Organic metal compound, organic light-emitting device including the same, and apparatus including the organic light-emitting device

Abstract

An organic metal compound is represented by Formula 1. An organic light-emitting device includes: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode, the organic layer including a light-emitting layer and at least one organic metal compound represented by Formula 1. A device includes the above organic light-emitting device.

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2018-0074983 filed in the Korean Intellectual Property Office on June 28, 2018, the entire contents of which are incorporated herein by reference. Technical Field

[0003] One or more embodiments of the present disclosure are directed to an organic metal compound, an organic light-emitting device including the organic metal compound, and an apparatus including the organic light-emitting device. Background Art

[0004] Organic light-emitting devices are self-luminous devices that produce full-color images and also have wide viewing angles, high contrast, short response times, and excellent brightness, driving voltage, and response speed characteristics compared to other devices in the art.

[0005] An example of such an organic light-emitting device may include a first electrode disposed on a substrate, and a hole transport region, a light-emitting layer, an electron transport region, and a second electrode sequentially disposed on the first electrode. Holes provided by the first electrode may move toward the light-emitting layer through the hole transport region, and electrons provided by the second electrode may move toward the light-emitting layer through the electron transport region. Carriers (such as holes and electrons) recombine in the light-emitting layer to generate excitons. These excitons transition (e.g., transition or relax) from an excited state to a ground state, thereby generating light. Summary of the invention

[0006] One or more embodiments of the present disclosure provide a novel organometallic compound, an organic light-emitting device including the organometallic compound, and an apparatus including the organic light-emitting device.

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

[0008] One aspect of an embodiment provides an organometallic compound represented by Formula 1:

[0009] Formula 1

[0010]

[0011] In formula 1,

[0012] M may be a transition metal,

[0013] Ring A 1 To Ring A 4 Can be independently C 5 -C 60 Carbocyclic or C1 -C 60 Heterocyclic group,

[0014] R 1 To R 4 and R 11 To R 14 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine (hydrazine group), hydrazone (hydrazone group), substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 1 -C 60 heteroaryl, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -O(Q 1 )、-S(Q 1 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) and -P(=O)(Q 1 )(Q 2 ),

[0015] a1 to a4 can each independently be an integer from 0 to 10,

[0016] a) R 11 To R14 may not be hydrogen at the same time, b) R 11 To R 14 may not be phenyl at the same time, c) R 11 To R 14 may not be mesityl at the same time, and d) R 11 To R 14 Methyl groups may not be present at the same time.

[0017] Selected from R 11 To R 14 The two may not be connected to each other,

[0018] The substituted C 1 -C 60 Alkyl, the substituted C 2 -C 60 Alkenyl, the substituted C 2 -C 60 Alkynyl, the substituted C 1 -C 60 Alkoxy, the substituted C 3 -C 10 Cycloalkyl, the substituted C 1 -C 10 Heterocycloalkyl, the substituted C 3 -C 10 Cycloalkenyl, the substituted C 1 -C 10 Heterocycloalkenyl, the substituted C 6 -C 60 Aryl, the substituted C 1 -C 60 At least one substituent of the heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group may be selected from:

[0019] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine (hydrazine group), hydrazone (hydrazone group), C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy;

[0020] Each of the C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60Alkynyl and C 1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine (hydrazine group), hydrazone (hydrazone group), C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 heteroaryl, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, -O(Q 11 )、-S(Q 11 )、-Si(Q 11 )(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-P(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 ) and -P(=O)(Q 11 )(Q 12 );

[0021] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups;

[0022] Each of the C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group and monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine (hydrazine group), hydrazone (hydrazone group), C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 heteroaryl, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, -O(Q 21 )、-S(Q 21 )、-Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-P(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 ) and -P(=O)(Q 21 )(Q 22 );as well as

[0023] -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32)、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ),

[0024] Q 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 Each is independently selected from hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; amidino; hydrazine (hydrazine group); hydrazone (hydrazone group); C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 Alkoxy; C 3 -C 10 Cycloalkyl; C 1 -C 10 Heterocycloalkyl; C 3 -C 10 Cycloalkenyl; C 1 -C 10 Heterocycloalkenyl; C 6 -C 60 Aryl; C 1 -C 60 heteroaryl; a monovalent non-aromatic fused polycyclic group; a monovalent non-aromatic fused heteropolycyclic group; a biphenyl group; a terphenyl group; a C substituted with at least one selected from the following 1 -C 60 Alkyl: deuterium, -F, cyano, C 1 -C 60 alkyl, phenyl and biphenyl; and C substituted by at least one selected from the following 6 -C 60 Aryl: deuterium, -F, cyano, C 1 -C 10 Alkyl, phenyl and biphenyl.

[0025] Another aspect of the embodiment provides an organic light-emitting device including a first electrode, a second electrode facing the first electrode, and an organic layer between the first electrode and the second electrode, the organic layer including a light-emitting layer and at least one of the organic metal compounds.

[0026] Another aspect of an embodiment provides an apparatus including the organic light-emitting device. BRIEF DESCRIPTION OF THE DRAWINGS

[0027] These and / or other aspects of the embodiments will become apparent and more easily understood through the following description of the embodiments in conjunction with the accompanying drawings. Figure 1 is a schematic diagram of an organic light emitting device according to one embodiment. DETAILED DESCRIPTION

[0028] The subject matter of the present disclosure will now be more fully described with reference to exemplary embodiments. However, the subject matter of the present disclosure may be embodied in a variety of different forms and should not be construed as being limited to the embodiments listed herein; rather, these embodiments are provided to make the present disclosure thorough and complete and to fully convey the concepts of the present disclosure to those skilled in the art. The features of the embodiments of the present disclosure and how to achieve these features will become apparent by reference to the embodiments and drawings that will be described in more detail below. However, the subject matter of the present invention may be embodied in a variety of different forms and should not be limited to exemplary embodiments.

[0029] One aspect of an embodiment provides an organometallic compound represented by Formula 1:

[0030] Formula 1

[0031]

[0032] In Formula 1, M may be a transition metal. For example, M may be a transition metal in the first row, a transition metal in the second row, or a transition metal in the third row of the periodic table.

[0033] For example, M can be iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), rhodium (Rh), manganese (Mn), cobalt (Co), copper (Cu), ruthenium (Ru), palladium (Pd), silver (Ag), rhenium (Re) or gold (Au).

[0034] In one embodiment, M may be Pt, Pd, or Au, but embodiments of the present disclosure are not limited thereto.

[0035] In Formula 1, Ring A 1 To Ring A 4 Can be independently C 5 -C 60 Carbocyclic or C 1 -C 60 Heterocyclic group. Ring A 1 To Ring A 4Each of can be fused (eg, bonded) to an adjacent 5-membered ring by sharing two carbon atoms.

[0036] For example, Ring A 1 To Ring A 4 Can be independently C 5 -C 60 Carbocyclic group.

[0037] In one embodiment, Ring A 1 To Ring A 4 Each of them can be independently phenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl, pyrenyl, chrysene, cyclopentadienyl, 1,2,3,4-tetrahydronaphthyl, thienyl, furanyl, pyrrolyl, indolyl, indenyl, benzothiolsyl, benzothiophenyl, benzofuranyl, carbazolyl, fluorenyl, dibenzothiolsyl, dibenzothiophenyl, dibenzofuranyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazine 1,2-dihydro-1,2-dihydro-2 ...2,2-dihydro-1,2-dihydro-2,2-dihydro-2,2-dihydro-1,2-dihydro-2,2-dihydro-2,2-dihydro-1,2-dihydro-2,2-dihydro-2,2-dihydro-1,2-dihydro-2,2-dihydro-2,2-dihydro-2,2-dihydro-1,2-dihydro-2,2-dihydro-2,2-dihydro-2,2-dihydro-2,2-dihydro-2,2-dihydro-2,2-dihydro-2,2-dihydro-2,2-dihydro-2,2-dihydro-2,2-dihydro-2,2-dihydro-2,2-dihydro-2,2-dihydro-2,

[0038] In one embodiment, Ring A 1 To Ring A 4 Each may independently be a phenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group, a quinolyl group or an isoquinolyl group, but the embodiments of the present disclosure are not limited thereto.

[0039] In one or more embodiments, Ring A 1 To Ring A 4 can be identical to each other (for example, Ring A 1 To Ring A 4 Any two of can be identical to each other).

[0040] In one or more embodiments, Ring A 1 and Ring A 2 can be different from each other (for example, Ring A 3 and Ring A 4 may be identical to each other and optionally 1 or Ring A 2 same), or ring A 1 and Ring A 3 can be different from each other (for example, Ring A 2 and Ring A 4 may be identical to each other, and optionally 1 or Ring A 3 same).

[0041] In one or more embodiments, Ring A 1 To A 4 Each may be independently selected from the groups represented by Formula 2-1 to Formula 2-13:

[0042]

[0043] In Formulae 2-1 to 2-13, * and *' represent the position of the carbon atom shared with the adjacent 5-membered ring, wherein Ring A 1 To Ring A 4 Each of is respectively fused (eg, bonded) to the 5-membered ring.

[0044] In formula 1, R 1 To R 4 and R 11 To R 14 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine (hydrazine group), hydrazone (hydrazone group), substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 1 -C 60 heteroaryl, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -O(Q 1 )、-S(Q 1 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-P(Q 1)(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) and -P(=O)(Q 1 )(Q 2 ), and Q 1 To Q 3 Each may be independently the same as defined above.

[0045] For example, R 1 To R 4 and R 11 To R 14 Can be independently selected from:

[0046] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine (hydrazine group) and hydrazone (hydrazone group);

[0047] Each unsubstituted or substituted by at least one selected from the following C 1 -C 20 Alkyl, C 2 -C 20 Alkenyl, C 2 -C 20 Alkynyl and C 1 -C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amidino, hydrazine (hydrazine group), hydrazone (hydrazone group), C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 20 Aryl, with at least one C 1 -C 10 Alkyl substituted C 6 -C 20 Aryl, C 1 -C 20 heteroaryl, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, -O(Q 31 )、-S(Q 31 )、-Si(Q31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 );

[0048] Each unsubstituted or substituted by at least one selected from the following C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 1 -C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group and monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amidino, hydrazine (hydrazine group), hydrazone (hydrazone group), C 1 -C 20 Alkyl, C 2 -C 20 Alkenyl, C 2 -C 20 Alkynyl, C 1 -C 20 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 20 Aryl, with at least one C 1 -C 10Alkyl substituted C 6 -C 20 Aryl, C 1 -C 60 heteroaryl, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 );as well as

[0049] -O(Q 1 )、-S(Q 1 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) and -P(=O)(Q 1 )(Q 2 ),and

[0050] Q 1 To Q 3 and Q 31 To Q 33 can be independently selected from hydrogen; deuterium; -F; -Cl; -Br; -I; -CD 3 ;-CD 2 H;-CDH 2 ;-CF 3 ;-CF 2 H; -CFH 2 ; Hydroxyl; Cyano; Nitro; Amidino; Hydrazino (hydrazine group); Hydrazono (hydrazono group); C 1 -C 20 Alkyl; C2 -C 20 Alkenyl; C 2 -C 20 Alkynyl; C 1 -C 20 Alkoxy; C 3 -C 10 Cycloalkyl; C 1 -C 10 Heterocycloalkyl; C 3 -C 10 Cycloalkenyl; C 1 -C 10 Heterocycloalkenyl; C 6 -C 20 Aryl; C 1 -C 20 heteroaryl; a monovalent non-aromatic fused polycyclic group; a monovalent non-aromatic fused heteropolycyclic group; a biphenyl group; a terphenyl group; a C substituted with at least one selected from the following 1 -C 20 Alkyl: deuterium, -F, cyano, C 1 -C 20 alkyl, phenyl and biphenyl; and C substituted by at least one selected from the following 6 -C 20 Aryl: deuterium, -F, cyano, C 1 -C 20 Alkyl, phenyl and biphenyl.

[0051] In one embodiment, R 1 To R 4 and R 11 To R 14 Can be independently selected from:

[0052] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine (hydrazine group) and hydrazone (hydrazone group);

[0053] Each unsubstituted or substituted by at least one selected from the following C 1 -C 10 Alkyl, C 2 -C 10 Alkenyl, C 2 -C 10 Alkynyl and C 1 -C 10 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2, hydroxyl, cyano, nitro, amidino, hydrazine (hydrazine group), hydrazone (hydrazone group), cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, tetrahydro-2H-pyranyl, morpholinyl, phenyl, (C 1 -C 10 alkyl)phenyl, di(C 1 -C 10 alkyl)phenyl, biphenyl, diphenyl, terphenyl, naphthyl, pyridyl, pyrimidyl, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 );

[0054] cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, tetrahydro-2H-pyranyl, morpholinyl, dioxanyl, phenyl, (C 1 -C 10 alkyl)phenyl, di(C 1 -C 10 alkyl)phenyl, biphenyl, diphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzyl imidazolyl, benzofuranyl, benzothiophenyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, 2,3-dihydro-1H-indenyl, 1,2,3,4-tetrahydronaphthyl, 2,3-dihydrobenzodioxolyl and benzodioxanyl: deuterium, -F, -Cl, -Br, -I, -CD 3、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amidino, hydrazine (hydrazine group), hydrazone (hydrazone group), C 1 -C 10 Alkyl, C 2 -C 10 Alkenyl, C 2 -C 10 Alkynyl, C 1 -C 10 alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, tetrahydro-2H-pyranyl, morpholinyl, dioxanyl, phenyl, (C 1 -C 10 alkyl)phenyl, di(C 1 -C 10 alkyl)phenyl, biphenyl, diphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazole yl, phenanthroline, benzimidazolyl, benzofuranyl, benzothiophenyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidyl, 2,3-dihydro-1H-indenyl, 1,2,3,4-tetrahydronaphthyl, 2,3-dihydrobenzodioxolyl, benzodioxanyl, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 );as well as

[0055] -O(Q 1 )、-S(Q 1 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 ) and -P(=O)(Q 1 )(Q 2 ),and

[0056] Q 1 To Q 3 and Q 31 To Q 33 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amidino, hydrazine (hydrazine group), hydrazone (hydrazone group), C 1 -C 10 Alkyl, C 2 -C 10 Alkenyl, C 2 -C 10 Alkynyl, C 1 -C 10 alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, tetrahydro-2H-pyranyl, morpholinyl, dioxanyl, phenyl, (C 1 -C 10 alkyl)phenyl, di(C 1 -C 10alkyl)phenyl, biphenyl, diphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthroline The invention also includes benzofuranyl, benzothiophenyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidinyl, 2,3-dihydro-1H-indenyl, 1,2,3,4-tetrahydronaphthyl, 2,3-dihydrobenzodioxolyl and benzodioxanyl, but the embodiments of the present disclosure are not limited thereto.

[0057] In one embodiment, R 1 To R 4 and R 11 To R 14 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, -CH 3 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amidino, hydrazine (hydrazine group), hydrazone (hydrazone group) and groups represented by formulae 3-1(1) to 3-1(29), 3-2(1) to 3-2(21), 3-3(1) to 3-3(19), 3-4(1) to 3-4(4), 3-5(1) to 3-5(107), 3-6(1) to 3-6(10) and 3-7(1) to 3-7(27):

[0058]

[0059]

[0060]

[0061]

[0062]

[0063] In Formulae 3-1(1) to 3-1(29), 3-2(1) to 3-2(21), 3-3(1) to 3-3(19), 3-4(1) to 3-4(4), 3-5(1) to 3-5(107), 3-6(1) to 3-6(10) and 3-7(1) to 3-7(27),

[0064] Z 1 To Z 10 can be independently selected from deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amidino, hydrazine (hydrazine group), hydrazone (hydrazone group), C 1 -C 10 Alkyl, C 2 -C 10 Alkenyl, C 2 -C 10 Alkynyl, C 1 -C 10 alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, tetrahydro-2H-pyranyl, morpholinyl, dioxanyl, phenyl, (C 1 -C 10 alkyl)phenyl, di(C 1 -C 10 alkyl)phenyl, biphenyl, diphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazole yl, phenanthroline, benzimidazolyl, benzofuranyl, benzothiophenyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidyl, 2,3-dihydro-1H-indenyl, 1,2,3,4-tetrahydronaphthyl, 2,3-dihydrobenzodioxolyl, benzodioxanyl, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ),and

[0065] Q 31 To Q 33 may be independently the same as defined above, and

[0066] *Indicates the binding site with the adjacent atom.

[0067] In Formula 1, a1 to a4 each represent R 1 To R 4 When a1 is 2 or more, two or more R 1 can be the same or different from each other; when a2 is 2 or more, two or more R 2 can be the same or different from each other; when a3 is 2 or more, two or more R 3 can be the same or different from each other; when a4 is 2 or more, two or more R 4 May be the same as or different from each other.

[0068] In one embodiment, R 1 To R 4 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , C 1 -C 10 Alkyl, C 2 -C 10 Alkenyl, C 2 -C 10 Alkynyl, C 1 -C 10 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, phenyl, (C 1 -C 10 alkyl)phenyl, di(C 1 -C 10 alkyl)phenyl, biphenyl, diphenyl, terphenyl, -O(Q1 ) and -S(Q 1 ),and

[0069] Q 1 Can be selected from C 1 -C 10 Alkyl, C 2 -C 10 Alkenyl, C 2 -C 10 Alkynyl, C 1 -C 10 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, phenyl, (C 1 -C 10 alkyl)phenyl, di(C 1 -C 10 alkyl)phenyl, biphenyl, di(phenyl)phenyl and terphenyl.

[0070] In one or more embodiments, selected from R 11 To R 14 At least one of (e.g., all R 11 To R 14 ) can be independently selected from C 2 -C 10 Alkyl, C 2 -C 10 Alkenyl, C 2 -C 10 Alkynyl and C 1 -C 10 Alkoxy groups, each of which is unsubstituted or substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amidino, hydrazine (hydrazine group), hydrazone (hydrazone group), cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, tetrahydro-2H-pyranyl, morpholinyl, phenyl, (C 1 -C 10 alkyl)phenyl, di(C 1 -C 10 alkyl)phenyl, biphenyl, diphenyl, terphenyl, naphthyl, pyridyl, pyrimidyl, -O(Q 31 )、-S(Q 31 )、-Si(Q 31 )(Q 32 )(Q 33 )、-N(Q31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ).

[0071] In one or more embodiments, selected from R 11 To R 14 At least one of the may be other than hydrogen, phenyl, mesityl or methyl.

[0072] In one or more embodiments, selected from R 11 To R 14 At least one of them can be independently selected from -O(Q 1 )、-S(Q 1 )、-Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) and a group represented by formula A5:

[0073] Formula A5

[0074]

[0075] Among them, Q 1 To Q 3 may be independently the same as defined above, and

[0076] A in formula A5 5 Can be substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 1 -C 60heteroaryl or substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and may be combined with the above R 11 The definition is the same.

[0077] For example, the group belonging to Formula A5 may be represented by one selected from Formulae 3-2(16) to 3-2(19) and 3-7(22) to 3-7(27), but the embodiments of the present disclosure are not limited thereto.

[0078] In one or more embodiments, R 11 To R 14 Can be identical to each other.

[0079] In one or more embodiments, R 11 With R 12 can be different from each other, or R 11 and R 13 Can be different from each other.

[0080] In one or more embodiments, in Formula 1,

[0081] a) R 11 With R 12 can be different from each other, R 13 With R 14 can be different from each other, R 11 With R 13 can be identical to each other, and R 12 With R 14 can be identical to one another;

[0082] b) R 11 With R 13 can be different from each other, R 12 With R 14 can be different from each other, R 11 With R 14 can be identical to each other, and R 12 With R 13 can be identical to one another;

[0083] c) R 11 With R 12 can be different from each other, and R 11 , R 13 and R 14 may be identical to one another; or

[0084] d) R 11 To R 14 They may be different from each other, but the embodiments of the present disclosure are not limited thereto.

[0085] For example, the organometallic compound represented by Formula 1 may be selected from Compounds 1 to 180, but embodiments of the present disclosure are not limited thereto:

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092] In Compounds 1 to 180, TMS represents a trimethylsilyl group, and Ph represents a phenyl group.

[0093] In one embodiment, in Formula 1, M may be selected from a transition metal (eg, a transition metal of the first row, a transition metal of the second row, or a transition metal of the third row of the periodic table), and ring A 1 To Ring A 4 Can be independently C 5 -C 60 Carbocyclic or C 1 -C 60 Therefore, the organometallic compound can emit near-infrared phosphorescence having a maximum emission wavelength in the range of 720 nm to 2500 nm.

[0094] In one or more embodiments, in Formula 1, a) R 11 To R 14 may not be hydrogen at the same time, b) R 11 To R 14 may not be phenyl at the same time, c) R 11 To R 14 may not be mesityl at the same time, and d) R 11 To R 14 Methyl groups may not be present at the same time, wherein R 11 To R 14 The two of them may not be connected to each other. 11 To R 14 Various embodiments. Since R in Formula 1 11 To R 14Same as defined above, therefore the organometallic compound represented by Formula 1 can be synthesized in high purity and can have high heat resistance. In this regard, the film formed by depositing the organometallic compound can have a high film density. Therefore, when such a film is exposed to heat generated by operating an electronic device (such as an organic light-emitting device) including the film, the decomposition of the organometallic compound contained in the film can be substantially prevented or reduced. Therefore, an electronic device (such as an organic light-emitting device) including an organometallic compound represented by Formula 1 can have a low driving voltage, high luminous efficiency and / or a long life.

[0095] The synthesis method of the organometallic compound represented by Formula 1 will be apparent to one of ordinary skill in the art by referring to the following examples.

[0096] At least one organic metal compound of Formula 1 can be used between a pair of electrodes of an organic light-emitting device. Therefore, another aspect of the embodiment provides an organic light-emitting device, including: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode, the organic layer including a light-emitting layer, wherein the organic layer includes at least one organic metal compound represented by Formula 1.

[0097] As used herein, the expression “(the organic layer) includes at least one organic metal compound” may include the case where “(the organic layer) includes the same organic metal compound represented by Formula 1” and the case where “(the organic layer) includes two or more different organic metal compounds represented by Formula 1”.

[0098] For example, the organic layer may include only Compound 1 as an organic metal compound. In this regard, Compound 1 may be present in the light-emitting layer of the organic light-emitting device. In one or more embodiments, the organic layer may include Compound 1 and Compound 2 as organic metal compounds. In this regard, Compound 1 and Compound 2 may be present in the same layer (for example, Compound 1 and Compound 2 may both be present in the light-emitting layer), or in different layers (for example, Compound 1 may be present in the light-emitting layer, and Compound 2 may be present in the electron transport region).

[0099] In an organic light emitting device according to one embodiment,

[0100] The first electrode of the organic light-emitting device may be an anode,

[0101] The second electrode of the organic light-emitting device may be a cathode,

[0102] The organic layer may further include a hole transport region between the first electrode and the light emitting layer and an electron transport region between the light emitting layer and the second electrode.

[0103] The hole transport region may include a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, an electron blocking layer, or any combination thereof, and

[0104] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0105] The term "organic layer" used herein refers to a single layer and / or multiple layers between a first electrode and a second electrode of an organic light-emitting device. Materials included in the "organic layer" are not limited to organic materials.

[0106] In one or more embodiments, the light emitting layer may include an organic metal compound represented by Formula 1. In addition to the organic metal compound, the light emitting layer may further include a host, wherein the amount of the organic metal compound may be less than the amount of the host in the light emitting layer. Here, the light emitting layer may emit near-infrared phosphorescence having a maximum emission wavelength in the range of 720 nm to 2500 nm.

[0107] In one or more embodiments, the hole transport region may include an electron blocking layer, and the electron blocking layer may include an organic metal compound; and / or the electron transport region may include a hole blocking layer, and the hole blocking layer may include an organic metal compound. The organic metal compound included in the electron blocking layer or the hole blocking layer does not act as an emitter.

[0108] In one or more embodiments,

[0109] At least one selected from the hole transport region and the light emitting layer may include at least one selected from a compound containing an aromatic amine group, a compound containing an acridine ring, and a compound containing a carbazole ring; and / or

[0110] At least one selected from the light-emitting layer and the electron transport region may include at least one selected from the following: a silicon-containing compound, a phosphine oxide-containing compound, a sulfur oxide-containing compound, a triazine ring-containing compound, a pyrimidine ring-containing compound, a pyridine ring-containing compound, a dibenzofuran ring-containing compound, and a dibenzothiophene ring-containing compound.

[0111] Description of the drawings

[0112] Figure 1 1 is a schematic diagram of an organic light-emitting device 10 according to an embodiment of the present invention. The organic light-emitting device 10 includes a first electrode 110 , an organic layer 150 , and a second electrode 190 .

[0113] The following will be combined Figure 1 A structure of an organic light-emitting device 10 and a method of manufacturing the organic light-emitting device 10 according to one embodiment are described.

[0114] First electrode 110

[0115] exist Figure 1 In the embodiment, a substrate may be additionally disposed below the first electrode 110 or above the second electrode 190. The substrate may be a glass substrate or a plastic substrate, which have excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance, respectively.

[0116] The first electrode 110 may be formed by depositing or sputtering a material for forming the first electrode 110 on a 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.

[0117] 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, a material for forming the first electrode 110 may be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO) and any combination thereof, but the embodiments of the present disclosure are not limited thereto. When the first electrode 110 is a semi-transmissive electrode or a reflective electrode, as a material for forming the first electrode 110, magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) or any combination thereof may be used. However, the material for forming the first electrode 110 is not limited thereto.

[0118] The first electrode 110 may have a single-layer structure or a multi-layer structure including 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.

[0119] Organic layer 150

[0120] The organic layer 150 is disposed on the first electrode 110. The organic layer 150 may include a light emitting layer.

[0121] The organic layer 150 may further include a hole transport region between the first electrode 110 and the light emitting layer and an electron transport region between the light emitting layer and the second electrode 190 .

[0122] [Hole Transport Region in Organic Layer 150]

[0123] The hole transport region may have i) a single layer structure including a single layer including a single material, ii) a single layer structure including a single layer including a plurality of different materials, or iii) a multilayer structure having a plurality of layers including a plurality of different materials.

[0124] The hole transport region may include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, and an electron blocking layer.

[0125] For example, the hole transport zone may have a single-layer structure or a multi-layer structure, wherein the single-layer structure includes a single layer containing a plurality of different materials, and the multi-layer structure has a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / luminescence auxiliary layer structure, a hole injection layer / luminescence auxiliary layer structure, a hole transport layer / luminescence auxiliary layer structure, or a hole injection layer / hole transport layer / electron blocking layer structure, wherein for each structure, the constituent layers are stacked in sequence from the first electrode 110 in the order stated, but the structure of the hole transport zone is not limited thereto.

[0126] The hole transport region may include at least one selected from the group consisting of m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), PEDOT / PSS (poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate)), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), a compound represented by Formula 201, and a compound represented by Formula 202:

[0127]

[0128] Formula 201

[0129]

[0130] Formula 202

[0131]

[0132] In equation 201 and equation 202,

[0133] L 201 To L 204 may be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60heteroarylene, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

[0134] L 205 Can be selected from *-O-*', *-S-*', *-N(Q 201 )-*', substituted or unsubstituted C 1 -C 20 Alkylene, substituted or unsubstituted C 2 -C 20 Alkenylene, substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

[0135] xa1 to xa4 may each independently be an integer from 0 to 3,

[0136] xa5 can be an integer from 1 to 10, and

[0137] R 201 To R 204 and Q 201 may be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

[0138] For example, in Equation 202, R 201 and R 202 may be optionally linked to each other via a single bond, a dimethyl-methylene group or a diphenyl-methylene group, and R 203 and R 204 They may optionally be linked to one another via single bonds, dimethyl-methylene groups or diphenyl-methylene groups.

[0139] In one or more embodiments, in formulas 201 and 202,

[0140] L 201 To L 205 Can be independently selected from:

[0141] phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acenaphthenylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylene, pyrenylene, chrysene, tetraphenylene, phrenylene, perylene, pentaphenylene, hexaphenylene, pentaphenylene, rubenylene, coronenylene, ovaphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzosilylene, and pyridinylene; and

[0142] each substituted by at least one of the following: phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acenaphthenylene, fluorenylene, spiro-difluorenylene, benzofluorenylene, dibenzofluorenylene, phenalenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylene, pyrenylene, chrysene, tetraphenylene, pyrenylene, perylene, pentaphenylene, hexaphenylene, pentphenylene, jasperylene, iodine, coronet, oxadiene, thienyl, furanyl, carbazolylene, indolyl, isoindolyl, benzofuranyl, benzothiophenylene, dibenzofuranyl, dibenzothiophenylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothiophenylene and pyridinyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine (hydrazine group), hydrazone (hydrazone group), C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C 1 -C10 Alkyl-substituted phenyl, -F-substituted phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, tetracenyl, phenanthrenyl, peryl, pentaphenyl, hexacenyl, pentacecenyl, rubenyl, coronenyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, pyridinyl, -Si(Q) 31 )(Q 32 )(Q 33 ) and -N(Q 31 )(Q 32 ),and

[0143] Q 31 To Q 33 Can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.

[0144] In one or more embodiments, xa1 to xa4 may each independently be 0, 1 or 2.

[0145] In one or more embodiments, xa5 can be 1, 2, 3 or 4.

[0146] In one or more embodiments, R 201 To R 204 and Q 201 Can be independently selected from:

[0147] phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, tetracenyl, phenanthrenyl, peryl, pentaphenyl, hexacenyl, pentacecenyl, rubenyl, coronenyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, and pyridinyl; and

[0148] phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, tetracenyl, pyrenyl, peryl, pentaphenenyl, hexacenyl, pentacenyl, rubin benzothiophene, dibenzofuranyl, dibenzothiophene, dibenzocarbazolyl, dibenzocarbazolyl, dibenzothiophene, and pyridyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine (hydrazine group), hydrazone (hydrazone group), C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C 1 -C 10 Alkyl-substituted phenyl, -F-substituted phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, tetracenyl, phenanthrenyl, peryl, pentaphenyl, hexacenyl, pentacecenyl, rubenyl, coronenyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilyl, pyridinyl, -Si(Q) 31 )(Q 32 )(Q 33 ) and -N(Q 31 )(Q 32 ),and

[0149] Q 31 To Q 33 may each independently be the same as defined above.

[0150] In one or more embodiments, in Formula 201, selected from R 201 To R 203 At least one of can be independently selected from:

[0151] fluorenyl, spiro-bifluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl; and

[0152] Fluorenyl, spiro-bifluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl, each substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine (hydrazine group), hydrazone (hydrazone group), C1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C 1 -C 10 alkyl-substituted phenyl, -F-substituted phenyl, naphthyl, fluorenyl, spiro-bifluorenyl, carbazolyl, dibenzofuranyl and dibenzothienyl,

[0153] However, the embodiments of the present disclosure are not limited thereto.

[0154] In one or more embodiments, in Formula 202, i) R 201 and R 202 can be connected via a single bond, and / or ii) R 203 and R 204 Connect via one-touch.

[0155] In one or more embodiments, in Formula 202, selected from R 201 To R 204 At least one of:

[0156] carbazolyl; and

[0157] A carbazolyl group substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine (hydrazine group), hydrazone (hydrazone group), C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C 1 -C 10 alkyl-substituted phenyl, -F-substituted phenyl, naphthyl, fluorenyl, spiro-bifluorenyl, carbazolyl, dibenzofuranyl and dibenzothienyl,

[0158] However, the embodiments of the present disclosure are not limited thereto.

[0159] The compound represented by Formula 201 can be represented by Formula 201A:

[0160] Formula 201A

[0161]

[0162] In one embodiment, the compound represented by Formula 201 may be represented by the following Formula 201A(1), but the embodiments of the present disclosure are not limited thereto:

[0163] Formula 201A(1)

[0164]

[0165] In one embodiment, the compound represented by Formula 201 may be represented by the following Formula 201A-1, but the embodiments of the present disclosure are not limited thereto:

[0166] Formula 201A-1

[0167]

[0168] In one embodiment, the compound represented by Formula 202 may be represented by Formula 202A:

[0169] Formula 202A

[0170]

[0171] In one embodiment, the compound represented by Formula 202 can be represented by Formula 202A-1:

[0172] Formula 202A-1

[0173]

[0174] In Formulas 201A, 201A(1), 201A-1, 202A and 202A-1,

[0175] L 201 To L 203 , xa1 to xa3, xa5 and R 202 To R 204 may be independently the same as defined above,

[0176] R 211 and R 212 Can be independently connected to R 203 are defined the same as

[0177] R 213 To R 217 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine (hydrazine group), hydrazone (hydrazone group), C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, biphenyl, terphenyl, C 1 -C 10Alkyl substituted phenyl, phenyl substituted with -F, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, tetracenyl, phenanthrenyl, peryl, pentaphenyl, hexacenyl, pentacecenyl, rubenyl, coronenyl, ovalenyl, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzosilolyl and pyridinyl.

[0178] The hole transport region may include at least one compound selected from compounds HT1 to HT39, but embodiments of the present disclosure are not limited thereto:

[0179]

[0180]

[0181]

[0182]

[0183] The thickness of the hole transport region can be about to about For example, about to about When the hole transport region includes at least one of a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be in the range of about to about For example, about to about and the thickness of the hole transport layer can be in the range of about to about For example, about to about When the thicknesses of the hole transport region, the hole injection layer and the hole transport layer are within the above ranges, suitable or satisfactory hole transport characteristics may be obtained without a significant increase in driving voltage.

[0184] The light-emitting auxiliary layer can increase light-emitting efficiency by compensating the optical resonance distance according to the wavelength of light emitted by the light-emitting layer, and the electron blocking layer can block the flow of electrons from the electron transport region. The light-emitting auxiliary layer and the electron blocking layer can include the materials described above.

[0185] p-type dopant

[0186] In addition to these materials, the hole transport region may further include a charge generating material to improve conductivity. The charge generating material may be dispersed uniformly or non-uniformly in the hole transport region.

[0187] The charge generating material may be, for example, a p-type dopant.

[0188] In one embodiment, the p-type dopant has a lowest unoccupied molecular orbital (LUMO) level below -3.5 eV.

[0189] The p-type dopant may include at least one selected from the group consisting of a quinone derivative, a metal oxide, and a cyano group-containing compound, but embodiments of the present disclosure are not limited thereto.

[0190] For example, the p-type dopant may include at least one selected from the following:

[0191] Quinone derivatives, such as tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ);

[0192] Metal oxides, such as tungsten oxide or molybdenum oxide;

[0193] 1,4,5,8,9,12-Hexaazatriphenylene-hexanitrile (HAT-CN); and

[0194] A compound represented by formula 221;

[0195] However, the embodiments of the present disclosure are not limited thereto:

[0196]

[0197] Formula 221

[0198]

[0199] In formula 221,

[0200] R 221 To R 223 may be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 1 -C 60 heteroaryl, substituted or unsubstituted monovalent non-aromatic fused polycyclic group and substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, wherein R is selected from 221 To R 223At least one of the following may have at least one substituent selected from the group consisting of cyano, -F, -Cl, -Br, -I, C substituted with -F 1 -C 20 Alkyl, C substituted by -Cl 1 -C 20 Alkyl, C substituted by -Br 1 -C 20 Alkyl and C substituted by -I 1 -C 20 alkyl.

[0201] The light emitting layer in the organic layer 150

[0202] When the organic light-emitting device 10 is a full-color organic light-emitting device, the light-emitting layer may be patterned into a red light-emitting layer, a green light-emitting layer, or a blue light-emitting layer according to the sub-pixel. In one or more embodiments, the light-emitting layer may have a stacked structure of two or more layers selected from the red light-emitting layer, the green light-emitting layer, and the blue light-emitting layer, wherein the two or more layers are in contact with each other or separated from each other. In one or more embodiments, the light-emitting layer may include two or more materials selected from the red light-emitting material, the green light-emitting material, and the blue light-emitting material, wherein the two or more materials are mixed with each other in a single layer to emit white light.

[0203] The light emitting layer may include a host and a dopant. The dopant may include at least one of a phosphorescent dopant and a fluorescent dopant.

[0204] In the light emitting layer, the amount of the dopant may be in the range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host, but embodiments of the present disclosure are not limited thereto.

[0205] The thickness of the light-emitting layer can be about to about For example, about to about When the thickness of the light-emitting layer is within this range, excellent light-emitting characteristics can be obtained without a significant increase in driving voltage.

[0206] Subject in the luminous layer

[0207] In one or more embodiments, the host may include a compound represented by Formula 301:

[0208] Formula 301

[0209] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 .

[0210] In formula 301,

[0211] Ar 301 It can be substituted or unsubstituted C 5 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group,

[0212] xb11 can be 1, 2 or 3,

[0213] L 301 may be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60 Arylene, substituted or unsubstituted C 1 -C 60 heteroarylene, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

[0214] xb1 can be an integer from 0 to 5.

[0215] R 301 It can be selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine (hydrazine group), hydrazone (hydrazone group), substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a 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 ),

[0216] xb21 can be an integer from 1 to 5, and

[0217] Q 301 To Q 303 Can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 An alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, but the embodiments of the present disclosure are not limited thereto.

[0218] In one embodiment, in Formula 301, Ar 301 Can be selected from:

[0219] naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, naphthacene, phenanthrenyl, peryl, pentaphenanthrenyl, indenoanthryl, dibenzofuranyl, and dibenzothienyl; and

[0220] naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, naphthacene, phenanthrenyl, peryl, pentaphenanthrenyl, indenoanthryl, dibenzofuranyl and dibenzothienyl, each substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine (hydrazine group), hydrazone (hydrazone group), C 1 -C 20 Alkyl, C 1 -C 20Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -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

[0221] Q 31 To Q 33 Can be independently selected from C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl. However, the embodiments of the present disclosure are not limited thereto.

[0222] When xb11 in Formula 301 is 2 or greater, two or more Ar 301 Connect via one-touch.

[0223] In one or more embodiments, the compound represented by Formula 301 may be represented by Formula 301-1 or Formula 301-2: Formula 301-1

[0224]

[0225] Formula 301-2

[0226]

[0227] In Formula 301-1 to Formula 301-2,

[0228] A 301 To A 304 The phenyl group may be independently selected from phenyl, naphthyl, phenanthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, pyridyl, pyrimidyl, indenyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, indolyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, furanyl, benzofuranyl, dibenzofuranyl, naphthofuranyl, benzonaphthofuranyl, dinaphthofuranyl, thienyl, benzothienyl, dibenzothienyl, naphthothienyl, benzonaphthothienyl and dinaphthothienyl,

[0229] X 301 Can be O, S or N-[(L 304 ) xb4 -R304 ],

[0230] R 311 To R 314 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine (hydrazine group), hydrazone (hydrazone group), C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -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 ),

[0231] xb22 and xb23 can each independently be 0, 1 or 2,

[0232] L 301 、xb1、R 301 and Q 31 To Q 33 may be independently the same as defined above,

[0233] L 302 To L 304 Can be independently connected to L 301 The same definition,

[0234] xb2 to xb4 can each independently be defined identically to xb1, and

[0235] R 302 To R 304 Can be independently connected to R 301 The definition is the same.

[0236] For example, in Formula 301, Formula 301-1, and Formula 301-2, L 301 To L 304 Can be independently selected from:

[0237] Phenylene, naphthylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, phenanthrenylene, pyrenylene, chrysene, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene, pyridinylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene, pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridinylene, quinoxalylene, quinazolinylene, cinnolinylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzimidazolylene, benzisothiazolylene, benzoxazolylene, benzisoxazolylene, triazolylene, tetrazolylene, imidazopyridinylene, imidazopyrimidinylene, and azacarbazolylene; and

[0238] phenylene, naphthylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, phenanthrenylene, pyrenylene, chrysene, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene, pyridinylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene yl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazinyl (hydrazinyl group), hydrazone (hydrazone group), C 1 -C 20 Alkyl, C 1 -C 20Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, peryl, pentaphenanthrenyl, hexacenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothioyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, -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

[0239] Q 31 To Q 33 may each independently be the same as defined above.

[0240] In one embodiment, in Formulas 301, 301-1, and 301-2, R 301 To R 304 Can be independently selected from:

[0241] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, peryl, pentaphenyl, hexacenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothioyl, pyridyl, imidazolyl, pyrazolyl, thiophene oxazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and

[0242] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, peryl, pentaphenanthrenyl, hexaphenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothioyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, oxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine (hydrazine group), hydrazone (hydrazone group), C 1 -C 20 Alkyl, C 1 -C 20Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, peryl, pentaphenanthrenyl, hexacenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothioyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, azacarbazolyl, -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

[0243] Q 31 To Q 33 may each independently be the same as defined above.

[0244] In one or more embodiments, the host may include an alkaline earth metal complex. For example, the host may be selected from a Be complex (eg, compound H55), a Mg complex, and a Zn complex.

[0245] The host may include at least one selected from the group consisting of 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalene-2-yl)anthracene (MADN), 9,10-di-(2-naphthyl)-2-tert-butyl-anthracene (TBADN), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-di-9-carbazolylbenzene (mCP), 1,3,5-tri(carbazolyl-9-yl)benzene (TCP), and compounds H1 to H55, but embodiments of the present disclosure are not limited thereto:

[0246]

[0247]

[0248]

[0249] In one embodiment, the host may include at least one selected from a silicon-containing compound (eg, BCPDS or the like used in the following examples) and a phosphine oxide-containing compound (eg, POPCPA or the like used in the following examples).

[0250] However, the embodiments of the present disclosure are not limited thereto. In one embodiment, the host may include only one compound, or two or more different compounds (for example, the host used in the following examples includes BCPDS and POPCPA).

[0251] The dopant included in the light emitting layer of the organic layer 150

[0252] The dopant may include an organic metal compound represented by Formula 1: The organic metal compound is the same as described above.

[0253] Electron transport region in the organic layer 150

[0254] The electron transport region may have i) a single-layer structure including a single layer including a single material, ii) a single-layer structure including a single layer including a plurality of different materials, or iii) a multi-layer structure having a plurality of layers including a plurality of different materials.

[0255] The electron transport region may include at least one selected from a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, and an electron injection layer, but embodiments of the present disclosure are not limited thereto.

[0256] For example, the electron transport region may have a structure of electron transport layer / electron injection layer, a structure of hole blocking layer / electron transport layer / electron injection layer, a structure of electron control layer / electron transport layer / electron injection layer, or a structure of buffer layer / electron transport layer / electron injection layer, wherein for each structure, the constituent layers are stacked sequentially from the light-emitting layer. However, the embodiment of the structure of the electron transport region is not limited thereto.

[0257] The electron transport region (eg, a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a metal-free compound including at least one π-electron-depleted nitrogen-containing ring.

[0258] As used herein, the term "π-electron-depleted nitrogen-containing ring" refers to a C-containing ring having at least one *-N=*' moiety as a ring-forming part. 1 -C 60 Heterocyclic group.

[0259] For example, the “π-electron-depleted nitrogen-containing ring” may be i) a five- to seven-membered heteromonocyclic group having at least one *-N=*' moiety, ii) a heteropolycyclic group in which two or more five- to seven-membered heteromonocyclic groups, each having at least one *-N=*' moiety, are fused to each other, or iii) a heteropolycyclic group in which at least one five- to seven-membered heteromonocyclic group, each having at least one *-N=*' moiety, is fused to at least one C 5 -C 60 The carbocyclic group is fused.

[0260] Examples of π-electron-depleted nitrogen-containing rings include, but are not limited to, imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, indazole, purine, quinoline, isoquinoline, benzoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, phenanthridine, acridine, phenanthroline, phenazine, benzimidazole, benzisothiazole, benzoxazole, benzisoxazole, triazole, tetrazole, oxadiazole, triazine, thiadiazole, imidazopyridine, imidazopyrimidine, and azacarbazole.

[0261] For example, the electron transport region may include a compound represented by Formula 601:

[0262] Formula 601

[0263] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 .

[0264] In formula 601,

[0265] Ar 601 It can be substituted or unsubstituted C 5 -C 60 Carbocyclic or substituted or unsubstituted C 1 -C 60 Heterocyclic group,

[0266] xe11 can be 1, 2 or 3,

[0267] L 601 may be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene, substituted or unsubstituted C 3 -C 10 Cycloalkenylene, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene, substituted or unsubstituted C 6 -C 60Arylene, substituted or unsubstituted C 1 -C 60 a heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group;

[0268] xe1 can be an integer from 0 to 5,

[0269] R 601 Can be selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 601 )(Q 602 )(Q 603 )、-C(=O)(Q 601 )、-S(=O) 2 (Q 601 ) and -P(=O)(Q 601 )(Q 602 ),

[0270] Q 601 To Q 603 Can be independently C 1 -C 10 Alkyl, C 1 -C 10 alkoxy, phenyl, biphenyl, terphenyl or naphthyl, and

[0271] xe21 can be an integer from 1 to 5.

[0272] In one embodiment, at least one Ar in number xe11 601 and at least one R of xe21 601 Pi-electron-depleted nitrogen-containing rings may be included.

[0273] In one embodiment, Ar in Formula 601 601 You can choose from:

[0274] Phenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, naphthacene, phenanthrenyl, peryl, peryl, pentaphenanthracene, indenoanthryl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and

[0275] phenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, naphthacene, pyrenyl, peryl, pentaphenanthracene, indenoanthryl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indazolyl, purinyl, quinolyl, isoquinolyl quinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine (hydrazine group), hydrazone (hydrazone group), C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, -Si(Q 31 )(Q 32 )(Q 33 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ),and

[0276] Q 31 To Q 33 Can be independently selected from C 1 -C 10 Alkyl, C 1 -C10 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.

[0277] When xe11 in Formula 601 is 2 or greater, two or more Ar 601 The groups may be linked to each other via single bonds.

[0278] In one or more embodiments, Ar in Formula 601 601 It may be anthracene.

[0279] In one or more embodiments, the compound represented by Formula 601 may be represented by Formula 601-1:

[0280] Formula 601-1

[0281]

[0282] In formula 601-1,

[0283] 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 selected from X 614 To X 616 At least one of may be N,

[0284] L 611 To L 613 Can be independently connected to L 601 The same definition,

[0285] xe611 to xe613 can be independently defined the same as xe1.

[0286] R 611 To R 613 Can be independently connected to R 601 The definitions are the same, and

[0287] R 614 To R 616 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine (hydrazine group), hydrazone (hydrazone group), C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl and naphthyl.

[0288] In one embodiment, L in Formula 601 and 601-1 601 and L 611To L 613 Can be independently selected from:

[0289] Phenylene, naphthylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, phenanthrenylene, pyrenylene, chrysene, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene, pyridinylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, thiadiazolylene, oxadiazolylene, pyrazinylene, pyrimidinylene, pyridazinylene, triazinylene, quinolylene, isoquinolylene, benzoquinolylene, phthalazinylene, naphthyridinylene, quinoxalylene, quinazolinylene, cinnolinylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzimidazolylene, benzisothiazolylene, benzoxazolylene, benzisoxazolylene, triazolylene, tetrazolylene, imidazopyridinylene, imidazopyrimidinylene, and azacarbazolylene; and

[0290] phenylene, naphthylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, phenanthrenylene, pyrenylene, chrysene, perylene, pentaphenylene, hexaphenylene, pentphenylene, thienylene, furanylene, carbazolylene, indolylene, isoindolylene, benzofuranylene, benzothienylene, dibenzofuranylene, dibenzothienylene, benzocarbazolylene, dibenzocarbazolylene, dibenzothioylene, pyridinylene, imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene yl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazinyl (hydrazinyl group), hydrazone (hydrazone group), C 1 -C 20 Alkyl, C 1 -C 20Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, peryl, pentaphenanthrenyl, hexacenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothioyl, pyridyl, imidazolyl, pyrazole oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl,

[0291] However, the embodiments of the present disclosure are not limited thereto.

[0292] In one or more embodiments, xe1 and xe611 to xe613 in Formulas 601 and 601-1 may each independently be 0, 1 or 2.

[0293] In one or more embodiments, in Formula 601 and Formula 601-1, R 601 and R 611 To R 613 Can be independently selected from:

[0294] Phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, peryl, pentaphenanthrenyl, hexacenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothioyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl;

[0295] phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, peryl, pentaphenanthrenyl, hexaphenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothioyl, pyridyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, oxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl and azacarbazolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine (hydrazine group), hydrazone (hydrazone group), C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-bifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, peryl, pentaphenanthrenyl, hexacenyl, pentacene, thienyl, furanyl, carbazolyl, indolyl, isoindolyl, benzofuranyl, benzothienyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, dibenzothioyl, pyridyl, imidazolyl, pyrazolyl , thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, thiadiazolyl, oxadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, imidazopyridinyl, imidazopyrimidinyl, and azacarbazolyl; and

[0296] -S(=O) 2 (Q 601 ) and -P(=O)(Q 601 )(Q 602 ),and

[0297] Q 601 and Q 602 Each can be independently defined the same as above.

[0298] The electron transport region may include at least one compound selected from compounds ET1 to ET36, but embodiments of the present disclosure are not limited thereto:

[0299]

[0300]

[0301]

[0302] In one or more embodiments, the electron transport region may include a plurality of selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq 3 , BAlq, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ) and NTAZ:

[0303]

[0304] In one embodiment, the electron transport region may include a phosphine oxide-containing compound (e.g., TSPO1 used in the following examples, etc.), but the embodiments of the present disclosure are not limited thereto. In one embodiment, the phosphine oxide-containing compound may be used in a hole blocking layer of the electron transport region, but the embodiments of the present disclosure are not limited thereto.

[0305] The thickness of the buffer layer, hole blocking layer or electron control layer can be independently about to about For example, in about to about When the thicknesses of the buffer layer, the hole blocking layer, and the electron control layer are within these ranges, the electron transport region may have excellent hole blocking properties or electron control properties without a significant increase in driving voltage.

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

[0307] The electron transport region (eg, an electron transport layer in the electron transport region) may further include a metal-containing material in addition to the above-mentioned materials.

[0308] The metal-containing material may include at least one selected from an alkali metal complex and an alkaline earth metal complex. The alkali metal complex may include a metal ion selected from the following: Li ion, Na ion, K ion, Rb ion and Cs ion, and the alkaline earth metal complex may include a metal ion selected from the following: Be ion, Mg ion, Ca ion, Sr ion and Ba ion. The ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth metal complex may be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline and cyclopentadiene, but the embodiments of the present disclosure are not limited thereto.

[0309] For example, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (8-hydroxyquinoline lithium, LiQ) or ET-D2:

[0310]

[0311] The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 190. The electron injection layer may directly contact the second electrode 190.

[0312] The electron injection layer may have i) a single layer structure including a single layer including a single material, ii) a single layer structure including a single layer including a plurality of different materials, or iii) a multilayer structure having a plurality of layers including a plurality of different materials.

[0313] The electron injection layer may include 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.

[0314] 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 one or more embodiments, the alkali metal may be Li or Cs, but the embodiments of the present disclosure are not limited thereto.

[0315] The alkaline earth metal may be selected from Mg, Ca, Sr and Ba.

[0316] The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb and Gd.

[0317] The alkali metal compound, alkaline earth metal compound and rare earth metal compound may be selected from oxides and halides (eg, fluorides, chlorides, bromides or iodides) of alkali metals, alkaline earth metals and rare earth metals.

[0318] The alkali metal compound can be selected from alkali metal oxides (such as Li2 O, Cs 2 O or K 2 O) and an alkali metal halide (such as LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI). In one embodiment, the alkali metal compound may be selected from LiF, Li 2 O, NaF, LiI, NaI, CsI, and KI, but the embodiments of the present disclosure are not limited thereto.

[0319] The alkaline earth metal compound may 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 may be selected from BaO, SrO, and CaO, but the embodiments of the present disclosure are not limited thereto.

[0320] The rare earth metal compound may be selected from YbF 3 、ScF 3 、Sc 2 O 3 、Y 2 O 3 、Ce 2 O 3 、GdF 3 and TbF 3 。In one embodiment, the rare earth metal compound may be selected from YbF 3 、ScF 3 、TbF 3 、YbI 3 、ScI 3 and TbI 3 ,but the embodiments of the present disclosure are not limited thereto.

[0321] The alkali metal complex, alkaline earth metal complex, and rare earth metal complex may include the ions of the alkali metal, alkaline earth metal, and rare earth metal described above. The ligands coordinated with the metal ions of the alkali metal complex, alkaline earth metal complex, or rare 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 of the present disclosure are not limited thereto.

[0322] The electron injection layer may include (e.g., consisting of) 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 as described above. In one or more embodiments, the electron injection layer may further include an organic material. When the electron injection layer further includes an organic material, 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 may be uniformly or non-uniformly dispersed in a matrix including an organic material.

[0323] The thickness of the electron injection layer can be about to about For example, in about to about When the thickness of the electron injection layer is within the above range, the electron injection layer may have suitable or satisfactory electron injection characteristics without a significant increase in driving voltage.

[0324] The second electrode 190

[0325] The second electrode 190 may be disposed on the organic layer 150 having such a structure. The second electrode 190 may be a cathode, which is an electron injection electrode, and in this regard, a material for forming the second electrode 190 may be a material having a low work function, such a material may be a metal, an alloy, a conductive compound, or a combination thereof.

[0326] The second electrode 190 may 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 of the present disclosure are not limited thereto. The second electrode 190 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.

[0327] The second electrode 190 may have a single-layer structure or a multi-layer structure including two or more layers.

[0328] The layer constituting the hole transport region, the light emitting layer and the layer constituting the electron transport region may be formed in certain regions 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.

[0329] When the layer constituting the hole transport region, the light emitting layer and / or the layer constituting the electron transport region is formed by vacuum deposition, the deposition may be performed at a deposition temperature of about 100° C. to about 500° C., at a ... -8About 10 -3 Torr vacuum and approx. to about The deposition rate was carried out at .

[0330] When the layer constituting the hole transport region, the light emitting layer and / or the layer constituting the electron transport region is formed by spin coating, the spin coating may be performed at a coating speed of about 2,000 rpm to about 5,000 rpm and a heat treatment temperature of about 80°C to 200°C, depending on the material to be included in the layer and the structure of the layer to be formed.

[0331] equipment

[0332] Organic light-emitting devices can be used in a variety of suitable devices.

[0333] Therefore, another aspect of the embodiment provides an apparatus including an organic light-emitting device.

[0334] For example, the device may be a lighting device, an identification device, or any other suitable electronic device, but embodiments of the present disclosure are not limited thereto.

[0335] The light emitting device can be used as various appropriate displays, light sources, and the like.

[0336] For example, the authentication device may be a biometric authentication device that uses biometric information of a biometric body (eg, a fingertip or pupil, etc.) for authenticating an individual.

[0337] In addition to the organic light emitting device, the authentication apparatus may further include a biometric information collector.

[0338] The electronic device can be applied to personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic notebooks, electronic dictionaries, electronic game consoles, medical instruments (e.g., electronic thermometers, blood pressure meters, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram (ECG) displays, ultrasonic diagnostic devices, or endoscope displays), fish finders, various suitable measuring instruments, meters (e.g., meters for vehicles, aircraft, and ships), projectors, and the like, but the embodiments of the present disclosure are not limited thereto.

[0339] In addition to the organic light-emitting device, the apparatus may further include a thin film transistor. The thin film transistor may include a source and a drain, and the first electrode of the organic light-emitting device may be electrically coupled (eg, electrically connected) to at least one selected from the source and the drain of the thin film transistor.

[0340] General definitions of some substituents

[0341] As used herein, the term "C 1 -C 60"Alkyl" refers to a linear or branched aliphatic saturated hydrocarbon monovalent group having 1 to 60 carbon atoms, and non-limiting examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl and hexyl. As used herein, the term "C 1 -C 60 "Alkylene" refers to 1 -C 60 The alkyl group has divalent groups of the same (eg, substantially the same) structure.

[0342] As used herein, the term "C 2 -C 60 "Alkenyl" means a group consisting of 2 -C 60 The main chain (e.g., in the middle) or terminal of the alkyl group is substituted with at least one carbon-carbon double bond to form a hydrocarbon group, and non-limiting examples thereof include ethenyl, propenyl, and butenyl. As used herein, the term "C 2 -C 60 "Alkenylene" refers to 2 -C 60 Alkenyl groups have divalent groups with the same (eg, substantially the same) structure.

[0343] As used herein, the term "C 2 -C 60 "Alkynyl" refers to a 2 -C 60 The main chain (e.g., in the middle) or terminal of the alkyl group is substituted with at least one carbon-carbon triple bond to form a hydrocarbon group, and non-limiting examples thereof include ethynyl and propynyl. As used herein, the term "C 2 -C 60 "Alkynylidene" refers to 2 -C 60 Alkynyl groups have divalent groups with the same (eg, substantially the same) structure.

[0344] As used herein, the term "C 1 -C 60 "Alkoxy" refers to -OA 101 (A 101 C 1 -C 60 The term "alkyl" refers to a monovalent group represented by an alkyl group, and non-limiting examples thereof include a methoxy group, an ethoxy group, and an isopropoxy group.

[0345] As used herein, the term "C 3 -C 10 "Cycloalkyl" refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl. As used herein, the term "Cycloalkyl" refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl. 3 -C10 "Cycloalkylene" refers to 3 -C 10 The cycloalkyl group has divalent groups of the same (eg, substantially the same) structure.

[0346] As used herein, the term "C 1 -C 10 "Heterocycloalkyl" refers to a monovalent saturated monocyclic group having at least one heteroatom selected from N, O, Si, P and S as a ring atom and 1 to 10 carbon atoms, and non-limiting examples thereof include 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl and tetrahydrothienyl. As used herein, the term "C 1 -C 10 "Heterocycloalkylene" refers to a C 1 -C 10 The heterocycloalkyl group has divalent groups with the same (eg, substantially the same) structure.

[0347] As used herein, the term "C 3 -C 10 "Cycloalkenyl" refers to a monovalent monocyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and not having aromaticity (e.g., the entire ring and / or group is not aromatic), and non-limiting examples thereof include cyclopentenyl, cyclohexenyl and cycloheptenyl. As used herein, the term "C 3 -C 10 "Cycloalkenylene" refers to 3 -C 10 The cycloalkenyl group has divalent groups of the same (eg, substantially the same) structure.

[0348] As used herein, the term "C 1 -C 10 The term "heterocycloalkenyl group" refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P and S as a ring atom, 1 to 10 carbon atoms and at least one double bond in its ring. 1 -C 10 Non-limiting examples of heterocycloalkenyl groups include 4,5-dihydro-1,2,3,4-oxatriazolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothienyl. As used herein, the term “C 1 -C 10 "Heterocycloalkenylene" refers to 1 -C 10 The heterocycloalkenyl group has divalent groups having the same (eg, substantially the same) structure.

[0349] As used herein, the term "C 6 -C 60"Aryl" refers to a monovalent group having a carbocyclic aromatic system (having 6 to 60 carbon atoms), and the term "C 6 -C 60 "Arylene" refers to a divalent group having a carbocyclic aromatic system (having 6 to 60 carbon atoms). 6 -C 60 Non-limiting examples of aryl groups include phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, and chrysene. 6 -C 60 Aryl and C 6 -C 60 When the arylene groups each include two or more rings, the rings may be fused to each other (eg, bonded together).

[0350] As used herein, the term "C 1 -C 60 "Heteroaryl" refers to a monovalent group having a heterocyclic aromatic system (having at least one heteroatom selected from N, O, Si, P and S as a ring atom in addition to 1 to 60 carbon atoms). As used herein, the term "C 1 -C 60 The term "heteroarylene group" refers to a divalent group having a heterocyclic aromatic system (having at least one heteroatom selected from N, O, Si, P and S as a ring atom in addition to 1 to 60 carbon atoms). 1 -C 60 Non-limiting examples of heteroaryl groups include pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. 1 -C 60 Heteroaryl and C 1 -C 60 When the heteroarylene groups each include two or more rings, the rings may be fused to each other.

[0351] As used herein, the term "C 6 -C 60 "Aryloxy" refers to -OA 102 (A 102 C 6 -C 60 aryl), and the term C used herein 6 -C 60 Arylthio refers to -SA 103 (A 103 C 6 -C 60 aryl).

[0352] As used herein, the term "monovalent non-aromatic fused polycyclic group" refers to a monovalent group (e.g., having 8 to 60 carbon atoms) having two or more rings fused to each other (e.g., bonded together), with only carbon atoms as ring-forming atoms, and the entire molecular structure is non-aromatic (e.g., the entire ring, group or molecule is not aromatic). An example of a monovalent non-aromatic fused polycyclic group is fluorenyl. As used herein, the term "divalent non-aromatic fused polycyclic group" refers to a divalent group having the same (e.g., substantially the same) structure as a monovalent non-aromatic fused polycyclic group.

[0353] As used herein, the term "monovalent non-aromatic fused heteropolycyclic group" refers to a monovalent group (e.g., having 1 to 60 carbon atoms) having two or more rings fused to each other (e.g., bonded together), having at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom in addition to carbon atoms, and its entire molecular structure does not have aromaticity (e.g., the entire ring, group, and / or molecule is not aromatic). An 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 (e.g., substantially the same) as a monovalent non-aromatic fused heteropolycyclic group.

[0354] As used herein, the term "C 5 -C 60 "Carbocyclic group" refers to a monocyclic or polycyclic group having 5 to 60 carbon atoms (only carbon atoms are ring-forming atoms). 5 -C 60 The carbocyclic group may be an aromatic carbocyclic group or a non-aromatic carbocyclic group. 5 -C 60 The carbocyclic group can be a ring (such as benzene), a monovalent group (such as phenyl), or a divalent group (such as phenylene). In one or more embodiments, depending on the bond to (e.g., connected to) C 5 -C 60 The number of substituents of the carbocyclic group, C 5 -C 60 The carbocyclic group may be a trivalent group or a tetravalent group.

[0355] As used herein, the term "C 1 -C 60 "Heterocyclic group" refers to a C 5 -C 60 The carbocyclic group has a group having the same (eg, substantially the same) structure except that, in addition to carbon (the number of carbon atoms may range from 1 to 60), at least one heteroatom selected from N, O, Si, P and S is used as a ring-forming atom.

[0356] Selected from the substituted C5 -C 60 Carbocyclic group, the substituted C 1 -C 60 Heterocyclic group, the substituted C 3 -C 10 Cycloalkylene, the substituted C 1 -C 10 Heterocycloalkylene, the substituted C 3 -C 10 Cycloalkenylene, the substituted C 1 -C 10 Heterocycloalkenylene, the substituted C 6 -C 60 Arylene, the substituted C 1 -C 60 heteroarylene, the substituted divalent non-aromatic condensed polycyclic group, the substituted divalent non-aromatic condensed heteropolycyclic group, the substituted C 1 -C 60 Alkyl, the substituted C 2 -C 60 Alkenyl, the substituted C 2 -C 60 Alkynyl, the substituted C 1 -C 60 Alkoxy, the substituted C 3 -C 10 Cycloalkyl, the substituted C 1 -C 10 Heterocycloalkyl, the substituted C 3 -C 10 Cycloalkenyl, the substituted C 1 -C 10 Heterocycloalkenyl, the substituted C 6 -C 60 Aryl, the substituted C 6 -C 60 Aryloxy, the substituted C 6 -C 60 Arylthio, the substituted C 1 -C 60 At least one of the substituents of the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:

[0357] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine (hydrazine group), hydrazone (hydrazone group), C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C60 Alkynyl and C 1 -C 60 Alkoxy;

[0358] Each of the C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl and C 1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine (hydrazine group), hydrazone (hydrazone group), C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, -O(Q 11 )、-S(Q 11 )、-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 );

[0359] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups;

[0360] Each of the C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group and monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine (hydrazine group), hydrazone (hydrazone group), C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, -O(Q 21 )、-S(Q 21 )、-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 );as well as

[0361] -O(Q 31 )、-S(Q 31 )、-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

[0362] Q 1 To Q 3 , Q 11 To Q 13 , Q 21 To Q 23 and Q 31 To Q 33 can be independently selected from hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; amidino; hydrazine (hydrazine group); hydrazone (hydrazone group); C 1 -C 60 Alkyl; C 2 -C 60 Alkenyl; C 2 -C 60 Alkynyl; C 1 -C 60 Alkoxy; C 3 -C 10 Cycloalkyl; C 1 -C 10 Heterocycloalkyl; C 3 -C 10 Cycloalkenyl; C 1 -C 10 Heterocycloalkenyl; C 6 -C 60 Aryl; C 1 -C 60heteroaryl; a monovalent non-aromatic fused polycyclic group; a monovalent non-aromatic fused heteropolycyclic group; a biphenyl group; a terphenyl group; a C substituted with at least one selected from the following 1 -C 60 Alkyl: deuterium, -F, cyano, C 1 -C 60 alkyl, phenyl and biphenyl; and C substituted by at least one selected from the following 6 -C 60 Aryl: deuterium, -F, cyano, C 1 -C 10 Alkyl, phenyl and biphenyl.

[0363] As used herein, the term "Ph" may refer to a phenyl group; as used herein, the term "Me" may refer to a methyl group; as used herein, the term "Et" may refer to an ethyl group; as used herein, the term "ter-Bu" or "Bu t " may refer to a tert-butyl group; and the term "OMe" as used herein may refer to a methoxy group.

[0364] As used herein, the term "biphenyl" refers to a phenyl group substituted with a phenyl group. In other words, a "biphenyl" group is a group having "C 6 -C 60 "substituted phenyl" having "aryl" as a substituent.

[0365] As used herein, the term "terphenyl" refers to a phenyl group substituted with a biphenyl group. In other words, a "terphenyl" is a phenyl group having "substituted with a C 6 -C 60 Aryl substituted C 6 -C 60 A phenyl group having an "aryl" group as a substituent.

[0366] Unless otherwise defined, * and *' used herein each refer to a binding site to an adjacent atom in the corresponding formula.

[0367] The compound according to the embodiment and the organic light-emitting device according to the embodiment will be described in more detail below with reference to Synthesis Examples and Examples. The phrase "using B instead of A" used when describing Synthesis Examples means using B instead of A in the same molar equivalent.

[0368] Example

[0369] Synthesis Example 1 (Compound 2)

[0370]

[0371] Synthetic intermediate 2(2)

[0372] 2,3-Naphthalene dicarboxylic acid imide (150 g, 0.76 mol), isopropylacetic acid (starting material 2A, 116 g, 1.14 mol) and isopropylacetic acid zinc (starting material 2B, 51 g, 0.19 mol) were mixed in a 250 ml reactor, and then refluxed and stirred at a temperature of 360° C. for 24 hours. After the reaction was completed, the temperature was cooled to room temperature, and the resulting product intermediate 2 (1) was dissolved in 3 L of tetrahydrofuran without further purification process, and then 700 ml of methanesulfonic acid was added dropwise thereto. After 2 hours, it was subjected to an extraction process with water and dichloromethane, and the organic layer obtained by the extraction was separated by silica gel column chromatography (using a mixed solvent of dichloromethane and methanol), thereby synthesizing intermediate 2 (2) (0.50 g, 0.57 mmol, yield: 0.3%).

[0373] Synthesis of compound 2

[0374] Dichloroplatinum (II) dichloride (0.30 g, 1.14 mmol) was added to a 20 ml reactor, and 3 ml of benzonitrile was added thereto. The mixed solution was then refluxed and stirred for 30 minutes at a temperature of 160 ° C in a nitrogen atmosphere. The product thus obtained was added dropwise to a mixture containing 30 ml of phenyl diether and intermediate 2 (2) (0.50 g, 0.57 mmol), and the resulting mixed solution was refluxed and stirred for 3 hours at a temperature of 190 ° C. After the reaction was completed, the temperature was cooled to room temperature, and the product obtained was separated by silica gel column chromatography (using dichloromethane), thereby synthesizing compound 2 (0.31 g, 0.29 mmol, yield: 50%).

[0375] MS (MALDI-TOF) m / z: 1072[M]+

[0376] Synthesis Example 2 (Compound 8)

[0377]

[0378] Compound 8 (0.28 g, 0.23 mmol, yield: 0.12%) was synthesized by a method basically the same as that in Synthesis Example 1, except that intermediate 8(2) was synthesized by replacing starting materials 2A and 2B in the synthesis of intermediate 2(2) with starting materials 8A and 8B, respectively, and intermediate 8(2) was used instead of intermediate 2(2) in the synthesis of compound 2.

[0379] MS (MALDI-TOF) m / z: 1232[M]+

[0380] Synthesis Example 3 (Compound 10)

[0381]

[0382] Compound 10 (0.43 g, 0.34 mmol, yield: 0.18%) was synthesized by a method basically the same as that in Synthesis Example 1, except that intermediate 10(2) was synthesized by using starting materials 10A and 10B instead of starting materials 2A and 2B in the synthesis of intermediate 2(2), and intermediate 10(2) was used instead of intermediate 2(2) in the synthesis of compound 2.

[0383] MS (MALDI-TOF) m / z: 1264[M]+

[0384] Synthesis Example 4 (Compound 22)

[0385]

[0386] Compound 22 (0.23 g, 0.15 mmol, yield: 0.08%) was synthesized by a method basically the same as that in Synthesis Example 1, except that intermediate 22(2) was synthesized by using starting materials 22A and 22B respectively instead of starting materials 2A and 2B when synthesizing intermediate 2(2), and intermediate 22(2) was used instead of intermediate 2(2) when synthesizing compound 2.

[0387] MS (MALDI-TOF) m / z: 1480 [M] +

[0388] Synthesis Example 5 (Compound 24)

[0389]

[0390] Compound 24 (0.27 g, 0.21 mmol, yield: 0.11%) was synthesized by a method basically the same as that in Synthesis Example 1, except that intermediate 24(2) was synthesized by using starting materials 24A and 24B respectively instead of starting materials 2A and 2B when synthesizing intermediate 2(2), and intermediate 24(2) was used instead of intermediate 2(2) when synthesizing compound 2.

[0391] MS (MALDI-TOF) m / z: 1280 [M] +

[0392] Synthesis Example 6 (Compound 39)

[0393]

[0394] Compound 39 (0.14 g, 0.11 mmol, yield: 0.06%) was synthesized by a method basically the same as that in Synthesis Example 1, except that intermediate 39(2) was synthesized by using starting materials 39A and 39B instead of starting materials 2A and 2B in the synthesis of intermediate 2(2), and intermediate 39(2) was used instead of intermediate 2(2) in the synthesis of compound 2.

[0395] MS (MALDI-TOF) m / z: 1212[M]+

[0396] Synthesis Example 7 (Compound 43)

[0397]

[0398] Compound 43 (0.25 g, 0.17 mmol, yield: 0.09%) was synthesized by a method basically the same as that in Synthesis Example 1, except that intermediate 43(2) was synthesized by using starting materials 43A and 43B instead of starting materials 2A and 2B in the synthesis of intermediate 2(2), and intermediate 43(2) was used instead of intermediate 2(2) in the synthesis of compound 2.

[0399] MS (MALDI-TOF) m / z: 1440 [M] +

[0400] Synthesis Example 8 (Compound 31)

[0401]

[0402] Compound 31 (0.29 g, 0.19 mmol, yield: 0.10%) was synthesized by a method basically the same as that in Synthesis Example 1, except that intermediate 31(2) was synthesized by using starting materials 31A and 31B instead of starting materials 2A and 2B in the synthesis of intermediate 2(2), and intermediate 31(2) was used instead of intermediate 2(2) in the synthesis of compound 2.

[0403] MS (MALDI-TOF) m / z: 1512 [M] +

[0404] Synthesis Example 9 (Compound 59)

[0405]

[0406] Compound 59 (0.06 g, 0.06 mmol, yield: 0.03%), which was produced as a by-product in Synthesis Example 1, was collected.

[0407] MS (MALDI-TOF) m / z:988[M]+

[0408] Synthesis Example 10 (Compound 75)

[0409]

[0410] Compound 75 (0.18 g, 0.15 mmol, yield: 0.08%) was synthesized by a method basically the same as that in Synthesis Example 1, except that when synthesizing intermediate 2(2), intermediate 75(2) was synthesized by using starting materials 75A and 75B instead of starting materials 2A and 2B, respectively, and when synthesizing compound 2, intermediate 75(2) was used instead of intermediate 2(2).

[0411] MS (MALDI-TOF) m / z: 1168[M]+

[0412] Comparative Synthesis Example A (Compound A)

[0413]

[0414] Compound A (0.46 g, 0.38 mmol, yield: 0.20%) was synthesized by a method basically the same as that in Synthesis Example 1, except that intermediate A(2) was synthesized by using starting materials AA and AB instead of starting materials 2A and 2B in the synthesis of intermediate 2(2), respectively, and intermediate A(2) was used instead of intermediate 2(2) in the synthesis of compound 2.

[0415] MS (MALDI-TOF) m / z: 1208[M]+

[0416] Comparative Synthesis Example B (Compound B)

[0417]

[0418] Compound B (0.26 g, 0.19 mmol, yield: 0.10%) was synthesized by a method basically the same as that in Synthesis Example 1, except that intermediate B(2) was synthesized by using starting materials BA and BB instead of starting materials 2A and 2B in the synthesis of intermediate 2(2), respectively, and intermediate B(2) was used instead of intermediate 2(2) in the synthesis of compound 2.

[0419] MS (MALDI-TOF) m / z: 1376[M]+

[0420] Comparative Synthesis Example C (Compound C)

[0421]

[0422] Compound C (0.11 g, 0.11 mmol, yield: 0.06%) was synthesized by a method basically the same as that in Synthesis Example 1, except that intermediate C(2) was synthesized by using starting materials CA and CB instead of starting materials 2A and 2B in the synthesis of intermediate 2(2), respectively, and intermediate C(2) was used instead of intermediate 2(2) in the synthesis of compound 2.

[0423] MS (MALDI-TOF) m / z: 960[M]+

[0424] Example 1

[0425] Corning 15Ω / cm 2 The ITO glass substrate as the substrate and anode 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 then cleaned by exposure to ultraviolet rays and ozone for 30 minutes. Then, the ITO glass substrate was provided to a vacuum deposition device.

[0426] 2-TNATA was vacuum deposited on an ITO glass substrate to form a The hole injection layer is vacuum deposited on the hole injection layer to form a Thickness of hole transport layer.

[0427] BCPDS and POPCPA (at a weight ratio of 1:1 BCPDS to POPCPA) (which is a common host) and Compound 2 (which is a dopant) at a weight ratio of 97:3 were co-deposited on the hole transport layer to form a Thickness of the luminous layer.

[0428] TSPO1 is deposited on the light-emitting layer to form a The hole blocking layer is Alq 3 deposited on the hole blocking layer to form a Then, LiF is deposited on the electron transport layer to form a The electron injection layer is formed by vacuum depositing Al on the electron injection layer to form a A cathode with a thickness of 100 nm is formed, thereby completing the manufacture of the organic light-emitting device.

[0429]

[0430] Examples 2 to 10 and Comparative Examples A to C

[0431] An organic light-emitting device was manufactured in substantially the same manner as in Example 1, except that the compounds shown in Table 1 were respectively used as dopants when forming the light-emitting layers.

[0432] Evaluation Example 1

[0433] The driving voltage, current density, external quantum efficiency (EQE) and maximum emission wavelength of the organic light-emitting devices manufactured according to Examples 1 to 10 and Comparative Examples AC were measured using a Keithley SMU 236 and a luminance meter PR650, and the results are shown in Table 1.95 ) represents the amount of time that has passed when the brightness is 95% of the initial brightness (100%).

[0434] Table 1

[0435]

[0436]

[0437]

[0438] Referring to Table 1, it was confirmed that the organic light-emitting devices of Examples 1 to 10 had low driving voltage and high EQE compared to the organic light-emitting devices of Comparative Examples A to C. Therefore, the organic light-emitting devices of Examples 1 to 10 were able to emit near-infrared light.

[0439] According to one or more embodiments, an organic light-emitting device including an organometallic compound may have a low driving voltage, high light emission efficiency, and / or a long lifetime, and in this regard, the organometallic compound may be used to realize high-quality organic light-emitting devices and electronic devices.

[0440] It should be understood that the embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should typically be considered as available for other similar features or aspects in other embodiments.

[0441] It should be understood that although the terms "first", "second", "third", etc. may be used herein to describe various elements, components, regions, layers and / or sections, these elements, components, regions, layers and / or sections should not be limited by these terms. These terms are used to distinguish one element, component, region, layer or section from another element, component, region, layer or section. Therefore, the first element, component, region, layer or section described above may be referred to as a second element, component, region, layer or section without departing from the spirit and scope of the present disclosure.

[0442] Spatially relative terms, such as "below," "lower," "below," "above," "above," and the like, may be used herein for convenience of explanation to describe the relationship of one element or feature to another element or feature, as shown in the figures. It will be understood that the spatially relative terms are intended to cover different orientations of the device in use or in operation, in addition to the orientation shown in the figures. For example, if the device in the figure is turned over, the elements described as being "below" or "below" or "below" other elements or features will then be positioned as being "above" the other elements or features. Thus, the example terms "below" or "below" can cover both the "above" and "below" orientations. The device can be oriented in other ways (e.g., rotated 90 degrees or in other orientations), and the spatially relative descriptors used herein should be interpreted accordingly.

[0443] It will be understood that when an element or layer is referred to as being “on,” “connected to,” or “coupled to” another element or layer, it can be directly on, connected to, or coupled to the other element or layer, or one or more intervening elements or layers may be present. Additionally, it will be understood that when an element or layer is referred to as being “between” two elements or layers, it can be the only element or layer between the two elements or layers, or one or more intervening elements or layers may also be present.

[0444] The terms used herein are only used for the purpose of describing specific embodiments and are not intended to limit the present disclosure. As used herein, unless the context clearly indicates otherwise, the singular forms of "one" and "a kind of" are also intended to include the plural forms. It should be further understood that the terms "comprise", "include", "contain" and "containing", when used in this specification, specify the presence of the features, integers, behaviors, operations, elements and / or components, but do not exclude the presence or addition of one or more other features, integers, behaviors, operations, elements, components and / or combinations thereof. As used herein, the term "and / or" includes any and all combinations of one or more related listed items. When "at least one of" is before a series of elements, it modifies the entire column of elements, rather than modifying a single element in the column.

[0445] As used herein, the terms "substantially," "about," and similar terms are used as approximate terms, rather than as terms of degree, and are intended to take into account the inherent deviations of measurements or calculations that one of ordinary skill in the art would recognize. In addition, when describing embodiments of the present disclosure, the use of "may" refers to "one or more embodiments of the present disclosure." As used herein, the terms "use," "using," and "used" may be considered synonymous with the terms "utilize," "utilizing," and "utilized," respectively. In addition, the term "exemplary" is intended to refer to an example or illustration.

[0446] In addition, any numerical range described herein is intended to include all sub-ranges of the same numerical precision contained in the range. For example, the range of "1.0 to 10.0" is intended to include all sub-ranges between the minimum value 1.0 and the maximum value 10.0 (including 1.0 and 10.0), that is, the minimum value is equal to or greater than 1.0, and the maximum value is equal to or less than 10.0, such as, for example, 2.4 to 7.6. Any maximum numerical limit described herein is intended to include all lower numerical limits included herein, and any minimum numerical limit described in this specification is intended to include all higher numerical limits included herein. Therefore, the applicant reserves the right to modify this specification (including claims) to explicitly describe any sub-ranges included in the range explicitly described herein.

[0447] Although one or more embodiments have been described with reference to the drawings, it will be understood by those skilled in the art that various changes in form and details may be made without departing from the spirit and scope defined by the claims and their equivalents.

Claims

1. An organometallic compound represented by Formula 1: Formula 1 in, In formula 1, M is platinum, Ring A 1 To Ring A 4 are each independently naphthyl, R 1 To R 4 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano and nitro, R 11 To R 14 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 6 -C 60 Aryl and substituted or unsubstituted C 1 -C 60 Heteroaryl, a1 to a4 are each independently an integer from 0 to 10, a) R 11 To R 14 are not hydrogen at the same time, b) R 11 To R 14 are not phenyl at the same time, c) R 11 To R 14 are not mesityl at the same time, and d) R 11 To R 14 Different from methyl at the same time, Selected from R 11 To R 14 The two are not connected to each other, The substituted C 1 -C 60 Alkyl, the substituted C 3 -C 10 Cycloalkyl, the substituted C 6 -C 60 The aryl group and the substituted C 1 -C 60 At least one substituent of the heteroaryl group is selected from: Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, and C 1 -C 60 alkyl; C substituted by at least one selected from the following 1 -C 60 Alkyl: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, and nitro; and C 6 -C 60 Aryl, The organometallic compound emits near-infrared phosphorescence having a maximum emission wavelength in the range of 720 nm to 2500 nm.

2. The organometallic compound according to claim 1, wherein ring A 1 To Ring A 4 Each is independently selected from the group represented by Formula 2-2 to Formula 2-4: in, In Formula 2-2 to Formula 2-4, * and *' respectively represent the position of the carbon atom shared with the adjacent 5-membered ring, wherein Ring A 1 To Ring A 4 Each of them is fused to the 5-membered ring.

3. The organometallic compound according to claim 1, in: R 11 To R 14 Each independently selected from: hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, and nitro; C is unsubstituted or substituted by at least one selected from the following 1 -C 10 Alkyl: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, phenyl, biphenyl, di(phenyl)phenyl, terphenyl, naphthyl; cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, phenyl, biphenyl, diphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysene, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, each unsubstituted or substituted by at least one selected from the following , benzofuranyl, benzothiophenyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl and imidazopyrimidinyl: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, C 1 -C 10 alkyl, phenyl, biphenyl, di(phenyl)phenyl, terphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl and chrysene.

4. The organometallic compound according to claim 1, in: R 1 To R 4 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br and -I.

5. The organometallic compound according to claim 1, in: Selected from R 11 To R 14 At least one of which is independently selected from C 2 -C 10 Alkyl, which is unsubstituted or substituted by at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxy, cyano, nitro, phenyl, biphenyl, di(phenyl)phenyl, terphenyl and naphthyl.

6. The organometallic compound according to claim 1, in: Selected from R 11 To R 14 At least one of the radicals is not any of hydrogen, phenyl, mesityl and methyl.

7. The organometallic compound according to claim 1, in: Selected from R 11 To R 14 At least one of them is independently a group represented by formula A5: Formula A5 A in formula A5 5 is substituted or unsubstituted C 1 -C 60 Heteroaryl.

8. The organometallic compound according to claim 1, in: a) R 11 With R 12 Different from each other, R 13 With R 14 Different from each other, R 11 With R 13 are the same as each other, and R 12 With R 14 are identical to one another; b) R 11 With R 13 Different from each other, R 12 With R 14 Different from each other, R 11 With R 14 are the same as each other, and R 12 With R 13 are identical to one another; c) R 11 With R 12 are different from each other, and R 11 , R 13 and R 14 are identical to each other; or d) R 11 To R 14 They are all different from each other.

9. The organometallic compound of claim 1, wherein the organometallic compound is selected from the following compounds: in, In the above compounds, Ph represents a phenyl group.

10. An organic light emitting device, include: a first electrode; a second electrode facing the first electrode; as well as an organic layer between the first electrode and the second electrode, The organic layer comprises a light-emitting layer and the light-emitting layer comprises at least one organic metal compound according to any one of claims 1 to 9.

11. The organic light-emitting device according to claim 10, in: The first electrode is an anode, The second electrode is a cathode, and The organic layer further includes a hole transport region between the first electrode and the light emitting layer and an electron transport region between the light emitting layer and the second electrode, The hole transport region includes a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, an electron blocking layer or any combination thereof, and The electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer or any combination thereof. 12 . The organic light-emitting device of claim 10 , wherein the light-emitting layer emits near-infrared phosphorescence having a maximum emission wavelength in the range of 720 nm to 2500 nm.

13. The organic light-emitting device according to claim 11, in: At least one selected from the hole transport region and the light emitting layer comprises a compound containing an aromatic amine group, a compound containing an acridine ring and a compound containing a carbazole ring, or At least one selected from the light-emitting layer and the electron transport region includes a silicon-containing compound, a phosphine oxide-containing compound, a sulfur oxide-containing compound, a triazine ring-containing compound, a pyrimidine ring-containing compound, a pyridine ring-containing compound, a dibenzofuran ring-containing compound, and a dibenzothiophene ring-containing compound.

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

15. The apparatus of claim 14, wherein the apparatus is an electronic device.

16. The apparatus of claim 14, in: The device further comprises a thin film transistor, The thin film transistor includes a source electrode and a drain electrode, and The first electrode of the organic light emitting device is electrically coupled to one of the source and the drain of the thin film transistor.

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