Organometallic Compound and Organic Light-Emitting Device Comprising the Same

Abstract

The present application provides an organometallic compound and an organic light-emitting device comprising the organometallic compound. The organometallic compound is represented by Formula 1: <Formula 1> M(L A ) n1 (L B ) n2 .

Description

[0001] Cross - reference to related applications

[0002] This application claims the priority and benefit of Korean Patent Application No. 10 - 2019 - 0154560, filed with the Korean Intellectual Property Office on November 27, 2019, the entire contents of which are incorporated herein by reference. Technical field

[0003] Embodiments relate to an organometallic compound and an organic light - emitting device including the organometallic compound. Background art

[0004] An organic light - emitting device is a self - emitting device that produces full - color images and also has a wide viewing angle, high contrast ratio, short response time, and excellent characteristics in terms of brightness, driving voltage, and response speed compared to devices in the art.

[0005] An organic light - emitting device may include a first electrode disposed on a substrate, and a hole - transport region, an emission layer, an electron - transport region, and a second electrode sequentially disposed on the first electrode. Holes provided by the first electrode may move to the emission layer through the hole - transport region, and electrons provided by the second electrode may move to the emission layer through the electron - transport region. Carriers (e.g., 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] Embodiments include an organometallic compound and an organic light - emitting device including the organometallic compound.

[0007] Additional embodiments will be set forth in part in the following description, and in part will be obvious from the description, or may be learned by practice of the embodiments of the present disclosure.

[0008] In an embodiment, the organometallic compound is represented by Formula 1.

[0009] <Formula 1>

[0010] M(L A ) n1 (L B ) n2

[0011] In Formula 1,

[0012] M may be selected from platinum (Pt), palladium (Pd), copper (Cu), zinc (Zn), silver (Ag), gold (Au), iridium (Ir), rhodium (Rh), cobalt (Co), ruthenium (Ru), rhenium (Re), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm),

[0013] n1 can be 1 or 2,

[0014] n2 can be 0 or 1,

[0015] The sum of n1 and n2 can be 2,

[0016] L A can be a tridentate ligand represented by Formula 1A,

[0017] L B can be a tridentate ligand represented by Formula 1B:

[0018]

[0019] In Formula 1A and Formula 1B,

[0020] *, *' and *” can each be a binding site to M,

[0021] Y1 and Y3 to Y6 can each independently be selected from N and C,

[0022] X 21 can be selected from C(Z 21 ), N(Z 21 ), N, O and S,

[0023] X 22 can be selected from C(Z 22 ), N(Z 22 ), N, O and S,

[0024] A1 and A3 to A6 can each independently be selected from C5-C 60 carbocyclic ring and C1-C 60 heterocyclic ring,

[0025] A2 can be selected from imidazole ring, oxazole ring, thiazole ring, selenazole ring, triazole ring, oxadiazole ring, thiadiazole ring and selenadiazole ring,

[0026] L1 and L2 can each independently be selected from *-O-*', *-S-*', *-C(R7)(R8)-*', *-C(R7)=*', *=C(R7)-*', *-C(R7)=C(R8)-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R7)-*', *-N(R7)-*', *-P(R7)-*', *-Si(R7)(R8)-*', *-P(R7)(R8)-*' and *-Ge(R7)(R8)-*',

[0027] a1 and a2 can each independently be selected from 0, 1 and 2,

[0028] Z21 , Z 22 , R1 and R3 to R8 can each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, substituted or unsubstituted C1-C 60 alkyl group, substituted or unsubstituted C2-C 60 alkenyl group, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 alkoxy group, substituted or unsubstituted C3-C 10 cycloalkyl group, substituted or unsubstituted C1-C 10 heterocycloalkyl group, substituted or unsubstituted C3-C 10 cycloalkenyl group, substituted or unsubstituted C1-C 10 heterocycloalkenyl group, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 arylthio group, substituted or unsubstituted C1-C 60 heteroaryl group, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) and -P(=O)(Q1)(Q2),

[0029] b1 and b3 to b6 can each independently be selected from 1, 2, 3, 4, 5, 6, 7 and 8,

[0030] provided that: at least one pair of substituents can optionally be joined together to form a substituted or unsubstituted C5-C 60 carbocyclic group or a substituted or unsubstituted C1-C 60 heterocyclic group, and the pair of substituents is selected from the group consisting of Z 21 and Z 22 , two adjacent R1 among b1 number of R1, two adjacent R3 among b3 number of R3, two adjacent R4 among b4 number of R4, two adjacent R5 among b5 number of R5, two adjacent R6 among b6 number of R6, R1 and R7, and R3 and R7,

[0031] can satisfy one of the following conditions i) to condition iii),

[0032] i) Y1 is N, and A1 is a 5-membered ring containing Y1, a 6-membered ring containing Y1, a C5-C fused with a 5-membered ring containing Y1 60 heterocyclic ring, or a C5-C fused with a 6-membered ring containing Y1 60 heterocyclic ring,

[0033] ii) Y1 is C and each of a1 and a2 is 0,

[0034] iii) Y1 is C and a1 and a2 are each independently selected from 1 and 2, and

[0035] the substituted C5-C 60 carbocyclic group, the substituted C1-C 60 heterocyclic group, the substituted C1-C 60 alkyl group, the substituted C2-C 60 alkenyl group, the substituted C2-C 60 alkynyl group, the substituted C1-C 60 alkoxy group, the substituted C3-C 10 cycloalkyl group, the substituted C1-C 10 heterocycloalkyl group, the substituted C3-C 10 cycloalkenyl group, the substituted C1-C 10 heterocycloalkenyl group, the substituted C6-C 60 aryl group, the substituted C6-C 60 aryloxy group, the substituted C6-C 60 arylthio group, the substituted C1-C 60 heteroaryl group, at least one substituent of the substituted monovalent non-aromatic fused polycyclic group and the substituted monovalent non-aromatic fused heteropolycyclic group may be selected from:

[0036] deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazone group, C1-C 60 alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group and C1-C 60 alkoxy group,

[0037] each independently selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazone group, C3-C 10 cycloalkyl group, C1-C 10 heterocycloalkyl group, C3-C 10 cycloalkenyl group, C1-C 10 heterocycloalkenyl group, C6-C60 Aryl group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C1-C 60 heteroaryl group, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O)2(Q 11 ) and -P(=O)(Q 11 )(Q 12 ) at least one substituted C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl groups and C1-C 60 Alkoxy groups,

[0038] C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C1-C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups and monovalent non-aromatic fused heteropolycyclic groups,

[0039] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group, C1-C 60 Alkoxy groups, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C1-C 60Heteroaryl group, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21 ) and -P(=O)(Q 21 )(Q 22 ) in which at least one of the substituted C3-C 10 cycloalkyl group, C1-C 10 heterocycloalkyl group, C3-C 10 cycloalkenyl group, C1-C 10 heterocycloalkenyl group, C6-C 60 aryl group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C1-C 60 heteroaryl group, monovalent non-aromatic fused polycyclic group and monovalent non-aromatic fused heteropolycyclic group, and

[0040] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) and -P(=O)(Q 31 )(Q 32 ),

[0041] wherein Q1 to Q3, Q 11 to Q 13 、Q 21 to Q 23 and Q 31 to Q 33 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazone group, C1-C 60 alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 alkoxy group, C3-C 10 cycloalkyl group, C1-C10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C1-C 60 Heteroaryl group, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, biphenyl group and terphenyl group.

[0042] In an embodiment, the organic light-emitting device may include: a first electrode, a second electrode facing the first electrode, and an organic layer disposed between the first electrode and the second electrode and including an emission layer, wherein the organic light-emitting device includes an organometallic compound represented by Formula 1.

[0043] In an embodiment, the organometallic compound may have a T1 energy of greater than or equal to about 2.25 eV.

[0044] In an embodiment, the organic layer may include the organometallic compound.

[0045] In an embodiment, the emission layer may include the organometallic compound.

[0046] In an embodiment, the emission layer may further include a host, and the amount of the host included in the emission layer may be greater than the amount of the organometallic compound included in the emission layer.

[0047] In an embodiment, the emission layer may emit light having a maximum emission wavelength of about 445 nm to about 550 nm.

[0048] In an embodiment, the first electrode may be an anode, the second electrode may be a cathode, and the organic layer may further include a hole transport region disposed between the first electrode and the emission layer and an electron transport region disposed between the emission layer and the second electrode. The hole transport region may include a hole injection layer, a hole transport layer, an emission assist layer, an electron blocking layer, or any combination thereof. The electron transport region may include a buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof. BRIEF DESCRIPTION OF THE DRAWINGS

[0049] The above and other aspects, features, and advantages of the embodiments of the present disclosure will become more apparent from the following description in conjunction with the accompanying drawings.

[0050] Figures 1 to 4 Each is a schematic cross-sectional view of an organic light-emitting device according to an embodiment. DETAILED DESCRIPTION

[0051] Reference will now be made in detail to the embodiments, examples of which are illustrated in the accompanying drawings. In this regard, the embodiments may have different forms and should not be construed as limited to the description set forth herein. Accordingly, the embodiments are described below by referring to the accompanying drawings to explain aspects of the present invention.

[0052] The same reference numerals refer to the same elements throughout. In the drawings, the dimensions of the structures are enlarged for clarity of illustration. It should be understood that although the terms first, second, etc. may be used herein to describe various elements, these elements should not be limited by these terms. These terms are only used to distinguish one element from another. Thus, a first element may be referred to as a second element without departing from the teachings of the present invention. Similarly, a second element may be referred to as a first element. As used herein, the singular forms are also intended to include the plural forms unless the context clearly indicates otherwise.

[0053] As used herein, for purposes of its meaning and interpretation, the term "and / or" includes any combination and all combinations of one or more of the related listed items. For example, "A and / or B" can be understood to mean "A, B, or A and B". The terms "and" and "or" may be used in a conjunctive or disjunctive sense and may be understood to be equivalent to "and / or". Throughout the disclosure, the phrase "at least one of (a, b, or c)" means only a, only b, only c, both a and b, both a and c, both b and c, all of a, b, and c, or variations thereof.

[0054] For purposes of its meaning and interpretation, the phrase "at least one of..." is intended to include the meaning of "at least one of the group consisting of...". For example, "at least one of A and B" can be understood to mean "A, B, or A and B". When the term "at least one of..." is placed before a list of elements, it modifies the entire list of elements and not a single element of the list.

[0055] It should be further understood that the terms "comprises", "comprising", "includes" and / or "including", when used in this specification, specify the presence of the stated feature, number, step, operation, element, component, or combination thereof, but do not preclude the presence or addition of one or more other features, numbers, steps, operations, elements, components, or combinations thereof.

[0056] It should be further understood that when a layer, film, region, plate, etc. is referred to as being "on" or "above" another component, it can be "directly" on the other component, or there can also be an intervening layer. It should also be understood that when a layer, film, region, plate, etc. is referred to as being "under" or "below" another component, it can be "directly" under the other component, or there can also be an intervening layer. When an element is referred to as being disposed "on" another element, it can be disposed below the other element.

[0057] Spatial relative terms such as "under", "below", "lower", "on", "upper", etc. may be used herein for ease of description to describe the relationship between one element or component and another element or component, as illustrated in the figures. It should be understood that, in addition to the directions described in the figures, spatial relative terms are intended to encompass different directions of the device in use or operation. For example, in the case where the device illustrated in the figures is flipped, a device positioned "under" or "below" another device can be placed "on" the other device. Thus, the exemplary term "under" can include both a lower position and an upper position. The device can also be oriented in other directions, and thus the spatially related terms can be differently interpreted depending on the orientation.

[0058] Unless otherwise defined, all terms used herein (including technical and scientific terms) have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure pertains. It should be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning consistent with their meaning in the context of the relevant art and will not be interpreted in an idealized or overly formal sense unless expressly defined in the specification.

[0059] In an embodiment, the organometallic compound is represented by the following formula 1:

[0060] <Formula 1>

[0061] M(L A ) n1 (L B ) n2

[0062] M in Formula 1 can be selected from platinum (Pt), palladium (Pd), copper (Cu), zinc (Zn), silver (Ag), gold (Au), iridium (Ir), rhodium (Rh), cobalt (Co), ruthenium (Ru), rhenium (Re), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm).

[0063] In one embodiment, M can be iridium or rhodium.

[0064] Regarding Formula 1, n1 can be 1 or 2, n2 can be 0 or 1, and the sum of n1 and n2 can be 2.

[0065] n1 represents the number of Ls included in Formula 1 A and n2 represents the number of Ls included in Formula 1 B .

[0066] In one embodiment, n1 can be 1 and n2 can be 1.

[0067] Regarding Formula 1, L A can be a tridentate ligand represented by Formula 1A, and L B can be a tridentate ligand represented by

[0068] Formula 1B:

[0069]

[0070] In Formulas 1A and 1B, *, *', and *'' represent the connection sites to M.

[0071] Y1 and Y3 to Y6 in Formulas 1A and 1B can each independently be selected from N and C.

[0072] Y1, the N in A2 connected to *', and Y3 to Y6 can each form a chemical bond with M. The chemical bond can be a covalent bond or a coordination bond.

[0073] In one embodiment, in Formula 1A, the bond between Y1 and M can be a covalent bond, the bond between M and the N in A2 connected to *' can be a coordination bond, and the bond between Y3 and M can be a covalent bond, and

[0074] in Formula 1B, the bond between Y4 and M can be a coordination bond, the bond between Y5 and M can be a covalent bond, and the bond between Y6 and M can be a coordination bond.

[0075] In Formula 1A, X 21 can be selected from C(Z 21 ), N(Z 21 ), N, O, and S, and X 22 can be selected from C(Z 22 ), N(Z 22 ), N, O, and S.

[0076] In Formulas 1A and 1B, A1 and A3 to A6 can each independently be selected from C5-C 60 carbocycles and C1-C 60 heterocycles, and A2 can be selected from imidazole rings, oxazole rings, thiazole rings, selenazole rings, triazole rings, oxadiazole rings, thiadiazole rings, and selenadiazole rings.

[0077] In one embodiment, A1 and A3 to A6 in Formula 1A and Formula 1B can each independently be selected from a cyclohexane ring, a cyclohexene ring, a cyclohexadiene ring, a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, an azulene ring, a benzo[a]pyrene ring, a cyclopentadiene ring, a 1,2,3,4-tetrahydronaphthalene ring, a furan ring, a thiophene ring, a borole ring, a silole ring, an indene ring, a fluorene ring, an indole ring, a carbazole ring, a benzofuran ring, a dibenzofuran ring, a benzothiophene ring, a dibenzothiophene ring, a benzosilole ring, a dibenzosilole ring, an indolopyridine ring, an indolopyridine ring, a benzofuranopyridine ring, a benzothiophenopyridine ring, a benzosilolepyridine ring, an indolopyrimidine ring, an indolopyrimidine ring, a benzofuranopyrimidine ring, a benzothiophenopyrimidine ring, a benzosilolepyrimidine ring, a dihydropyridine ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, a pyridazine ring, a triazine ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, a quinazoline ring, a phenanthroline ring, a pyrrole ring, a pyrazole ring, an imidazole ring, a 2,3-dihydroimidazole ring, a triazole ring, a 2,3-dihydrotriazole ring, a tetrazole ring, an oxazole ring, an isoxazole ring, an oxadiazole ring, an isoxadiazole ring, an oxatriazole ring, an isoxatriazole ring, a thiazole ring, an isothiazole ring, a thiadiazole ring, an isothiadiazole ring, a thiatriazole ring, an isothiatriazole ring, aazasilole ring, diazasilole ring, triazasilole ring, benzopyrazole ring, pyrazolopyridine ring, furanopyrazole ring, thiophenopyrazole ring, benzimidazole ring, 2,3-dihydrobenzimidazole ring, imidazopyridine ring, 2,3-dihydroimidazopyridine ring, furanimidazole ring, thiophenimidazole ring, imidazopyrimidine ring, 2,3-dihydroimidazopyrimidine ring, imidazopyrazine ring, 2,3-dihydroimidazopyrazine ring, benzoxazole ring, benzothiazole ring, benzoxadiazole ring, benzothiadiazole ring, 5,6,7,8-tetrahydroisoquinoline ring, and 5,6,7,8-tetrahydroquinoline ring.

[0078] The oxadiazole rings described herein can include 1,2,3-oxadiazole rings, 1,2,4-oxadiazole rings, 1,2,5-oxadiazole rings, and 1,3,4-oxadiazole rings. The thiadiazole rings can include 1,2,3-thiadiazole rings, 1,2,4-thiadiazole rings, 1,2,5-thiadiazole rings, and 1,3,4-thiadiazole rings. The triazole rings can include 1,2,3-triazole rings and 1,2,4-triazole rings.

[0079] In an embodiment, A1 in Formula 1A can be selected from a cyclohexane ring, a cyclohexene ring, a cyclohexadiene ring, a benzene ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, a pyridazine ring, a triazine ring, a furan ring, a thiophene ring, a pyrrole ring, a borole ring, a silole ring, an oxazole ring, an isoxazole ring, an oxadiazole ring, an isoxadiazole ring, an oxatriazole ring, an isoxatriazole ring, a thiazole ring, an isothiazole ring, a thiadiazole ring, an isothiadiazole ring, a thiatriazole ring, an isothiatriazole ring, a pyrazole ring, an imidazole ring, a triazole ring, a tetrazole ring, aazasilole ring, diazasilole ring, and triazasilole ring.

[0080] In an embodiment, in Formula 1A, A1 can be selected from the groups represented by Formulae A1-1 to A1-21, and A3 can be selected from the groups represented by Formulae A3-1 to A3-13:

[0081]

[0082]

[0083] In Formulae A1-1 to A1-21 and Formulae A3-1 to A3-13,

[0084] X 11 can be N or C(R 11 ), X 12 can be N or C(R 12 ), X 13 can be N or C(R 13 ), X 14 can be N or C(R 14 ), X 15 can be N or C(R 15 ), X 16 can be N or C(R 16 ), X 17 can be N or C(R 17 ), X 18 can be N or C(R 18 ),

[0085] X 19 can be C(R 19a )(R 19b ), Si(R 19a )(R 19b ), N(R 19 ), O or S,

[0086] X 31 can be N or C(R 31 ), X 32 can be N or C(R 32 ), X 33 can be N or C(R 33 ), X 34 can be N or C(R 34 ), X 35 can be N or C(R 35 ), X 36 can be N or C(R 36 ), X 37 can be N or C(R 37 ), X 38 can be N or C(R 38 ),

[0087] X 39 may be C(R 39a )(R 39b ), Si(R 39a )(R 39b ), N(R 39 ), O or S,

[0088] R 11 to R 19 and R 15a to R 19b may each independently be the same as described for R1 in Formula 1A,

[0089] R 31 to R 39 and R 35a to R 39b may each independently be the same as described for R3 in Formula 1A,

[0090] * and *” may each be a linking site to M, and

[0091] *' represents a linking site to an adjacent atom.

[0092] In one embodiment, A1 in Formula 1A may be selected from the groups represented by Formula A1-1, Formula A1-15, and Formula A1-19.

[0093] In one embodiment, when A1 is a group represented by Formula A1-1, i) A1 may be a group represented by Formula A1-1, where X 11 is C(R 11 ), X 12 is C(R 12 ), X 13 is C(R 13 ), and X 14 is C(R 14 ), such as a benzene ring, or ii) A1 may be a group represented by Formula A1-1, where one of X 11 to X 14 is N, for example, a pyridine ring.

[0094] In one embodiment, A3 in Formula 1A may be a group represented by Formula A3-1. For example, i) A3 may be a group represented by Formula A3-1, where X 31 is C(R 31 ), X 32 is C(R 32 ), X 33 is C(R 33 ), and X 34 is C(R 34), such as a benzene ring, or ii) A3 can be a group represented by formula A3-1, where X 31 to X 34 in one of them is N, for example, a pyridine ring.

[0095] In one embodiment, A2 in formula 1A can be selected from the groups represented by formula A2-1 to formula A2-18:

[0096]

[0097] In formula A2-1 to formula A2-18,

[0098] X 23 can be N or C(R 21 ), X 24 can be N or C(R 22 ), X 25 can be N or C(R 23 ), X 26 can be N or C(R 24 ),

[0099] Z 21 and Z 22 can be the same as described above for formula 1A,

[0100] R 21 to R 24 can be the same as described for R1 in formula 1A,

[0101] * can be the attachment site to L1,

[0102] *' can be the attachment site to M, and

[0103] *” can be the attachment site to L2.

[0104] In one embodiment, A2 in formula 1A can be selected from the groups represented by formula A2-1, formula A2-3, formula A2-9, formula A2-10, formula A2-12 and formula A2-18. For example, A2 can be selected from the groups represented by formula A2-1, formula A2-3 and formula A2-9.

[0105] In one embodiment, in formula 1A, A2 can be a group represented by formula A2-9, where X 23 can be C(R 21 ), X 24 can be C(R 22 ), X 25 can be C(R 23 ), and X 26 can be C(R 24 ).

[0106] In one embodiment, in Formula 1B, A4 can be selected from the groups represented by Formula A4-1 to Formula A4-26, and A6 can be selected from the groups represented by Formula A6-1 to Formula A6-26:

[0107]

[0108]

[0109] In Formulas A4-1 to A4-26 and Formulas A6-1 to A6-26,

[0110] X 42 can be N or C(R 42 ), X 43 can be N or C(R 43 ), X 44 can be N or C(R 44 ), X 45 can be N or C(R 45 ), X 46 can be N or C(R 46 ), X 47 can be N or C(R 47 ),

[0111] X 62 can be N or C(R 62 ), X 63 can be N or C(R 63 ), X 64 can be N or C(R 64 ), X 65 can be N or C(R 65 ), X 66 can be N or C(R 66 ), X 67 can be N or C(R 67 ),

[0112] R 41 to R 47 can each independently be the same as described for R4 in Formula 1B,

[0113] R 61 to R 67 can each independently be the same as described for R6 in Formula 1B,

[0114] * and *” can each be the attachment site to M, and

[0115] *' represents the attachment site to an adjacent atom.

[0116] In one embodiment, in Formula 1B, A4 may be selected from the groups represented by Formula A4-25 and Formula A4-26, and A6 may be selected from the groups represented by Formula A6-25 and Formula A6-26:

[0117]

[0118] The descriptions of the substituents already described for Formula A4-25, Formula A4-26, Formula A6-25 and Formula A6-26 may be the same as those described above for Formula A4-1 to Formula A4-26 and Formula A6-1 to Formula A6-26.

[0119] In one embodiment, in Formula A4-25 and Formula A6-25, a) X 42 may be C(R 42 ), X 43 may be C(R 43 ), X 62 may be C(R 62 ), and X 63 may be C(R 63 ), or b) X 42 may be N, X 43 may be C(R 43 ), X 62 may be N, and X 63 may be C(R 63 ).

[0120] In one embodiment, in Formula A4-26 and Formula A6-26, X 44 may be C(R 44 ), X 45 may be C(R 45 ), X 46 may be C(R 46 ), X 47 may be C(R 47 ), X 64 may be C(R 64 ), X 65 may be C(R 65 ), X 66 may be C(R 66 ), and X 67 may be C(R 67 ).

[0121] In one embodiment, A5 in Formula 1B may be selected from the groups represented by Formula A5-1 or Formula A5-2:

[0122]

[0123] In Formula A5-1 and Formula A5-2,

[0124] X 51 may be N or C(R 51 ) and X 52 may be N or C(R 52 ) and X 53 may be N or C(R 53 ).

[0125] R 51 to R 53 may each independently be the same as described for R5 in Formula 1B

[0126] * may be the attachment site to A4

[0127] *' may be the attachment site to M, and

[0128] *” may be the attachment site to A6

[0129] In one embodiment, in Formulas A5-1 and A5-2, X 51 may be C(R 51 ) and X 52 may be C(R 52 ) and X 53 may be C(R 53 ).

[0130] L1 and L2 in Formula 1A may each independently be selected from *-O-*', *-S-*', *-C(R7)(R8)-*', *-C(R7)=*', *=C(R7)-*', *-C(R7)=C(R8)-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R7)-*', *-N(R7)-*', *-P(R7)-*', *-Si(R7)(R8)-*', *-P(R7)(R8)-*' and *-Ge(R7)(R8)-*'.

[0131] In Formula 1A, a1 and a2 may each independently be selected from 0, 1, and 2. When a1 is 0, the bond represented by *-(L1) a1 -*' may be a single bond. For example, A1 and A2 may be connected to each other via a single bond. When a2 is 0, the bond represented by *-(L2) a2 -*' may be a single bond. For example, A2 and A3 may be connected to each other via a single bond.

[0132] The organometallic compound represented by Formula 1 satisfies one of the following conditions i) to iii).

[0133] i) Y1 is N, and A1 is a 5-membered ring containing Y1, a 6-membered ring containing Y1, a C5-C heterocyclic ring fused with a 5-membered ring containing Y1, or a C5-C heterocyclic ring fused with a 6-membered ring containing Y1, 60 a C5-C heterocyclic ring fused with a 5-membered ring containing Y1, 60 heterocyclic ring,

[0134] ii) Y1 is C and each of a1 and a2 is 0,

[0135] iii) Y1 is C and a1 and a2 are each independently selected from 1 and 2.

[0136] As used herein, the term "5-membered ring containing Y1" refers to a 5-membered ring in which Y1 serves as a ring-forming atom. The term "6-membered ring containing Y1" as used herein refers to a 6-membered ring in which Y1 serves as a ring-forming atom. "C5-C heterocyclic ring fused with a 5-membered ring containing Y1" refers to a polycyclic group in which the 5-membered ring containing Y1 is fused with at least one C5-C 60 carbocyclic ring. "C5-C heterocyclic ring fused with a 6-membered ring containing Y1" refers to a polycyclic group in which the 6-membered ring containing Y1 is fused with at least one C5-C 60 carbocyclic ring. 60 carbocyclic ring. 60 carbocyclic ring.

[0137] In one embodiment, when the organometallic compound satisfies condition i), A1 can be selected from a pyrrole ring, an oxazole ring, an isoxazole ring, an oxadiazole ring, an isoxadiazole ring, an oxatriazole ring, an isoxatriazole ring, a thiazole ring, an isothiazole ring, a thiadiazole ring, an isothiadiazole ring, a thiatriazole ring, an isothiatriazole ring, a pyrazole ring, an imidazole ring, a triazole ring, a tetrazole ring, an azathiophene ring, a diazathiophene ring, and a triazathiophene ring.

[0138] In one embodiment, when the organometallic compound satisfies condition i), A1 can be a group represented by Formula A1-14 to Formula A1-21.

[0139] In one embodiment, in Formula 1A, Y1 can be N, and A1 can be a 5-membered ring containing Y1, a 6-membered ring containing Y1, a C5-C 60 heterocyclic ring fused with a 5-membered ring containing Y1, or a C5-C 60 heterocyclic ring fused with a 6-membered ring containing Y1, a1 can be 0, and a2 can be 1. For example, L2 can be *-O-*' or *-N(R7)-*'.

[0140] In an embodiment, in Formula 1A, Y1 can be C, and each of a1 and a2 can be 1. For example, L1 and L2 can be *-O-*' or *-N(R7)-*'.

[0141] Z in Formula 1A and Formula 1B 21 , Z 22, R1 and R3 to R8 can each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxy group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a carboxylic acid or its salt, a sulfonic acid or its salt, a phosphoric acid 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 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, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) and -P(=O)(Q1)(Q2),

[0142] b1 and b3 to b6 can each independently be selected from 1, 2, 3, 4, 5, 6, 7 and 8, and

[0143] provided that: at least one pair of substituents can optionally be joined together to form a substituted or unsubstituted C5-C 60 carbocyclic group or a substituted or unsubstituted C1-C 60 heterocyclic group, the pair of substituents being selected from the group consisting of Z 21 and Z 22 , two adjacent R1s out of the b1 number of R1s, two adjacent R3s out of the b3 number of R3s, two adjacent R4s out of the b4 number of R4s, two adjacent R5s out of the b5 number of R5s, two adjacent R6s out of the b6 number of R6s, R1 and R7, and R3 and R7.

[0144] In one embodiment, Z 21 , Z 22 , R1 and R3 to R8 in Formulas 1A and 1B can each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxy group, a cyano group, a nitro group, a C1-C20 Alkyl groups and C1-C 20 alkoxy groups;

[0145] C1-C each independently substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, cyano group, phenyl group, and biphenyl group 20 Alkyl groups and C1-C 20 alkoxy groups;

[0146] Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorene group, spiro-bifluorene group, spiro-fluoro-benzofluorene group, benzofluorene group, dibenzofluorene group, pyrene group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, benzophenanthrenyl group, pyrrolyl group, thienyl group, furyl group, silolyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, indolyl group, isoindolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, benzofuranyl group, benzothienyl group, benzosilolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothienyl group, dibenzosilolyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, thiadiazolyl group, imidazopyridyl group, imidazopyrimidinyl group, oxazolopyridyl group, thiazolopyridyl group, benzonaphthyridinyl group, azafluorene group, azaspiro-bifluorene group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothienyl group, azadibenzosilolyl group, -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), and -B(Q1)(Q2); and

[0147] each independently substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazone group, C1-C 20 alkyl groups, C1-C 20A cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-difluorenyl group, a spiro-fluoro-benzofluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a pyrenyl group, a phenalenyl group, a phenanthryl group, an anthryl group, a fluoranthenyl group, a benzo[ghi]phenanthrenyl group, a pyrrolyl group, a thienyl group, a furyl group, a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothienyl group, a benzosilolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothienyl group, a dibenzosilolyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an oxazolopyridinyl group, a thiazolopyridinyl group, a benzonaphthyridinyl group, an azafuranyl group, an azaspiro-difluorenyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothienyl group, an azadibenzosilolyl group, a biphenyl group, and a terphenyl group, wherein at least one of the above substituents is selected from the group consisting of a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-difluorenyl group, a spiro-fluoro-benzofluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a pyrenyl group, a phenalenyl group, a phenanthryl group, an anthryl group, a fluoranthenyl group, a benzo[ghi]phenanthrenyl group, a pyrrolyl group, a thienyl group, a furyl group, a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothienyl group, a benzosilolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothienyl groupDibenzothiophene-based group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, thiadiazolyl group, imidazopyridyl group, imidazopyrimidinyl group, oxazolopyridyl group, thiazolopyridyl group, benzonaphthyridinyl group, azafluorene group, azaspiro-difluorene group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group, and azadibenzothiophene-based group.

[0148] In an embodiment, Z 21 、Z 22 、R1 and R3 to R8 can each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, C1-C 20 alkyl group, and C1-C 20 alkoxy group;

[0149] C1-C 20 alkyl group and C1-C 20 alkoxy group each substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, cyano group, phenyl group, and biphenyl group;

[0150] phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorene group, spiro-difluorene group, phenanthryl group, anthryl group, pyridyl group, pyrimidinyl group, carbazolyl group, and triazinyl group; and

[0151] phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorene group, spiro-difluorene group, phenanthryl group, anthryl group, pyridyl group, pyrimidinyl group, carbazolyl group, and triazinyl group each substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, cyano group, C1-C 20 alkyl group, C1-C 20 alkoxy group, -CF3, -CCl3, -CBr3, -CI3, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorene group, spiro-difluorene group, phenanthryl group, anthryl group, pyridyl group, pyrimidinyl group, carbazolyl group, and triazinyl group.

[0152] In an embodiment, Z 21 、Z 22 、R1 and R3 to R8 can each independently be selected from: hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, methyl group, -CF3, -CCl3, -CBr3, -CI3, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, and tert-butyl group;

[0153] phenyl group and pyridyl group; and

[0154] Phenyl and pyridyl groups each substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, a cyano group, a methyl group, -CF3, -CCl3, -CBr3, -CI3, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group.

[0155] In an embodiment, in Formulae 1A and 1B, at least one selected from Z 21 、Z 22 、the b1 number of R1, the b3 number of R3, the b4 number of R4, the b5 number of R5, and the b6 number of R6 may be an electron-withdrawing group. The electron-withdrawing group may be selected from, for example, -F, a cyano group, a C1-C 10 alkyl group substituted with at least one -F, a C1-C 10 alkyl group substituted with at least one -Cl, a C1-C 10 alkyl group substituted with at least one -Br, and a C1-C 10 alkyl group substituted with at least one -I.

[0156] In an embodiment, in Formulae 1A and 1B, at least one of Z 21 、Z 22 、the b1 number of R1, the b3 number of R3, the b4 number of R4, the b5 number of R5, and the b6 number of R6 may be selected from -F, a cyano group, -CF3, -CCl3, -CBr3, and -CI3.

[0157] When the organometallic compound represented by Formula 1 includes at least one electron-withdrawing group, the emission wavelength of the organometallic compound can be shifted to a shorter wavelength (blue shift) to generate blue light with high color purity. The emission wavelength can be controlled by controlling the number of electron-withdrawing groups substituted into the compound.

[0158] In one embodiment, in Formula 1A, L2 may be selected from *-B(R7)-*', *-N(R7)-*', *-P(R7)-*', and *-Ge(R7)(R8)-*', and R7 may be connected to an adjacent R3 to form a substituted or unsubstituted C5-C 60 carbocyclic group or a substituted or unsubstituted C1-C 60 heterocyclic group.

[0159] In one embodiment, the moiety represented by in Formula 1A may be represented by one of Formulae AL-1 to AL-28:

[0160]

[0161]

[0162]

[0163] In Formulas AL-1 to AL-28,

[0164] R 31 to R 33 can each independently be the same as described for R3 in Formula 1A,

[0165] R 71 to R 74 can be the same as described for R7 in Formula 1A,

[0166] *” can be the attachment site to M, and

[0167] * can be the attachment site to A2.

[0168] In one embodiment, L in Formula 1 A can be selected from the tridentate ligands represented by Formulas 1AA-1 to 1AA-3, Formulas 1AB-1 to 1AB-3, and Formulas 1AC-1 to 1AC-3:

[0169]

[0170]

[0171] In Formulas 1AA-1 to 1AA-3, Formulas 1AB-1 to 1AB-3, and Formulas 1AC-1 to 1AC-3,

[0172] Y3, A1, A3, L1, L2, a1, a2, Z 21 , Z 22 , R1, R3, b1, and b3 are the same as described above for Formula 1A,

[0173] X 23 can be N or C(R 21 ), X 24 is N or C(R 22 ), X 25 is N or C(R 23 ), X 26 can be N or C(R 24 ),

[0174] R 21 to R 24 can be the same as described above for R1 in Formula 1A, and

[0175] *, *', and *” can each be the attachment site to M.

[0176] In one embodiment, in Formulae 1AA-3, 1AB-3 and 1AC-3, X 23 can be C(R 21 ), X 24 can be C(R 22 ), X 25 can be C(R 23 ), and X 26 can be C(R 24 ).

[0177] In one embodiment, L in Formula 1 B can be selected from the tridentate ligands represented by Formulae 1B-1 and 1B-2:

[0178]

[0179] In Formulae 1B-1 and 1B-2,

[0180] X 42 to X 47 , X 51 to X 53 , X 62 to X 67 , R 41 and R 61 are the same as those described above, and

[0181] *, *' and *” are each a binding site to M.

[0182] In one embodiment, in Formula 1B-1, a) X 42 can be C(R 42 ), X 43 can be C(R 43 ), X 62 can be C(R 62 ), and X 63 can be C(R 63 ), or b) X 42 can be N, X 43 can be C(R 43 ), X 62 can be N, and X 63 can be C(R 63 ).

[0183] In one embodiment, in Formula 1B-2, X 44 can be C(R 44 ), X 45 can be C(R 45 ), X 46 can be C(R 46 ), X 47 can be C(R47 ),X 51 may be C(R 51 ),X 52 may be C(R 52 ),X 53 may be C(R 53 ),X 64 may be C(R 64 ),X 65 may be C(R 65 ),X 66 may be C(R 66 ),and X 67 may be C(R 67 ).

[0184] In one embodiment, the organometallic compound may have a T1 energy greater than or equal to about 2.25 eV.

[0185] In one embodiment, the organometallic compound may be selected from Compound 1 to Compound 65:

[0186]

[0187]

[0188] Since the ligand represented by Formula 1A includes the A2 ring which is a 5-membered ring containing N, the organometallic compound represented by Formula 1 may have an increased lowest unoccupied molecular orbital (LUMO) energy level. Accordingly, the emission wavelength of the organometallic compound may be blue-shifted.

[0189] A2 in the organometallic compound may be a 5-membered ring containing N, and the bond between M and the N atom connected to M may be a coordination bond. Most of the LUMO exists in the A2 moiety. The organometallic compound represented by Formula 1 includes a tridentate ligand L A , wherein A1 and A3 are covalently connected to both sides of the A2 ring, thereby improving the bonding stability by increasing the bonding energy between A2 and the central metal M. Accordingly, the bond dissociation energy between the L A ligand and the central metal can be increased, and thus, the possibility of the organometallic compound transferring to the dissociation path can be reduced. Accordingly, since the stability of the organometallic compound is improved, the organic light-emitting device including the organometallic compound has a long service life.

[0190] The central metal M and the ligand L in the organometallic compound A may form a cyclometalated ring. For example, in the organometallic compound, the central metal M and the ligand L ATwo cyclometalated rings can be formed. In the organometallic compound according to the embodiment, when Y1 is C, the two cyclometalated rings can each be a 5-membered ring or a 6-membered ring. By satisfying these conditions, compared with a compound in which one of the two cyclometalated rings is a 5-membered ring and the other is a 6-membered ring, the stability of the compound is increased due to the increase in the σ-electron donor property from the ligand to the central metal M and the MLCT (metal-ligand charge transfer state) ratio.

[0191] Since it contains the tridentate ligand L B , based on a principle similar to the case where the tridentate ligand L A is applied, the organometallic compound represented by Formula 1 can have high stability.

[0192] The organometallic compound according to the embodiment can include at least one electron-withdrawing group in its molecular structure. Therefore, the emission wavelength of the organometallic compound can be blue-shifted, and thus blue light with high color purity can be emitted.

[0193] By referring to the following examples, the synthesis method for the organometallic compound represented by Formula 1 will be obvious to those of ordinary skill in the art.

[0194] The organometallic compound of Formula 1 can be used between a pair of electrodes of an organic light-emitting device. For example, the organometallic compound can be included in the emission layer. The organometallic compound can act as a dopant in the emission layer. In an embodiment, the organometallic compound of Formula 1 can be used as a material for a cover layer provided outside a pair of electrodes of an organic light-emitting device.

[0195] Therefore, an organic light-emitting device is provided, which includes: a first electrode; a second electrode facing the first electrode; and an organic layer provided between the first electrode and the second electrode and including an emission layer; and wherein the organic light-emitting device contains the organometallic compound represented by Formula 1.

[0196] In one embodiment, the organic layer of the organic light-emitting device can include at least one organometallic compound represented by Formula 1.

[0197] The expression "(the organic layer) includes at least one organometallic compound" used herein can include the case where "(the organic layer) includes the same organometallic compound represented by Formula 1" and the case where "(the organic layer) includes two or more different organometallic compounds represented by Formula 1".

[0198] For example, the organic layer may contain only Compound 1 as the organometallic compound. In this regard, Compound 1 may be present only in the emission layer of the organic light-emitting device. In an embodiment, the organic layer may contain Compound 1 and Compound 2 as the organometallic compounds. In this regard, Compound 1 and Compound 2 may be present in the same layer (e.g., both Compound 1 and Compound 2 may be present in the emission layer), or in different layers (e.g., Compound 1 may be present in the emission layer, and Compound 2 may be present in the electron transport region).

[0199] In one embodiment, the emission layer of the organic light-emitting device may contain an organometallic compound.

[0200] In an embodiment, the emission layer of the organic light-emitting device may contain an organometallic compound, the emission layer may further contain a host, and the amount of the host contained in the emission layer may be greater than the amount of the organometallic compound contained in the emission layer. For example, based on 100 parts by weight of the emission layer, the amount of the organometallic compound may be about 0.01 part by weight to 30 parts by weight.

[0201] In one embodiment, the emission layer may contain an organometallic compound, and light having a maximum emission wavelength of about 445 nm to about 550 nm may be emitted from the emission layer. For example, blue light having a maximum emission wavelength of about 445 nm to about 480 nm or green light having a maximum emission wavelength of about 481 nm to about 550 nm may be emitted.

[0202] The maximum emission wavelength of the organometallic compound may be a value calculated by using the TD-DFT method at B3LYP / LanL2DZ / / m062x&6-311G(d,p) using a function and a basis set by using the Gaussian 09 program. In one embodiment, the maximum emission wavelength of the organometallic compound may be an actual value measured by a photoluminescence (PL) measurement device.

[0203] In one embodiment, in the organic light-emitting device, the first electrode is an anode, and the second electrode is a cathode, and the organic layer further includes a hole transport region provided between the first electrode and the emission layer and an electron transport region provided between the emission layer and the second electrode. The hole transport region includes a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, or any combination thereof. The electron transport region includes a buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0204] As used herein, the term "organic layer" refers to a single layer and / or multiple layers provided between the first electrode and the second electrode of the organic light-emitting device. The materials contained in the "organic layer" are not limited to organic materials.

[0205] ​Figure 1 Description]

[0206] Figure 1 is a cross-sectional schematic view of an organic light-emitting device 10 according to an embodiment. The organic light-emitting device 10 includes a first electrode 110, an organic layer 150, and a second electrode 190.

[0207] Hereinafter, in conjunction with Figure 1 the structure of the organic light-emitting device 10 according to an embodiment and a method of manufacturing the organic light-emitting device 10 will be described.

[0208] [First electrode 110]

[0209] In Figure 1 , a substrate may be disposed below the first electrode 110 or above the second electrode 190. The substrate may be a glass substrate or a plastic substrate each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.

[0210] The first electrode 110 may be formed by depositing or sputtering a material for forming the first electrode 110 on the substrate. When the first electrode 110 is an anode, the material for forming the first electrode 110 may be selected from materials having a high work function to facilitate hole injection.

[0211] The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, the material for forming the first electrode may be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), and any combination thereof, but the embodiments are not limited thereto. In an embodiment, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, the material for forming the first electrode may be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination thereof, but the embodiments are not limited thereto.

[0212] The first electrode 110 may have a single-layer structure or include a multi-layer structure of two or more layers. For example, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO, but the structure of the first electrode 110 is not limited thereto.

[0213] [Organic layer 150]

[0214] The organic layer 150 is disposed on the first electrode 110. The organic layer 150 may include an emission layer.

[0215] The organic layer 150 may further include a hole transport region disposed between the first electrode 110 and the emission layer and an electron transport region disposed between the emission layer and the second electrode 190.

[0216] [Hole transport region in the organic layer 150]

[0217] The hole transport region may have i) a single-layer structure including a single layer containing a single material, ii) a single-layer structure including a single layer containing different materials, or iii) a multi-layer structure having multiple layers containing different materials.

[0218] The hole transport region may include a hole injection layer, a hole transport layer, an emission assisting layer, an electron blocking layer, or any combination thereof.

[0219] For example, the hole transport region may have a single-layer structure including a single layer containing different materials, or a multi-layer structure having a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission assisting layer structure, a hole injection layer / emission assisting layer structure, a hole transport layer / emission assisting layer structure, or a hole injection layer / hole transport layer / electron blocking layer structure, where for each structure, the constituent layers may be stacked (or disposed) in this specified order successively from the first electrode 110, but the structure of the hole transport region is not limited thereto.

[0220] The hole transport region may contain at least one selected from m-MTDATA, TDATA, 2-TNATA, NPB (NPD), 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), the compound represented by Formula 201, and the compound represented by Formula 202:

[0221]

[0222]

[0223] In Formula 201 and Formula 202,

[0224] L 201 to L 204 may each independently be selected from substituted or unsubstituted C3-C 10 subcycloalkyl groups, substituted or unsubstituted C1-C 10 subheterocycloalkyl groups, substituted or unsubstituted C3-C 10 subcycloalkenyl groups, substituted or unsubstituted C1-C 10 subheterocycloalkenyl groups, substituted or unsubstituted C6-C60 Arylene group, substituted or unsubstituted C1-C 60 Heteroarylene group, substituted or unsubstituted divalent non-aromatic fused polycyclic group and substituted or unsubstituted divalent non-aromatic fused heteropolycyclic group,

[0225] L 205 may be selected from *-O-*', *-S-*', *-N(Q 201 )-*', substituted or unsubstituted C1-C 20 Alkylene group, substituted or unsubstituted C2-C 20 Alkenylene group, substituted or unsubstituted C3-C 10 Cycloalkylene group, substituted or unsubstituted C1-C 10 Heterocycloalkylene group, substituted or unsubstituted C3-C 10 Cycloalkenylene group, substituted or unsubstituted C1-C 10 Heterocycloalkenylene group, substituted or unsubstituted C6-C 60 Arylene group, substituted or unsubstituted C1-C 60 Heteroarylene group, substituted or unsubstituted divalent non-aromatic fused polycyclic group and substituted or unsubstituted divalent non-aromatic fused heteropolycyclic group,

[0226] xa1 to xa4 may each independently be an integer from 0 to 3,

[0227] xa5 may be an integer from 1 to 10, and

[0228] R 201 to R 204 and Q 201 may each independently be selected from substituted or unsubstituted C3-C 10 Cycloalkyl group, substituted or unsubstituted C1-C 10 Heterocycloalkyl group, substituted or unsubstituted C3-C 10 Cycloalkenyl group, substituted or unsubstituted C1-C 10 Heterocycloalkenyl group, substituted or unsubstituted C6-C 60 Aryl group, substituted or unsubstituted C6-C 60 Aryloxy group, substituted or unsubstituted C6-C 60 Arylthio group, substituted or unsubstituted C1-C 60 Heteroaryl group, substituted or unsubstituted monovalent non-aromatic fused polycyclic group and substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group.

[0229] For example, in Formula 202, R 201 and R 202may optionally be connected to each other via a single bond, a dimethyl-methylene group or a diphenyl-methylene group, and R 203 and R 204 may optionally be connected to each other via a single bond, a dimethyl-methylene group or a diphenyl-methylene group.

[0230] In one embodiment, in Formulas 201 and 202,

[0231] L 201 to L 205 may each independently be selected from:

[0232] a phenylene group, a pentacenylene group, an indenylene group, a naphthylene group, a azulylene group, a heptacenylene group, an indacenylene group, an acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, an aceanthrylene group, an phenanthrylene group, an anthrylene group, a fluoranthene group, a benzophenanthrene group, a pyrene group, a yl group, a tetracenylene group, a picene group, a perylene group, a pentaphenylene group, a hexacenylene group, a pentacenequinone group, a corannulenyl group, an ovalene group, a thienyl group, a furyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, a dibenzothienyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group and a pyridyl group; and

[0233] each independently being selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C 20 alkyl group, a C1-C 20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C1-C 10 alkyl group, a phenyl group substituted with -F, a pentacenyl group, an indenyl group, a naphthyl group, an azulyl group, a heptacenyl group, an indacenyl group, an acenaphthyl group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, an aceanthrylene group, an phenanthrylene group, an anthrylene group, a fluoranthene group, a benzophenanthrene group, a pyrene group, A base group, a tetraphenyl group, a picene group, a perylene group, a pentaphenyl group, a hexaphenyl group, a pentacene group, a rubicene group, a coronene group, an ovalene group, a thienyl group, a furyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, a dibenzothienyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridyl group, -Si(Q 31 )(Q 32 )(Q 33 ) and -N(Q 31 )(Q 32 ), and at least one of the substituted phenylene group, pentalenylene group, indenylene group, naphthylene group, azulylene group, heptalenylene group, indacenylene group, acenaphthylene group, fluorenylene group, spiro-bifluorenylene group, benzo[ b ]fluorenylene group, dibenzo[ b,d ]fluorenylene group, phenalenylene group, phenanthrylene group, anthrylene group, fluoranthenylene group, benzo[ def ]phenanthrylene group, pyrenylene group, yl group, sub-tetraphenyl group, sub-picene group, sub-perylene group, sub-pentaphenyl group, sub-hexaphenyl group, sub-pentacene group, sub-rubicene group, sub-coronene group, sub-ovalene group, sub-thienyl group, sub-furyl group, sub-carbazolyl group, sub-indolyl group, sub-isoindolyl group, sub-benzofuranyl group, sub-benzothienyl group, sub-dibenzofuranyl group, sub-dibenzothienyl group, sub-benzocarbazolyl group, sub-dibenzocarbazolyl group, sub-dibenzosilolyl group and sub-pyridyl group,

[0234] wherein Q 31 to Q 33 can each independently be selected from C1-C 10 alkyl group, C1-C 10 alkoxy group, phenyl group, biphenyl group, terphenyl group and naphthyl group.

[0235] In an embodiment, xa1 to xa4 can each independently be 0, 1 or 2.

[0236] In an embodiment, xa5 can be 1, 2, 3 or 4.

[0237] In an embodiment, R 201 to R 204 and Q 201 can each independently be selected from:

[0238] phenyl group, biphenyl group, terphenyl group, pentacenyl group, indenyl group, naphthyl group, azulene group, heptacenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, benzo[a]phenanthrenyl group, pyrenyl group, yl group, tetraphenyl group, picenyl group, perylenyl group, pentaphenyl group, hexaphenyl group, pentacenyl group, rubicenyl group, coronenyl group, ovalene group, thienyl group, furyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, dibenzothienyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group and pyridyl group; and

[0239] each independently selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 alkyl group, C1-C 20 alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, phenyl group substituted with C1-C 10 alkyl group, phenyl group substituted with -F, pentacenyl group, indenyl group, naphthyl group, azulene group, heptacenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, benzo[a]phenanthrenyl group, pyrenyl group, yl group, tetraphenyl group, picenyl group, perylenyl group, pentaphenyl group, hexaphenyl group, pentacenyl group, rubicenyl group, coronenyl group, ovalene group, thienyl group, furyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, dibenzothienyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridyl group, -Si(Q 31 )(Q 32 )(Q 33 ) and -N(Q 31 )(Q 32at least one of the substituted phenyl group, biphenyl group, terphenyl group, pentacenyl group, indenyl group, naphthyl group, azulene group, heptacenyl group, indacenyl group, acenaphthylenyl group, fluorenyl group, spiro - bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, benzo[ghi]phenanthrenyl group, pyrenyl group, the perylene group, tetracenyl group, picene group, pentaphenyl group, hexaphenyl group, pentacene group, rubicene group, coronene group, ovalene group, thienyl group, furyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, dibenzothienyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group and pyridyl group,

[0240] wherein Q 31 to Q 33 is the same as described above.

[0241] In an embodiment, at least one of R 201 to R 203 selected from Formula 201 can each independently be selected from:

[0242] fluorenyl group, spiro - bifluorenyl group, carbazolyl group, dibenzofuranyl group and dibenzothienyl group; and

[0243] each independently substituted by at least one selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazone group, C1 - C 20 alkyl group, C1 - C 20 alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, phenyl group substituted by C1 - C 10 alkyl group, phenyl group substituted by -F, naphthyl group, fluorenyl group, spiro - bifluorenyl group, carbazolyl group, dibenzofuranyl group and dibenzothienyl group, fluorenyl group, spiro - bifluorenyl group, carbazolyl group, dibenzofuranyl group and dibenzothienyl group substituted by at least one of naphthyl group, fluorenyl group, spiro - bifluorenyl group, carbazolyl group, dibenzofuranyl group and dibenzothienyl group,

[0244] However, the embodiments are not limited thereto.

[0245] In an embodiment, in Formula 202, i) R 201 and R 202 can be connected to each other via a single bond, and / or ii) R 203 and R 204 can be connected to each other via a single bond.

[0246] In an embodiment, R selected from those in Formula 202 201 to R 204 at least one of which may each independently be selected from:

[0247] a carbazolyl group; and

[0248] substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C 20 alkyl group, a C1-C 20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C1-C 10 alkyl group, a phenyl group substituted with -F, a naphthyl group, a fluorene group, a spiro-difluorene group, a carbazolyl group, a dibenzofuranyl group, and a carbazolyl group substituted with at least one of a dibenzothiophenyl group,

[0249] However, the embodiments are not limited thereto.

[0250] The compound represented by Formula 201 may be represented by the following Formula 201-1:

[0251] <Formula 201-1>

[0252]

[0253] In one embodiment, the compound represented by Formula 201 may be represented by the following Formula 201-2, however, the embodiments are not limited thereto:

[0254] <Formula 201-2>

[0255]

[0256] In an embodiment, the compound represented by Formula 201 may be represented by the following Formula 201-2(1), however, the embodiments are not limited thereto:

[0257] <Formula 201-2(1)>

[0258]

[0259] In an embodiment, the compound represented by Formula 201 may be represented by the following Formula 201A:

[0260] <Formula 201A>

[0261]

[0262] In an embodiment, the compound represented by Formula 201 may be represented by the following Formula 201A(1), but the embodiment is not limited thereto:

[0263] <Formula 201A(1)>

[0264]

[0265] In an embodiment, the compound represented by Formula 201 may be represented by the following Formula 201A-1, but the embodiment is not limited thereto:

[0266] <Formula 201A-1>

[0267]

[0268] In one embodiment, the compound represented by Formula 202 may be represented by the following Formula 202-1:

[0269] <Formula 202-1>

[0270]

[0271] In an embodiment, the compound represented by Formula 202 may be represented by the following Formula 202-1(1):

[0272] <Formula 202-1(1)>

[0273]

[0274] In an embodiment, the compound represented by Formula 202 may be represented by the following Formula 202A:

[0275] <Formula 202A>

[0276]

[0277] In an embodiment, the compound represented by Formula 202 may be represented by the following Formula 202A-1:

[0278] <Formula 202A-1>

[0279]

[0280] In Formula 201-1, Formula 201-2, Formula 201-2(1), Formula 201A, Formula 201A(1), Formula 201A-1, Formula 202-1, Formula 202-1(1), Formula 202A and Formula 202A-1,

[0281] L 201 to L 203 , xa1 to xa3, xa5 and R 202 to R 204Same as described above,

[0282] L 205 may be selected from a phenylene group and a fluoreneylene group,

[0283] X 211 may be selected from O, S and N(R 211 )

[0284] X 212 may be selected from O, S and N(R 212 )

[0285] R 211 and R 212 are the same as those described with respect to R 203 and, in addition,

[0286] R 213 to R 217 may each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C 20 alkyl group, a C1-C 20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C1-C 10 alkyl group, a phenyl group substituted with -F, a pentaphenylenyl group, an indenyl group, a naphthyl group, an azulene group, a heptaphenylenyl group, an indacenyl group, an acenaphthylenyl group, a fluorene group, a spiro-bifluorene group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a benzo[a]phenanthrenyl group, a pyrenyl group, yl group, a tetraphenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexaphenyl group, a pentacene group, a rubicene group, a coronene group, an ovalene group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group and a pyridyl group.

[0287] The hole transport region may contain at least one compound selected from Compounds HT1 to HT48, but the embodiments are not limited thereto:

[0288]

[0289]

[0290]

[0291]

[0292]

[0293] The thickness of the hole transport region can be about to about In an embodiment, the thickness of the hole transport region can be about to about When the hole transport region includes at least one selected from a hole injection layer and a hole transport layer, the thickness of the hole injection layer can be about to about and the thickness of the hole transport layer can be about to about In an embodiment, the thickness of the hole injection layer can be about to about In an embodiment, the thickness of the hole transport layer can be about to 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.

[0294] The emission assisting layer can improve the light emission efficiency by compensating for the optical resonance distance according to the wavelength of the light emitted from the emission layer, and the electron blocking layer can block the flow of electrons from the electron transport region. The emission assisting layer and the electron blocking layer can include the materials described above.

[0295] [p-dopant]

[0296] The hole transport region can further include a charge generation material for improving the conductive properties. The charge generation material can be uniformly or non-uniformly dispersed in the hole transport region.

[0297] The charge generation material can be, for example, a p-dopant.

[0298] In one embodiment, the lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant can be -3.5 eV or less than -3.5 eV.

[0299] The p-dopant can include at least one selected from quinone derivatives, metal oxides, and compounds containing a cyano group, but the embodiments are not limited thereto.

[0300] In one embodiment, the p-dopant can include at least one selected from the following:

[0301] Quinone derivatives such as tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ);

[0302] Metal oxides such as tungsten oxide or molybdenum oxide;

[0303] 1,4,5,8,9,12-hexaazatriphenylene-hexacarbonitrile (HAT-CN); and

[0304] A compound represented by the following formula 221,

[0305] but the embodiments are not limited thereto:

[0306]

[0307] <Formula 221>

[0308]

[0309] In formula 221,

[0310] R 221 to R 223 may each independently be selected from substituted or unsubstituted C3-C 10 cycloalkyl groups, substituted or unsubstituted C1-C 10 heterocycloalkyl groups, substituted or unsubstituted C3-C 10 cycloalkenyl groups, substituted or unsubstituted C1-C 10 heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 aryl groups, substituted or unsubstituted C1-C 60 heteroaryl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups and substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic groups, wherein at least one selected from R 221 to R 223 may have at least one substituent selected from a cyano group, -F, -Cl, -Br, -I, a C1-C 20 alkyl group substituted with -F, a C1-C 20 alkyl group substituted with -Cl, a C1-C 20 alkyl group substituted with -Br, and a C1-C 20 alkyl group substituted with -I.

[0311] [Emission layer in organic layer 150]

[0312] When the organic light-emitting device 10 is a full-color organic light-emitting device, the emission layer can be patterned into a red emission layer, a green emission layer, or a blue emission layer according to the sub-pixels. In an embodiment, the emission layer can have a stacked structure of two or more layers selected from a red emission layer, a green emission layer, and a blue emission layer, where the two or more layers are in contact with each other or spaced apart from each other. In an embodiment, the emission layer can contain two or more materials selected from a material that emits red light, a material that emits green light, and a material that emits blue light, where the two or more materials are mixed with each other in a single layer to emit white light.

[0313] The emission layer can contain a host and a dopant. The dopant can include at least one selected from a phosphorescent dopant and a fluorescent dopant.

[0314] In the emission layer, based on 100 parts by weight of the host, the amount of the dopant can be about 0.01 part by weight to about 15 parts by weight, but the embodiment is not limited thereto.

[0315] The thickness of the emission layer can be about to about In an embodiment, the thickness of the emission layer can be about to about When the thickness of the emission layer is within this range, excellent light emission characteristics can be obtained without a significant increase in the driving voltage.

[0316] [Host in the emission layer]

[0317] In an embodiment, the host can include a compound represented by the following formula 301:

[0318] <Formula 301>

[0319] [Ar 301 xb11 -[(L 301 ) xb1 -R 301 xb21

[0320] In formula 301,

[0321] Ar 301 can be a substituted or unsubstituted C5-C 60 carbocyclic group or a substituted or unsubstituted C1-C 60 heterocyclic group,

[0322] xb11 can be 1, 2, or 3,

[0323] L 301 can be selected from a substituted or unsubstituted C3-C 10 subcycloalkyl group, a substituted or unsubstituted C1-C​​10 Azaheterocycloalkyl group, substituted or unsubstituted C3-C 10 Aza cycloalkenyl group, substituted or unsubstituted C1-C 10 Azaheterocycloalkenyl group, substituted or unsubstituted C6-C 60 Arylene group, substituted or unsubstituted C1-C 60 Azaheteroaryl group, substituted or unsubstituted divalent non-aromatic fused polycyclic group and substituted or unsubstituted divalent non-aromatic fused heteropolycyclic group,

[0324] xb1 can be an integer from 0 to 5,

[0325] R 301 can be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazone group, substituted or unsubstituted C1-C 60 alkyl group, substituted or unsubstituted C2-C 60 alkenyl group, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 alkoxy group, substituted or unsubstituted C3-C 10 cycloalkyl group, substituted or unsubstituted C1-C 10 heterocycloalkyl group, substituted or unsubstituted C3-C 10 cycloalkenyl group, substituted or unsubstituted C1-C 10 heterocycloalkenyl group, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 arylthio group, substituted or unsubstituted C1-C 60 heteroaryl group, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 301 )(Q 302 )(Q 303 )、-N(Q 301 )(Q 302 )、-B(Q 301 )(Q 302 )、-C(=O)(Q 301 )、-S(=O)2(Q 301 ) and -P(=O)(Q 301 )(Q 302 ),

[0326] xb21 can be an integer from 1 to 5, and

[0327] Q301 to Q 303 may each independently be selected from C1-C 10 alkyl groups, C1-C 10 alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, and naphthyl groups, but the embodiments are not limited thereto.

[0328] In one embodiment, Ar in Formula 301 301 may be selected from:

[0329] naphthyl groups, fluorene groups, spiro-bifluorene groups, benzo[b]fluorene groups, dibenzo[b,d]fluorene groups, phenalenyl groups, phenanthrenyl groups, anthracenyl groups, fluoranthenyl groups, benzo[a]phenanthrenyl groups, pyrenyl groups, groups, tetracenyl groups, picenyl groups, perylenyl groups, pentacenyl groups, indeno[1,2,3-cd]anthracenyl groups, dibenzofuranyl groups, and dibenzothiophenyl groups; and

[0330] each naphthyl group, fluorene group, spiro-bifluorene group, benzo[b]fluorene group, dibenzo[b,d]fluorene group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, benzo[a]phenanthrenyl group, pyrenyl group, 20 alkyl groups, C1-C 20 alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, naphthyl groups, -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ), and -P(=O)(Q 31 )(Q 32 ) substituted with at least one of and naphthyl groups, fluorene groups, spiro-bifluorene groups, benzo[b]fluorene groups, dibenzo[b,d]fluorene groups, phenalenyl groups, phenanthrenyl groups, anthracenyl groups, fluoranthenyl groups, benzo[a]phenanthrenyl groups, pyrenyl groups, groups, tetracenyl groups, picenyl groups, perylenyl groups, pentacenyl groups, indeno[1,2,3-cd]anthracenyl groups, dibenzofuranyl groups, and dibenzothiophenyl groups,

[0331] wherein Q 31 to Q 33 may each independently be selected from C1-C 10 alkyl groups, C1-C 10 alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups, and naphthyl groups, but the embodiments are not limited thereto.

[0332] When xb11 in Formula 301 is 2 or greater than 2, two or more than two Ars 301Can be connected to each other via a single key.

[0333] In an embodiment, the compound represented by Formula 301 can be represented by Formula 301-1 or Formula 301-2:

[0334] <Formula 301-1>

[0335]

[0336] <Formula 301-2>

[0337]

[0338] In Formula 301-1 and Formula 301-2,

[0339] A 301 to A 304 can each independently be selected from a benzene ring, a naphthalene ring, a phenanthrene ring, a fluoranthene ring, a benzo[a]phenanthrene ring, a pyrene ring, a cyclopenta[a]phenanthrene ring, a pyridine ring, a pyrimidine ring, an indene ring, a fluorene ring, a spiro-bifluorene ring, a benzo[a]fluorene ring, a dibenzo[a,h]fluorene ring, an indole ring, a carbazole ring, a benzo[a]carbazole ring, a dibenzo[a,h]carbazole ring, a furan ring, a benzofuran ring, a dibenzofuran ring, a naphtho[2,3-b]furan ring, a benzo[def]naphtho[2,1-b]furan ring, a dinaphtho[2,3-b:2',3'-f]furan ring, a thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a naphtho[2,3-b]thiophene ring, a benzo[def]naphtho[2,1-b]thiophene ring, and a dinaphtho[2,3-b:2',3'-f]thiophene ring,

[0340] X 301 can be O, S, or N-[(L 304 ) xb4 -R 304 ,

[0341] R 311 to R 314 can each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxy group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C 20 alkyl group, a C1-C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, -Si(Q 31 )(Q 32 )(Q 33 ), -N(Q 31 )(Q 32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ), and -P(=O)(Q 31 )(Q 32 ),

[0342] xb22 and xb23 can each independently be 0, 1 or 2,

[0343] L 301 , xb1, R 301 and Q 31 to Q 33 each is the same as described above,

[0344] L 302 to L 304 each independently is the same as that described with respect to L 301 described,

[0345] xb2 to xb4 can each independently be the same as that described with respect to xb1, and

[0346] R 302 to R 304 each independently is the same as that described with respect to R 301 described.

[0347] For example, in Formula 301, Formula 301-1 and Formula 301-2, L 301 to L 304 can each independently be selected from:

[0348] a phenylene group, a naphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenanthrene group, an anthracene group, a fluoranthene group, a benzophenanthrene group, a pyrene group, a ylene group, a perylene group, a pentaphenylene group, a hexacenylene group, a quinquephenylene group, a thiophene group, a furan group, a carbazole group, an indole group, an isoindole group, a benzofuran group, a benzothiophene group, a dibenzofuran group, a dibenzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzosilole group, a pyridine group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a thiadiazole group, an oxadiazole group, a pyrazine group, a pyrimidine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an imidazopyridine group, an imidazopyrimidine group and an azacarbazole group; and

[0349] Each independently selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazone group, C1-C 20 alkyl group, C1-C 20 alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthryl group, anthryl group, fluoranthenyl group, benzophenanthryl group, pyrenyl group, yl group, perylenyl group, pentaphenyl group, hexaphenyl group, quaterphenyl group, thienyl group, furyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, dibenzothienyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) and -P(=O)(Q 31 )(Q 32 ) and at least one substituted phenylene group, naphthylene group, fluorenylene group, spiro-bifluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrylene group, anthrylene group, fluoranthenylene group, benzophenanthrylene group, pyrenylene group, sub- Group, perylene diimide group, pentacene diimide group, hexacene diimide group, pentaphene diimide group, thiophene diimide group, furan diimide group, carbazole diimide group, indole diimide group, isoindole diimide group, benzofuran diimide group, benzothiophene diimide group, dibenzofuran diimide group, dibenzothiophene diimide group, benzocarbazole diimide group, dibenzocarbazole diimide group, dibenzosilole diimide group, pyridine diimide group, imidazole diimide group, pyrazole diimide group, thiazole diimide group, isothiazole diimide group, oxazole diimide group, isoxazole diimide group, thiadiazole diimide group, oxadiazole diimide group, pyrazine diimide group, pyrimidine diimide group, pyridazine diimide group, s-triazine diimide group, quinoline diimide group, isoquinoline diimide group, benzoquinoline diimide group, phthalazine diimide group, naphthyridine diimide group, quinoxaline diimide group, quinazoline diimide group, cinnoline diimide group, phenanthridine diimide group, acridine diimide group, phenanthroline diimide group, phenazine diimide group, benzimidazole diimide group, isobenzothiazole diimide group, benzoxazole diimide group, isobenzoxazole diimide group, triazole diimide group, tetrazole diimide group, imidazopyridine diimide group, imidazopyrimidine diimide group, and azacarbazole diimide group,

[0350] wherein Q 31 to Q 33 is the same as described above.

[0351] In one embodiment, in Formula 301, Formula 301-1 and Formula 301-2, R 301 to R 304 can each independently be selected from:

[0352] phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorene group, spiro-bifluorene group, benzofluorenyl group, dibenzofluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, benzo[a]phenanthryl group, pyrenyl group, Group, perylene group, pentaphenyl group, hexaphenyl group, pentacene group, thiophene group, furan group, carbazole group, indole group, isoindole group, benzofuran group, benzothiophene group, dibenzofuran group, dibenzothiophene group, benzocarbazole group, dibenzocarbazole group, dibenzosilole group, pyridine group, imidazole group, pyrazole group, thiazole group, isothiazole group, oxazole group, isoxazole group, thiadiazole group, oxadiazole group, pyrazine group, pyrimidine group, pyridazine group, triazine group, quinoline group, isoquinoline group, benzoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, quinazoline group, cinnoline group, phenanthridine group, acridine group, phenanthroline group, phenazine group, benzimidazole group, isobenzothiazole group, benzoxazole group, isobenzoxazole group, triazole group, tetrazole group, imidazopyridine group, imidazopyrimidine group, and azacarbazole group; and

[0353] each independently selected from deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 20 alkyl group, C1-C 20 alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenanthryl group, anthryl group, fluoranthenyl group, benzo[a]phenanthryl group, pyrenyl group, Group, perylene group, pentaphenyl group, hexaphenyl group, pentacene group, thiophene group, furan group, carbazole group, indole group, isoindole group, benzofuran group, benzothiophene group, dibenzofuran group, dibenzothiophene group, benzocarbazole group, dibenzocarbazole group, dibenzosilole group, pyridine group, imidazole group, pyrazole group, thiazole group, isothiazole group, oxazole group, isoxazole group, thiadiazole group, oxadiazole group, pyrazine group, pyrimidine group, pyridazine group, triazine group, quinoline group, isoquinoline group, benzoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, quinazoline group, cinnoline group, phenanthridine group, acridine group, phenanthroline group, phenazine group, benzimidazole group, isobenzothiazole group, benzoxazole group, isobenzoxazole group, triazole group, tetrazole group, imidazopyridine group, imidazopyrimidine group, azacarbazole group, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q32 ), -B(Q 31 )(Q 32 ), -C(=O)(Q 31 ), -S(=O)2(Q 31 ), and -P(=O)(Q 31 )(Q 32 ), and at least one substituted phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro - bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthryl group, anthryl group, fluoranthenyl group, benzophenanthryl group, pyrenyl group, -yl group, perylenyl group, pentaphenyl group, hexaphenyl group, quinquephenyl group, thienyl group, furyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuryl group, benzothienyl group, dibenzofuryl group, dibenzothienyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, imidazopyridyl group, imidazopyrimidinyl group, and azacarbazolyl group,

[0354] where Q 31 to Q 33 is the same as described above.

[0355] In one embodiment, the host may include an alkaline earth metal complex. For example, the host may be selected from Be complexes (e.g., compound H55), Mg complexes, and Zn complexes.

[0356] In an embodiment, the host may include at least one selected from 9,10 - bis(2 - naphthyl)anthracene (ADN), 2 - methyl - 9,10 - bis(naphthalen - 2 - yl)anthracene (MADN), 9,10 - bis(2 - naphthyl)-2 - tert - butyl - anthracene (TBADN), 4,4′ - bis(N - carbazolyl)-1,1′ - biphenyl (CBP), 1,3 - bis(carbazol - 9 - yl)benzene (mCP), 1,3,5 - tris(carbazol - 9 - yl)benzene (TCP), and compounds H1 to H55, but the embodiment is not limited thereto:

[0357]

[0358]

[0359]

[0360]

[0361] [The phosphorescent dopant contained in the emission layer in the organic layer 150]

[0362] The phosphorescent dopant may include an organometallic compound represented by Formula 1.

[0363] The phosphorescent dopant may further include an organometallic complex represented by the following Formula 401:

[0364] <Formula 401>

[0365] M(L 401 ) xc1 (L 402 ) xc2

[0366] <Formula 402>

[0367]

[0368] In Formula 401 and Formula 402,

[0369] M may be selected from iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), and thulium (Tm),

[0370] L 401 may be selected from the ligands represented by Formula 402, and xc1 may be 1, 2, or 3, where when xc1 is 2 or greater than 2, two or more L 401 may be the same as or different from each other,

[0371] L 402 may be an organic ligand, and xc2 may be an integer from 0 to 4, where when xc2 is 2 or greater than 2, two or more L 402 may be the same as or different from each other,

[0372] X 401 to X 404 may each independently be nitrogen or carbon,

[0373] X 401 and X 403 may be connected to each other via a single bond or a double bond, and X 402 and X 404 may be connected to each other via a single bond or a double bond,

[0374] A 401 and A 402 may each independently be selected from C5-C 60 carbocyclic groups or C1-C 60 heterocyclic groups,

[0375] X 405 may be a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 411 ))-*', *-C(Q 411 )(Q 412 ))-*', *-C(Q 411 ))=C(Q 412 ))-*', *-C(Q 411 ))=*' or *=C=*', where Q 411 and Q 412 may each independently be hydrogen, deuterium, C1-C 20 alkyl groups, C1-C 20 alkoxy groups, phenyl groups, biphenyl groups, terphenyl groups or naphthyl groups,

[0376] X 406 may be a single bond, O or S,

[0377] R 401 and R 402 may each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy groups, cyano groups, nitro groups, amidino groups, hydrazino groups, hydrazone groups, substituted or unsubstituted C1-C 20 alkyl groups, substituted or unsubstituted C1-C 20 alkoxy groups, substituted or unsubstituted C3-C 10 cycloalkyl groups, substituted or unsubstituted C1-C 10 heterocycloalkyl groups, substituted or unsubstituted C3-C 10 cycloalkenyl groups, substituted or unsubstituted C1-C 10 heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 aryl groups, substituted or unsubstituted C6-C 60 aryloxy groups, substituted or unsubstituted C6-C 60 arylthio groups, substituted or unsubstituted C1-C 60 heteroaryl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups and substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic groups, -Si(Q 401 )(Q 402 )(Q 403 ), -N(Q 401 )(Q402 ), -B(Q 401 )(Q 402 ), -C(=O)(Q 401 ), -S(=O)2(Q 401 ), and -P(=O)(Q 401 )(Q 402 ), and Q 401 to Q 403 can each independently be selected from C1-C 10 alkyl groups, C1-C 10 alkoxy groups, C6-C 20 aryl groups, and C1-C 20 heteroaryl groups,

[0378] xc11 and xc12 can each independently be an integer from 0 to 10, and

[0379] * and *' in formula 402 each represent the attachment site to M in formula 401.

[0380] In one embodiment, A in formula 402 401 and A 402 can each independently be selected from benzene groups, naphthalene groups, fluorene groups, spiro-bifluorene groups, indene groups, pyrrole groups, thiophene groups, furan groups, imidazole groups, pyrazole groups, thiazole groups, isothiazole groups, oxazole groups, isoxazole groups, pyridine groups, pyrazine groups, pyrimidine groups, pyridazine groups, quinoline groups, isoquinoline groups, benzoquinoline groups, quinoxaline groups, quinazoline groups, carbazole groups, benzimidazole groups, benzofuran groups, benzothiophene groups, isobenzothiophene groups, benzoxazole groups, isobenzoxazole groups, triazole groups, tetrazole groups, oxadiazole groups, triazine groups, dibenzofuran groups, and dibenzothiophene groups.

[0381] In an embodiment, in formula 402, i) X 401 can be nitrogen and X 402 can be carbon, or ii) each of X 401 and X 402 can be nitrogen.

[0382] In an embodiment, R in formula 402 401 and R 402 can each independently be selected from:

[0383] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy groups, cyano groups, nitro groups, amidino groups, hydrazino groups, hydrazono groups, C1-C 20 alkyl groups, and C1-C 20 alkoxy groups;

[0384] C1-C substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazone group, a phenyl group, a naphthyl group, a cyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornyl group, and a norbornenyl group 20 alkyl group and C1-C 20 alkoxy group;

[0385] cyclopentyl group, cyclohexyl group, adamantyl group, norbornyl group, norbornenyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorene group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, dibenzofuranyl group, and dibenzothiophenyl group;

[0386] each substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazone group, C1-C 20 alkyl group, C1-C 20 alkoxy group, cyclopentyl group, cyclohexyl group, adamantyl group, norbornyl group, norbornenyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorene group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, dibenzofuranyl group, and dibenzothiophenyl group; and

[0387] -Si(Q 401 )(Q 402 )(Q 403 ), -N(Q 401 )(Q 402 ), -B(Q 401 )(Q 402 ), -C(=O)(Q 401 ), -S(=O)2(Q 401 ), and -P(=O)(Q 401 )(Q 402 ),

[0388] Wherein Q 401 to Q 403 can each independently be selected from C1-C 10 alkyl groups, C1-C 10 alkoxy groups, phenyl groups, biphenyl groups, and naphthyl groups, but the embodiments are not limited thereto.

[0389] In an embodiment, when xc1 in Formula 401 is 2 or greater than 2, two or more of the two A's in L 401 can optionally be connected to each other via X which is a linking group 401 , or two or more of the two A's in L 407 can optionally be connected to each other via X which is a linking group 401 (see Compound PD1 to Compound PD4 and Compound PD7). X 402 and X 408 can each independently be a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q 407 )-*', *-C(Q 408 )(Q 413 )-*' or *-C(Q 413 )(Q 414 )=C(Q 413 )(Q 414 )-*' (wherein Q 413 and Q 414 can each independently be hydrogen, deuterium, a C1-C 20 alkyl group, a C1-C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group), but the embodiments are not limited thereto.

[0390] L in Formula 401 402 can be a monovalent organic ligand, a divalent organic ligand, or a trivalent organic ligand. For example, L 402 can be selected from halogens, diketones (e.g., acetylacetonates), carboxylic acids (e.g., picolinates), -C(=O), isonitriles, -CN, and phosphorus compounds (e.g., phosphines or phosphites), but the embodiments are not limited thereto.

[0391] In an embodiment, the phosphorescent dopant can be selected from, for example, Compound PD1 to Compound PD25, but the embodiments are not limited thereto:

[0392]

[0393]

[0394] [Fluorescent dopant in the emitting layer]

[0395] The fluorescent dopant may include an arylamine compound or a styrylamine compound.

[0396] The fluorescent dopant may include a compound represented by the following Formula 501:

[0397] <Formula 501>

[0398]

[0399] In Formula 501,

[0400] Ar 501 may be a substituted or unsubstituted C5-C 60 carbocyclic group or a substituted or unsubstituted C1-C 60 heterocyclic group,

[0401] L 501 to L 503 may each independently be selected from a substituted or unsubstituted C3-C 10 subcycloalkyl group, a substituted or unsubstituted C1-C 10 subheterocycloalkyl group, a substituted or unsubstituted C3-C 10 subcycloalkenyl group, a substituted or unsubstituted C1-C 10 subheterocycloalkenyl group, a substituted or unsubstituted C6-C 60 subaryl group, a substituted or unsubstituted C1-C 60 subheteroaryl group, a substituted or unsubstituted divalent non-aromatic fused polycyclic group, and a substituted or unsubstituted divalent non-aromatic fused heteropolycyclic group,

[0402] xd1 to xd3 may each independently be an integer from 0 to 3,

[0403] R 501 and R 502 may each independently be selected from 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, and a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, and

[0404] xd4 can be an integer from 1 to 6.

[0405] In one embodiment, Ar in Formula 501 501 may be selected from:

[0406] a naphthalene group, a heptalene group, a fluorene group, a spiro-difluorene group, a benzo[b]fluorene group, a dibenzo[b,k]fluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a benzo[a]phenanthrene group, a pyrene group, a group, a tetracene group, a picene group, a perylene group, a pentacene group, an indeno[1,2,3-cd]anthracene group, and an indeno[1,2,3-cd]phenanthrene group; and

[0407] each naphthalene group, heptalene group, fluorene group, spiro-difluorene group, benzo[b]fluorene group, dibenzo[b,k]fluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, benzo[a]phenanthrene group, pyrene group, 20 alkyl group, C1-C 20 alkoxy group, phenyl group, biphenyl group, terphenyl group, and naphthyl group, which is substituted by at least one selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C a group, a tetracene group, a picene group, a perylene group, a pentacene group, an indeno[1,2,3-cd]anthracene group, and an indeno[1,2,3-cd]phenanthrene group.

[0408] In an embodiment, L in Formula 501 501 to L 503 may each independently be selected from:

[0409] a phenylene group, a naphthylene group, a fluorenylene group, a spiro-difluorenylene group, a benzo[b]fluorenylene group, a dibenzo[b,k]fluorenylene group, a phenanthrylene group, an anthrylene group, a fluoranthenylene group, a benzo[a]phenanthrylene group, a pyrenylene group, a group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, and a pyridinylene group; and

[0410] each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C 20 alkyl group, C1-C 20An alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzo[fluorene] group, a dibenzo[fluorene] group, a phenanthryl group, an anthryl group, a fluoranthenyl group, a benzo[phenanthrene] group, a pyrenyl group, a group, a perylenyl group, a pentaphenyl group, a hexaphenyl group, a quinquephenyl group, a thienyl group, a furyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, a dibenzothienyl group, a benzo[carbazole] group, a dibenzo[carbazole] group, a dibenzosilolyl group, and a pyridyl group-substituted phenylene group, naphthylene group, fluorenylene group, spiro-bifluorenylene group, benzo[fluorene]ylene group, dibenzo[fluorene]ylene group, phenanthrylene group, anthrylene group, fluoranthenylene group, benzo[phenanthrene]ylene group, pyrenylene group, a group, a perylenylene group, a pentaphenylene group, a hexaphenylene group, a quinquephenylene group, a thienylene group, a furylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothienylene group, a dibenzofuranylene group, a dibenzothienylene group, a benzo[carbazole]ylene group, a dibenzo[carbazole]ylene group, a dibenzosilolylene group, and a pyridinylene group.

[0411] In an embodiment, R in Formula 501 501 and R 502 can each independently be selected from:

[0412] a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzo[fluorene] group, a dibenzo[fluorene] group, a phenanthryl group, an anthryl group, a fluoranthenyl group, a benzo[phenanthrene] group, a pyrenyl group, a group, a perylenyl group, a pentaphenyl group, a hexaphenyl group, a quinquephenyl group, a thienyl group, a furyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, a dibenzothienyl group, a benzo[carbazole] group, a dibenzo[carbazole] group, a dibenzosilolyl group, and a pyridyl group; and

[0413] each independently substituted with deuterium, -F, -Cl, -Br, -I, a hydroxy group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C 20 alkyl group, a C1-C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzo[fluorene] group, a dibenzo[fluorene] group, a phenanthryl group, an anthryl group, a fluoranthenyl group, a benzo[phenanthrene] group, a pyrenyl group, At least one of the phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenanthryl group, anthracenyl group, fluoranthenyl group, benzophenanthryl group, pyrenyl group, 31 )(Q 32 )(Q 33 ) substituted by a group, perylene group, pentaphenyl group, hexaphenyl group, quaterphenyl group, thiophenyl group, furyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuryl group, benzothiophenyl group, dibenzofuryl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridyl group and -Si(Q A group, perylene group, pentaphenyl group, hexaphenyl group, quaterphenyl group, thiophenyl group, furyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuryl group, benzothiophenyl group, dibenzofuryl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group and pyridyl group,

[0414] wherein Q 31 to Q 33 can each independently be selected from C1-C 10 alkyl group, C1-C 10 alkoxy group, phenyl group, biphenyl group, terphenyl group and naphthyl group.

[0415] In an embodiment, xd4 in Formula 501 can be 2, but the embodiment is not limited thereto.

[0416] For example, the fluorescent dopant can be selected from Compound FD1 to Compound FD22:

[0417]

[0418]

[0419]

[0420] In an embodiment, the fluorescent dopant can be selected from the following compounds, but the embodiment is not limited thereto:

[0421]

[0422] [Electron transport region in organic layer 150]

[0423] The electron transport region may have i) a single-layer structure including a single layer containing a single material, ii) a single-layer structure including a single layer containing different materials, or iii) a multi-layer structure having multiple layers containing different materials.

[0424] The electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof, but the embodiments are not limited thereto.

[0425] For example, the electron transport region may have an electron transport layer / electron injection layer structure, a hole blocking layer / electron transport layer / electron injection layer structure, an electron control layer / electron transport layer / electron injection layer structure, or a buffer layer / electron transport layer / electron injection layer structure, where for each structure, the constituent layers may be stacked (or disposed) in sequence from the emission layer. However, the embodiments of the structure of the electron transport region are not limited thereto.

[0426] The electron transport region (e.g., the buffer layer, hole blocking layer, electron control layer, or electron transport layer in the electron transport region) may contain a metal-free compound containing at least one ring having a nitrogen lacking π electrons.

[0427] "Ring having a nitrogen lacking π electrons" means a C1-C 60 heterocyclic group.

[0428] For example, "ring having a nitrogen lacking π electrons" may be i) a 5- to 7-membered hetero-monocyclic group having at least one *-N=*' moiety, ii) a hetero-polycyclic group in which two or more 5- to 7-membered hetero-monocyclic groups each having at least one *-N=*' moiety are fused to each other, or iii) a hetero-polycyclic group in which at least one of the 5- to 7-membered hetero-monocyclic groups each having at least one *-N=*' moiety is fused to at least one C5-C 60 carbocyclic group.

[0429] Examples of rings having a nitrogen lacking π electrons include an imidazole ring, a pyrazole ring, a thiazole ring, an isothiazole ring, an oxazole ring, an isoxazole ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, an indazole ring, a purine ring, a quinoline ring, an isoquinoline ring, a benzoquinoline ring, a phthalazine ring, a naphthyridine ring, a quinoxaline ring, a quinazoline ring, a cinnoline ring, a phenanthridine ring, an acridine ring, a phenanthroline ring, a phenazine ring, a benzimidazole ring, an isobenzothiazole ring, a benzoxazole ring, an isobenzoxazole ring, a triazole ring, a tetrazole ring, an oxadiazole ring, a triazine ring, a thiadiazole ring, an imidazopyridine ring, an imidazopyrimidine ring, and an azacarbazole ring, but are not limited thereto.

[0430] For example, the electron transport region may contain a compound represented by the following formula 601:

[0431] <Formula 601>

[0432] [Ar 601 xe11 -[(L 601 ) xe1 -R 601 xe21 。

[0433] In formula 601,

[0434] Ar 601 can be a substituted or unsubstituted C5-C 60 carbocyclic group or a substituted or unsubstituted C1-C 60 heterocyclic group,

[0435] xe11 can be 1, 2, or 3,

[0436] L 601 can be selected from substituted or unsubstituted C3-C 10 cycloalkylidene groups, substituted or unsubstituted C1-C 10 heterocycloalkylidene groups, substituted or unsubstituted C3-C 10 cycloalkenylidene groups, substituted or unsubstituted C1-C 10 heterocycloalkenylidene groups, substituted or unsubstituted C6-C 60 arylidene groups, substituted or unsubstituted C1-C 60 heteroarylidene groups, substituted or unsubstituted divalent non-aromatic fused polycyclic groups, and substituted or unsubstituted divalent non-aromatic fused heteropolycyclic groups;

[0437] xe1 can be an integer from 0 to 5,

[0438] R 601 can be selected from substituted or unsubstituted C3-C 10 cycloalkyl groups, substituted or unsubstituted C1-C 10 heterocycloalkyl groups, substituted or unsubstituted C3-C 10 cycloalkenyl groups, substituted or unsubstituted C1-C 10 heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 aryl groups, substituted or unsubstituted C6-C 60 aryloxy groups, substituted or unsubstituted C6-C 60 arylthio groups, substituted or unsubstituted C1-C 60 heteroaryl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic groups, -Si(Q 601 )(Q 602 )(Q 603 )、-C(=O)(Q 601 )、-S(=O)2(Q​​601 ) and -P(=O)(Q 601 )(Q 602 ),

[0439] Q 601 to Q 603 can each independently be a C1-C 10 alkyl group, a C1-C 10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group or a naphthyl group, and

[0440] xe21 can be an integer from 1 to 5.

[0441] In one embodiment, at least one of the xe11 number of Ar 601 and the xe21 number of R 601 can contain a ring with nitrogen lacking π electrons.

[0442] In one embodiment, Ar in Formula 601 601 can be selected from

[0443] a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzo[b]fluorene group, a dibenzo[b,d]fluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a benzo[a]phenanthrene group, a pyrene group, a perylene group, a picene group, a pentacene group, an indeno[1,2,3-cd]anthracene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzo[c]quinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group and an azacarbazole group; and

[0444] each independently substituted with a group selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C 20 alkyl group, a C1-C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, -Si(Q 31 )(Q 32 )(Q 33 )、-S(=O)2(Q 31 ) and -P(=O)(Q 31 )(Q 32) at least one substituted benzene group, naphthalene group, fluorene group, spiro - bifluorene group, benzofluorene group, dibenzofluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, benzo[a]phenanthrene group, pyrene group, group, tetracene group, picene group, perylene group, pentacene group, indeno[1,2,3 - cd]anthracene group, dibenzofuran group, dibenzothiophene group, carbazole group, imidazole group, pyrazole group, thiazole group, isothiazole group, oxazole group, isoxazole group, pyridine group, pyrazine group, pyrimidine group, pyridazine group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, quinazoline group, cinnoline group, phenanthridine group, acridine group, phenanthroline group, phenazine group, benzimidazole group, isobenzothiazole group, benzoxazole group, isobenzoxazole group, triazole group, tetrazole group, oxadiazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group, and azacarbazole group,

[0445] wherein Q 31 to Q 33 can each independently be selected from C1 - C 10 alkyl group, C1 - C 10 alkoxy group, phenyl group, biphenyl group, terphenyl group, and naphthyl group.

[0446] When xe11 in formula 601 is 2 or greater than 2, two or more than two Ar 601 can be connected to each other via a single bond.

[0447] In an embodiment, Ar in formula 601 601 can be an anthracene group.

[0448] In an embodiment, the compound represented by formula 601 can be represented by the following formula 601 - 1:

[0449] <Formula 601 - 1>

[0450]

[0451] In formula 601 - 1,

[0452] X 614 can be N or C(R 614 ), X 615 can be N or C(R 615 ), X 616 can be N or C(R 616 ), and at least one selected from X 614 to X 616 can be N,

[0453] L 611to L 613 can each independently be the same as those described with respect to L 601 described,

[0454] xe611 to xe613 can each independently be the same as those described with respect to xe1,

[0455] R 611 to R 613 can each independently be the same as those described with respect to R 601 described, and

[0456] R 614 to R 616 can each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C 20 alkyl group, a C1-C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

[0457] In one embodiment, L 601 and L 611 to L 613 in Formula 601 and Formula 601-1 can each independently be selected from:

[0458] a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzo[a]fluorenylene group, a dibenzo[a,h]fluorenylene group, a phenanthrylene group, an anthrylene group, a fluoranthenylene group, a benzo[a]phenanthrylene group, a pyrenylene group, a ylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a quaterrylene group, a thienylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothienylene group, a dibenzofuranylene group, a dibenzothienylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, a pyridinylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a thiadiazolylene group, an oxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a triazinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzimidazolylene group, an isobenzothiazolylene group, a benzoxazolylene group, an isobenzoxazolylene group, a triazolylene group, a tetrazolylene group, an imidazopyridinylene group, an imidazopyrimidinylene group, and an azacarbazolylene group; and

[0459] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazone group, C1-C 20 alkyl group, C1-C 20 alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, benzo[a]phenanthrenyl group, pyrenyl group, anthracenyl group, perylenyl group, pentaphenyl group, hexaphenyl group, quaterphenyl group, thienyl group, furyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, dibenzothienyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, imidazopyridyl group, imidazopyrimidinyl group, and an azacarbazolyl group, and at least one of the substituted phenylene group, naphthylene group, fluorenylene group, spiro-bifluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, benzo[a]phenanthrenylene group, pyrenylene group, sub- Group, perylene diimide group, pentacene diimide group, hexacene diimide group, pentacenequinone diimide group, thiophene diimide group, furan diimide group, carbazole diimide group, indole diimide group, isoindole diimide group, benzofuran diimide group, benzothiophene diimide group, dibenzofuran diimide group, dibenzothiophene diimide group, benzocarbazole diimide group, dibenzocarbazole diimide group, dibenzosilole diimide group, pyridine diimide group, imidazole diimide group, pyrazole diimide group, thiazole diimide group, isothiazole diimide group, oxazole diimide group, isoxazole diimide group, thiadiazole diimide group, oxadiazole diimide group, pyrazine diimide group, pyrimidine diimide group, pyridazine diimide group, s-triazine diimide group, quinoline diimide group, isoquinoline diimide group, benzoquinoline diimide group, phthalazine diimide group, naphthyridine diimide group, quinoxaline diimide group, quinazoline diimide group, cinnoline diimide group, phenanthridine diimide group, acridine diimide group, phenanthroline diimide group, phenazine diimide group, benzimidazole diimide group, isobenzothiazole diimide group, benzoxazole diimide group, isobenzoxazole diimide group, triazole diimide group, tetrazole diimide group, imidazopyridine diimide group, imidazopyrimidine diimide group, and azacarbazole diimide group,

[0460] However, the embodiments are not limited thereto.

[0461] In an embodiment, xe1 and xe611 to xe613 in Formula 601 and Formula 601-1 may each independently be 0, 1, or 2.

[0462] In an embodiment, R in Formula 601 and Formula 601-1 601 and R 611 to R 613 may each independently be selected from:

[0463] phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenanthryl group, anthracenyl group, fluoranthenyl group, benzo[a]phenanthryl group, pyrenyl group, a base group, a perylene group, a pentaphenyl group, a hexaphenyl group, a quinquephenyl group, a thienyl group, a furyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuryl group, a benzothienyl group, a dibenzofuryl group, a dibenzothienyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group;

[0464] each independently selected from deuterium, -F, -Cl, -Br, -I, a hydroxy group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C1-C 20 alkyl group, C1-C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthryl group, an anthryl group, a fluoranthenyl group, a benzoanthryl group, a pyrenyl group, a phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorene group, spiro-bifluorene group, benzo[h]fluorene group, dibenzo[h,k]fluorene group, phenanthryl group, anthracenyl group, fluoranthenyl group, benzo[a]phenanthryl group, pyrenyl group, substituted by at least one of a radical group, perylene radical group, pentaphenyl radical group, hexaphenyl radical group, quaterphenyl radical group, thiophenyl radical group, furyl radical group, carbazolyl radical group, indolyl radical group, isoindolyl radical group, benzofuryl radical group, benzothienyl radical group, dibenzofuryl radical group, dibenzothienyl radical group, benzocarbazolyl radical group, dibenzocarbazolyl radical group, dibenzosilolyl radical group, pyridyl radical group, imidazolyl radical group, pyrazolyl radical group, thiazolyl radical group, isothiazolyl radical group, oxazolyl radical group, isoxazolyl radical group, thiadiazolyl radical group, oxadiazolyl radical group, pyrazinyl radical group, pyrimidinyl radical group, pyridazinyl radical group, triazinyl radical group, quinolinyl radical group, isoquinolinyl radical group, benzoquinolinyl radical group, phthalazinyl radical group, naphthyridinyl radical group, quinoxalinyl radical group, quinazolinyl radical group, cinnolinyl radical group, phenanthridinyl radical group, acridinyl radical group, phenanthrolinyl radical group, phenazinyl radical group, benzimidazolyl radical group, isobenzothiazolyl radical group, benzoxazolyl radical group, isobenzoxazolyl radical group, triazolyl radical group, tetrazolyl radical group, imidazopyridinyl radical group, imidazopyrimidinyl radical group and azacarbazolyl radical group a radical group, perylene radical group, pentaphenyl radical group, hexaphenyl radical group, quaterphenyl radical group, thiophenyl radical group, furyl radical group, carbazolyl radical group, indolyl radical group, isoindolyl radical group, benzofuryl radical group, benzothienyl radical group, dibenzofuryl radical group, dibenzothienyl radical group, benzocarbazolyl radical group, dibenzocarbazolyl radical group, dibenzosilolyl radical group, pyridyl radical group, imidazolyl radical group, pyrazolyl radical group, thiazolyl radical group, isothiazolyl radical group, oxazolyl radical group, isoxazolyl radical group, thiadiazolyl radical group, oxadiazolyl radical group, pyrazinyl radical group, pyrimidinyl radical group, pyridazinyl radical group, triazinyl radical group, quinolinyl radical group, isoquinolinyl radical group, benzoquinolinyl radical group, phthalazinyl radical group, naphthyridinyl radical group, quinoxalinyl radical group, quinazolinyl radical group, cinnolinyl radical group, phenanthridinyl radical group, acridinyl radical group, phenanthrolinyl radical group, phenazinyl radical group, benzimidazolyl radical group, isobenzothiazolyl radical group, benzoxazolyl radical group, isobenzoxazolyl radical group, triazolyl radical group, tetrazolyl radical group, imidazopyridinyl radical group, imidazopyrimidinyl radical group and azacarbazolyl radical group; and

[0465] -S(=O)2(Q 601 ), and -P(=O)(Q 601 )(Q 602 ),

[0466] wherein Q 601 and Q 602 are the same as those described above.

[0467] The electron transport region may include at least one compound selected from Compound ET1 to Compound ET36, but the embodiments are not limited thereto:

[0468]

[0469]

[0470]

[0471]

[0472] In an embodiment, the electron transport region may include at least one compound selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), and NTAZ.

[0473]

[0474] The thicknesses of the buffer layer, the hole blocking layer, and the electron control layer may each independently be about to about In an embodiment, the thickness of the buffer layer may be about to about In an embodiment, the thickness of the hole blocking layer may be about to about In an embodiment, the thickness of the electron control layer may be about to about When the thicknesses of the buffer layer, the hole blocking layer, and the electron control layer are within these ranges, excellent hole blocking characteristics or excellent electron control characteristics can be obtained without a significant increase in the driving voltage.

[0475] The thickness of the electron transport layer may be about to about In an embodiment, the thickness of the electron transport layer may be about to 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.

[0476] The electron transport region (e.g., the electron transport layer in the electron transport region) may further include a metal-containing material.

[0477] The metal-containing material may include at least one selected from alkali metal complexes and alkaline earth metal complexes. The alkali metal complex may contain metal ions selected from Li ions, Na ions, K ions, Rb ions, and Cs ions, and the alkaline earth metal complex may contain metal ions selected from Be ions, Mg ions, Ca ions, Sr ions, and Ba ions. The ligand coordinated with the metal ions of the alkali metal complex or alkaline earth metal complex may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxyphenyl oxadiazole, hydroxyphenyl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzimidazole, hydroxyphenyl benzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but the embodiments are not limited thereto.

[0478] For example, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (lithium hydroxyquinoline, LiQ) or compound ET-D2:

[0479]

[0480] The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 190. The electron injection layer may be in direct contact with the second electrode 190.

[0481] The electron injection layer may have i) a single-layer structure including a single layer containing a single material, ii) a single-layer structure including a single layer containing different materials, or iii) a multi-layer structure having multiple layers containing different materials.

[0482] The electron injection layer may contain an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.

[0483] The alkali metal may be selected from Li, Na, K, Rb, and Cs. In one embodiment, the alkali metal may be Li, Na, or Cs. In an embodiment, the alkali metal may be Li or Cs, but the embodiments are not limited thereto.

[0484] The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.

[0485] The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb, and Gd.

[0486] The alkali metal compounds, alkaline earth metal compounds, and rare earth metal compounds may be selected from oxides and halides (e.g., fluorides, chlorides, bromides, or iodides) of alkali metals, alkaline earth metals, and rare earth metals.

[0487] The alkali metal compound can be selected from alkali metal oxides (such as Li2O, Cs2O or K2O) and alkali metal halides (such as LiF, NaF, CsF, KF, LiI, NaI, CsI or KI). In one embodiment, the alkali metal compound can be selected from LiF, Li2O, NaF, LiI, NaI, CsI and KI, but the embodiment is not limited thereto.

[0488] The alkaline earth metal compound can be selected from alkaline earth metal oxides, such as BaO, SrO, CaO, Ba x Sr 1-x O(0 < x < 1) or Ba x Ca 1-x O(0 < x < 1). In one embodiment, the alkaline earth metal compound can be selected from BaO, SrO and CaO, but the embodiment is not limited thereto.

[0489] The rare earth metal compound can be selected from YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3 and TbF3. In one embodiment, the rare earth metal compound can be selected from YbF3, ScF3, TbF3, YbI3, ScI3 and TbI3, but the embodiment is not limited thereto.

[0490] The alkali metal complex, alkaline earth metal complex and rare earth metal complex can contain ions of alkali metal, alkaline earth metal and rare earth metal as described above, and the ligands coordinated with the metal ions of the alkali metal complex, alkaline earth metal complex or rare earth metal complex can be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxyphenyl oxadiazole, hydroxyphenyl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzimidazole, hydroxyphenyl benzothiazole, bipyridine, phenanthroline and cyclopentadiene, but the embodiment is not limited thereto.

[0491] The electron injection layer can be composed of alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex or any combination thereof as described above. In an embodiment, the electron injection layer can further contain an organic material. When the electron injection layer further contains an organic material, the alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex or any combination thereof can be uniformly or non-uniformly dispersed in the matrix containing the organic material.

[0492] The thickness of the electron injection layer can be about to about In an embodiment, the thickness of the electron injection layer can be about to about When the thickness of the electron injection layer is within the range described above, the electron injection layer can have satisfactory electron injection characteristics without a significant increase in driving voltage.

[0493] [Second electrode 190]

[0494] The second electrode 190 can be disposed on the organic layer 150 having such a structure. The second electrode 190 can be a cathode, which is an electron injection electrode, and in this regard, the material used to form the second electrode 190 can be selected from metals, alloys, conductive compounds, and combinations thereof having a relatively low work function.

[0495] The second electrode 190 can include at least one selected from lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ITO, and IZO, but the embodiments are not limited thereto. The second electrode 190 can be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.

[0496] The second electrode 190 can have a single-layer structure or include a multi-layer structure of two or more layers.

[0497] Figures 2 to 4 description]

[0498] Figure 2 is a schematic cross-sectional view of an organic light-emitting device 20 according to an embodiment. The organic light-emitting device 20 includes a first cover layer 210, a first electrode 110, an organic layer 150, and a second electrode 190, which are sequentially stacked (or disposed) in this specified order. Figure 3 is a schematic cross-sectional view of an organic light-emitting device 30 according to an embodiment. The organic light-emitting device 30 includes a first electrode 110, an organic layer 150, a second electrode 190, and a second cover layer 220, which are sequentially stacked (or disposed) in this specified order. Figure 4 is a schematic cross-sectional view of an organic light-emitting device 40 according to an embodiment. The organic light-emitting device 40 includes a first cover layer 210, a first electrode 110, an organic layer 150, a second electrode 190, and a second cover layer 220, which are sequentially stacked (or disposed) in this specified order.

[0499] Regarding Figures 2 to 4 , the first electrode 110, the organic layer 150, and the second electrode 190 can be understood by referring to the description presented regarding Figure 1 .

[0500] ​In the organic layer 150 of each of the organic light-emitting device 20 and the organic light-emitting device 40, the light generated in the emission layer can pass through the first electrode 110 and the first cover layer 210 toward the outside, where the first electrode 110 can be a semi-transmissive electrode or a transmissive electrode. In the organic layer 150 of each of the organic light-emitting device 30 and the organic light-emitting device 40, the light generated in the emission layer can pass through the second electrode 190 and the second cover layer 220 toward the outside, where the second electrode 190 can be a semi-transmissive electrode or a transmissive electrode.

[0501] The first cover layer 210 and the second cover layer 220 can increase the external light-emitting efficiency according to the principle of constructive interference.

[0502] The first cover layer 210 and the second cover layer 220 can each independently be an organic cover layer containing an organic material, an inorganic cover layer containing an inorganic material, or a composite cover layer containing an organic material and an inorganic material.

[0503] At least one selected from the first cover layer 210 and the second cover layer 220 can each independently contain at least one material selected from a carbocyclic compound, a heterocyclic compound, an amine-based compound, a porphyrin derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, and an alkaline earth metal complex. The carbocyclic compound, the heterocyclic compound, and the amine-based compound can optionally be substituted with a substituent containing at least one element selected from O, N, S, Se, Si, F, Cl, Br, and I. In one embodiment, at least one selected from the first cover layer 210 and the second cover layer 220 can each independently contain an amine-based compound.

[0504] In one embodiment, at least one selected from the first cover layer 210 and the second cover layer 220 can each independently contain a compound represented by Formula 201 or a compound represented by Formula 202.

[0505] In an embodiment, at least one selected from the first cover layer 210 and the second cover layer 220 can each independently contain a compound selected from Compound HT28 to Compound HT33 and Compound CP1 to Compound CP5, but the embodiment is not limited thereto:

[0506]

[0507] Above, the organic light-emitting device according to the embodiment has been described, but the embodiment is not limited thereto. Figures 1 to 4

[0508] ​The layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region can be formed in a certain region by using one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, and laser-induced thermal imaging.

[0509] When the layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region are formed by vacuum deposition, considering the materials to be included in the layer to be formed and the structure of the layer to be formed, the deposition can be carried out at a deposition temperature of about 100 °C to about 500 °C, a vacuum degree of about 10 -8 Torr to about 10 -3 Torr, and a deposition rate of about seconds to about / second.

[0510] When the layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region are formed by spin coating, considering the materials to be included in the layer to be formed and the structure of the layer to be formed, the spin coating can be carried out at a coating speed of about 2,000 rpm to about 5,000 rpm and a heat treatment temperature of about 80 °C to about 200 °C.

[0511] [Definition of substituents]

[0512] As used herein, the term "C1-C 60 alkyl group" refers to a straight-chain or branched-chain aliphatic saturated hydrocarbon monovalent group having 1 to 60 carbon atoms, and examples thereof include methyl group, ethyl group, propyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, isopentyl group, and hexyl group. In some embodiments, the C1-C 60 alkyl group can be a C1-C 30 alkyl group, a C1-C 20 alkyl group, or a C1-C 10 alkyl group. As used herein, the term "C1-C 60 alkylene group" refers to a divalent group having the same structure as the C1-C 60 alkyl group.

[0513] As used herein, the term "C2-C 60 alkenyl group" refers to a hydrocarbon group having at least one carbon-carbon double bond in the middle or at the end of the C2-C 60 alkyl group, and examples thereof include vinyl group, propenyl group, and butenyl group. In some embodiments, the C2-C 60 alkenyl group can be a C2-C 30 alkenyl group, a C2-C 20 alkenyl group, or a C2-C10 Alkenyl group. As used herein, the term "C2-C 60 alkenylene group" refers to a divalent group having the same structure as a C2-C 60 alkenyl group.

[0514] As used herein, the term "C2-C 60 alkynyl group" refers to a hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the end of a C2-C 60 alkyl group, and examples thereof include ethynyl group and propynyl group. In some embodiments, the C2-C 60 alkynyl group can be a C2-C 30 alkynyl group, a C2-C 20 alkynyl group or a C2-C 10 alkynyl group. As used herein, the term "C2-C 60 alkynylene group" refers to a divalent group having the same structure as a C2-C 60 alkynyl group.

[0515] As used herein, the term "C1-C 60 alkoxy group" refers to a monovalent group represented by -OA 101 (where A 101 is a C1-C 60 alkyl group), and examples thereof include methoxy group, ethoxy group and isopropoxy group.

[0516] As used herein, the term "C3-C 10 cycloalkyl group" refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and examples thereof include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group and cycloheptyl group. As used herein, the term "C3-C 10 cycloalkylene group" refers to a divalent group having the same structure as a C3-C 10 cycloalkyl group.

[0517] As used herein, the term "C1-C 10 heterocycloalkyl group" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P and S as ring-forming atoms (e.g., 1 to 5 or 1 to 3 heteroatoms, e.g., 1, 2, 3, 4 or 5 heteroatoms) and 1 to 10 carbon atoms, and examples thereof include 1,2,3,4-oxadiazolyl group, tetrahydrofuranyl group and tetrahydrothienyl group. As used herein, the term "C1-C 10 heterocycloalkylene group" refers to a divalent group having the same structure as a C1-C 10 heterocycloalkyl group.

[0518] As used herein, the term "C3-C 10 cycloalkenyl group" refers to a monovalent monocyclic group having 3 to 10 carbon atoms and at least one double bond in its ring and having no aromaticity, and examples thereof include cyclopentenyl group, cyclohexenyl group, and cycloheptenyl group. As used herein, the term "C3-C 10 subcycloalkenyl group" refers to a divalent group having the same structure as the C3-C 10 cycloalkenyl group.

[0519] As used herein, the term "C1-C 10 heterocycloalkenyl group" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P, and S as ring-forming atoms (e.g., 1 to 5 or 1 to 3 heteroatoms, e.g., 1, 2, 3, 4, or 5 heteroatoms), 1 to 10 carbon atoms, and at least one double bond in its ring. Non-limiting examples of the C1-C 10 heterocycloalkenyl group include 4,5-dihydro-1,2,3,4-oxadiazolyl group, 2,3-dihydrofuryl group, and 2,3-dihydrothienyl group. As used herein, the term "C1-C 10 subheterocycloalkenyl group" refers to a divalent group having the same structure as the C1-C 10 heterocycloalkenyl group.

[0520] As used herein, the term "C6-C 60 aryl group" refers to a monovalent group having a carbocyclic aromatic system containing 6 to 60 carbon atoms, and the "C6-C 60 subaryl group" as used herein refers to a divalent group having a carbocyclic aromatic system containing 6 to 60 carbon atoms. Examples of the C6-C 60 aryl group include phenyl group, naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, and yl group. In some embodiments, the C6-C 60 aryl group can be a C6-C 30 aryl group, a C6-C 24 aryl group, or a C6-C 18 aryl group. When the C6-C 60 aryl group and the C6-C 60 subaryl group each contain two or more rings, the two or more rings can be fused to each other.

[0521] As used herein, the term "C1-C 60"Heteroaryl group" refers to a monovalent group of a heteroaromatic system having at least one heteroatom selected from N, O, Si, P, and S (e.g., 1 to 5 or 1 to 3 heteroatoms, e.g., 1, 2, 3, 4, or 5 heteroatoms) in addition to 1 to 60 carbon atoms as ring-forming atoms. As used herein, the term "C1-C 60 "Heteroarylene group" refers to a divalent group of a heteroaromatic system having at least one heteroatom selected from N, O, Si, P, and S (e.g., 1 to 5 or 1 to 3 heteroatoms, e.g., 1, 2, 3, 4, or 5 heteroatoms) in addition to 1 to 60 carbon atoms as ring-forming atoms. C1-C 60 Examples of heteroaryl groups include pyridyl groups, pyrimidinyl groups, pyrazinyl groups, pyridazinyl groups, triazinyl groups, quinolinyl groups, and isoquinolinyl groups. In some embodiments, C1-C 60 The heteroaryl group can be a C1-C 30 heteroaryl group, a C1-C 24 heteroaryl group, or a C1-C 18 heteroaryl group. When the C1-C 60 heteroaryl group and the C1-C 60 heteroarylene group each contain two or more than two rings, the two or more than two rings can be fused to each other.

[0522] As used herein, the term "C6-C 60 aryloxy group" refers to -OA 102 (where A 102 is a C6-C 60 aryl group), and the "C6-C 60 arylthio group" as used herein refers to -SA 103 (where A 103 is a C6-C 60 aryl group).

[0523] As used herein, the term "monovalent non-aromatic fused polycyclic group" refers to a monovalent group (e.g., having 8 to 60 carbon atoms, e.g., 8 to 30 or 8 to 24 carbon atoms) having two or more than two rings fused to each other, having only carbon atoms as ring-forming atoms, and not having aromaticity in its entire molecular structure. A detailed example of a monovalent non-aromatic fused polycyclic group is a fluorenyl group. 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.

[0524] As used herein, the term "monovalent non-aromatic fused heteropolycyclic group" refers to a monovalent group (e.g., having 1 to 60 carbon atoms, such as 1 to 30 or 1 to 24 carbon atoms) that has two or more rings fused to each other, has at least one heteroatom selected from N, O, Si, P, and S (e.g., 1 to 5 or 1 to 3 heteroatoms, such as 1, 2, 3, 4, or 5 heteroatoms) other than carbon as ring-forming atoms, and does not have aromaticity in its entire molecular structure. A detailed example of a monovalent non-aromatic fused heteropolycyclic group is 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.

[0525] As used herein, the term "C5-C 60 carbocyclic group" refers to a monocyclic or polycyclic group that contains only carbon as ring-forming atoms and is composed of 5 to 60 carbon atoms. The C5-C 60 carbocyclic group can be an aromatic carbocyclic group or a non-aromatic carbocyclic group. The C5-C 60 carbocyclic group can be a ring, such as benzene; a monovalent group, such as a phenyl group; or a divalent group, such as a phenylene group. In an embodiment, depending on the number of substituents attached to the C5-C 60 carbocyclic group, the C5-C 60 carbocyclic group can be a trivalent or tetravalent group. In some embodiments, the C5-C 60 carbocyclic group can be a C5-C 30 carbocyclic group, a C5-C 24 carbocyclic group, or a C5-C 18 carbocyclic group.

[0526] As used herein, the term "C1-C 60 heterocyclic group" refers to a group having the same structure as the C5-C 60 carbocyclic group, but using at least one heteroatom selected from N, O, Si, P, and S (e.g., 1 to 5 or 1 to 3 heteroatoms, such as 1, 2, 3, 4, or 5 heteroatoms) other than carbon (the number of carbon atoms can be 1 to 60, such as 1 to 30 or 1 to 24 carbon atoms) as ring-forming atoms.

[0527] In the specification, substituted C5-C 60 carbocyclic groups, substituted C1-C 60 heterocyclic groups, substituted C3-C 10 subcycloalkyl groups, substituted C1-C 10 subheterocycloalkyl groups, substituted C3-C 10 subcycloalkenyl groups, substituted C1-C 10Azacycloalkenyl group, substituted C6-C 60 Arylene group, substituted C1-C 60 Heteroarylene group, substituted divalent non-aromatic fused polycyclic group, substituted divalent non-aromatic fused heteropolycyclic group, substituted C1-C 60 Alkyl group, substituted C2-C 60 Alkenyl group, substituted C2-C 60 Alkynyl group, substituted C1-C 60 Alkoxy group, substituted C3-C 10 Cycloalkyl group, substituted C1-C 10 Heterocycloalkyl group, substituted C3-C 10 Cycloalkenyl group, substituted C1-C 10 Heterocycloalkenyl group, substituted C6-C 60 Aryl group, substituted C6-C 60 Aryloxy group, substituted C6-C 60 Arylthio group, substituted C1-C 60 At least one substituent of the heteroaryl group, substituted monovalent non-aromatic fused polycyclic group, and substituted monovalent non-aromatic fused heteropolycyclic group may be selected from:

[0528] Deuterium, -F, -Cl, -Br, -I, hydroxy group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 60 Alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group and C1-C 60 Alkoxy group;

[0529] Each independently selected from deuterium, -F, -Cl, -Br, -I, hydroxy group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl group, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O)2(Q 11 ) and -P(=O)(Q 11 )(Q 12 ) at least one substituted C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl groups and C1-C 60 Alkoxy groups;

[0530] C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C1-C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups;

[0531] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl group, C1-C 60 Alkoxy groups, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C1-C 60 heteroaryl group, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O)2(Q 21) and -P(=O)(Q 21 )(Q 22 ) in at least one substituted C3-C 10 cycloalkyl group, C1-C 10 heterocycloalkyl group, C3-C 10 cycloalkenyl group, C1-C 10 heterocycloalkenyl group, C6-C 60 aryl group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C1-C 60 heteroaryl group, monovalent non-aromatic fused polycyclic group and monovalent non-aromatic fused heteropolycyclic group; and

[0532] -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 ) and -P(=O)(Q 31 )(Q 32 ),

[0533] wherein Q 11 to Q 13 , Q 21 to Q 23 and Q 31 to Q 33 can each independently be selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C1-C 60 alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 alkoxy group, C3-C 10 cycloalkyl group, C1-C 10 heterocycloalkyl group, C3-C 10 cycloalkenyl group, C1-C 10 heterocycloalkenyl group, C6-C 60 aryl group, C1-C 60 heteroaryl group, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, biphenyl group and terphenyl group.

[0534] As used herein, the term "Ph" refers to a phenyl group, the term "Me" refers to a methyl group, the term "Et" refers to an ethyl group, and the term "tert-Bu" or "t-Bu" or "Bu t " refers to a tert-butyl group, and the term "OMe" refers to a methoxy group as used herein.

[0535] As used herein, the term "biphenyl group" refers to "a phenyl group substituted with a phenyl group". In other words, a "biphenyl group" is a substituted phenyl group having a C6-C 60 aryl group as a substituent.

[0536] As used herein, the term "terphenyl group" refers to "a phenyl group substituted with a biphenyl group". In other words, a "terphenyl group" is a substituted phenyl group having a C6-C 60 aryl group substituted with a C6-C 60 aryl group as a substituent.

[0537] As used herein, unless otherwise defined, *, *', and *" each refer to the bonding site to an adjacent atom in the corresponding formula.

[0538] Hereinafter, the compounds according to the embodiments and the organic light-emitting devices according to the embodiments will be described in detail with reference to Synthesis Examples and Examples. The expression "using B in place of A" used in the description of the Synthesis Examples means that an equimolar equivalent of B is used in place of A.

[0539] [Synthesis Example]

[0540] Synthesis Example 1: Synthesis of Compound 1

[0541]

[0542] (1) Synthesis of Intermediate Compound [1-A]

[0543] 1,3-Dibromo-5-(trifluoromethyl)benzene (1.0 equivalent), imidazole (3.0 equivalents), CuI (0.02 equivalent), K2CO3 (3.0 equivalents), and L-proline (0.04 equivalent) were dissolved in dimethyl sulfonate (0.1 M), and the mixture was stirred at 160 °C for 48 hours. The reaction mixture was cooled to room temperature, and the extraction process was performed three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate and concentrated using column chromatography to obtain Intermediate Compound [1-A] (yield: 43%).

[0544] (2) Synthesis of Intermediate Compound [1-B]

[0545] The intermediate compound [1-A] (1.0 equivalent) and methyl iodide (3.0 equivalents) were dissolved in toluene (1.0 M), and stirred at a temperature of 120 °C for 12 hours. The reaction mixture was cooled to room temperature, washed with toluene and filtered to obtain a solid. The obtained solid was dried to obtain the intermediate compound [1-B] (yield: 71%).

[0546] (3) Synthesis of intermediate compound [1-C]

[0547] 5-Bromo-1H-imidazole (1.0 equivalent), (2,4-difluorophenyl)boronic acid (1.1 equivalents), PdCl2(PPh3)2 (0.002 equivalent) and K2CO3 (2.0 equivalents) were dissolved in dioxane:H2O (2:1, 0.1 M), and stirred at a temperature of 90 °C for 12 hours. The reaction mixture was cooled to room temperature, and extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate and concentrated using column chromatography to obtain the intermediate compound [1-C] (yield: 66%).

[0548] (4) Synthesis of intermediate compound [1-D]

[0549] The intermediate compound [1-C] (1.0 equivalent), 2-bromo-1,3,5-trimethylbenzene (1.2 equivalents), Pd2(dba)3 (0.002 equivalent) and K3PO4 (2.0 equivalents) were dissolved in toluene (0.1 M), and stirred at a temperature of 120 °C for 24 hours. The reaction mixture was cooled to room temperature, and extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate and concentrated using column chromatography to obtain the intermediate compound [1-D] (yield: 63%).

[0550] (5) Synthesis of intermediate compound [1-E]

[0551] The intermediate compound [1-D] (1.0 equivalent) was dissolved in tetrahydrofuran (0.5 M), and at a temperature of -78 °C, n-butyllithium (1 M in THF, 1.0 equivalent) was slowly added thereto. After stirring the resulting mixture at -78 °C for 30 minutes, N,N-dimethylacetamide (1.2 equivalents) was added thereto. The reaction product was stirred at room temperature for 3 hours. The reaction product was extracted three times with ether and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate and concentrated using column chromatography to obtain the intermediate compound [1-E] (yield: 77%).

[0552] (6) Synthesis of intermediate compound [1-F]

[0553] The intermediate compound [1-E] (1.0 equivalent) and sodium ethoxide (1.2 equivalents) were dissolved in tetrahydrofuran (1.0 M), and ethyl 2,2,2-trifluoroacetate (1.1 equivalents) was added thereto at a temperature of 0 °C. The reaction product was stirred at a temperature of 70 °C for 12 hours. The reaction product was cooled to room temperature and neutralized with 2N aqueous HCl solution. After removing the remaining tetrahydrofuran solvent under reduced pressure, the reaction product was extracted three times with ethyl acetate to obtain an organic layer. The obtained organic layer was dried using sodium sulfate and concentrated. Hydrazine monohydrate (3.0 equivalents), a catalytic amount of NaH, and ethanol (1.0 M) were added thereto, and then stirred at a temperature of 60 °C for 12 hours. After cooling the reaction product to room temperature, the solvent was removed under reduced pressure, and the extraction process with ethyl acetate and H2O was performed three times to obtain an organic layer. The obtained organic layer was dried using sodium sulfate and concentrated using column chromatography to obtain the intermediate compound [1-F] (yield: 72%).

[0554] (7) Synthesis of Compound 1

[0555] The intermediate compound [1-B] (1.0 equivalent), the intermediate compound [1-F] (1.0 equivalent), iridium(III) chloride hydrate (1.1 equivalents), and K2CO3 (10 equivalents) were dissolved in propionic acid (0.2 M), and stirred at a temperature of 140 °C for 12 hours. The reaction was cooled to room temperature, and the solvent was removed therefrom under reduced pressure. The organic layer was extracted three times using dichloromethane and water. The obtained organic layer was dried using magnesium sulfate and concentrated using column chromatography to obtain Compound 1 (yield: 23%).

[0556] Synthesis Example 2: Synthesis of Compound 2

[0557]

[0558] (1) Synthesis of Intermediate Compound [2-F]

[0559] The intermediate compound [1-E] (1.0 equivalent) and sodium ethoxide (1.2 equivalents) were dissolved in tetrahydrofuran (1.0 M), and ethyl acetate (1.1 equivalents) was added thereto at a temperature of 0 °C. The reaction product was stirred at a temperature of 70 °C for 12 hours. The reaction product was cooled to room temperature and neutralized with 2N aqueous HCl solution. After removing the remaining tetrahydrofuran solvent under reduced pressure, the reaction product was extracted three times with ethyl acetate to obtain an organic layer. The obtained organic layer was dried using sodium sulfate and concentrated. Hydrazine monohydrate (3.0 equivalents), a catalytic amount of NaH and ethanol (1.0 M) were added thereto, and then stirred at a temperature of 60 °C for 12 hours. After cooling the reaction product to room temperature, the solvent was removed under reduced pressure, and the extraction process with ethyl acetate and H2O was carried out three times to obtain an organic layer. The obtained organic layer was dried using sodium sulfate and concentrated using column chromatography to obtain the intermediate compound [2-F] (yield: 72%).

[0560] (2) Synthesis of Compound 2

[0561] The intermediate compound [1-B] (2.0 equivalents), the intermediate compound [2-F] (1.0 equivalent), iridium chloride hydrate (1.1 equivalents) and K2CO3 (10 equivalents) were dissolved in propionic acid (0.2 M), and stirred at a temperature of 140 °C for 12 hours. The reaction was cooled to room temperature, and the solvent was removed therefrom under reduced pressure. The organic layer was extracted three times using dichloromethane and water. The obtained organic layer was dried using magnesium sulfate and concentrated using column chromatography to obtain Compound 2 (yield: 23%).

[0562] Synthesis Example 3: Synthesis of Compound 6

[0563]

[0564] (1) Synthesis of Intermediate Compound [6-D]

[0565] The intermediate compound [1-C] (1.0 equivalent) and sodium hydroxide (1.0 equivalent) were dissolved in THF (0.1 M) at a temperature of 65 °C for 10 minutes while stirring. After cooling to room temperature, iodomethane (0.9 equivalent) dissolved in THF (0.1 M) was slowly added thereto. The reaction mixture was cooled to room temperature, and the extraction process with dichloromethane and water was carried out three times to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate and concentrated using column chromatography to obtain the intermediate compound [6-D] (yield: 78%).

[0566] (2) Synthesis of Intermediate Compound [6-E]

[0567] Dissolve the intermediate compound [6-D] (1.0 equivalent) in tetrahydrofuran (0.5 M), and slowly add n-butyllithium (1 M in THF, 1.0 equivalent) thereto at a temperature of -78 °C. After stirring the resulting mixture at -78 °C for 30 minutes, add N,N-dimethylacetamide (1.2 equivalents) thereto. Stir the reaction product at room temperature for 3 hours. Extract the reaction product three times with diethyl ether and water to obtain the organic layer. Dry the obtained organic layer using magnesium sulfate and concentrate it using column chromatography to obtain the intermediate compound [6-E] (yield: 75%).

[0568] (3) Synthesis of intermediate compound [6-F]

[0569] Dissolve the intermediate compound [6-E] (1.0 equivalent) and sodium ethoxide (1.2 equivalents) in tetrahydrofuran (1.0 M), and add ethyl 2,2,2-trifluoroacetate (1.1 equivalents) thereto at a temperature of 0 °C. Stir the reaction product at 70 °C for 12 hours. Cool the reaction product to room temperature and neutralize it with 2N aqueous HCl solution. After removing the remaining tetrahydrofuran solvent under reduced pressure, extract the reaction product three times with ethyl acetate to obtain the organic layer. Dry the obtained organic layer using sodium sulfate and concentrate it. Add hydrazine monohydrate (3.0 equivalents), a catalytic amount of NaH, and ethanol (1.0 M) thereto, and then stir it at 60 °C for 12 hours. After cooling the reaction product to room temperature, remove the solvent under reduced pressure, and extract it three times with ethyl acetate and H2O to obtain the organic layer. Dry the obtained organic layer using sodium sulfate and concentrate it using column chromatography to obtain the intermediate compound [6-F] (yield: 74%).

[0570] (4) Synthesis of compound 6

[0571] Dissolve the intermediate compound [1-B] (1.0 equivalent), the intermediate compound [6-F] (1.0 equivalent), iridium(III) chloride hydrate (1.1 equivalents), and K2CO3 (10 equivalents) in propionic acid (0.2 M), and stir it at 140 °C for 12 hours. Cool the reaction to room temperature and remove the solvent therefrom under reduced pressure. Extract the organic layer three times with dichloromethane and water. Dry the obtained organic layer using magnesium sulfate and concentrate it using column chromatography to obtain compound 6 (yield: 19%).

[0572] Synthesis Example 4: Synthesis of compound 7

[0573]

[0574] (1) Synthesis of intermediate compound [7-D]

[0575] Intermediate compound [1-C] (1.0 equiv), methyl iodide (1.5 equiv), Pd2(dba)3 (0.002 equiv), and K3PO4 (2.0 equiv) were dissolved in toluene (0.1 M) and stirred at 120 °C for 24 h. The reaction mixture was cooled to room temperature and extracted three times with dichloromethane and water to obtain the organic layer. The obtained organic layer was dried over magnesium sulfate and concentrated by column chromatography to obtain intermediate compound [7-D] (yield: 72%).

[0576] (2) Synthesis of intermediate compound [7-E]

[0577] Intermediate compound [7-D] (1.0 equiv) was dissolved in tetrahydrofuran (0.5 M), and n-butyllithium (1 M in THF, 1.0 equiv) was slowly added thereto at -78 °C. After stirring the resulting mixture at -78 °C for 30 min, N,N-dimethylacetamide (1.2 equiv) was added thereto. The reaction product was stirred at room temperature for 3 h. The reaction product was extracted three times with diethyl ether and water to obtain the organic layer. The obtained organic layer was dried over magnesium sulfate and concentrated by column chromatography to obtain intermediate compound [7-E] (yield: 77%).

[0578] (3) Synthesis of intermediate compound [7-F]

[0579] Intermediate compound [7-E] (1.0 equiv) and sodium ethoxide (1.2 equiv) were dissolved in tetrahydrofuran (1.0 M), and ethyl acetate (1.1 equiv) was added thereto at 0 °C. The reaction product was stirred at 70 °C for 12 h. The reaction product was cooled to room temperature and neutralized with 2N aqueous HCl solution. After removing the remaining tetrahydrofuran solvent under reduced pressure, the reaction product was extracted three times with ethyl acetate to obtain the organic layer. The obtained organic layer was dried over sodium sulfate and concentrated. Hydrazine monohydrate (3.0 equiv), a catalytic amount of NaH, and ethanol (1.0 M) were added thereto, and then the mixture was stirred at 60 °C for 12 h. After cooling the reaction product to room temperature, the solvent was removed under reduced pressure, and the reaction product was extracted three times with ethyl acetate and H2O to obtain the organic layer. The obtained organic layer was dried over sodium sulfate and concentrated by column chromatography to obtain intermediate compound [7-F] (yield: 72%).

[0580] (4) Synthesis of compound 7

[0581] The intermediate compound [1-B] (1.0 equivalent), intermediate compound [7-F] (1.0 equivalent), iridium(III) chloride hydrate (1.1 equivalents), and K2CO3 (10 equivalents) were dissolved in propionic acid (0.2 M), and the mixture was stirred at 140 °C for 12 hours. The reaction was cooled to room temperature, and the solvent was removed therefrom under reduced pressure. The organic layer was extracted three times using dichloromethane and water. The obtained organic layer was dried over magnesium sulfate and concentrated by column chromatography to obtain Compound 7 (yield: 23%).

[0582] Synthesis Example 5: Synthesis of Compound 11

[0583]

[0584] (1) Synthesis of Intermediate Compound [11-C]

[0585] 5-Bromo-1H-imidazole (1.0 equivalent), carbazole (1.1 equivalents), Pd(PPh3)4 (0.05 equivalent), and K2CO3 (2.0 equivalents) were dissolved in dioxane:H2O (4:1, 0.1 M), and the mixture was stirred at 110 °C for 12 hours. The reaction mixture was cooled to room temperature, and the extraction process was carried out three times with dichloromethane and water to obtain the organic layer. The obtained organic layer was dried over magnesium sulfate and concentrated by column chromatography to obtain Intermediate Compound [11-C] (yield: 87%).

[0586] (2) Synthesis of Intermediate Compound [11-D]

[0587] Intermediate Compound [11-C] (1.0 equivalent) and sodium hydroxide (1.0 equivalent) were dissolved in THF (0.1 M) at 65 °C for 10 minutes with stirring. After cooling to room temperature, iodomethane (0.9 equivalent) dissolved in THF (0.1 M) was slowly added thereto. The reaction mixture was cooled to room temperature, and the extraction process was carried out three times with dichloromethane and water to obtain the organic layer. The obtained organic layer was dried over magnesium sulfate and concentrated by column chromatography to obtain Intermediate Compound [11-D] (yield: 81%).

[0588] (3) Synthesis of Intermediate Compound [11-E]

[0589] Dissolve intermediate compound [11-D] (1.0 equivalent) in tetrahydrofuran (0.5 M), and slowly add n-butyllithium (1 M in THF, 1.0 equivalent) thereto at a temperature of -78 °C. After stirring the resulting mixture at -78 °C for 30 minutes, add N,N-dimethylacetamide (1.2 equivalents) thereto. Stir the reaction product at room temperature for 3 hours. Extract the reaction product three times with diethyl ether and water to obtain an organic layer. Dry the obtained organic layer using magnesium sulfate, and concentrate it using column chromatography to obtain intermediate compound [11-E] (yield: 77%).

[0590] (4) Synthesis of intermediate compound [11-F]

[0591] Dissolve intermediate compound [11-E] (1.0 equivalent) and sodium ethoxide (1.2 equivalents) in tetrahydrofuran (1.0 M), and add ethyl 2,2,2-trifluoroacetate (1.1 equivalents) thereto at a temperature of 0 °C. Stir the reaction product at 70 °C for 12 hours. Cool the reaction product to room temperature and neutralize it with 2N aqueous HCl solution. After removing the remaining tetrahydrofuran solvent under reduced pressure, extract the reaction product three times with ethyl acetate to obtain an organic layer. Dry the obtained organic layer using sodium sulfate and concentrate it. Add hydrazine monohydrate (3.0 equivalents), a catalytic amount of NaH, and ethanol (1.0 M) thereto, and then stir at 60 °C for 12 hours. After cooling the reaction product to room temperature, remove the solvent under reduced pressure, and extract it three times with ethyl acetate and H2O to obtain an organic layer. Dry the obtained organic layer using sodium sulfate, and concentrate it using column chromatography to obtain intermediate compound [11-F] (yield: 72%).

[0592] (5) Synthesis of compound 11

[0593] Dissolve intermediate compound [1-B] (1.0 equivalent), intermediate compound [11-F] (1.0 equivalent), iridium(III) chloride hydrate (1.1 equivalents), and K2CO3 (10 equivalents) in propionic acid (0.2 M), and stir at 140 °C for 12 hours. Cool the reaction to room temperature, and remove the solvent therefrom under reduced pressure. Extract the organic layer three times with dichloromethane and water. Dry the obtained organic layer using magnesium sulfate, and concentrate it using column chromatography to obtain compound 11 (yield: 21%).

[0594] Synthesis Example 6: Synthesis of compound 12

[0595]

[0596] (1) Synthesis of intermediate compound [12-C]

[0597] 5-Bromo-1H-imidazole (1.0 equiv), carbazole (1.1 equiv), Pd(PPh3)4 (0.05 equiv), and K2CO3 (2.0 equiv) were dissolved in dioxane:H2O (4:1, 0.1 M), and stirred at 110 °C for 12 h. The reaction mixture was cooled to room temperature and extracted three times with dichloromethane and water to obtain the organic layer. The obtained organic layer was dried over magnesium sulfate and concentrated by column chromatography to obtain intermediate compound [12-C] (yield: 88%).

[0598] (2) Synthesis of intermediate compound [12-D]

[0599] Intermediate compound [12-C] (1.0 equiv) and sodium hydroxide (1.0 equiv) were dissolved in THF (0.1 M) at 65 °C for 10 min with stirring. After cooling to room temperature, iodomethane (0.9 equiv) dissolved in THF (0.1 M) was slowly added thereto. The reaction mixture was cooled to room temperature and extracted three times with dichloromethane and water to obtain the organic layer. The obtained organic layer was dried over magnesium sulfate and concentrated by column chromatography to obtain intermediate compound [12-D] (yield: 77%).

[0600] (3) Synthesis of intermediate compound [12-E]

[0601] Intermediate compound [12-D] (1.0 equiv) was dissolved in tetrahydrofuran (0.5 M), and n-butyllithium (1 M in THF, 1.0 equiv) was slowly added thereto at -78 °C. After stirring the resulting mixture at -78 °C for 30 min, N,N-dimethylacetamide (1.2 equiv) was added thereto. The reaction product was stirred at room temperature for 3 h. The reaction product was extracted three times with diethyl ether and water to obtain the organic layer. The obtained organic layer was dried over magnesium sulfate and concentrated by column chromatography to obtain intermediate compound [12-E] (yield: 76%).

[0602] (4) Synthesis of intermediate compound [12-F]

[0603] The intermediate compound [12-E] (1.0 equivalent) and sodium ethoxide (1.2 equivalents) were dissolved in tetrahydrofuran (1.0 M), and ethyl acetate (1.1 equivalents) was added thereto at a temperature of 0 °C. The reaction product was stirred at a temperature of 70 °C for 12 hours. The reaction product was cooled to room temperature and neutralized with 2N aqueous HCl solution. After removing the remaining tetrahydrofuran solvent under reduced pressure, the reaction product was extracted three times with ethyl acetate to obtain an organic layer. The obtained organic layer was dried using sodium sulfate and concentrated. Hydrazine monohydrate (3.0 equivalents), a catalytic amount of NaH, and ethanol (1.0 M) were added thereto, and then it was stirred at a temperature of 60 °C for 12 hours. After cooling the reaction product to room temperature, the solvent was removed under reduced pressure, and it was extracted three times with ethyl acetate and H2O to obtain an organic layer. The obtained organic layer was dried using sodium sulfate and concentrated using column chromatography to obtain the intermediate compound [12-F] (yield: 72%).

[0604] (5) Synthesis of Compound 12

[0605] The intermediate compound [1-B] (1.0 equivalent), the intermediate compound [12-F] (1.0 equivalent), iridium(III) chloride hydrate (1.1 equivalents), and K2CO3 (10 equivalents) were dissolved in propionic acid (0.2 M), and it was stirred at a temperature of 140 °C for 12 hours. The reaction was cooled to room temperature, and the solvent was removed therefrom under reduced pressure. The organic layer was extracted three times with dichloromethane and water. The obtained organic layer was dried using magnesium sulfate and concentrated using column chromatography to obtain Compound 12 (yield: 23%).

[0606] Synthesis Example 7: Synthesis of Compound 21

[0607]

[0608] (1) Synthesis of Intermediate Compound [21-A]

[0609] 1,3-Dibromo-5-(trifluoromethyl)benzene (1.0 equivalent), imidazole (3.0 equivalents), CuI (0.02 equivalent), K2CO3 (3.0 equivalents), and L-proline (0.04 equivalent) were dissolved in dimethyl sulfonate (0.1 M), and it was stirred at a temperature of 160 °C for 48 hours. The reaction mixture was cooled to room temperature, and the extraction process was carried out three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate and concentrated using column chromatography to obtain the intermediate compound [21-A] (yield: 43%).

[0610] (2) Synthesis of Intermediate Compound [21-B]

[0611] The intermediate compound [21-A] (1.0 equivalent) was dissolved in 2-iodopropane (3.0 equivalents) and stirred at a temperature of 120 °C for 12 hours. The reaction mixture was cooled to room temperature, washed with diethyl ether and filtered to obtain a solid. The obtained solid was dried to obtain the intermediate compound [21-B] (yield: 52%).

[0612] (3) Synthesis of intermediate compound [21-D]

[0613] The intermediate compound [1-C] (1.0 equivalent) and sodium hydroxide (1.0 equivalent) were dissolved in THF (0.1 M) at a temperature of 65 °C for 10 minutes with stirring. After cooling to room temperature, methyl iodide (0.9 equivalent) dissolved in THF (0.1 M) was slowly added thereto. The reaction mixture was cooled to room temperature and extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate and concentrated using column chromatography to obtain the intermediate compound [21-D] (yield: 78%).

[0614] (4) Synthesis of intermediate compound [21-E]

[0615] The intermediate compound [21-D] (1.0 equivalent) was dissolved in tetrahydrofuran (0.5 M), and at a temperature of -78 °C, n-butyllithium (1 M in THF, 1.0 equivalent) was slowly added thereto. After stirring the resulting mixture at -78 °C for 30 minutes, N,N-dimethylacetamide (1.2 equivalents) was added thereto. The reaction product was stirred at room temperature for 3 hours. The reaction product was extracted three times with diethyl ether and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate and concentrated using column chromatography to obtain the intermediate compound [21-E] (yield: 75%).

[0616] (5) Synthesis of intermediate compound [21-F]

[0617] The intermediate compound [21-E] (1.0 equivalent) and sodium ethoxide (1.2 equivalents) were dissolved in tetrahydrofuran (1.0 M), and ethyl 2,2,2-trifluoroacetate (1.1 equivalents) was added thereto at a temperature of 0 °C. The reaction product was stirred at a temperature of 70 °C for 12 hours. The reaction product was cooled to room temperature and neutralized with 2N aqueous HCl solution. After removing the remaining tetrahydrofuran solvent under reduced pressure, the reaction product was extracted three times with ethyl acetate to obtain an organic layer. The obtained organic layer was dried using sodium sulfate and concentrated. Hydrazine monohydrate (3.0 equivalents), a catalytic amount of NaH, and ethanol (1.0 M) were added thereto, and then it was stirred at a temperature of 60 °C for 12 hours. After cooling the reaction product to room temperature, the solvent was removed under reduced pressure, and it was extracted three times with ethyl acetate and H2O to obtain an organic layer. The obtained organic layer was dried using sodium sulfate and concentrated using column chromatography to obtain the intermediate compound [21-F] (yield: 74%).

[0618] (6) Synthesis of Compound 21

[0619] The intermediate compound [21-B] (1.0 equivalent), the intermediate compound [21-F] (1.0 equivalent), iridium(III) chloride hydrate (1.1 equivalents), and K2CO3 (10 equivalents) were dissolved in propionic acid (0.2 M), and it was stirred at a temperature of 140 °C for 12 hours. The reaction was cooled to room temperature, and the solvent was removed therefrom under reduced pressure. The organic layer was extracted three times with dichloromethane and water. The obtained organic layer was dried using magnesium sulfate and concentrated using column chromatography to obtain Compound 21 (yield: 18%).

[0620] Synthesis Example 8: Synthesis of Compound 22

[0621]

[0622] (1) Synthesis of Intermediate Compound [22-D]

[0623] The intermediate compound [1-C] (1.0 equivalent), methyl iodide (1.5 equivalents), Pd2(dba)3 (0.002 equivalent), and K3PO4 (2.0 equivalents) were dissolved in toluene (0.1 M), and it was stirred at a temperature of 120 °C for 24 hours. The reaction mixture was cooled to room temperature, and it was extracted three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate and concentrated using column chromatography to obtain the intermediate compound [22-D] (yield: 74%).

[0624] (2) Synthesis of Intermediate Compound [22-E]

[0625] The intermediate compound [22-D] (1.0 equivalent) was dissolved in tetrahydrofuran (0.5 M), and at a temperature of -78 °C, n-butyllithium (1 M in THF, 1.0 equivalent) was slowly added thereto. After stirring the resulting mixture at -78 °C for 30 minutes, N,N-dimethylacetamide (1.2 equivalents) was added thereto. The reaction product was stirred at room temperature for 3 hours. The reaction product was extracted three times with diethyl ether and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate and concentrated using column chromatography to obtain intermediate compound [22-E] (yield: 78%).

[0626] (3) Synthesis of intermediate compound [22-F]

[0627] The intermediate compound [22-E] (1.0 equivalent) and sodium ethoxide (1.2 equivalents) were dissolved in tetrahydrofuran (1.0 M), and ethyl acetate (1.1 equivalents) was added thereto at a temperature of 0 °C. The reaction product was stirred at 70 °C for 12 hours. The reaction product was cooled to room temperature and neutralized with 2N aqueous HCl solution. After removing the remaining tetrahydrofuran solvent under reduced pressure, the reaction product was extracted three times with ethyl acetate to obtain an organic layer. The obtained organic layer was dried using sodium sulfate and concentrated. Hydrazine monohydrate (3.0 equivalents), a catalytic amount of NaH, and ethanol (1.0 M) were added thereto, and then the mixture was stirred at 60 °C for 12 hours. After cooling the reaction product to room temperature, the solvent was removed under reduced pressure, and the mixture was extracted three times with ethyl acetate and H2O to obtain an organic layer. The obtained organic layer was dried using sodium sulfate and concentrated using column chromatography to obtain intermediate compound [22-F] (yield: 75%).

[0628] (4) Synthesis of compound 22

[0629] The intermediate compound [21-B] (1.0 equivalent), the intermediate compound [22-F] (1.0 equivalent), iridium(III) chloride hydrate (1.1 equivalents), and K2CO3 (10 equivalents) were dissolved in propionic acid (0.2 M), and the mixture was stirred at 140 °C for 12 hours. The reaction was cooled to room temperature, and the solvent was removed therefrom under reduced pressure. The organic layer was extracted three times with dichloromethane and water. The obtained organic layer was dried using magnesium sulfate and concentrated using column chromatography to obtain compound 22 (yield: 19%).

[0630] Synthesis Example 9: Synthesis of compound 36

[0631]

[0632] (1) Synthesis of intermediate compound [36-A]

[0633] 3,5-Dibromobenzyl cyanide (1.0 eq), imidazole (3.0 eq), CuI (0.02 eq), K2CO3 (3.0 eq) and N,N-dimethylglycine (0.05 eq) were dissolved in N,N-dimethylformamide (0.1 M) and stirred at 160 °C for 48 h. The reaction mixture was cooled to room temperature and extracted three times with dichloromethane and water to obtain the organic layer. The obtained organic layer was dried over magnesium sulfate and concentrated by column chromatography to obtain intermediate compound [36-A] (yield: 80%).

[0634] (2) Synthesis of intermediate compound [36-B]

[0635] Intermediate compound [36-A] (1.0 eq) and methyl iodide (3.0 eq) were dissolved in toluene (1.0 M) and stirred at 120 °C for 12 h. The reaction mixture was cooled to room temperature, washed with toluene and filtered to obtain a solid. The obtained solid was dried to obtain intermediate compound [36-B] (yield: 71%).

[0636] (3) Synthesis of intermediate compound [36-D]

[0637] Intermediate compound [1-C] (1.0 eq) and sodium hydroxide (1.0 eq) were dissolved in THF (0.1 M) at 65 °C for 10 min with stirring. After cooling to room temperature, methyl iodide (0.9 eq) dissolved in THF (0.1 M) was slowly added thereto. The reaction mixture was cooled to room temperature and extracted three times with dichloromethane and water to obtain the organic layer. The obtained organic layer was dried over magnesium sulfate and concentrated by column chromatography to obtain intermediate compound [36-D] (yield: 79%).

[0638] (4) Synthesis of intermediate compound [36-E]

[0639] Intermediate compound [36-D] (1.0 eq) was dissolved in tetrahydrofuran (0.5 M), and n-butyllithium (1 M in THF, 1.0 eq) was slowly added thereto at -78 °C. After stirring the resulting mixture at -78 °C for 30 min, N,N-dimethylacetamide (1.2 eq) was added thereto. The reaction product was stirred at room temperature for 3 h. The reaction product was extracted three times with ether and water to obtain the organic layer. The obtained organic layer was dried over magnesium sulfate and concentrated by column chromatography to obtain intermediate compound [36-E] (yield: 76%).

[0640] (5) Synthesis of intermediate compound [36-F]

[0641] The intermediate compound [36-E] (1.0 equivalent) and sodium ethoxide (1.2 equivalents) were dissolved in tetrahydrofuran (1.0 M), and ethyl 2,2,2-trifluoroacetate (1.1 equivalents) was added thereto at a temperature of 0 °C. The reaction product was stirred at a temperature of 70 °C for 12 hours. The reaction product was cooled to room temperature and neutralized with 2N aqueous HCl solution. After removing the remaining tetrahydrofuran solvent under reduced pressure, the reaction product was extracted three times with ethyl acetate to obtain an organic layer. The obtained organic layer was dried using sodium sulfate and concentrated. Hydrazine monohydrate (3.0 equivalents), a catalytic amount of NaH, and ethanol (1.0 M) were added thereto, and then it was stirred at a temperature of 60 °C for 12 hours. After the reaction product was cooled to room temperature, the solvent was removed under reduced pressure, and it was extracted three times with ethyl acetate and H2O to obtain an organic layer. The obtained organic layer was dried using sodium sulfate and concentrated using column chromatography to obtain the intermediate compound [36-F] (yield: 78%).

[0642] (6) Synthesis of Compound 36

[0643] The intermediate compound [36-B] (1.0 equivalent), the intermediate compound [36-F] (1.0 equivalent), iridium(III) chloride hydrate (1.1 equivalents), and K2CO3 (10 equivalents) were dissolved in propionic acid (0.2 M), and it was stirred at a temperature of 140 °C for 12 hours. The reaction was cooled to room temperature, and the solvent was removed therefrom under reduced pressure. The organic layer was extracted three times with dichloromethane and water. The obtained organic layer was dried using magnesium sulfate and concentrated using column chromatography to obtain Compound 36 (yield: 23%).

[0644] Synthesis Example 10: Synthesis of Compound 37

[0645]

[0646] (1) Synthesis of Intermediate Compound [37-D]

[0647] The intermediate compound [1-C] (1.0 equivalent), methyl iodide (1.5 equivalents), Pd2(dba)3 (0.002 equivalents), and K3PO4 (2.0 equivalents) were dissolved in toluene (0.1 M), and it was stirred at a temperature of 120 °C for 24 hours. The reaction mixture was cooled to room temperature, and the extraction process was carried out three times with dichloromethane and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate and concentrated using column chromatography to obtain the intermediate compound [37-D] (yield: 71%).

[0648] (2) Synthesis of Intermediate Compound [37-E]

[0649] Dissolve the intermediate compound [37-D] (1.0 equivalent) in tetrahydrofuran (0.5 M), and slowly add n-butyllithium (1 M in THF, 1.0 equivalent) thereto at a temperature of -78 °C. After stirring the resulting mixture at -78 °C for 30 minutes, add N,N-dimethylacetamide (1.2 equivalents) thereto. Stir the reaction product at room temperature for 3 hours. Extract the reaction product three times with ether and water to obtain the organic layer. Dry the obtained organic layer with magnesium sulfate and concentrate it by column chromatography to obtain the intermediate compound [37-E] (yield: 76%).

[0650] (3) Synthesis of intermediate compound [37-F]

[0651] Dissolve the intermediate compound [37-E] (1.0 equivalent) and sodium ethoxide (1.2 equivalents) in tetrahydrofuran (1.0 M), and add ethyl acetate (1.1 equivalents) thereto at a temperature of 0 °C. Stir the reaction product at a temperature of 70 °C for 12 hours. Cool the reaction product to room temperature and neutralize it with 2N aqueous HCl solution. After removing the remaining tetrahydrofuran solvent under reduced pressure, extract the reaction product three times with ethyl acetate to obtain the organic layer. Dry the obtained organic layer with sodium sulfate and concentrate it. Add hydrazine monohydrate (3.0 equivalents), a catalytic amount of NaH, and ethanol (1.0 M) thereto, and then stir it at a temperature of 60 °C for 12 hours. After cooling the reaction product to room temperature, remove the solvent under reduced pressure, and extract it three times with ethyl acetate and H2O to obtain the organic layer. Dry the obtained organic layer with sodium sulfate and concentrate it by column chromatography to obtain the intermediate compound [37-F] (yield: 75%).

[0652] (4) Synthesis of compound 37

[0653] Dissolve the intermediate compound [36-B] (1.0 equivalent), the intermediate compound [37-F] (1.0 equivalent), iridium(III) chloride hydrate (1.1 equivalents), and K2CO3 (10 equivalents) in propionic acid (0.2 M), and stir it at a temperature of 140 °C for 12 hours. Cool the reaction to room temperature and remove the solvent therefrom under reduced pressure. Extract the organic layer three times with dichloromethane and water. Dry the obtained organic layer with magnesium sulfate and concentrate it by column chromatography to obtain compound 37 (yield: 22%).

[0654] Synthesis Example 11: Synthesis of compound 41

[0655]

[0656] (1) Synthesis of intermediate compound [41-A]

[0657] 1,3 - dibromobenzene (1.0 eq), imidazole (3.0 eq), CuI (0.02 eq), K₂CO₃ (3.0 eq), and N,N - dimethylglycine (0.05 eq) were dissolved in N,N - dimethylformamide (0.1 M) and stirred at 160 °C for 48 h. The reaction mixture was cooled to room temperature and extracted three times with dichloromethane and water to obtain the organic layer. The obtained organic layer was dried over magnesium sulfate and concentrated by column chromatography to obtain intermediate compound [41 - A] (yield: 79%).

[0658] (2) Synthesis of intermediate compound [41 - B]

[0659] Intermediate compound [41 - A] (1.0 eq) and iodomethane (3.0 eq) were dissolved in toluene (1.0 M) and stirred at 120 °C for 12 h. The reaction mixture was cooled to room temperature, washed with toluene, and filtered to obtain a solid. The obtained solid was dried to obtain intermediate compound [41 - B] (yield: 76%).

[0660] (3) Synthesis of intermediate compound [41 - D]

[0661] Intermediate compound [1 - C] (1.0 eq) and sodium hydroxide (1.0 eq) were dissolved in THF (0.1 M) at 65 °C for 10 min with stirring. After cooling to room temperature, iodomethane (0.9 eq) dissolved in THF (0.1 M) was slowly added thereto. The reaction mixture was cooled to room temperature and extracted three times with dichloromethane and water to obtain the organic layer. The obtained organic layer was dried over magnesium sulfate and concentrated by column chromatography to obtain intermediate compound [41 - D] (yield: 79%).

[0662] (4) Synthesis of intermediate compound [41 - E]

[0663] Intermediate compound [41 - D] (1.0 eq) was dissolved in tetrahydrofuran (0.5 M), and n - butyllithium (1 M in THF, 1.0 eq) was slowly added thereto at - 78 °C. After stirring the resulting mixture at - 78 °C for 30 min, N,N - dimethylacetamide (1.2 eq) was added thereto. The reaction product was stirred at room temperature for 3 h. The reaction product was extracted three times with diethyl ether and water to obtain the organic layer. The obtained organic layer was dried over magnesium sulfate and concentrated by column chromatography to obtain intermediate compound [41 - E] (yield: 76%).

[0664] (5) Synthesis of intermediate compound [41 - F]

[0665] Dissolve intermediate compound [41-E] (1.0 equivalent) and sodium ethoxide (1.2 equivalents) in tetrahydrofuran (1.0 M), and add ethyl 2,2,2-trifluoroacetate (1.1 equivalents) thereto at a temperature of 0 °C. Stir the reaction product at a temperature of 70 °C for 12 hours. Cool the reaction product to room temperature and neutralize it with 2N aqueous HCl solution. After removing the remaining tetrahydrofuran solvent under reduced pressure, extract the reaction product with ethyl acetate three times to obtain an organic layer. Dry the obtained organic layer with sodium sulfate and concentrate it. Add hydrazine monohydrate (3.0 equivalents), a catalytic amount of NaH, and ethanol (1.0 M) thereto, and then stir at a temperature of 60 °C for 12 hours. After cooling the reaction product to room temperature, remove the solvent under reduced pressure, and perform an extraction process with ethyl acetate and H2O three times to obtain an organic layer. Dry the obtained organic layer with sodium sulfate, and concentrate it using column chromatography to obtain intermediate compound [41-F] (yield: 78%).

[0666] (6) Synthesis of Compound 41

[0667] Dissolve intermediate compound [41-B] (1.0 equivalent), intermediate compound [41-F] (1.0 equivalent), iridium(III) chloride hydrate (1.1 equivalents), and K2CO3 (10 equivalents) in propionic acid (0.2 M), and stir at a temperature of 140 °C for 12 hours. Cool the reaction to room temperature and remove the solvent therefrom under reduced pressure. Extract the organic layer therefrom three times with dichloromethane and water. Dry the obtained organic layer with magnesium sulfate, and concentrate it using column chromatography to obtain Compound 41 (yield: 23%).

[0668] Synthesis Example 12: Synthesis of Compound 42

[0669]

[0670] (1) Synthesis of Intermediate Compound [42-D]

[0671] Dissolve intermediate compound [1-C] (1.0 equivalent), methyl iodide (1.5 equivalents), Pd2(dba)3 (0.002 equivalent), and K3PO4 (2.0 equivalents) in toluene (0.1 M), and stir at a temperature of 120 °C for 24 hours. Cool the reaction mixture to room temperature, and perform an extraction process with dichloromethane and water three times to obtain an organic layer. Dry the obtained organic layer with magnesium sulfate, and concentrate it using column chromatography to obtain intermediate compound [42-D] (yield: 71%).

[0672] (2) Synthesis of Intermediate Compound [42-E]

[0673] The intermediate compound [42-D] (1.0 equivalent) was dissolved in tetrahydrofuran (0.5 M), and n-butyllithium (1 M in THF, 1.0 equivalent) was slowly added thereto at a temperature of -78 °C. After stirring the resulting mixture at -78 °C for 30 minutes, N,N-dimethylacetamide (1.2 equivalents) was added thereto. The reaction product was stirred at room temperature for 3 hours. The reaction product was extracted three times with ether and water to obtain an organic layer. The obtained organic layer was dried using magnesium sulfate and concentrated using column chromatography to obtain the intermediate compound [42-E] (yield: 76%).

[0674] (3) Synthesis of intermediate compound [42-F]

[0675] The intermediate compound [42-E] (1.0 equivalent) and sodium ethoxide (1.2 equivalents) were dissolved in tetrahydrofuran (1.0 M), and ethyl acetate (1.1 equivalents) was added thereto at a temperature of 0 °C. The reaction product was stirred at a temperature of 70 °C for 12 hours. The reaction product was cooled to room temperature and neutralized with 2N aqueous HCl solution. After removing the remaining tetrahydrofuran solvent under reduced pressure, the reaction product was extracted three times with ethyl acetate to obtain an organic layer. The obtained organic layer was dried using sodium sulfate and concentrated. Hydrazine monohydrate (3.0 equivalents), a catalytic amount of NaH, and ethanol (1.0 M) were added thereto, and then the mixture was stirred at a temperature of 60 °C for 12 hours. After cooling the reaction product to room temperature, the solvent was removed under reduced pressure, and the mixture was extracted three times with ethyl acetate and H2O to obtain an organic layer. The obtained organic layer was dried using sodium sulfate and concentrated using column chromatography to obtain the intermediate compound [42-F] (yield: 75%).

[0676] (4) Synthesis of compound 42

[0677] The intermediate compound [41-B] (1.0 equivalent), the intermediate compound [42-F] (1.0 equivalent), iridium chloride hydrate (1.1 equivalents), and K2CO3 (10 equivalents) were dissolved in propionic acid (0.2 M), and the mixture was stirred at a temperature of 140 °C for 12 hours. The reaction was cooled to room temperature, and the solvent was removed therefrom under reduced pressure. The organic layer was extracted three times with dichloromethane and water. The obtained organic layer was dried using magnesium sulfate and concentrated using column chromatography to obtain compound 42 (yield: 22%).

[0678] For the compounds synthesized in Synthesis Examples 1 to 12 1 1H NMR and LC-MS are shown in Table 1 below.

[0679] Those skilled in the art can even easily recognize compounds other than the compounds shown in Table 1 by referring to the above synthetic routes and starting materials.

[0680] [Table 1]

[0681]

[0682]

[0683] [Evaluation Example]

[0684] Measure the highest occupied molecular orbital (HOMO) energy level, LUMO energy level, and T1 energy of the compounds synthesized according to Synthesis Examples 1 to 12, and perform quantum simulation of the bond dissociation energy (BDE) between Ir and the nitrogen atom in the imidazole ring and 3 the MC state energy, and the results are shown in Table 2. The HOMO, LUMO, and T1 energies are measured by differential pulse voltammetry and UV-Vis spectroscopy. The bond dissociation energy is calculated by structural optimization at the B3LYP, 6-31G(d,p) level using the density functional theory (DFT) calculation method of the Gaussian program.

[0685] [Table 2]

[0686]

[0687]

[0688] T1 (nm) is the wavelength calculated from the T1 energy (eV) according to the photon energy formula E = hc / λ.

[0689] <Compound C1>

[0690]

[0691] <Compound C2>

[0692]

[0693] <Compound C3>

[0694]

[0695] [Example]

[0696] Example 1

[0697] For the anode, Corning 15 Ω / cm 2 The ITO glass substrate was cut into a size of 50 mm × 50 mm × 0.7 mm, ultrasonically cleaned with isopropyl alcohol and pure water for 5 minutes each, and irradiated with ultraviolet light for 30 minutes, and then exposed to ozone for cleaning. The resulting structure was placed in a vacuum deposition apparatus. 2-TNATA was vacuum deposited on the glass substrate to form a hole injection layer with a thickness of , and 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter referred to as NPB) was vacuum deposited on the hole injection layer to form a hole transport layer with a thickness of . Compound 1 (10% by weight) as a dopant and 3,3-bis(9H-carbazol-9-yl)biphenyl (mCBP) as a host were co-deposited on the hole transport layer to form an emission layer with a thickness of . Diphenyl(4-(triphenylsilyl)phenyl)-phosphine oxide (TSPO1) was vacuum deposited on the emission layer to form a hole blocking layer with a thickness of . Alq3 was deposited on the hole blocking layer to form an electron transport layer with a thickness of , and LiF as an alkali metal halide was deposited on the electron transport layer to form an electron injection layer with a thickness of , and Al was vacuum deposited thereon to form a cathode with a thickness of to form a LiF / Al electrode, thus completing the fabrication of the organic light-emitting device.

[0698] Examples 2 to 12

[0699] An organic light-emitting device was fabricated in the same manner as in Example 1, but in forming the emission layer, the compounds shown in Table 3 were used instead of Compound 1 as the dopant.

[0700] Comparative Examples 1 to 3

[0701] An organic light-emitting device was fabricated in the same manner as in Example 1, but in forming the emission layer, Compounds C1 to C3 were used instead of Compound 1 as the dopant.

[0702] The driving voltage, luminance, luminous efficiency, and maximum emission wavelength of the organic light-emitting devices fabricated according to Examples 1 to 12 and Comparative Examples 1 to 3 were measured by using a Keithley SMU 236 and a luminance meter PR650 at a current density of 50 mA / cm 2 . The results are shown in Table 3.

[0703] [Table 3]

[0704]

[0705] As shown in Table 3, compared with the organic light-emitting devices of Comparative Examples 1 to 3, the organic light-emitting devices of Examples 1 to 12 using the compound according to one embodiment as a dopant in the emission layer have a lower driving voltage, higher efficiency, and higher color purity.

[0706] For example, when an organometallic compound is used in an organic light-emitting device, high color purity can be achieved, and excellent effects can be obtained in terms of driving voltage, efficiency, and service life.

[0707] The organic light-emitting device containing the organometallic compound can have a low driving voltage, high efficiency, and long service life, and its emission wavelength can be easily controlled, resulting in high color purity.

[0708] It should be understood that the embodiments described herein should be considered only in a descriptive sense and not for purposes of limitation. The description of features or aspects within each embodiment should generally be considered applicable to other similar features or aspects in other embodiments. Although the embodiments have been described with reference to the accompanying drawings, those of ordinary skill in the art should understand that various changes in form and detail may be made herein without departing from the spirit and scope defined by the claims.

Claims

1. An organic light-emitting device, comprising: a first electrode; a second electrode facing the first electrode; and an organic layer disposed between the first electrode and the second electrode and including an emission layer, wherein the organic light-emitting device contains an organometallic compound represented by Formula 1: <Formula 1> M(L A ) n1 (L B ) n2 wherein in Formula 1, M is selected from iridium and rhodium, n1 is 1, n2 is 1, L A is a tridentate ligand represented by Formula 1A, and L B which is a tridentate ligand represented by Formula 1B-1: wherein in Formula 1A and Formula 1B-1, *, *' and *” are each a bonding site to M, Y1 is N, and Y3 is C, X 21 selected from C(Z 21 ), N(Z 21 ), N, O and S, X 22 selected from C(Z 22 ), N(Z 22 ), N, O, and S, X 42 is C(R 42 ), and X 43 is C(R 43 ), X 51 is C(R 51 ), X 52 is C(R 52 ), and X 53 is C(R 53 ), X 62 is C(R 62 ), and X 63 is C(R 63 ), (R1) b1 - A1 is selected from the groups represented by formula A1-15 and formula A1-19: in Formula A1-15 and Formula A1-19, * is a bonding site to M, and *' represents a bonding site to an adjacent atom; A3 is a benzene ring; A2 is selected from the groups represented by Formula A2-1 to Formula A2-6 and Formula A2-10 to Formula A2-15: in Formula A2-1 to Formula A2-6 and Formula A2-10 to Formula A2-15, * is a bonding site to L1, *' is a bonding site to M, and *” is a bonding site to L2; L1 and L2 are each independently selected from *-O-*', *-S-*', *-C(R7)(R8)-*' and *-N(R7)-*', a1 and a2 are each independently selected from 0 and 1, Z 21 、Z 22 、R 11 、R 12 、R3, R7, R8, R 41 to R 43 、R 51 to R 53 and R 61 to R 63 each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, a substituted or unsubstituted C1-C 60 alkyl group, a substituted or unsubstituted C1-C 60 alkoxy group, a substituted or unsubstituted C6-C 60 aryl group and a substituted or unsubstituted C1-C 60 heteroaryl group, b3 is selected from 1, 2, 3 and 4, The condition is that R3 and R7 are optionally joined together to form a substituted or unsubstituted C5-C 24 carbocyclic group or a substituted or unsubstituted C1-C 24 heterocyclic group, and The substituted C5-C 24 carbocyclic group, the substituted C1-C 24 heterocyclic group, the substituted C1-C 60 alkyl group, the substituted C1-C 60 alkoxy group, the substituted C6-C 60 aryl group and at least one substituent of the substituted C1-C 60 heteroaryl group is selected from: Deuterium, -F, -Cl, -Br, -I, hydroxy group, cyano group, nitro group, C1-C 10 alkyl group and C1-C 10 alkoxy group.

2. The organic light-emitting device according to claim 1, wherein the organometallic compound has a T1 energy of greater than or equal to 2.25 eV.

3. The organic light-emitting device according to claim 1, wherein the organic layer contains the organometallic compound.

4. The organic light-emitting device according to claim 1, wherein the emission layer contains the organometallic compound.

5. The organic light-emitting device according to claim 4, wherein the emission layer further contains a host, and the amount of the host contained in the emission layer is greater than the amount of the organometallic compound contained in the emission layer.

6. The organic light-emitting device according to claim 4, wherein the emission layer emits light having a maximum emission wavelength of 445 nm to 550 nm.

7. The organic light-emitting device according to claim 1, wherein the first electrode is an anode, the second electrode is a cathode, the organic layer further includes: a hole transport region disposed between the first electrode and the emission layer; and an electron transport region disposed between the emission layer and the second electrode, the hole transport region includes a hole injection layer, a hole transport layer, an emission assist layer, an electron blocking layer or any combination thereof, and the electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer or any combination thereof.

8. An organometallic compound represented by Formula 1: <Formula 1> M(L A ) n1 (L B ) n2 wherein in Formula 1, M is selected from iridium and rhodium, n1 is 1, n2 is 1, L A is a tridentate ligand represented by Formula 1A, and L B is a tridentate ligand represented by Formula 1B-1: wherein in Formula 1A and Formula 1B-1, *, *' and *” are each a bonding site to M, Y1 is N, and Y3 is C, X 21 selected from C(Z 21 ), N(Z 21 ), N, O, and S, X 22 selected from C(Z 22 ), N(Z 22 ), N, O, and S, X 42 is C(R 42 ), and X 43 is C(R 43 ), X 51 is C(R 51 ), X 52 is C(R 52 ), and X 53 is C(R 53 ). X 62 is C(R 62 ), and X 63 is C(R 63 ). (R1) b1 - A1 is selected from the groups represented by formula A1-15 and formula A1-19: in Formula A1-15 and Formula A1-19, * is a bonding site to M, and *' represents a bonding site to an adjacent atom; A3 is a benzene ring; A2 is selected from the groups represented by Formula A2-1 to Formula A2-6 and Formula A2-10 to Formula A2-15: In Formulas A2-1 to A2-6 and Formulas A2-10 to A2-15, * is the bonding site to L1, *' is the bonding site to M, and *" is the bonding site to L2; L1 and L2 are each independently selected from *-O-*', *-S-*', *-C(R7)(R8)-*', and *-N(R7)-*'; a1 and a2 are each independently selected from 0 and 1; Z 21 、Z 22 、R 11 、R 12 、R3, R7, R8, R 41 to R 43 、R 51 to R 53 and R 61 to R 63 each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxy group, a cyano group, a nitro group, a substituted or unsubstituted C1-C 60 alkyl group, a substituted or unsubstituted C1-C 60 alkoxy group, a substituted or unsubstituted C6-C 60 aryl group and a substituted or unsubstituted C1-C 60 heteroaryl group, b3 is selected from 1, 2, 3, and 4; The condition is that R3 and R7 are optionally connected together to form a substituted or unsubstituted C5-C 24 carbocyclic group or a substituted or unsubstituted C1-C 24 heterocyclic group, and The at least one substituent of the substituted C5-C 24 carbocyclic group, the substituted C1-C 24 heterocyclic group, the substituted C1-C 60 alkyl group, the substituted C1-C 60 alkoxy group, the substituted C6-C 60 aryl group and the substituted C1-C 60 heteroaryl group is selected from: Deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, a C1-C 10 alkyl group and a C1-C 10 alkoxy group.

9. The organometallic compound according to claim 8, wherein in Formula 1A, the bond between Y1 and M is a covalent bond, the bond between M and the N in A2 that is connected to *' is a coordination bond, and the bond between Y3 and M is a covalent bond, and in Formula 1B-1, the bond between * and M is a coordination bond, the bond between *' and M is a covalent bond, and the bond between *" and M is a coordination bond.

10. The organometallic compound according to claim 8, wherein the moiety represented by in Formula 1A is represented by one of Formula AL-1 to Formula AL-5, Formula AL-9 to Formula AL-11, Formula AL-15, Formula AL-16, and Formula AL-20: Wherein in Formulas AL-1 to AL-5, Formulas AL-9 to AL-11, Formula AL-15, Formula AL-16, and Formula AL-20, R 31 to R 33 each independently is the same as described for R3 in Formula 1A, R 71 to R 74 is the same as that described for R7 in Formula 1A, *" is the bonding site to M, and * is the bonding site to A2.

11. The organometallic compound according to claim 8, wherein Z 21 、Z 22 、R 11 、R 12 、R3 of the quantity b3, R 41 to R 43 、R 51 to R 53 and R 61 to R 63 and at least one of them is selected from: -F, a cyano group, a C1-C 10 alkyl group substituted with at least one -F, a C1-C 10 alkyl group substituted with at least one -Cl, a C1-C 10 alkyl group substituted with at least one -Br, and a C1-C 10 alkyl group substituted with at least one -I.

12. The organometallic compound according to claim 8, wherein the organometallic compound is one selected from the following compounds: wherein Me represents a methyl group.

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