10]phenanthrenyl, a pyrenyl, a yl, a tetracenylene, a picenyl, a perylenyl, or a pentacenylene group, each of which is unsubstituted or substituted with: deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C 60 alkyl group, a C2-C 60 alkenyl group, a C2-C 60 alkynyl group, a C1-C 60 alkoxy group, a C3-C 10 cycloalkyl group, a C3-C 10 cycloalkenyl group, a C1-C 10 heterocycloalkyl group, a C1-C 10 heterocycloalkenyl group, a C6-C 60 aryl group, a C6-C 60 aryloxy group, a C6-C 60 arylthio group, a C1-C 60 heteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, or any combination thereof.

[0263] In Formula 201, the symbols xa and xb can each independently be an integer from 0 to 5, or can be 0, 1, or 2. For example, xa can be 1 and xb can be 0. However, the embodiments are not limited thereto.

[0264] In Formulas 201 and 202, R 101 -R 108 、R 111 -R 119 and R 121 -R 124 can each independently be:

[0265] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, a carboxylic acid group or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, C1-C 10 alkyl (e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl, etc.), or C1-C 10 alkoxy (e.g., methoxy, ethoxy, propoxy, butoxy, pentyloxy, etc.);

[0266] C1-C 10 alkyl or C1-C 10 alkoxy that is each unsubstituted or substituted with: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, a carboxylic acid group or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, or any combination thereof; or

[0267] phenyl, naphthyl, anthryl, fluorenyl, or pyrenyl that is each unsubstituted or substituted with: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, a carboxylic acid group or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, C1-C 10 alkyl, C1-C 10 alkoxy, or any combination thereof.

[0268] In Formula 201, R 109 can be phenyl, naphthyl, anthryl, or pyridyl that is each unsubstituted or substituted with: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazino, hydrazono, a carboxylic acid group or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, C1-C 20 alkyl, C1-C 20 alkoxy, phenyl, naphthyl, anthryl, pyridyl, or any combination thereof.

[0269] In one or more embodiments, the compound represented by Formula 201 can be represented by Formula 201A.

[0270] <Formula 201A>

[0271]

[0272] R in Formula 201A 101 , R 111 , R 112 and R 109 are described in detail in the same way as the above description.

[0273] For example, the hole transport region may include one or any combination of compounds HT1 to HT21:

[0274]

[0275]

[0276]

[0277] The thickness of the hole transport region may be about - about For example, about - about When the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, the thickness of the hole injection layer may be in the range of about - about For example, about - about and the thickness of the hole transport layer may be in the range of about - about For example, about - about When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transport characteristics can be obtained without a significant increase in the driving voltage.

[0278] In addition to the above materials, the hole transport region may further include a charge generation material for improving the conductive property. The charge generation material may be uniformly or non-uniformly dispersed in the hole transport region.

[0279] The charge generation material may be, for example, a p-dopant. The p-dopant may be a quinone derivative, a metal oxide, a compound containing a cyano group, or any combination thereof. For example, the p-dopant may be a quinone derivative such as tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ), or F6-TCNNQ; a metal oxide such as tungsten oxide or molybdenum oxide; or a compound containing a cyano group such as compound HT-D1; or any combination thereof.

[0280]

[0281]

[0282] The hole transport region may further include a buffer layer.

[0283] The buffer layer may compensate for the optical resonance distance according to the wavelength of light emitted from the emission layer, and thus improve the efficiency.

[0284] Meanwhile, when the hole transport region includes an electron blocking layer, the material for the electron blocking layer may be the material for the hole transport region described above, the material for the host to be described later, or any combination thereof. For example, when the hole transport region includes an electron blocking layer, the material for the electron blocking layer may be mCP, compound H21, or any combination thereof to be described later.

[0285] Then, the emission layer may be formed on the hole transport region by vacuum deposition, spin coating, casting, LB deposition, etc. When the emission layer is formed by vacuum deposition or spin coating, although the deposition or coating conditions may vary depending on the compound used to form the emission layer, the deposition or coating conditions may be similar to those applied when forming the hole injection layer.

[0286] The emission layer may include a host and a dopant, and the dopant may include the organometallic compound represented by Formula 1 described herein.

[0287] The host may include TPBi, TBADN, ADN (also referred to as "DNA"), CBP, CDBP, TCP, mCP, compound H50, compound H51, compound H52, or any combination thereof.

[0288]

[0289]

[0290] When the organic light-emitting device is a full-color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and / or a blue emission layer. In one or more embodiments, the emission layer may emit white light due to having a stacked structure including a red emission layer, a green emission layer, and / or a blue emission layer.

[0291] When the emission layer includes a host and a dopant, based on 100 parts by weight of the host, the amount of the dopant may be in the range of about 0.01 part by weight - about 15 parts by weight.

[0292] The thickness of the emission layer may be about - about For example, about - about Within this range. When the thickness of the emission layer is within this range, excellent light-emitting characteristics can be obtained without a significant increase in the driving voltage.

[0293] Then, an electron transport region can be provided on the emission layer.

[0294] The electron transport region can include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0295] For example, the electron transport region can have a hole blocking layer / electron transport layer / electron injection layer structure or an electron transport layer / electron injection layer structure. The electron transport layer can have a multi-layer structure or a single-layer structure including two or more different materials.

[0296] 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 that constitute the electron transport region can be understood.

[0297] When the electron transport region includes a hole blocking layer, the hole blocking layer can include, for example, BCP, Bphen, BAlq, or any combination thereof.

[0298]

[0299] In one or more embodiments, the hole blocking layer can include the host, materials for the electron transport layer and the electron injection layer to be described later, or any combination thereof.

[0300] The thickness of the hole blocking layer can be about - about For example, about - about 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 the driving voltage.

[0301] The electron transport layer can include BCP, Bphen, TPBi, Alq3, BAlq, TAZ, NTAZ, or any combination thereof.

[0302]

[0303] In one or more embodiments, the electron transport layer can include one of compounds ET1 to ET25, or any combination thereof.

[0304]

[0305]

[0306] The thickness of the electron transport layer may be about - about For example, about - about When the thickness of the electron transport layer is within the range described above, the electron transport layer may have satisfactory electron transport characteristics without a significant increase in the driving voltage.

[0307] In addition to the materials described above, the electron transport layer may further include a metal-containing material.

[0308] The metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1(LiQ), compound ET-D2, or any combination thereof:

[0309]

[0310] The electron transport region may include an electron injection layer that facilitates the flow of electrons from the second electrode 19.

[0311] The electron injection layer may include LiF, NaCl, CsF, Li2O, BaO, or any combination thereof.

[0312] The thickness of the electron injection layer may be about - about For example, about - about When the thickness of the electron injection layer is within these ranges, satisfactory electron injection characteristics can be obtained without a significant increase in the driving voltage.

[0313] The second electrode 19 is disposed on the organic layer 15. The second electrode 19 may be a cathode. The material for forming the second electrode 19 may be a metal, an alloy, a conductive compound, or any combination thereof having a relatively low work function. For example, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag) may be used as the material for forming the second electrode 19. For manufacturing a top-emission type light-emitting device, a transmissive electrode formed of ITO or IZO may be used as the second electrode 19.

[0314] Previously, an organic light-emitting device according to an embodiment has been described with reference to Figure 1 However, the embodiment is not limited thereto.

[0315] In one or more embodiments, the organic light-emitting device may be included in an electronic device. Accordingly, on the other hand, an electronic device including the organic light-emitting device is provided. For example, the electronic device may be a display, a lighting device, or a sensor.

[0316] Another aspect of the present disclosure provides a diagnostic composition comprising at least one organometallic compound represented by Formula 1.

[0317] The organometallic compound represented by Formula 1 provides high luminescence efficiency. Thus, the diagnostic composition comprising the organometallic compound can have high diagnostic efficiency.

[0318] The diagnostic composition can have various applications, such as in diagnostic kits, diagnostic reagents, biosensors, and biomarkers.

[0319] As used herein, the term "C1-C 60 alkyl" refers to a straight-chain or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms. As used herein, the term "C1-C 60 alkylene" refers to a divalent group having the same structure as C1-C 60 alkyl.

[0320] As used herein, C1-C 60 alkyl, C1-C 20 alkyl, and / or C1-C 10 alkyl non-limiting examples may include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl, or tert-decyl, each unsubstituted or substituted by: 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, isodecyl, sec-decyl, tert-decyl, or any combination thereof. For example, the group represented by Formula 9-33 as described above for branched C6 alkyl can be tert-butyl substituted by two methyl groups.

[0321] As used herein, the term "C1-C 60 alkoxy" refers to a monovalent group represented by -OA 101 (where A 101 is C1-C 60 alkyl). C1-C 60 alkoxy, C1-C 20 alkoxy, or C1-C 10Non-limiting examples of alkoxy groups can include methoxy, ethoxy, propoxy, butoxy, and pentyloxy.

[0322] As used herein, the term "C2-C 60 alkenyl" refers to a hydrocarbyl group having at least one carbon-carbon double bond at the middle or end of a C2-C 60 alkyl group, and examples thereof include vinyl, propenyl, and butenyl. As used herein, the term "C2-C 60 alkenylene" refers to a divalent group having the same structure as a C2-C 60 alkenyl group.

[0323] As used herein, the term "C2-C 60 alkynyl" refers to a hydrocarbyl group having at least one carbon-carbon triple bond at the middle or end of a C2-C 60 alkyl group, and examples thereof include ethynyl and propynyl. As used herein, the term "C2-C 60 alkynylene" refers to a divalent group having the same structure as a C2-C 60 alkynyl group.

[0324] As used herein, the term "C3-C 10 cycloalkyl" refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and as used herein, the term "C3-C 10 cycloalkylene" refers to a divalent group having the same structure as a C3-C 10 cycloalkyl group.

[0325] C3-C 10 Non-limiting examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl (norbornanyl), and bicyclo[2.2.2]octyl.

[0326] As used herein, the term "C1-C 10 heterocycloalkyl" refers to a monovalent monocyclic group having 1 to 10 carbon atoms and including at least one selected from N, O, P, Si, and S as ring-forming atoms. As used herein, the term "C1-C 10 heterocycloalkylene" refers to a divalent group having the same structure as a C1-C 10 heterocycloalkyl group.

[0327] Examples of C1-C 10 heterocycloalkyl groups herein can include silacyclopentyl, silacyclohexyl, tetrahydrofuranyl, tetrahydro-2H-pyranyl, and tetrahydrothienyl.

[0328] As used herein, the term "C3-C 10 cycloalkenyl" refers to a monovalent monocyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring but not having aromaticity, and non-limiting examples thereof include cyclopentenyl, cyclohexenyl, and cycloheptenyl. As used herein, the term "C3-C 10 subcycloalkenyl" refers to a divalent group having the same structure as C3-C 10 cycloalkenyl.

[0329] As used herein, the term "C1-C 10 heterocycloalkenyl" refers to a monovalent monocyclic group having 1 to 10 carbon atoms and including at least one N, O, P, Si, S, or any combination thereof as ring-forming atoms in its ring, and at least one double bond. Non-limiting examples of C1-C 10 heterocycloalkenyl include 2,3-dihydrofuranyl and 2,3-dihydrothienyl. As used herein, the term "C1-C 10 subheterocycloalkenyl" refers to a divalent group having the same structure as C1-C 10 heterocycloalkenyl.

[0330] As used herein, the term "C6-C 60 aryl" refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and as used herein, the term "C6-C 60 subaryl" refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Non-limiting examples of C6-C 60 aryl include phenyl, naphthyl, anthracenyl, phenanthryl, pyrenyl, and yl. When C6-C 60 aryl and C6-C 60 subaryl each include two or more rings, the rings may be fused to each other.

[0331] As used herein, the term "C7-C 60 alkaryl" refers to a C6-C 60 aryl substituted with at least one C1-C 60 alkyl.

[0332] As used herein, the term "C1-C 60 heteroaryl" refers to a monovalent group having a heterocyclic aromatic system as follows: the heterocyclic aromatic system has 1 to 60 carbon atoms and includes at least one heteroatom selected from N, O, P, Si, and S as ring-forming atoms. As used herein, the term "C1-C 60"Hetarylene" refers to a divalent group having a heterocyclic aromatic system as follows: the heterocyclic aromatic system has 1 - 60 carbon atoms and includes at least one heteroatom selected from N, O, P, Si, and S as ring-forming atoms. C1 - C 60 Non-limiting examples of heteroaryl include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. When C1 - C 60 heteroaryl and C1 - C 60 hetarylene each include two or more rings, the rings may be fused to each other.

[0333] As used herein, the term "C2 - C 60 alkylheteroaryl" refers to a C1 - C 60 heteroaryl substituted with at least one C1 - C 60 alkyl.

[0334] As used herein, the term "C6 - C 60 aryloxy" means - OA 102 (where A 102 is a C6 - C 60 aryl as described above), the term "C6 - C 60 arylthio" as used herein means - SA 103 (where A 103 is a C6 - C 60 aryl as described above), and the term "C1 - C 60 alkylthio" as used herein means - SA 104 (where A 104 represents a C1 - C 60 alkyl as described above).

[0335] As used herein, the term "monovalent non-aromatic fused polycyclic group" refers to a monovalent group having two or more rings fused to each other, having only carbon atoms as ring-forming atoms, and the entire molecular structure being non-aromatic (e.g., having 8 - 60 carbon atoms). Examples of monovalent non-aromatic fused polycyclic groups include fluorenyl. As used herein, the term "divalent non-aromatic fused polycyclic group" refers to a divalent group having the same structure as the monovalent non-aromatic fused polycyclic group.

[0336] As used herein, the term "monovalent non-aromatic fused heteropolycyclic group" refers to a monovalent group having two or more rings fused to each other, including at least one heteroatom selected from N, O, P, Si, and S in addition to carbon atoms as ring-forming atoms, and wherein the entire molecular structure is non-aromatic (e.g., having 1-60 carbon atoms). Non-limiting examples of the monovalent non-aromatic fused heteropolycyclic group include a carbazolyl group. As used herein, the term "divalent non-aromatic fused heteropolycyclic group" refers to a divalent group having the same structure as the monovalent non-aromatic fused heteropolycyclic group.

[0337] As used herein, the term "C5-C 30 carbocyclic group" refers to a saturated or unsaturated cyclic group having only 5-30 carbon atoms as ring-forming atoms. The C5-C 30 carbocyclic group may be a monocyclic group or a polycyclic group. The term "(unsubstituted or substituted by at least one R 1a substituted)C5-C 30 carbocyclic group" may include, for example, an adamantyl group, a norbornene group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group (norbornanyl group), a bicyclo[2.2.2]octyl group, a cyclopentyl group, a cyclohexyl group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a benzo[9,10]phenanthrene group, a pyrene group, group, a 1,2,3,4-tetrahydronaphthalene group, a cyclopentadiene group, a silole group, and a fluorene group (each of which is unsubstituted or substituted by at least one R 1a substituted).

[0338] As used herein, the term "C1-C 30 heterocyclic group" refers to a saturated or unsaturated cyclic group having at least one heteroatom selected from N, O, P, Si, Se, Ge, B, and S in addition to 1-30 carbon atoms as ring-forming atoms. The C1-C 30 heterocyclic group may be a monocyclic group or a polycyclic group. "(Unsubstituted or substituted by at least one R 1a substituted)C1-C 30The "heterocyclic group" may be, for example, a thiophene group, a furan group, a pyrrole group, a silole group, a borole group, a phosphole group, a selenophene group, a germole group, a benzothiophene group, a benzofuran group, an indole group, an indene group, a benzosilole group, a benzoborole group, a benzophosphole group, a benzoselenophene group, a benzogermole group, a dibenzothiophene group, a dibenzofuran group, a carbazole group, a dibenzosilole group, a dibenzoborole group, a dibenzophosphole group, a dibenzoselenophene group, a dibenzogermole group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, a dibenzothiophene 5,5-dioxide group, an azabenzothiophene group, an azabenzofuran group, an azaindole group, an azaindene group, an azabenzosilole group, an azabenzoborole group, an azabenzophosphole group, an azabenzoselenophene group, an azabenzogermole group, an azadibenzothiophene group, an azadibenzofuran group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzoborole group, an azadibenzophosphole group, an azadibenzoselenophene group, an azadibenzogermole group, an azadibenzothiophene 5-oxide group, an aza-9H-fluoren-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrazole group, an imidazole group, a triazole group, azole group, is azole group, a thiazole group, an isothiazole group, diazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, benzo azole group, a benzothiazole group, benzo diazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group (each of which is unsubstituted or substituted by at least one R 1a substituted).

[0339] As used herein, the term "fluorinated C1-C 60 alkyl (or fluorinated C1-C 20 alkyl, etc.)", "fluorinated C3-C 10 cycloalkyl", "fluorinated C1-C 10 heterocycloalkyl", and "fluorinated phenyl" respectively refer to a C1-C 60 alkyl, a C3-C 10 cycloalkyl, a C1-C 10Heterocycloalkyl, and phenyl. Examples of "fluorinated C1 alkyl (i.e., fluorinated methyl)" may include -CF3, -CF2H, and -CFH2. The term "fluorinated C1-C 60 alkyl (or fluorinated C1-C 20 alkyl, etc.)", "fluorinated C3-C 10 cycloalkyl", "fluorinated C1-C 10 heterocycloalkyl", or "fluorinated phenyl" may be i) a fully fluorinated C1-C 60 alkyl (or fully fluorinated C1-C 20 alkyl, etc.), a fully fluorinated C3-C 10 cycloalkyl, a fully fluorinated C1-C 10 heterocycloalkyl, a fully fluorinated phenyl, where all hydrogens in each group are replaced by fluorine groups, or ii) a partially fluorinated C1-C 60 alkyl (or partially fluorinated C1-C 20 alkyl, etc.), a partially fluorinated C3-C 10 cycloalkyl, a partially fluorinated C1-C 10 heterocycloalkyl, or a partially fluorinated phenyl, where all hydrogens in each group are partially i.e., not completely replaced by fluorine groups.

[0340] As used herein, the term "deuterated C1-C 60 alkyl (or deuterated C1-C 20 alkyl, etc.)", "deuterated C3-C 10 cycloalkyl", "deuterated C1-C 10 heterocycloalkyl", and "deuterated phenyl" may respectively refer to a C1-C 60 alkyl (or C1-C 20 alkyl, etc.), a C3-C 10 cycloalkyl, a C1-C 10 heterocycloalkyl, and a phenyl, each of which is substituted with at least one deuterium. Examples of "deuterated C1 alkyl (i.e., deuterated methyl)" may include -CD3, -CD2H, and -CDH2. Examples of "deuterated C3-C 10 cycloalkyl" may be the groups represented by Formula 10-501 as described above. The term "deuterated C1-C 60 alkyl (or deuterated C1-C 20 alkyl, etc.)", "deuterated C3-C 10 cycloalkyl", "deuterated C1-C 10 heterocycloalkyl", or "deuterated phenyl" may be i) a fully deuterated C1-C 60 alkyl (or fully deuterated C1-C 20 alkyl, etc.), a fully deuterated C3-C 10 cycloalkyl, a fully deuterated C1-C 10A heterocycloalkyl group, or a fully deuterated phenyl group in which all hydrogens in each group are replaced by deuterium, or ii) a partially deuterated C1-C 60 alkyl group (or a partially deuterated C1-C 20 alkyl group, etc.), a partially deuterated C3-C 10 cycloalkyl group, a partially deuterated C1-C 10 heterocycloalkyl group, or a partially deuterated phenyl group in which all hydrogens in each group are partially, i.e., not completely, replaced by deuterium.

[0341] As used herein, the term “(C1-C 20 alkyl)‘X’ group” refers to an ‘X’ group substituted with at least one C1-C 20 alkyl group. For example, as used herein, the term “(C1-C 20 alkyl)C3-C 10 cycloalkyl” represents a C3-C 20 cycloalkyl group substituted with at least one C1-C 10 alkyl group, and the term “(C1-C 20 alkyl)phenyl” represents a phenyl group substituted with at least one C1-C 20 alkyl group. For example, (C1 alkyl)phenyl can be tolyl.

[0342] As used herein, an azaindole group, an azabenzo[b]borole group, an azabenzo[b]phosphole group, an azaindene group, an azabenzo[b]silole group, an azabenzo[b]germole group, an azabenzo[b]thiophene group, an azabenzo[b]selenophene group, an azabenzo[b]furan group, an azacarbazole group, an azadibenzo[b]borole group, an azadibenzo[b]phosphole group, an azafluorene group, an azadibenzo[b]silole group, an azadibenzo[b]germole group, an azadibenzo[b]thiophene group, an azadibenzo[b]selenophene group, an azadibenzo[b]furan group, an azadibenzo[b]thiophene 5-oxide group, an azo-9H-fluoren-9-one group, and an azadibenzo[b]thiophene 5,5-dioxide group may respectively refer to heterocycles having the same skeletons as an indole group, a benzo[b]borole group, a benzo[b]phosphole group, an indene group, a benzo[b]silole group, a benzo[b]germole group, a benzo[b]thiophene group, a benzo[b]selenophene group, a benzo[b]furan group, a carbazole group, a dibenzo[b]borole group, a dibenzo[b]phosphole group, a fluorene group, a dibenzo[b]silole group, a dibenzo[b]germole group, a dibenzo[b]thiophene group, a dibenzo[b]selenophene group, a dibenzo[b]furan group, a dibenzo[b]thiophene 5-oxide group, a 9H-fluoren-9-one group, and a dibenzo[b]thiophene 5,5-dioxide group, in which at least one of the ring-forming carbons of each group is replaced by nitrogen.

[0343] Substituted C5-C 30 carbocyclic group, substituted C2-C30 Heterocyclic group, substituted C1-C 60 alkyl, substituted C2-C 60 alkenyl, substituted C2-C 60 alkynyl, substituted C1-C 60 alkoxy, substituted C1-C 60 alkylthio, substituted C3-C 10 cycloalkyl, substituted C1-C 10 heterocycloalkyl, substituted C3-C 10 cycloalkenyl, substituted C1-C 10 heterocycloalkenyl, substituted C6-C 60 aryl, substituted C7-C 60 alkaryl, substituted C6-C 60 aryloxy, substituted C6-C 60 arylthio, substituted C1-C 60 heteroaryl, substituted C2-C 60 One or more substituents of alkyl heteroaryl, substituted monovalent non-aromatic fused polycyclic group, and substituted monovalent non-aromatic fused heteropolycyclic group may each independently be:

[0344] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, amidino, hydrazino, hydrazono, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 alkoxy;

[0345] C1-C each substituted by the following 60 alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl, or C1-C 60 alkoxy: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, amidino, hydrazino, hydrazono, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C3-C 10 cycloalkyl, C1-C 10 heterocycloalkyl, C3-C 10 cycloalkenyl, C1-C 10 heterocycloalkenyl, C6-C 60 aryl, C7-C 60 alkaryl, C6-C 60 aryloxy, C6-C 60Arylthio, C1-C 60 Heteroaryl, C2-C 60 Alkylheteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 11 )(Q 12 )、-Si(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;

[0346] C3-C each unsubstituted or substituted by the following 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C7-C 60 Alkylaryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, C2-C 60 Alkylheteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxy, cyano, nitro, amidino, hydrazino, hydrazono, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C7-C 60 Alkylaryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, C2-C 60 Alkylheteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 21 )(Q 22)、 -Si(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;

[0347] -N(Q 31 )(Q 32 )、 -Si(Q 33 )(Q 34 )(Q 35 )、 -B(Q 36 )(Q 37 )、 -P(=O)(Q 38 )(Q 39 )、 or -P(Q 38 )(Q 39 ); or

[0348] any combination thereof.

[0349] As used herein, Q1 - Q9, Q 11 -Q 19 、 Q 21 -Q 29 、 and Q 31 -Q 39 can each independently be hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxy; cyano; nitro; amidino; hydrazino; hydrazono; a carboxylic acid group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphoric acid group or a salt thereof; a C1 - C 60 alkyl group unsubstituted or substituted with deuterium, a C1 - C 60 alkyl group, a C6 - C 60 aryl group, or any combination thereof; a C2 - C 60 alkenyl group; a C2 - C 60 alkynyl group; a C1 - C 60 alkoxy group; a C3 - C 10 cycloalkyl group; a C1 - C 10 heterocycloalkyl group; a C3 - C 10 cycloalkenyl group; a C1 - C 10 heterocycloalkenyl group; a C6 - C 60 aryl group unsubstituted or substituted with deuterium, a C1 - C 60 alkyl group, a C6 - C 60 aryl group, or any combination thereof; a C6 - C 60 aryloxy group; a C6 - C 60 arylthio group; a C1 - C 60A heteroaryl group; a monovalent non-aromatic fused polycyclic group; or a monovalent non-aromatic fused heteropolycyclic group.

[0350] Hereinafter, compounds and organic light-emitting devices according to embodiments will be described in detail with reference to synthesis examples and examples. However, these examples are for illustrative purposes only and are not intended to limit the scope of one or more embodiments of the present disclosure. The phrase "using B in place of A" used in describing the synthesis examples means that, in terms of molar equivalents, the amount of A used is the same as the amount of B used.

[0351] Example

[0352] Synthesis Example 1 (Compound 2)

[0353]

[0354] Synthesis of Compound L2-4

[0355] 5 g (29.1 mmol) of 3-bromo-4-methylpyridine was mixed with 60 mL of acetonitrile and 15 mL of water, and then 1.43 g (2.04 mmol) of PdCl2(PPh3)2, 4.88 g (29.1 mmol) of (4-fluoro-2-formylphenyl)boronic acid, and 10.04 g (72.8 mmol) of K2CO3 were added thereto, and the mixture was heated at 80 °C under reflux for 18 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure and then extracted with dichloromethane and water to obtain an organic phase. The obtained organic phase was dried over magnesium sulfate, distilled under reduced pressure, and then purified by liquid chromatography to obtain 5.13 g of compound L2-4 (yield: 82%).

[0356] HRMS (MALDI): For C 13 H 10 FNO, calculated value: m / z 215.0746, measured value: 215.0747

[0357] Synthesis of Compound L2-3

[0358] 5.13 g (23.8 mmol) of compound L2-4 was mixed with 70 mL of dimethylformamide (DMF). A solution of 3.49 g (47.6 mmol) of t-BuOK dissolved in 10 mL of DMF was slowly added dropwise to the mixture, and then the reaction mixture was stirred at room temperature for one day. After completion of the reaction, the reaction mixture was concentrated under reduced pressure and then extracted with dichloromethane and water to obtain an organic phase. The obtained organic phase was dried over magnesium sulfate, distilled under reduced pressure, and then purified by liquid chromatography to obtain 3.57 g of compound L2-3 (yield: 76%).

[0359] HRMS (MALDI): For C 13 Calculated value for C 13 H8FN: m / z 197.0641, measured value: 197.0642

[0360] Synthesis of Compound L2-2

[0361] After dissolving 3.57 g (18.1 mmol) of compound L2-3 in 60 mL of CH2Cl2, m-chloroperbenzoic acid (mCPBA) was slowly added dropwise thereto at 0 °C, and then it was stirred for one day. After the reaction was completed, the reaction mixture was extracted with 6N aqueous KOH solution to obtain an organic phase. The obtained organic phase was dried over magnesium sulfate, distilled under reduced pressure, and then purified by liquid chromatography to obtain 3.67 g of compound L2-2 (yield: 95%).

[0362] Synthesis of Compound L2-1

[0363] After mixing 3.67 g (17.2 mmol) of compound L2-2 with 80 mL of CH2Cl2, 5.68 g (19.8 mmol) of POBr3 was slowly added dropwise thereto at 0 °C, then 0.3 mL of DMF was added thereto and it was stirred at room temperature for one day. After the reaction was completed, the reaction mixture was extracted with saturated aqueous sodium bicarbonate solution to obtain an organic phase. The obtained organic phase was dried over magnesium sulfate, distilled under reduced pressure, and then purified by liquid chromatography to obtain 3.23 g of compound L2-1 (yield: 68%).

[0364] HRMS (MALDI): For C 13 Calculated value for C 13 H7BrFN: m / z 274.9746, measured value: 274.9747

[0365] Synthesis of Compound L2

[0366] After mixing 3.23 g (11.7 mmol) of compound L2-1 with 45 mL of THF and 15 mL of water, 1.93 g (12.9 mmol) of 3,5-dimethylphenylboronic acid, 1.23 g (0.82 mmol) of Pd(PPh3)4, and 4.04 g (29.3 mmol) of K2CO3 were added thereto, and then it was heated at 75 °C under reflux for one day. After the reaction was completed, the reaction mixture was extracted with ethyl acetate and water to obtain an organic phase. The obtained organic phase was dried over magnesium sulfate, distilled under reduced pressure, and then purified by liquid chromatography to obtain 2.61 g of compound L2 (yield: 74%).

[0367] HRMS (MALDI): For C 21 H 16Calculated value of FN: m / z 301.1267, measured value: 301.1268

[0368] Synthesis of Compound L2 Dimer

[0369] 2.00 g (6.6 mmol) of compound L2 and 1.11 g (3.1 mmol) of iridium chloride were mixed with 40 mL of ethoxyethanol and 15 mL of distilled water, and then heated under reflux for 24 hours. After the reaction was completed, the temperature was lowered to room temperature to obtain a solid product. The solid product was filtered and then washed thoroughly with water, methanol, and then hexane. The obtained solid was dried in a vacuum oven to obtain 2.4 g of compound L2 Dimer.

[0370] Synthesis of Compound 2

[0371] 2.4 g (1.45 mmol) of compound L2 Dimer, 1.33 g (7.25 mmol) of 2,2,6,6-tetramethylheptane-3,5-dione, and 0.76 g (7.25 mmol) of Na2CO3 were mixed with 40 mL of ethoxyethanol and then stirred at 90 °C for 24 hours to allow the reaction. After the reaction was completed, the temperature was lowered to room temperature to obtain a solid product. The solid product formed by lowering the temperature to room temperature was filtered and then purified by liquid chromatography to obtain 1.56 g of compound 2 (yield: 55%).

[0372] HRMS (MALDI): For C 53 H 49 Calculated value of F2FIrN2O2: m / z 976.3391, measured value: 976.3393

[0373] Synthesis Example 2 (Compound 10)

[0374]

[0375] Synthesis of Compound L10

[0376] 1.50 g of compound L10 (yield: 76%) was obtained in the same manner as in the synthesis method of compound L2 in Synthesis Example 1, except that: compound L10-1 (1-bromo-6-fluorobenzo[h]isoquinoline) was used instead of compound L2-1.

[0377] HRMS (MALDI): For C 21 H 16 Calculated value of FN: m / z 301.3644, measured value: 301.3646

[0378] Synthesis of Compound L10 Dimer

[0379] 1.82 g of compound L10 Dimer was obtained in the same manner as in the synthesis method of compound L2 Dimer in Synthesis Example 1, except that compound L10 was used instead of compound L2.

[0380] Synthesis of Compound 10

[0381] 1.10 g of compound 10 (yield: 52.0%) was obtained in the same manner as in the synthesis method of compound 2 in Synthesis Example 1, except that compound L10 Dimer was used instead of compound L2 Dimer.

[0382] HRMS (MALDI): For C 53 H 49 Calculated for F2IrN2O2: m / z 976.2008, found: 976.2009

[0383] Synthesis Example 3 (Compound 11)

[0384]

[0385] Synthesis of Compound L11

[0386] 1.42 g of compound L11 (yield: 77%) was obtained in the same manner as in the synthesis method of compound L2 in Synthesis Example 1, except that compound L11-1 (1-bromo-7-fluorobenzo[h]isoquinoline) was used instead of compound L2-1.

[0387] HRMS (MALDI): For C 21 H 16 Calculated for FN: m / z 301.3644, found: 301.3645

[0388] Synthesis of Compound L11 Dimer

[0389] 1.70 g of compound 11 Dimer was obtained in the same manner as in the synthesis method of compound L2 Dimer in Synthesis Example 1, except that compound L11 was used instead of compound L2.

[0390] Synthesis of Compound 11

[0391] 0.98 g of compound 11 (yield: 49.0%) was obtained in the same manner as in the synthesis method of compound 2 in Synthesis Example 1, except that compound L11 Dimer was used instead of compound L2 Dimer.

[0392] HRMS(MALDI): For C 53 H 49 Calculated for F2IrN2O2: m / z 976.2008, found: 976.2008

[0393] Synthesis Example 4 (Compound 22)

[0394]

[0395] Synthesis of Compound L22

[0396] 1.65 g of compound L22 (yield: 64.0%) was obtained in the same manner as in the synthesis method of compound L2 in Synthesis Example 1, except that: compound L22-1 was used instead of compound L2-1.

[0397] HRMS(MALDI): For C 22 H 16 Calculated for F3N: m / z 351.3722, found: 351.3724

[0398] Synthesis of Compound L22 Dimer

[0399] 1.62 g of compound L22 Dimer was obtained in the same manner as in the synthesis method of compound L2 Dimer in Synthesis Example 1, except that: compound L22 was used instead of compound L2.

[0400] Synthesis of Compound 22

[0401] 0.71 g of compound 22 (yield: 40%) was obtained in the same manner as in the synthesis method of compound 2 in Synthesis Example 1, except that: compound L22 Dimer was used instead of compound L2 Dimer.

[0402] HRMS(MALDI): For C 55 H 49 Calculated for F6IrN2O2: m / z 1076.2164, found: 1076.2166

[0403] Synthesis Example 5 (Compound 41)

[0404]

[0405] Synthesis of Compound L41

[0406] 2.10 g of compound L41 was obtained in the same manner as in the synthesis method of compound L2 in Synthesis Example 1, except that compound L41-1 was used instead of compound L2-1 (yield: 78%).

[0407] HRMS (MALDI): For C 24 H 22 FN calculated value: m / z 343.4454, measured value: 343.445

[0408] Synthesis of Compound L41 Dimer

[0409] 2.2 g of compound L41 Dimer was obtained in the same manner as in the synthesis method of compound L2 Dimer in Synthesis Example 1, except that compound L41 was used instead of compound L2.

[0410] Synthesis of Compound 41

[0411] 1.44 g of compound 41 was obtained in the same manner as in the synthesis method of compound 2 in Synthesis Example 1, except that compound L41 Dimer and 3,7-diethylnonane-4,6-dione were used instead of compound L2 Dimer and 2,2,6,6-tetramethylheptane-3,5-dione, respectively (yield: 55.0%).

[0412] HRMS (MALDI): For C 61 H 65 Calculated value for F2IrN2O2: m / z 1088.4168, measured value: 1088.4169

[0413] Synthesis Example 6 (Compound 42)

[0414]

[0415] 1.58 g of compound 42 was obtained in the same manner as in the synthesis method of compound 2 in Synthesis Example 1, except that compound L41 Dimer and 3,7-diethyl-3,7-dimethylnonane-4,6-dione were used instead of compound L2 Dimer and 2,2,6,6-tetramethylheptane-3,5-dione, respectively (yield: 52.0%).

[0416] HRMS (MALDI): For C 63 H 69 Calculated value for F2IrN2O2: m / z 1116.4708, measured value: 1116.4709

[0417] Synthesis Example 7 (Compound 56)

[0418]

[0419] Synthesis of Compound L56

[0420] 1.65 g of compound L56 (yield: 68.0%) was obtained in the same manner as in the synthesis method of compound L2 in Synthesis Example 1, except that compound L56-1 was used instead of compound L2-1.

[0421] HRMS (MALDI): For C 28 H 28 Calculated value for C

[0422] Synthesis of Compound L56 Dimer

[0423] 1.70 g of compound L56 Dimer was obtained in the same manner as in the synthesis method of compound L2 Dimer in Synthesis Example 1, except that compound L56 was used instead of compound L2.

[0424] Synthesis of Compound 56

[0425] 0.78 g of compound 56 (yield: 39.0%) was obtained in the same manner as in the synthesis method of compound 2 in Synthesis Example 1, except that compound L56 Dimer and 3,7-diethylnonane-4,6-dione were used instead of compound L2 Dimer and 2,2,6,6-tetramethylheptane-3,5-dione, respectively.

[0426] HRMS (MALDI): For C 69 H 77 Calculated value for C

[0427] Synthesis Example 8 (Compound 57)

[0428]

[0429] 1.00 g of compound 57 (yield: 42.0%) was obtained in the same manner as in the synthesis method of compound 2 in Synthesis Example 1, except that compound L56 Dimer and 3,7-diethyl-3,7-dimethylnonane-4,6-dione were used instead of compound L2 Dimer and 2,2,6,6-tetramethylheptane-3,5-dione, respectively.

[0430] HRMS (MALDI): For C71 H 81 Calculated value of F2IrN2O2: m / z 1224.6548, measured value: 1224.6550

[0431] Evaluation Example 1: Evaluation of Photoluminescence Quantum Yield (PLQY)

[0432] Compound H52 and Compound 2 with a weight ratio of 98:2 were co-deposited under a vacuum of 10 -7 Torr to fabricate a film with a thickness of 40 nm.

[0433] The photoluminescence quantum yield (PLQY) of Compound 2 in the film was evaluated using a Hamamatsu Photonics absolute PL quantum yield measurement system (Hamamatsu Photonics, Ltd., Shizuoka, Japan) equipped with a xenon light source, a monochromator, a photon multi-channel analyzer, an integrating sphere, and PLQY measurement software. The same evaluation was repeated using Compounds 10, 11, 22, 41, 42, 56, and 57. The results are shown in Table 2.

[0434] [Table 2]

[0435]

[0436]

[0437]

[0438] Example 1

[0439] A glass substrate with a thick ITO pattern as the anode was cut into a size of 50 mm × 50 mm × 0.5 mm, ultrasonically treated with isopropyl alcohol and pure water for 5 minutes each, then irradiated with ultraviolet light for 30 minutes and exposed to ozone for cleaning. Then, the obtained glass substrate was loaded onto a vacuum deposition apparatus.

[0440] Compound HT3 and F6-TCNNQ were co-deposited on the ITO anode under a vacuum at a weight ratio of 98:2 to form a hole injection layer with a thickness, and Compound HT3 was vacuum-deposited on the hole injection layer to form a hole transport layer with a thickness, and then Compound HT21 was vacuum-deposited on the hole transport layer to form an electron blocking layer with a thickness.

[0441] Subsequently, Compound H52 (host) and Compound 2 (dopant) were co-deposited on the electron blocking layer at a weight ratio of 98:2 to form a emitting layer with a thickness of

[0442] Then, compounds ET3 and ET-D1 were co-deposited on the emitting layer at a volume ratio of 50:50 to form an electron transport layer with a thickness of ET-D1 was vacuum-deposited on the electron transport layer to form an electron injection layer with a thickness of and Al was vacuum-deposited on the electron injection layer to form a cathode with a thickness of Thereby, an organic light-emitting device having a structure of ITO / HT3+F6-TCNNQ (2 wt%) / HT3 / HT21 / H52+Compound 2 (2 wt%) / ET3+ET-D1 (50%) / ET-D1 / Al was fabricated.

[0443]

[0444] Examples 2-8 and Comparative Examples A-F

[0445] An organic light-emitting device was fabricated in the same manner as in Example 1, except that: when forming the emitting layer, the compounds shown in Table 3 were used respectively instead of Compound 2 as the dopant.

[0446] Evaluation Example 2: Evaluation of Characteristics of Organic Light-Emitting Devices

[0447] The driving voltage, current density, external quantum efficiency (EQE), roll-off ratio, full width at half maximum (FWHM) of the emission peak in the EL spectrum, color coordinates, and lifetime (LT 97 ) of each of the organic light-emitting devices fabricated in Examples 1-8 and Comparative Examples A-F were evaluated. The results are shown in Table 3. This evaluation was performed using a current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1,000A), and the lifetime (LT 97 ) (at 3500 nits) was evaluated as the time (hours) until the luminance decreased to 97% of the initial luminance with respect to 100% and presented as a relative value (%) in Table 3. The roll-off ratio was calculated using Equation 1.

[0448] <Equation 1>

[0449] Roll-off ratio = {1 - (efficiency (at 3500 nits) / maximum luminous efficiency)} × 100%

[0450] [Table 3]

[0451]

[0452]

[0453]

[0454] Referring to Table 3, it is found that, compared with the organic light-emitting devices of Comparative Examples A-F, the organic light-emitting devices of Examples 1-8 emit red light with high color purity and simultaneously have improved driving voltage, improved EQE, improved roll-off ratio, relatively small FWHM, and improved lifetime characteristics.

[0455] According to one or more of the embodiments, the organometallic compound represented by Formula 1 has excellent electronic properties and stability, and thus an electronic device including the organometallic compound, such as an organic light-emitting device, can have improved driving voltage, improved external quantum efficiency, improved roll-off ratio, relatively small FWHM, and improved lifetime characteristics. Accordingly, high-quality organic light-emitting devices or electronic devices can be implemented using the organometallic compound.

[0456] It should be understood that the embodiments described herein should be considered only in the descriptive sense and not for purposes of limitation. The description of a feature or aspect in each embodiment should typically be considered applicable to other similar features or aspects in other embodiments.

[0457] Although one or more embodiments have been described with reference to the accompanying drawings, those of ordinary skill in the art will understand that various changes in form and detail may be made therein without departing from the spirit and scope of the disclosure as defined by the appended claims.

Claims

1. An organometallic compound represented by Formula 1, <Formula 1> wherein, In Formula 1, Y2 is C, Ring CY1 is a C5-C polycyclic group in which three or more monocyclic groups are fused to each other, where the group represented by in Formula 1 is the group represented by CY1-1: 30 a polycyclic group, where the group represented by is the group represented by Formula CY1-1: X1 - X8 are each independently C, * is a binding site to iridium (Ir) in Formula 1, and *" is a binding site to ring CY2 in Formula 1, ring CY2 is a phenyl group, T1 and A1 - A7 are each independently hydrogen, deuterium, -F, substituted or unsubstituted C1 - C 20 alkyl, or substituted or unsubstituted C3 - C 10 cycloalkyl, T2 is deuterium, or a substituted or unsubstituted C1-C 20 alkyl group, a1 is an integer from 1 to 20; when a1 is 2 or greater, two or more T1s are the same as or different from each other; and at least one of the a1 number of T1s includes at least one fluorine group, Substituted C1-C 20 alkyl and one or more substituents of substituted C3-C 10 cycloalkyl are each independently: Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, or C1-C 20 alkyl; C3-C 10 cycloalkyl; or in any combination, where a2 is 1, 2, or 3, and when a2 is 2 or greater, two or more T2s are the same as or different from each other, and where in Formula 1, the following cases are excluded: 1) A7 is hydrogen, and 2) both the group represented by *-C(A1)(A2)(A3) and the group represented by *-C(A4)(A5)(A6) are methyl.

2. The organometallic compound according to claim 1, wherein T1 and A1 - A7 are each independently: hydrogen, deuterium, -F, C1 - C 20 alkyl, or C3 - C 10 cycloalkyl; fluorinated C1 - C 20 alkyl or fluorinated C3 - C 10 cycloalkyl, each unsubstituted or substituted with: deuterium, C1 - C 20 alkyl, C3 - C 10 cycloalkyl, or any combination thereof; or deuterated C1 - C 20 alkyl or deuterated C3 - C 10 cycloalkyl, each unsubstituted or substituted with: -F, C1 - C 20 alkyl, C3 - C 10 cycloalkyl, or any combination thereof.

3. The organometallic compound according to claim 1, wherein A1 - A7 are each independently: hydrogen, deuterium, C1 - C 20 alkyl, or C3 - C 10 cycloalkyl; or deuterated C1 - C 20 alkyl or deuterated C3 - C10 Naphthenyl: C1-C 20 Alkyl, C3-C 10 Naphthenyl, or any combination thereof, T2 is: Deuterium, or C1-C 20 Alkyl; or Each unsubstituted or substituted deuterated C1-C 20 Alkyl: C1-C 20 Alkyl, C3-C 10 Naphthenyl, or any combination thereof.

4. The organometallic compound according to claim 1, wherein the group represented by in Formula 1 is the group represented by Formula CY1(1): Wherein, In Formula CY1(1), T 11 -T 18 is the same as that defined for T1 in claim 1, provided that T 11 -T 18 at least one of which comprises at least one fluorine group * represents a binding site to Ir in Formula 1, and *" represents a binding site to ring CY2 in Formula 1.

5. The organometallic compound according to claim 1, wherein the group represented by in Formula 1 is one of the groups represented by Formulae CY1(1)-1 to CY1(1)-64: Wherein, In Formulas CY1(1)-1 to CY1(1)-64, T 11 -T 18 Same as defined in claim 1 with respect to T1, provided that T 11 -T 18 Each is not hydrogen, T 101 -T 108 Each includes at least one fluorine group, * represents a binding site to Ir in Formula 1, and *" represents a binding site to ring CY2 in Formula 1.

6. The organometallic compound according to claim 5, wherein, In Formulas CY1(1)-1 to CY1(1)-64, T 11 -T 18 Each independently is: Deuterium, C1-C 20 alkyl, or C3-C 10 cycloalkyl; or Each deuterated C1-C which is unsubstituted or substituted as follows 20 alkyl or deuterated C3-C 10 cycloalkyl: C1-C 20 alkyl, C3-C 10 cycloalkyl, or any combination thereof, and T 101 -T 108 Each independently is: -F; or Each fluorinated C1-C which is unsubstituted or substituted as follows 20 alkyl or fluorinated C3-C 10 cycloalkyl: deuterium, C1-C 20 alkyl, C3-C 10 cycloalkyl, or any combination thereof.

7. The organometallic compound according to claim 1, wherein the group represented by in Formula 1 is the group of Formula CY2-1: wherein, In Formula CY2-1, Y2 and T2 are the same as those defined in claim 1, a24 is an integer from 0 to 4, *" represents a binding site to ring CY1 in Formula 1, and *' represents a binding site to Ir in Formula 1.

8. The organometallic compound according to claim 1, wherein the group represented by in Formula 1 is one of the groups represented by Formula CY2(1) to CY2(16): wherein, In Formulas CY2(1) to CY2(16), Y2 is the same as that defined in claim 1, T 21 -T 24 is the same as that defined for T2 in claim 1, but T 21 -T 24 each is not hydrogen, *" represents a binding site to ring CY1 in Formula 1, and *' represents a binding site to Ir in Formula 1.

9. The organometallic compound according to claim 1, wherein the organometallic compound satisfies at least one of <Condition 1> to <Condition 3>: <Condition 1> Each of A1 - A6 in Formula 1 is independently a substituted or unsubstituted C1 - C 20 alkyl group, or a substituted or unsubstituted C3 - C 10 cycloalkyl group; <Condition 2> At least one of A1 - A6 in Formula 1 is independently a substituted or unsubstituted C2 - C 20 alkyl group, or a substituted or unsubstituted C3 - C 10 cycloalkyl group; and <Condition 3> A7 in Formula 1 is deuterium, a substituted or unsubstituted C1 - C 20 alkyl group, or a substituted or unsubstituted C3 - C 10 cycloalkyl group.

10. 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 emission layer, the organic layer including at least one organometallic compound represented by Formula 1 as described in any one of claims 1 - 9.

11. The organic light - emitting device according to claim 10, wherein the first electrode is an anode, the second electrode is a cathode, The organic layer further includes a hole transport region between the first electrode and the emission layer and an electron transport region between the emission 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, and 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 according to claim 10, wherein the organometallic compound is in the emission layer.

13. The organic light-emitting device according to claim 12, wherein the emission layer further includes a host, and the amount of the host in the emission layer is greater than the amount of the organometallic compound in the emission layer.

14. An electronic device comprising the organic light-emitting device according to any one of claims 10-13.

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