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

Abstract

An organic light-emitting device, a device including the organic light-emitting device, and an organic metal compound represented by Formula 1 are provided. The organic light-emitting device includes: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode and including an emission layer, wherein: the organic layer includes the organic metal compound represented by Formula 1. Formula 1: M 1 (L 1 ) n1 (L 2 ) n2 .

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2018-0114361, filed on September 21, 2018, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field

[0003] One or more embodiments relate to an organic light-emitting device, and, for example, to an apparatus and an organometallic compound including the organic light-emitting device. Background Art

[0004] Organic light-emitting devices are self-emitting devices, and compared with other devices in the related art, they have a wide viewing angle, a high contrast ratio, and a short response time, and exhibit excellent characteristics in terms of brightness, driving voltage, and response speed.

[0005] In an exemplary organic light-emitting device, a first electrode is on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode are sequentially formed on the first electrode. Holes provided by the first electrode can move to the emission layer through the hole transport region, and electrons provided by the second electrode can move to the emission layer through the electron transport region. Holes and electrons, which are carriers, recombine in the emission layer to generate excitons. These excitons transition (e.g., relax) from an excited state to a ground state, thereby generating light. Summary of the invention

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

[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 presented embodiments.

[0008] According to one or more embodiments, an organic light-emitting device includes a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode and including an emission layer, wherein the organic layer includes an organic metal compound represented by Formula 1.

[0009] Formula 1

[0010] M 1 (L 1 ) n1 (L 2 ) n2

[0011] Formula 1-1

[0012]

[0013]

[0014] In Formula 1, Formula 1-1, Formula 2-1, Formula 2-2, Formula 3-1 and Formula 3-2,

[0015] M 1 Selected from the group consisting of period 1 transition metals, period 2 transition metals and period 3 transition metals;

[0016] *1 to *4 each represent the same 1 The attachment site of

[0017] L 1 is a ligand represented by formula 1-1;

[0018] L 2 is selected from a monodentate ligand and a bidentate ligand;

[0019] n1 is 1,

[0020] n2 is selected from 0, 1 and 2;

[0021] A 11 To A 14 Each independently selected from the group represented by Formula 2-1, the group represented by Formula 2-2, the group represented by Formula 3-1, the group represented by Formula 3-2, C 5 -C 60 Carbocyclic groups and C 1 -C 60 Heterocyclic groups;

[0022] Selected from A 11 To A 14 At least one of the groups selected from the group represented by formula 2-1 and the group represented by formula 2-2;

[0023] Selected from A 11 To A 14 At least one of the groups selected from the group represented by formula 3-1 and the group represented by formula 3-2;

[0024] Y 11 To Y 14 may be independently selected from N and C;

[0025] T 11 To T 14 may each be independently selected from a single bond, *-O-*' and *-S-*';

[0026] L 11 To L 14 can be independently selected from a single bond, *-O-*', *-S-*', *-C(R 17 )(R18 )-*'、*-C(R 17 )=*'、*=C(R 17 )-*'、*-C(R 17 )=C(R 18 )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 17 )-*'、*-N(R 17 )-*'、*-P(R 17 )-*'、*-Si(R 17 )(R 18 )-*'、*-P(R 17 )(R 18 )-*' and *-Ge(R 17 )(R 18 )-*';

[0027] a11 to a14 may be each independently selected from 0, 1, 2 and 3, and at least three selected from a11 to a14 are each independently selected from 1, 2 and 3;

[0028] When a11 is 0, A 11 and A 12 They may not be connected to each other. When a12 is 0, A 12 and A 13 They may not be connected to each other. When a13 is 0, A 13 and A 14 may not be connected to each other, and when a14 is 0, A 14 and A 11 They can not be linked to each other.

[0029] R 11 To R 14 , R 17 and R 18 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a substituted or unsubstituted C 1 -C 60 Alkyl groups, substituted or unsubstituted C 2 -C 60 Alkenyl groups, substituted or unsubstituted C 2 -C 60 Alkynyl group, substituted or unsubstituted C 1 -C 60 Alkoxy groups, substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10Heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl group, substituted or unsubstituted C 6 -C 60 Aryl group, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio group, substituted or unsubstituted C 1 -C 60 Heteroaryl groups, substituted or unsubstituted C 1 -C 60 Heteroaryloxy group, substituted or unsubstituted C 1 -C 60 heteroarylthio group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 );

[0030] R 17 and R 11 , R 17 and R 12 , R 17 and R 13 and / or R 17 and R 14 may be optionally linked to each other to form a substituted or unsubstituted C 5 -C 60 A carbocyclic group or a substituted or unsubstituted C 1 -C 60 Heterocyclic groups,

[0031] R 17 and R 18may be optionally linked to each other to form a substituted or unsubstituted C 5 -C 60 A carbocyclic group or a substituted or unsubstituted C 1 -C 60 Heterocyclic groups,

[0032] b11 to b14 may each be independently selected from 1, 2, 3, 4, 5, 6, 7 and 8;

[0033] X 21 Can be selected from O, S, N (R 24 ) and C(R 24 )(R 25 );

[0034] X 22 To X 25 may be independently selected from N and C,

[0035] A 21 and A 22 Can be independently selected from C 5 -C 60 Carbocyclic groups and C 1 -C 60 Heterocyclic groups;

[0036] X 31 Can be N, N-* or C(R 31 ), X 32 Can be N, N-* or C(R 32 ), X 33 Can be N, N-* or C(R 33 ), X 34 Can be N, N-* or C(R 34 ), X 35 Can be N, N-* or C(R 35 ), X 36 Can be N, N-* or C(R 36 ), X 37 Can be N, N-* or C(R 37 ), and X 38 Can be N, N-* or C(R 38 ),

[0037] Selected from X 31 To X 34 Two or more of may be independently N or N-*,

[0038] Selected from X 35 To X 38 One or more than one of them may be independently N or N-*, A 31 Can be selected from C 5-C 60 Carbocyclic groups and C 1 -C 60 Heterocyclic groups;

[0039] A 32 It can be a C containing at least one N 1 -C 60 Heterocyclic group.

[0040] R 21 To R 25 and R 31 To R 39 can be independently selected from the group consisting of a linking site, hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a substituted or unsubstituted C 1 -C 60 Alkyl groups, substituted or unsubstituted C 2 -C 60 Alkenyl groups, substituted or unsubstituted C 2 -C 60 Alkynyl group, substituted or unsubstituted C 1 -C 60 Alkoxy groups, substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl group, substituted or unsubstituted C 6 -C 60 Aryl group, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio group, substituted or unsubstituted C 1 -C 60 Heteroaryl groups, substituted or unsubstituted C 1 -C 60 Heteroaryloxy group, substituted or unsubstituted C 1 -C 60 heteroarylthio group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2)、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 );

[0041] Selected from R 21 To R 25 One, two or three of the may be attachment sites,

[0042] Selected from R 31 To R 34 and R 39 One, two or three of the may be attachment sites,

[0043] Selected from R 35 To R 39 One, two or three of the may be attachment sites,

[0044] Q 1 To Q 3 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60Heteroaryl groups, C 1 -C 60 Heteroaryloxy groups, C 1 -C 60 a heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group; and

[0045] * and *' each represent a bonding site to an adjacent atom.

[0046] According to one or more embodiments, an apparatus comprises the organic light-emitting device.

[0047] According to one or more embodiments, the organometallic compound is represented by Formula 1. BRIEF DESCRIPTION OF THE DRAWINGS

[0048] The drawings, together with the specification, illustrate embodiments of the subject matter of the present disclosure, and, together with the description, serve to explain principles of the embodiments of the subject matter of the present disclosure.

[0049] Figure 1 A schematic view showing an organic light emitting device according to an embodiment;

[0050] Figure 2 A schematic view showing an organic light emitting device according to an embodiment;

[0051] Figure 3 A schematic view showing an organic light emitting device according to an embodiment; and

[0052] Figure 4 A schematic view showing an organic light emitting device according to an embodiment is shown. DETAILED DESCRIPTION

[0053] Because the present disclosure allows for various suitable variations and numerous embodiments, exemplary embodiments will be illustrated in the drawings and described in more detail in the written description. The effects and characteristics of the embodiments of the present disclosure and methods of implementing them will become apparent with reference to the embodiments described in more detail with reference to the drawings. However, the present disclosure is implemented in many different forms and should not be construed as being limited to the embodiments set forth herein.

[0054] Hereinafter, the subject matter of the present disclosure will be described in more detail by explaining embodiments of the present disclosure with reference to the accompanying drawings. The same reference numerals in the accompanying drawings represent the same elements, and therefore repeated description thereof will not be repeated.

[0055] In the following embodiments, an expression used in the singular encompasses an expression in the plural unless it has a clearly different meaning in the context.

[0056] In the following embodiments, it should be understood that terms such as "including", "having" and "comprising" are intended to indicate the presence of features or components disclosed in the specification, and are not intended to exclude the possibility that one or more other features or components may exist or may be added.

[0057] In the following embodiments, when a film, region or component is on or over another film, region or component, the film, region or component may be directly on the other film, region or component, or the other film, region or component may be present therebetween.

[0058] For convenience of explanation, the sizes of components in the drawings may be exaggerated. In other words, since the sizes and thicknesses of components in the drawings may be arbitrarily shown for convenience of explanation, the following embodiments are not limited thereto.

[0059] An aspect of the embodiment provides an organic light-emitting device including: a first electrode; a second electrode; and an organic layer including an emission layer between the first electrode and the second electrode, wherein the organic layer includes an organic metal compound represented by Formula 1:

[0060] Formula 1

[0061] M 1 (L 1 ) n1 (L 2 ) n2

[0062] M in Formula 1 1 It can be selected from the group consisting of period 1 transition metals, period 2 transition metals and period 3 transition metals.

[0063] For example, M in Formula 1 1 It can be selected from platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) and thulium (Tm), but the embodiments of the present disclosure are not limited thereto.

[0064] In one embodiment, M in Formula 1 1 It may be selected from Pt, Pd, Cu, Ag, Au, Rh, Ir, Ru, and Os, but the embodiments of the present disclosure are not limited thereto.

[0065] In one embodiment, M in Formula 1 1 It may be selected from Pt, Pd, Cu, Ag, Au, Ru, and Os, but the embodiments of the present disclosure are not limited thereto.

[0066] In one embodiment, M in Formula 1 1It may be selected from Pt, Pd, Ru, and Os, but the embodiments of the present disclosure are not limited thereto.

[0067] L in Formula 1 1 is a ligand represented by formula 1-1:

[0068] Formula 1-1

[0069]

[0070] In Formula 1-1, *1 to *4 may each represent 1 A can be understood by referring to the following description of this article. 11 To A 14 , Y 11 To Y 14 , T 11 To T 14 , L 11 To L 14 、a11 to a14、R 11 To R 14 and b11 to b14.

[0071] In formula 1, n1 represents L 1 number, and n1 can be 1.

[0072] L in Formula 1 2 Selected from monodentate ligands and bidentate ligands.

[0073] In formula 1, n2 represents L 2 and n2 can be selected from 0, 1 and 2.

[0074] For example, n2 in Formula 1 may be 0 or 2, but embodiments of the present disclosure are not limited thereto.

[0075] In formula 1-1, A 11 To A 14 Each independently selected from the group represented by Formula 2-1, the group represented by Formula 2-2, the group represented by Formula 3-1, the group represented by Formula 3-2, C 5 -C 60 Carbocyclic groups and C 1 -C 60 Heterocyclic groups;

[0076] Selected from A 11 To A 14 At least one of the groups selected from the group represented by Formula 2-1 and the group represented by Formula 2-2; and

[0077] Selected from A 11 To A 14At least one of the groups is selected from the group represented by Formula 3-1 and the group represented by Formula 3-2.

[0078] For example, A in formula 1-1 11 To A 14 Each of the above may be independently selected from the group represented by Formula 2-1, the group represented by Formula 2-2, the group represented by Formula 3-1, the group represented by Formula 3-2, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a phenanthrenene group, a triphenylene group, a pyrene group, group, a cyclopentadiene group, a 1,2,3,4-tetralinyl group, a furan group, a thiophene group, a silole group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzosilole group, a dibenzosilole group, an indenopyridine group, an indolopyridine group, a benzofuranopyridine group, a benzothienopyridine group, a benzothiorrolopyridine group, an indenopyrimidine group, an indolopyrimidine group, a benzofuranopyrimidine group, a benzothienopyrimidine group, a benzothiorrolopyrimidine group, a dihydropyridine group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazolinyl group, a phenanthroline group, a benzoquinoline group, a benzoisoquinoline group group, a benzoquinoxaline group, a benzoquinazoline group, a pyrrole group, a pyrazole group, an imidazole group, a 2,3-dihydroimidazole group, a triazole group, a 2,3-dihydrotriazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a 2,3-dihydrobenzimidazole group, an imidazopyridine group, a 2,3-dihydroimidazopyridine group, an imidazopyrimidine group, a 2,3-dihydroimidazopyrimidine group, an imidazopyrazine group, a 2,3-dihydroimidazopyrazine group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, and a 5,6,7,8-tetrahydroquinoline group, but the embodiments of the present disclosure are not limited thereto.

[0079] In one embodiment, A in Formula 1-1 11 To A 14The group represented by formula 2-1, the group represented by formula 2-2, the group represented by formula 3-1, the group represented by formula 3-2, a phenyl group, a naphthalene group, an anthracene group, a phenanthrene group, a phenanthene group, a furan group, a thiophene group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, an indenopyridine group, an indolepyridine group, a benzofuranopyridine group, a benzothienopyridine group, an indenopyrimidine group, an indolepyrimidine group, a benzofuranopyridine group, a benzothienopyridine group, an indenopyrimidine group, an indolepyrimidine group, a benzofuranopyridine group, a benzothiophenepyridine group, a benzopyrimidine group, an indenopyrimidine group, a benzofuranopyridine group, a benzopyrim ... The invention also includes pyrimidine groups, benzothiophenopyrimidine groups, pyridine groups, pyrimidine groups, pyrazine groups, pyridazine groups, triazine groups, quinoline groups, isoquinoline groups, quinoxaline groups, quinazoline groups, phenanthroline groups, benzoquinoline groups, benzoisoquinoline groups, benzoquinoxaline groups, benzoquinazoline groups, pyrrole groups, pyrazole groups, imidazole groups, triazole groups, oxazole groups, isoxazole groups, thiazole groups, isothiazole groups, oxadiazole groups, thiadiazole groups, benzopyrazole groups, and benzimidazole groups, but the embodiments of the present disclosure are not limited thereto.

[0080] In one embodiment, A in Formula 1-1 11 To A 14 Each may be independently selected from a group represented by Formula 2-1, a group represented by Formula 2-2, a group represented by Formula 3-1, a group represented by Formula 3-2, a phenyl group, a naphthyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, and an isoquinoline group, but the embodiments of the present disclosure are not limited thereto.

[0081] Y in formula 1-1 11 To Y 14 can be each independently selected from N and C.

[0082] For example, Y selected from Formula 1-1 11 To Y 14 Two of them may be C, and the remaining two may be N, but embodiments of the present disclosure are not limited thereto.

[0083] T in formula 1-1 11 To T 14 may each be independently selected from a single bond, *-O-*' and *-S-*'.

[0084] For example, T in Formula 1 11 To T 14 Can be a single key.

[0085] L in formula 1-1 11 To L 14 can be independently selected from a single bond, *-O-*', *-S-*', *-C(R 17 )(R18 )-*'、*-C(R 17 )=*'、*=C(R 17 )-*'、*-C(R 17 )=C(R 18 )-*', *-C(=O)-*', *-C(=S)-*', *-C≡C-*', *-B(R 17 )-*'、*-N(R 17 )-*'、*-P(R 17 )-*'、*-Si(R 17 )(R 18 )-*'、*-P(R 17 )(R 18 )-*' and *-Ge(R 17 )(R 18 )-*';

[0086] You can understand R by referring to the following relevant descriptions in this article 17 and R 18 ;

[0087] * and *' each represent a bonding site to an adjacent atom.

[0088] For example, L in formula 1-1 11 To L 14 The *-O-*' and *-S-*' may each be independently selected from a single bond, *-O-*' and *-S-*', but the embodiments of the present disclosure are not limited thereto.

[0089] In Formula 1-1, a11 to a14 may each be independently selected from 0, 1, 2 and 3, and at least three selected from a11 to a14 may be selected from 1, 2 and 3, and

[0090] When a11 is 0, A 11 and A 12 They may not be connected to each other. When a12 is 0, A 12 and A 13 They may not be connected to each other. When a13 is 0, A 13 and A 14 may not be connected to each other, and when a14 is 0, A 14 and A 11 May not be linked to each other.

[0091] For example, a11 to a14 in Formula 1-1 may each be independently selected from 0 and 1, and

[0092] The sum of a11 to a14 may be selected from 3 and 4, but embodiments of the present disclosure are not limited thereto.

[0093] In one embodiment, comprising M1 , T 11 , Y 11 ,(L 11 ) a11 , Y 12 and T 12 (or composed of) an organometallic compound ring, comprising M 1 , T 12 , Y 12 ,(L 12 ) a12 , Y 13 and T 13 (or composed of) an organometallic compound ring, comprising M 1 , T 13 , Y 13 ,(L 13 ) a13 , Y 14 and T 14 (or consisting of) an organometallic compound ring, and a ring containing M 1 , T 14 , Y 14 ,(L 14 ) a14 , Y 11 and T 11 The rings of the organometallic compound of (or consisting of) the same may each independently be a 5-membered ring, a 6-membered ring, or a 7-membered ring, but embodiments of the present disclosure are not limited thereto.

[0094] R in Formula 1-1 11 To R 14 , R 17 and R 18 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a substituted or unsubstituted C 1 -C 60 Alkyl groups, substituted or unsubstituted C 2 -C 60 Alkenyl groups, substituted or unsubstituted C 2 -C 60 Alkynyl group, substituted or unsubstituted C 1 -C 60 Alkoxy groups, substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C10 Heterocycloalkenyl group, substituted or unsubstituted C 6 -C 60 Aryl group, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio group, substituted or unsubstituted C 1 -C 60 Heteroaryl groups, substituted or unsubstituted C 1 -C 60 Heteroaryloxy group, substituted or unsubstituted C 1 -C 60 heteroarylthio group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 );

[0095] R 17 and R 11 , R 17 and R 12 , R 17 and R 13 and / or R 17 and R 14 may be optionally linked to each other to form a substituted or unsubstituted C 5 -C 60 A carbocyclic group or a substituted or unsubstituted C 1 -C 60 Heterocyclic groups,

[0096] R 17 and R 18 may be optionally linked to each other to form a substituted or unsubstituted C 5 -C 60 A carbocyclic group or a substituted or unsubstituted C 1-C 60 Heterocyclic groups,

[0097] Q 1 To Q 3 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 1 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl groups, C 1 -C 60 Heteroaryloxy groups, C 1 -C 60 a heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group.

[0098] For example, R in Formula 1-1 11 To R 14 , R 17 and R 18 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a cyano group, C 1 -C 20 Alkyl groups and C 1 -C 20 Alkoxy groups;

[0099] C each substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, a cyano group, a phenyl group, a biphenyl group, and a terphenyl group 1 -C 20 Alkyl groups and C 1 -C 20Alkoxy groups;

[0100] a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a phenyl group, a peryl group, a pentacene group, a pyrrolyl group, a thienyl group, a furanyl group, a thiolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindoleyl group, an indazolyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a a benzophenanthryl group, a benzofuranyl group, a benzothiophenyl group, a benzothiophenyl group, a benzothiazolyl group, a benzothiazolyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzophenanthridine group, a benzophenanthridine group, a benzofuranyl group, a benzothiophenyl group, a benzothiazolyl group, a benzoisothiazolyl group, a benzoxazolyl group group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, a thiadiazolyl group, an oxadiazolyl group, a triazine group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilyl group, a benzocarbazolyl group, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, a naphthobenzosilyl group, a dibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenyl group, a di a naphthothirolyl group, an imidazopyridyl group, an imidazopyrimidyl group, an oxazolopyridyl group, a thiazopyridyl group, a benzonaphthyridinyl group, an azafluorenyl group, an azaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothienyl group, an azadibenzothirolyl group, an indenopyrrolyl group, an indolopyrrolyl group, an indenocarbazolyl group, and an indolocarbazolyl group;

[0101] Each is selected from deuterium, -F, -Cl, -Br, -I, a cyano group, C 1 -C 20 Alkyl group, C 1 -C 20an alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a phenyl group, a peryl group, a pentacene group, a pyrrolyl group, a thienyl group, a furanyl group, a thiolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindoleyl group, an indazolyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a benzoquinoline group, a a benzofuranyl group, a benzothiophenyl group, a benzothiosilyl group, a benzothiazolyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzoquinoxalinyl group, a quinazoline group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzosilyl group, a benzothiazolyl group, a benzisothiazolyl group, a benzoxazolyl group, Benzisoxazolyl group, triazolyl group, tetrazolyl group, thiadiazolyl group, oxadiazolyl group, triazine group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzosilyl group, benzocarbazolyl group, naphthobenzofuranyl group, naphthobenzothiophenyl group, naphthobenzosilyl group, dibenzocarbazolyl group, dinaphthofuranyl group, dinaphthothiophenyl group, dinaphthosilyl group azadibenzofuranyl group, azadibenzothiophenyl group, azadibenzothiophenyl group, azadibenzothiophenyl group, an indenopyrrolyl group, an indolepyrrolyl group, an indenocarbazolyl group, an indolecarbazolyl group, a -Si(Q)- 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) and -P(=S)(Q31 )(Q 32 ) is at least one substituted cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, indacenyl group, acenaphthenyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenaltenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a phenyl group, a peryl group, a pentacene group, a pyrrolyl group, a thienyl group, a furanyl group, a thiolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindoleyl group, an indazolyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzosilyl group, a benzothiazolyl group, a benzisothiazolyl group, a benzoxazolyl group group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, a thiadiazolyl group, an oxadiazolyl group, a triazine group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilyl group, a benzocarbazolyl group, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, a naphthobenzosilyl group, a dibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenyl group, a dinaphthobenzosilyl group thiolyl group, imidazopyridyl group, imidazopyrimidyl group, oxazolopyridyl group, thiazopyridyl group, benzonaphthyridinyl group, azafluorenyl group, azaspiro-bifluorenyl group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group, azadibenzosilyl group, indenopyrrolyl group, indolopyrrolyl group, indenocarbazolyl group and indolocarbazolyl group; and

[0102] -Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1)、-P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 ),

[0103] Where Q 1 To Q 3 and Q 31 To Q 33 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 1 -C 60 A heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group, but the embodiments of the present disclosure are not limited thereto.

[0104] In one embodiment, R in Formula 1-1 11 To R 14 , R 17 and R 18 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a cyano group and C 1 -C 20 Alkyl groups;

[0105] C substituted by at least one selected from deuterium, -F, -Cl, -Br, -I and cyano groups 1 -C 20 Alkyl groups;

[0106] A group represented by one of Formula 5-1 to Formula 5-138; and

[0107] -Si(Q 1 )(Q 2 )(Q3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 ), but the embodiments of the present disclosure are not limited thereto:

[0108]

[0109]

[0110]

[0111]

[0112]

[0113] In equations 5-1 to 5-138,

[0114] X 51 Can be selected from O, S, N (R 51 ) and C(R 51 )(R 60 );

[0115] X 52 Can be N or C (R 52 ), X 53 Can be N or C (R 53 ), X 54 Can be N or C (R 54 ), X 55 Can be N or C (R 55 ), X 56 Can be N or C (R 56 ), X 57 Can be N or C (R 57 ), X 58 Can be N or C (R 58 ), and X 59 Can be N or C (R 59 );

[0116] R 51 To R 60can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C 1 -C 20 Alkyl group, C 1 -C 20 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthryl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a benzofuranyl group, a benzothiophenyl group, a benzothiophenyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzothiophenyl group, a -Si(Q)- 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) and -P(=S)(Q 31 )(Q 32 );

[0117] Q 1 To Q 3 and Q 31 To Q 33 Can be independently selected from C 1 -C 60 Alkyl groups, phenyl groups, biphenyl groups and terphenyl groups;

[0118] b51 can be selected from 1, 2, 3, 4 and 5;

[0119] b52 can be selected from 1, 2, 3, 4, 5, 6 and 7;

[0120] b53 can be selected from 1, 2, 3, 4, 5, 6, 7, 8 and 9;

[0121] b54 can be selected from 1, 2, 3 and 4;

[0122] b55 can be selected from 1, 2 and 3;

[0123] b56 can be selected from 1 and 2;

[0124] b57 may be selected from 1, 2, 3, 4, 5 and 6; and

[0125] * indicates the connection site with the adjacent atom.

[0126] In one embodiment, R in Formula 1-1 11 To R 14 , R 17 and R 18 may be each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a cyano group, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group and a tert-butyl group;

[0127] a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group, each of which is substituted with at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, and a cyano group; and

[0128] A group represented by one of Formula 6-1 to Formula 6-257, but the embodiments of the present disclosure are not limited thereto:

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138] In equations 6-1 to 6-257,

[0139] t-Bu is a tert-butyl group;

[0140] Ph is a phenyl group;

[0141] 1-Naph is a 1-naphthyl group;

[0142] 2-Naph is a 2-naphthyl group; and

[0143] * indicates the connection site with the adjacent atom.

[0144] b11 to b14 in Formula 1-1 may be each independently selected from 1, 2, 3, 4, 5, 6, 7 and 8.

[0145] In formula 2-1 and formula 2-2, X 21 Can be selected from O, S, N (R 24 ) and C(R 24 )(R 25 );as well as

[0146] The following article further describes R 24 and R 25 .

[0147] For example, X in Formula 2-1 and Formula 2-2 21 It can be N(R 24 ), but the embodiments of the present disclosure are not limited thereto.

[0148] X in Formula 2-1 and Formula 2-2 22 To X 25 can be N and C independently.

[0149] For example, X in Formula 2-1 and Formula 2-2 22 To X 25 It may be C, but the embodiments of the present disclosure are not limited thereto.

[0150] A in Formula 2-1 and Formula 2-2 21 and A 22 Can be independently selected from C 5 -C 60 Carbocyclic groups and C 1 -C 60 Heterocyclic group.

[0151] For example, A in Formula 2-1 and Formula 2-2 21 and A 22 Each may be independently selected from a phenyl group, a naphthyl group, a phenanthrene group, a phenalene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, and a quinazoline group, but the embodiments of the present disclosure are not limited thereto.

[0152] In one embodiment, A in Formula 2-1 and Formula 2-2 21 and A 22 The groups may be each independently selected from a phenyl group, a naphthyl group, a phenanthrene group, a phenalene group, a pyridine group, a quinoline group, and an isoquinoline group, but the embodiments of the present disclosure are not limited thereto.

[0153] R in Formula 2-1 and Formula 2-2 21 To R 25 can be independently selected from the group consisting of a linking site, hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a substituted or unsubstituted C 1 -C 60 Alkyl groups, substituted or unsubstituted C 2 -C 60 Alkenyl groups, substituted or unsubstituted C 2 -C 60 Alkynyl group, substituted or unsubstituted C 1 -C 60 Alkoxy groups, substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl group, substituted or unsubstituted C 6 -C 60 Aryl group, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio group, substituted or unsubstituted C 1 -C 60 Heteroaryl groups, substituted or unsubstituted C 1 -C 60 Heteroaryloxy group, substituted or unsubstituted C 1 -C 60 heteroarylthio group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1)、-P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 );

[0154] Selected from R 21 To R 25 One, two or three of the may be attachment sites,

[0155] Q 1 To Q 3 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 1 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl groups, C 1 -C 60 Heteroaryloxy groups, C 1 -C 60 a heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group.

[0156] For example, R in Formula 2-1 and Formula 2-2 21 To R 25 can be independently selected from the group consisting of a linking site, hydrogen, deuterium, -F, -Cl, -Br, -I, a cyano group, C 1 -C 20 Alkyl groups and C 1 -C 20 Alkoxy groups;

[0157] C each substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, a cyano group, a phenyl group, a biphenyl group, and a terphenyl group 1 -C 20 Alkyl groups and C 1 -C 20 Alkoxy groups;

[0158] a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a phenyl group, a peryl group, a pentacene group, a pyrrolyl group, a thienyl group, a furanyl group, a thiolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindoleyl group, an indazolyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a a benzophenanthryl group, a benzofuranyl group, a benzothiophenyl group, a benzothiophenyl group, a benzothiazolyl group, a benzothiazolyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzophenanthridine group, a benzophenanthridine group, a benzofuranyl group, a benzothiophenyl group, a benzothiazolyl group, a benzoisothiazolyl group, a benzoxazolyl group group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, a thiadiazolyl group, an oxadiazolyl group, a triazine group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilyl group, a benzocarbazolyl group, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, a naphthobenzosilyl group, a dibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenyl group, a di a naphthothirolyl group, an imidazopyridyl group, an imidazopyrimidyl group, an oxazolopyridyl group, a thiazopyridyl group, a benzonaphthyridinyl group, an azafluorenyl group, an azaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothienyl group, an azadibenzothirolyl group, an indenopyrrolyl group, an indolopyrrolyl group, an indenocarbazolyl group, and an indolocarbazolyl group;

[0159] Each is selected from deuterium, -F, -Cl, -Br, -I, a cyano group, C 1 -C 20 Alkyl group, C 1 -C 20an alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a phenyl group, a peryl group, a pentacene group, a pyrrolyl group, a thienyl group, a furanyl group, a thiolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindoleyl group, an indazolyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a benzoquinoline group, a a benzofuranyl group, a benzothiophenyl group, a benzothiosilyl group, a benzothiazolyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzoquinoxalinyl group, a quinazoline group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzosilyl group, a benzothiazolyl group, a benzisothiazolyl group, a benzoxazolyl group, Benzisoxazolyl group, triazolyl group, tetrazolyl group, thiadiazolyl group, oxadiazolyl group, triazine group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzosilyl group, benzocarbazolyl group, naphthobenzofuranyl group, naphthobenzothiophenyl group, naphthobenzosilyl group, dibenzocarbazolyl group, dinaphthofuranyl group, dinaphthothiophenyl group, dinaphthosilyl group azadibenzofuranyl group, azadibenzothiophenyl group, azadibenzothiophenyl group, azadibenzothiophenyl group, an indenopyrrolyl group, an indolepyrrolyl group, an indenocarbazolyl group, an indolecarbazolyl group, a -Si(Q)- 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q 32 ) and -P(=S)(Q31 )(Q 32 ) is at least one substituted cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, indacenyl group, acenaphthenyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenaltenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a phenyl group, a peryl group, a pentacene group, a pyrrolyl group, a thienyl group, a furanyl group, a thiolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindoleyl group, an indazolyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzosilyl group, a benzothiazolyl group, a benzisothiazolyl group, a benzoxazolyl group group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, a thiadiazolyl group, an oxadiazolyl group, a triazine group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilyl group, a benzocarbazolyl group, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, a naphthobenzosilyl group, a dibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenyl group, a dinaphthobenzosilyl group thiolyl group, imidazopyridyl group, imidazopyrimidyl group, oxazolopyridyl group, thiazopyridyl group, benzonaphthyridinyl group, azafluorenyl group, azaspiro-bifluorenyl group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group, azadibenzosilyl group, indenopyrrolyl group, indolopyrrolyl group, indenocarbazolyl group and indolocarbazolyl group; and

[0160] -Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1)、-P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 );

[0161] Q 1 To Q 3 and Q 31 To Q 33 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 1 -C 60 A heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group, but the embodiments of the present disclosure are not limited thereto.

[0162] In one embodiment, R in Formula 2-1 and Formula 2-2 21 To R 25 can be independently selected from the group consisting of a linking site, hydrogen, deuterium, -F, -Cl, -Br, -I, a cyano group, C 1 -C 20 Alkyl groups;

[0163] C substituted by at least one selected from deuterium, -F, -Cl, -Br, -I and cyano groups 1 -C 20 Alkyl groups;

[0164] A group represented by one of Formula 5-1 to Formula 5-138; and

[0165] -Si(Q 1 )(Q 2 )(Q 3 )、-N(Q1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 ), but the embodiments of the present disclosure are not limited thereto.

[0166] In one embodiment, R in Formula 2-1 and Formula 2-2 21 To R 25 may each be independently selected from the group consisting of a linking site, hydrogen, deuterium, -F, -Cl, -Br, -I, a cyano group, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group;

[0167] a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group, each of which is substituted with at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, and a cyano group; and

[0168] A group represented by one of Formula 6-1 to Formula 6-257, but the embodiments of the present disclosure are not limited thereto.

[0169] In one embodiment, the group represented by Formula 2-1 and the group represented by Formula 2-2 may each independently be a group represented by one of Formulas 2-11 to 2-26, but embodiments of the present disclosure are not limited thereto:

[0170]

[0171] In equations 2-11 to 2-26,

[0172] X 21 Can be selected from O, S, N (R 24 ) and C(R 24 )(R 25 ),

[0173] X 26a Can be N, N-* or C(R 26a ), X 26b Can be N, N-* or C(R 26b ), X 26c Can be N, N-* or C(R 26c ), X26d Can be N, N-* or C(R 26d ), X 26e Can be N, N-* or C(R 26e ), X 26f Can be N, N-* or C(R 26f ), X 26g Can be N, N-* or C(R 26g ), X 26h Can be N, N-* or C(R 26h ), X 26i Can be N, N-* or C(R 26i ), X 26j Can be N, N-* or C(R 26j ), X 26k Can be N, N-* or C(R 26k ), X 26l Can be N, N-* or C(R 26l ),

[0174] By referring to the R provided by Formula 2-1 and Formula 2-2 21 The definitions of R are understood independently 24 , R 25 and R 26a To R 26l ,

[0175] R selected from formula 2-11 24 , R 25 and R 26a To R 26h One, two or three of them are the attachment sites,

[0176] R is selected from Formula 2-12 to Formula 2-14 24 , R 25 and R 26a To R 26j One, two or three of them are the attachment sites,

[0177] R is selected from Formula 2-15 to Formula 2-23 24 , R 25 and R 26a To R 26l One, two or three of them are the attachment sites,

[0178] R selected from Formula 2-24 and Formula 2-25 24 , R 25 and R 26a To R 26k One, two or three of them are the attachment sites,

[0179] R selected from formula 2-26 24, R 25 and R 26a To R 26h One, two or three of the are attachment sites, and

[0180] * indicates the connection site with the adjacent atom.

[0181] In one embodiment, the group represented by Formula 2-1 and the group represented by Formula 2-2 may each independently be a group represented by one of Formulas 2-31 to 2-44, but embodiments of the present disclosure are not limited thereto:

[0182]

[0183]

[0184] In Formula 2-31 to Formula 2-44,

[0185] X 26a Can be N, N-* or C(R 26a ), X 26b Can be N, N-* or C(R 26b ), X 26c Can be N or C (R 26c ), X 26d Can be N or C (R 26d ), X 26e Can be N or C (R 26e ), X 26f Can be N or C (R 26f ), X 26g Can be N or C (R 26g ), X 26h Can be N or C (R 26h ), X 26i Can be N or C (R 26i ), X 26j Can be N or C (R 26j ), X 26k Can be N or C (R 26k ), and X 26l Can be N or C (R 26l ),

[0186] R 26a To R 26l can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a substituted or unsubstituted C 1 -C 60 Alkyl groups, substituted or unsubstituted C 2 -C 60Alkenyl groups, substituted or unsubstituted C 2 -C 60 Alkynyl group, substituted or unsubstituted C 1 -C 60 Alkoxy groups, substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl group, substituted or unsubstituted C 6 -C 60 Aryl group, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio group, substituted or unsubstituted C 1 -C 60 Heteroaryl groups, substituted or unsubstituted C 1 -C 60 Heteroaryloxy group, substituted or unsubstituted C 1 -C 60 heteroarylthio group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 );

[0187] Q 1 To Q 3 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C 1 -C60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl groups, C 1 -C 60 Heteroaryloxy groups, C 1 -C 60 a heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group; and

[0188] *, *' and *" each represent a site of attachment to an adjacent atom.

[0189] In equations 3-1 and 3-2, X 31 Can be N, N-* or C(R 31 ), X 32 Can be N, N-* or C(R 32 ), X 33 Can be N, N-* or C(R 33 ), X 34 Can be N, N-* or C(R 34 ), X 35 Can be N, N-* or C(R 35 ), X 36 Can be N, N-* or C(R 36 ), X 37 Can be N, N-* or C(R 37 ), X 38 Can be N, N-* or C(R 38 ),

[0190] Selected from X 31 To X 34Two or more of may be N or N-*, and

[0191] Selected from X 35 To X 38 Two or more of may be N or N-*.

[0192] For example, in formula 3-1,

[0193] X 31 and X 32 can each independently be N or N-*;

[0194] X 31 and X 33 can each independently be N or N-*;

[0195] X 31 and X 34 can each independently be N or N-*;

[0196] X 32 and X 33 can each independently be N or N-*;

[0197] X 32 and X 34 may each independently be N or N-*; or

[0198] X 33 and X 34 can each independently be N or N-*;

[0199] In formula 3-2,

[0200] X 35 Can be N or N-*;

[0201] X 36 Can be N or N-*;

[0202] X 37 Can be N or N-*; or

[0203] X 38 It may be N or N-*, but the embodiments of the present disclosure are not limited thereto.

[0204] A in Formula 3-1 31 Can be selected from C 5 -C 60 Carbocyclic groups and C 1 -C 60 Heterocyclic group.

[0205] For example, A in formula 3-1 31 It can be selected from a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a phenanthrenene group, a triphenylene group, a pyrene group, group, a cyclopentadiene group, a 1,2,3,4-tetralinyl group, a furan group, a thiophene group, a silole group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzosilole group, a dibenzosilole group, an indenopyridine group, an indolopyridine group, a benzofuranopyridine group, a benzothienopyridine group, a benzothiorrolopyridine group, an indenopyrimidine group, an indolopyrimidine group, a benzofuranopyrimidine group, a benzothienopyrimidine group, a benzothiorrolopyrimidine group, a dihydropyridine group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazolinyl group, a phenanthroline group, a benzoquinoline group, a benzoisoquinoline group group, a benzoquinoxaline group, a benzoquinazoline group, a pyrrole group, a pyrazole group, an imidazole group, a 2,3-dihydroimidazole group, a triazole group, a 2,3-dihydrotriazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a 2,3-dihydrobenzimidazole group, an imidazopyridine group, a 2,3-dihydroimidazopyridine group, an imidazopyrimidine group, a 2,3-dihydroimidazopyrimidine group, an imidazopyrazine group, a 2,3-dihydroimidazopyrazine group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, and a 5,6,7,8-tetrahydroquinoline group, but the embodiments of the present disclosure are not limited thereto.

[0206] In one embodiment, A in Formula 3-1 31 It can be selected from a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a phenanthene group, a furan group, a thiophene group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, an indenopyridine group, an indolepyridine group, a benzofuranopyridine group, a benzothienopyridine group, an indenopyrimidine group, an indolepyrimidine group, a benzofuranopyrimidine group, a benzothienopyrimidine group, a pyridine group, a pyrimidine group, a pyrimidine group Groups include, but are not limited to, pyrazine groups, pyridazine groups, triazine groups, quinoline groups, isoquinoline groups, quinoxaline groups, quinazoline groups, phenanthroline groups, benzoquinoline groups, benzoisoquinoline groups, benzoquinoxaline groups, benzoquinazoline groups, pyrrole groups, pyrazole groups, imidazole groups, triazole groups, oxazole groups, isoxazole groups, thiazole groups, isothiazole groups, oxadiazole groups, thiadiazole groups, benzopyrazole groups, and benzimidazole groups, but the embodiments of the present disclosure are not limited thereto.

[0207] In one embodiment, A in Formula 3-1 31The group may be selected from a phenyl group, a naphthyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, and an isoquinoline group, but the embodiments of the present disclosure are not limited thereto.

[0208] A in formula 3-2 32 It can be a C containing at least one N 1 -C 60 Heterocyclic group.

[0209] For example, A in formula 3-2 32 It may be selected from an indole group, a carbazole group, an indenopyridine group, an indolopyridine group, a benzofuranopyridine group, a benzothienopyridine group, a benzothiorrolopyridine group, an indenopyrimidine group, an indolopyrimidine group, a benzofuranopyrimidine group, a benzothiorrolopyrimidine group, a benzothiorrolopyrimidine group, a dihydropyridine group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a benzoquinoline group, a benzoisoquinoline group, a benzoquinoxaline group, a benzoquinazoline group, a pyrrole group, a pyrazole group, an imidazole group, a 2,3-dihydroimidazole group , a triazole group, a 2,3-dihydrotriazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a 2,3-dihydrobenzimidazole group, an imidazopyridine group, a 2,3-dihydroimidazopyridine group, an imidazopyrimidine group, a 2,3-dihydroimidazopyrimidine group, an imidazopyrazine group, a 2,3-dihydroimidazopyrazine group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, and a 5,6,7,8-tetrahydroquinoline group, but the embodiments of the present disclosure are not limited thereto.

[0210] In one embodiment, A in Formula 3-2 32 It may be selected from an indole group, a carbazole group, an indenopyridine group, an indolopyridine group, a benzofuranopyridine group, a benzothienopyridine group, an indenopyrimidine group, an indolopyrimidine group, a benzofuranopyrimidine group, a benzothienopyrimidine group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a benzoquinoline group, a benzoisoquinoline group, a benzoquinoxaline group, a benzoquinazoline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, and a benzimidazole group, but the embodiments of the present disclosure are not limited thereto.

[0211] In one embodiment, A in Formula 3-232 The group may be selected from a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, and an isoquinoline group, but the embodiments of the present disclosure are not limited thereto.

[0212] In one embodiment, in Formula 3-1,

[0213] X 31 and X 32 can each independently be N or N-*;

[0214] X 31 and X 33 can each independently be N or N-*;

[0215] X 31 and X 34 can each independently be N or N-*;

[0216] X 32 and X 33 can each independently be N or N-*;

[0217] X 32 and X 34 may each independently be N or N-*; or

[0218] X 33 and X 34 can each independently be N or N-*;

[0219] A 31 may be selected from a phenyl group, a naphthyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group and an isoquinoline group; and

[0220] In formula 3-2,

[0221] X 35 Can be N or N-*;

[0222] X 36 Can be N or N-*;

[0223] X 37 Can be N or N-*; or

[0224] X 38 Can be N or N-*;

[0225] A 32 The group may be selected from a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, and an isoquinoline group, but the embodiments of the present disclosure are not limited thereto.

[0226] R in Formula 3-1 and Formula 3-2 31 To R39 can be independently selected from the group consisting of a linking site, hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a substituted or unsubstituted C 1 -C 60 Alkyl groups, substituted or unsubstituted C 2 -C 60 Alkenyl groups, substituted or unsubstituted C 2 -C 60 Alkynyl group, substituted or unsubstituted C 1 -C 60 Alkoxy groups, substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl group, substituted or unsubstituted C 6 -C 60 Aryl group, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio group, substituted or unsubstituted C 1 -C 60 Heteroaryl groups, substituted or unsubstituted C 1 -C 60 Heteroaryloxy group, substituted or unsubstituted C 1 -C 60 heteroarylthio group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-B(Q 1 )(Q 2 )、-N(Q 1 )(Q 2 )、-P(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1)(Q 2 );

[0227] Selected from R 31 To R 34 and R 39 One, two or three of can be attachment sites, and

[0228] Selected from R 35 To R 39 One, two or three of the may be attachment sites,

[0229] Where Q 1 To Q 3 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl groups, C 1 -C 60 Heteroaryloxy groups, C 1 -C 60 a heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group.

[0230] For example, R in Formula 3-1 and Formula 3-2 31 To R 39 can be independently selected from the group consisting of a linking site, hydrogen, deuterium, -F, -Cl, -Br, -I, a cyano group, C 1 -C 20 Alkyl groups and C 1 -C 20Alkoxy groups;

[0231] C each substituted with at least one selected from deuterium, -F, -Cl, -Br, -I, a cyano group, a phenyl group, a biphenyl group, and a terphenyl group 1 -C 20 Alkyl groups and C 1 -C 20 Alkoxy groups;

[0232] a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a phenyl group, a peryl group, a pentacene group, a pyrrolyl group, a thienyl group, a furanyl group, a thiolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindoleyl group, an indazolyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a a benzophenanthryl group, a benzofuranyl group, a benzothiophenyl group, a benzothiophenyl group, a benzothiazolyl group, a benzothiazolyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzophenanthridine group, a benzophenanthridine group, a benzofuranyl group, a benzothiophenyl group, a benzothiazolyl group, a benzoisothiazolyl group, a benzoxazolyl group group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, a thiadiazolyl group, an oxadiazolyl group, a triazine group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilyl group, a benzocarbazolyl group, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, a naphthobenzosilyl group, a dibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenyl group, a di a naphthothirolyl group, an imidazopyridyl group, an imidazopyrimidyl group, an oxazolopyridyl group, a thiazopyridyl group, a benzonaphthyridinyl group, an azafluorenyl group, an azaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothienyl group, an azadibenzothirolyl group, an indenopyrrolyl group, an indolopyrrolyl group, an indenocarbazolyl group, and an indolocarbazolyl group;

[0233] Each is selected from deuterium, -F, -Cl, -Br, -I, a cyano group, C 1 -C 20 Alkyl group, C1 -C 20 an alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a phenyl group, a peryl group, a pentacene group, a pyrrolyl group, a thienyl group, a furanyl group, a thiolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindoleyl group, an indazolyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a benzoquinoline group, a a benzofuranyl group, a benzothiophenyl group, a benzothiosilyl group, a benzothiazolyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzoquinoxalinyl group, a quinazoline group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzosilyl group, a benzothiazolyl group, a benzisothiazolyl group, a benzoxazolyl group, Benzisoxazolyl group, triazolyl group, tetrazolyl group, thiadiazolyl group, oxadiazolyl group, triazine group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzosilyl group, benzocarbazolyl group, naphthobenzofuranyl group, naphthobenzothiophenyl group, naphthobenzosilyl group, dibenzocarbazolyl group, dinaphthofuranyl group, dinaphthothiophenyl group, dinaphthosilyl group azadibenzofuranyl group, azadibenzothiophenyl group, azadibenzothiophenyl group, azadibenzothiophenyl group, an indenopyrrolyl group, an indolepyrrolyl group, an indenocarbazolyl group, an indolecarbazolyl group, a -Si(Q)- 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)(Q 31 )、-S(=O) 2 (Q 31 )、-P(=O)(Q 31 )(Q32 ) and -P(=S)(Q 31 )(Q 32 ) is at least one substituted cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, indacenyl group, acenaphthenyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenaltenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a phenyl group, a peryl group, a pentacene group, a pyrrolyl group, a thienyl group, a furanyl group, a thiolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindoleyl group, an indazolyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzosilyl group, a benzothiazolyl group, a benzisothiazolyl group, a benzoxazolyl group group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, a thiadiazolyl group, an oxadiazolyl group, a triazine group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilyl group, a benzocarbazolyl group, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, a naphthobenzosilyl group, a dibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenyl group, a dinaphthobenzosilyl group thiolyl group, imidazopyridyl group, imidazopyrimidyl group, oxazolopyridyl group, thiazopyridyl group, benzonaphthyridinyl group, azafluorenyl group, azaspiro-bifluorenyl group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group, azadibenzosilyl group, indenopyrrolyl group, indolopyrrolyl group, indenocarbazolyl group and indolocarbazolyl group; and

[0234] -Si(Q 1 )(Q 2 )(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O)2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 ),

[0235] Where Q 1 To Q 3 and Q 31 To Q 33 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 1 -C 60 A heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group, but the embodiments of the present disclosure are not limited thereto.

[0236] In one embodiment, R in Formula 3-1 and Formula 3-2 31 To R 39 can be independently selected from the group consisting of a linking site, hydrogen, deuterium, -F, -Cl, -Br, -I, a cyano group, C 1 -C 20 Alkyl groups;

[0237] C substituted by at least one selected from deuterium, -F, -Cl, -Br, -I and cyano groups 1 -C 20 Alkyl groups;

[0238] A group represented by one of Formula 5-1 to Formula 5-138; and

[0239] -Si(Q 1 )(Q 2)(Q 3 )、-N(Q 1 )(Q 2 )、-B(Q 1 )(Q 2 )、-C(=O)(Q 1 )、-S(=O)(Q 1 )、-S(=O) 2 (Q 1 )、-P(=O)(Q 1 )(Q 2 ) and -P(=S)(Q 1 )(Q 2 ), but the embodiments of the present disclosure are not limited thereto.

[0240] In one embodiment, R in Formula 3-1 and Formula 3-2 31 To R 39 may each be independently selected from the group consisting of a linking site, hydrogen, deuterium, -F, -Cl, -Br, -I, a cyano group, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group;

[0241] a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group, each of which is substituted with at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, and a cyano group; and

[0242] A group represented by one of Formula 6-1 to Formula 6-257, but the embodiments of the present disclosure are not limited thereto.

[0243] In one embodiment, L in Formula 1 1 The ligand may be a ligand represented by Formula 1-11, but the embodiments of the present disclosure are not limited thereto:

[0244] Formula 1-11

[0245]

[0246] In formula 1-11,

[0247] *1 to *4, A can be understood by referring to the description provided with respect to Formula 1-1. 11 To A 14 , Y 11 To Y 14 , T 11 To T 14 , L 11 To L 13 、a11 to a13、R 11 To R 14 and b11 to b14.

[0248] In one embodiment, L in Formula 1 1 The ligand may be a ligand represented by Formula 1-21, but the embodiments of the present disclosure are not limited thereto:

[0249] Formula 1-21

[0250]

[0251] Among them, in formula 1-21,

[0252] *1 to *4, A can be understood by referring to the description provided with respect to Formula 1-1. 11 To A 14 , Y 11 To Y 14 , L 11 To L 13 , R 11 To R 14 and b11 to b14.

[0253] In one or more than one embodiment, L in Formula 1 1 It may be a ligand represented by Formula 1-31 or Formula 1-32, but the embodiments of the present disclosure are not limited thereto:

[0254]

[0255] Among them, in Formula 1-31 and Formula 1-32,

[0256] *1 to *4, A can be understood by referring to the description provided with respect to Formula 1-1. 11 To A 14 , Y 11 To Y 14 , L 12 , R 11 To R 14 and b11 to b14.

[0257] L in Formula 1 2 It may be a ligand represented by one of Formula 7-1 to Formula 7-11, but the embodiments of the present disclosure are not limited thereto:

[0258]

[0259]

[0260] Among them, in Formula 7-1 to Formula 7-11,

[0261] A 71 and A 72 Can be independently selected from C 5 -C20 Carbocyclic groups and C 1 -C 20 Heterocyclic groups;

[0262] X 71 and X 72 may be independently selected from C and N;

[0263] X 73 Can be N or C (Q 73 );X 74 Can be N or C (Q 74 );X 75 Can be N or C (Q 75 );X 76 Can be N or C (Q 76 );X 77 Can be N or C (Q 77 );

[0264] X 78 Can be O, S or N (Q 78 );X 79 Can be O, S or N (Q 79 );

[0265] Y 71 and Y 72 can be independently selected from a single bond, a double bond, a substituted or unsubstituted C 1 -C 5 Alkylene group, substituted or unsubstituted C 2 -C 5 an alkenylene group and a substituted or unsubstituted C 6 -C 10 arylene groups;

[0266] Z 71 and Z 72 can be independently selected from N, O, N(R 75 )、P(R 75 )(R 76 ) and As(R 75 )(R 76 );

[0267] Z 73 Can be selected from P and As;

[0268] Z 74 Can be selected from CO and CH 2 ;

[0269] R 71 To R 73 and R 75 To R 80 and Q 73 To Q79 The substituted or unsubstituted C 1 -C 60 Alkyl groups, substituted or unsubstituted C 2 -C 60 Alkenyl groups, substituted or unsubstituted C 2 -C 60 Alkynyl group, substituted or unsubstituted C 1 -C 60 Alkoxy groups, substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl group, substituted or unsubstituted C 6 -C 60 Aryl group, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio group, substituted or unsubstituted C 1 -C 60 heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group; R 71 and R 72 may be optionally linked to form a ring; R 77 and R 78 may be optionally linked to form a ring; R 78 and R 79 may be optionally linked to form a ring; and R 79 and R 80 may optionally be linked to form a ring;

[0270] b71 and b72 may each be independently selected from 1, 2 and 3; and

[0271] * and *' each represent a bonding site to an adjacent atom.

[0272] For example, A in formula 7-11 71 and A 72The groups may be each independently selected from a phenyl group, a naphthyl group, an imidazole group, a benzimidazole group, a pyridine group, a pyrimidine group, a triazine group, a quinoline group, and an isoquinoline group, but the embodiments of the present disclosure are not limited thereto.

[0273] For example, X in formula 7-11 72 and X 79 It may be N, but the embodiments of the present disclosure are not limited thereto.

[0274] For example, in Formula 7-7, X 73 It can be C(Q 73 );X 74 It can be C(Q 74 );X 75 It can be C(Q 75 );X 76 It can be C(Q 76 ); and X 77 It can be C(Q 77 ), but the embodiments of the present disclosure are not limited thereto.

[0275] For example, in formula 7-8, X 78 It can be N(Q 78 ); and X 79 It can be N(Q 79 ), but the embodiments of the present disclosure are not limited thereto.

[0276] For example, Y in Formula 7-2, Formula 7-3, and Formula 7-8 71 and Y 72 The groups may be each independently selected from a substituted or unsubstituted methylene group and a substituted or unsubstituted phenylene group, but the embodiments of the present disclosure are not limited thereto.

[0277] For example, Z in Equation 7-1 and Equation 7-2 71 and Z 72 It may be 0, but the embodiments of the present disclosure are not limited thereto.

[0278] For example, Z in formula 7-4 73 It may be P, but the embodiments of the present disclosure are not limited thereto.

[0279] For example, R in Formula 7-1 to Formula 7-8 71 To R 73 and R 75 To R 80 and Q 73 To Q 79can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 Alkyl groups and C 1 -C 20 Alkoxy groups;

[0280] each of which is substituted with at least one selected from the group consisting of deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a phenyl group, a naphthyl group, a pyridyl group, and a pyrimidinyl group; 1 -C 20 Alkyl groups and C 1 -C 20 Alkoxy groups;

[0281] phenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, and an imidazopyridyl group; and

[0282] Each is selected from deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C 1 -C 20 Alkyl group, C 1 -C 20an alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthryl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a pyrrolyl group, a thienyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a a phenyl group substituted by at least one of an oxazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group and an imidazopyridyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a pyridyl group, a pyrrolyl group, a thienyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group , a carbazolyl group, a phenanthroline group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazine group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, and an imidazopyridyl group, but the embodiments of the present disclosure are not limited thereto.

[0283] For example, L in Formula 1 2 It may be a ligand represented by one of Formula 8-1 to Formula 8-11, but the embodiments of the present disclosure are not limited thereto:

[0284]

[0285] The * indicates the connection site with the adjacent atom.

[0286] In one embodiment, in Formula 1, n1 is 1 and n2 is 0; or n1 is 1 and n2 is 2, but embodiments of the present disclosure are not limited thereto.

[0287] In one embodiment, the organometallic compound represented by Formula 1 may be selected from Compound 1 to Compound 50, but embodiments of the present disclosure are not limited thereto:

[0288]

[0289]

[0290]

[0291] The organometallic compound can be configured to emit red light or near infrared (NIR) light having a maximum emission wavelength of, for example, 720 nm or greater, about 720 nm or greater and about 2,500 nm or less, about 750 nm or greater and about 2,500 nm or less, or about 750 nm or greater and about 1500 nm or less.

[0292] In one embodiment, the organometallic compound can be configured to emit near infrared light having a maximum emission wavelength of about 720 nm or more and about 2,500 nm or less, or about 750 nm or more and about 1500 nm or less. Organometallic compounds emitting near infrared light having such a maximum emission wavelength range are clearly distinguished from organometallic compounds configured to emit red visible light having a maximum emission wavelength of, for example, 650 nm or more and less than 720 nm.

[0293] An organic light-emitting device using the organic metal compound represented by Formula 1 can have a low driving voltage and a high external quantum efficiency while emitting red light or near-infrared light having a maximum emission wavelength of 720 nm or more, about 720 nm or more and about 2,500 nm or less, about 750 nm or more and about 2,500 nm or less, or 750 nm or more, or 1500 nm or less.

[0294] A person of ordinary skill in the art can recognize a method for synthesizing the organometallic compound represented by Formula 1 by referring to the examples provided below.

[0295] At least one of such organometallic compounds represented by Formula 1 can be used between a pair of electrodes of an organic light-emitting device. Therefore, an organic light-emitting device is provided, comprising: a first electrode; a second electrode facing the first electrode; and an organic layer including an emission layer between the first electrode and the second electrode, wherein the organic layer comprises at least one of the organometallic compounds represented by Formula 1.

[0296] The expression “(organic layer) contains at least one of the organic metal compounds” used herein may include the case where “(organic layer) contains the same organic metal compound represented by Formula 1” and the case where “(organic layer) contains two or more different organic metal compounds represented by Formula 1”.

[0297] For example, the organic layer may contain only compound 1 as an organic metal compound. In this regard, compound 1 may be present only in the emission layer of the organic light-emitting device. In one or more than one embodiments, the organic layer may contain compound 1 and compound 2 as organic metal compounds. In this case, 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 emission layer), or in different layers (for example, compound 1 may be present in the emission layer, and compound 2 may be present in the electron transport layer).

[0298] In one embodiment,

[0299] The first electrode of the organic light-emitting device may be an anode,

[0300] The second electrode of the organic light-emitting device may be a cathode,

[0301] The organic layer further includes a hole transport region between the first electrode and the emission layer and / or an electron transport region between the emission layer and the second electrode,

[0302] The hole transport region includes a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer or any combination thereof, and

[0303] The electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer or any combination thereof.

[0304] As used herein, the term "organic layer" refers to a single layer and / or all layers between the first electrode and the second electrode of the organic light-emitting device. The material contained in the "organic layer" is not limited to an organic material. For example, the organic layer may contain an inorganic material.

[0305] In one embodiment, the organic metal compound represented by Formula 1 may not be included in the emission layer. The emission layer may further include a host in addition to the organic metal compound, and the amount of the organic metal compound in the emission layer may be less than that of the host.

[0306] In one or more embodiments, the hole transport region may include an electron blocking layer and the organometallic compound may be included in the electron blocking layer; and / or the electron transport region may include a hole blocking layer and the organometallic compound may be included in the hole blocking layer.

[0307] In one or more than one embodiments, at least one selected from the hole transport region and the emissive layer may comprise at least one selected from an arylamine-containing compound, an acridine-containing compound, and a carbazole-containing compound; and / or

[0308] At least one selected from the emission layer and the electron transport region may contain at least one selected from silicon-containing compounds, phosphine oxide-containing compounds, sulfur oxide-containing compounds, phosphorus oxide-containing compounds, triazine-containing compounds, pyrimidine-containing compounds, pyridine-containing compounds, dibenzofuran-containing compounds and dibenzothiophene-containing compounds.

[0309] Figure 1 Description

[0310] Figure 1 is a schematic view of an organic light-emitting device 10 according to an embodiment. The organic light-emitting device 10 includes a first electrode 110 , an organic layer 150 , and a second electrode 190 .

[0311] In the following, we will combine Figure 1 A structure of an organic light-emitting device 10 and a method of manufacturing the organic light-emitting device 10 according to the embodiment are described.

[0312] First electrode 110

[0313] refer to Figure 1 , a substrate may be additionally located under the first electrode 110 or over the second electrode 190. The substrate may be a glass substrate or a plastic substrate each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.

[0314] The first electrode 110 may be formed by depositing or sputtering, on a substrate, a material for forming the first electrode 110. When the first electrode 110 is an anode, the material for the first electrode may be selected from materials having a high work function to facilitate hole injection.

[0315] 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 may be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO) and any combination thereof, but not limited thereto. In one or more than one embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, the material used to form the first electrode may be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) and any combination thereof, but not limited thereto.

[0316] 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.

[0317] Organic layer 150

[0318] The organic layer 150 is located on the first electrode 110. The organic layer 150 may include an emission layer.

[0319] The organic layer 150 may further include a hole transport region between the first electrode 110 and the emission layer and an electron transport region between the emission layer and the second electrode 190 .

[0320] Hole transport region in the organic layer 150

[0321] The hole transport region may have i) a single-layer structure including a single layer containing a single material, ii) a single-layer structure including a single layer containing a plurality of different materials, or iii) a multi-layer structure having a plurality of layers containing a plurality of different materials.

[0322] The hole transport region may include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an emission assisting layer, and an electron blocking layer.

[0323] For example, the hole transport zone may have a single-layer structure including a single layer containing a plurality of different materials, or a multi-layer structure having a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission auxiliary layer structure, a hole injection layer / emission auxiliary layer structure, a hole transport layer / emission auxiliary layer structure, or a hole injection layer / hole transport layer / emission auxiliary layer structure, wherein for each structure, the constituent layers are stacked in sequence from the first electrode 110 in this prescribed order, but the structure of the hole transport zone is not limited thereto.

[0324] The hole transport region may include at least one selected from m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), a compound represented by Formula 201, and a compound represented by Formula 202:

[0325]

[0326]

[0327] Formula 201

[0328]

[0329] Formula 202

[0330]

[0331] Among them, in equation 201 and equation 202,

[0332] L 201 To L 204 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene group, substituted or unsubstituted C 3 -C 10 Cycloalkenylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene group, substituted or unsubstituted C 6 -C 60 Arylene group, 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,

[0333] L 205 Can be selected from *-O-*', *-S-*', *-N(Q 201 )-*', substituted or unsubstituted C 1 -C 20 Alkylene group, substituted or unsubstituted C 2 -C 20 Alkenylene group, substituted or unsubstituted C 3 -C 10 Cycloalkylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene group, substituted or unsubstituted C 3 -C 10 Cycloalkenylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene group, substituted or unsubstituted C 6 -C 60 Arylene group, substituted or unsubstituted C 1 -C 60a heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

[0334] xa1 to xa4 can each independently be an integer from 0 to 3,

[0335] xa5 can be an integer from 1 to 10, and

[0336] R 201 To R 204 and Q 201 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl group, substituted or unsubstituted C 6 -C 60 Aryl group, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio group, substituted or unsubstituted C 1 -C 60 a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

[0337] In one embodiment, in Formula 202, R 201 and R 202 may optionally be linked via a single bond, a dimethyl-methylene group, or a diphenyl-methylene group, and R 203 and R 204 Attachment may optionally be via a single bond, a dimethyl-methylene group, or a diphenyl-methylene group.

[0338] In one embodiment, in Formula 201 and Formula 202,

[0339] L 201 To L 205 Can be independently selected from:

[0340] a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthenylene group, a fluorenylene group, a spiro-difluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a phenylene group, a phenanthrenylene group, a py ... a phenylene group, a tetraphenylene group, a perylene group, a perylene group, a pentphenylene group, a hexaphenylene group, a pentphenylene group, a rubinylene group, a coronene group, an ovphenylene group, a thienylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothienylene group, a dibenzofuranylene group, a dibenzothienylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilylene group, and a pyridylene group; and

[0341] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C 1 -C 10 a phenyl group substituted with an alkyl group, a phenyl group substituted with -F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenaltenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a phenyl group, a tetraphenyl group, a pyrenyl group, a peryl group, a pentaphenyl group, a hexaphenyl group, a pentacene group, a rubinyl group, a coronet group, an ovaphenyl group, a thienyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, a dibenzothienyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilyl group, a pyridyl group, -Si(Q 31 )(Q 32 )(Q 33 ) and -N(Q 31 )(Q 32) is at least one substituted phenylene group, pentalenylene group, indenylene group, naphthylene group, azulenylene group, heptalenylene group, indacenylene group, acenaphthenylene group, fluorenylene group, spiro-difluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, phenanthrenylene group, py ... a phenylene group, a tetraphenylene group, a perylene group, a perylene group, a pentphenylene group, a hexaphenylene group, a pentphenylene group, a rubidinyl group, a coronetyl group, an ovphenylene group, a thienylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothienylene group, a dibenzofuranylene group, a dibenzothienylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilylene group, and a pyridylene group,

[0342] Where Q 31 To Q 33 Can be independently selected from C 1 -C 10 Alkyl group, C 1 -C 10 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

[0343] In one or more than one embodiments, xa1 to xa4 can each independently be 0, 1 or 2.

[0344] In one or more than one embodiments, xa5 can be 1, 2, 3 or 4.

[0345] In one or more than one embodiment, R 201 To R 204 and Q 201 The phenyl group, biphenyl group, terphenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthenyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenaltenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilyl group, and a pyridyl group; and

[0346] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C 1 -C 10 a phenyl group substituted with an alkyl group, a phenyl group substituted with -F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenaltenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a phenyl group, a tetraphenyl group, a pyrenyl group, a peryl group, a pentaphenyl group, a hexaphenyl group, a pentacene group, a rubinyl group, a coronet group, an ovaphenyl group, a thienyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, a dibenzothienyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilyl group, a pyridyl group, -Si(Q 31 )(Q 32 )(Q 33 ) and -N(Q 31 )(Q 32 ) is at least one substituted phenyl group, biphenyl group, terphenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthenyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenaltenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilyl group, and a pyridyl group,

[0347] Where Q 31 To Q 33 Same as described above.

[0348] In one or more than one embodiment, R selected from Formula 201 201 To R 203 At least one of can be independently selected from:

[0349] fluorenyl groups, spiro-bifluorenyl groups, carbazolyl groups, dibenzofuranyl groups, and dibenzothiophenyl groups; and

[0350] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C 1 -C 10 a phenyl group substituted with an alkyl group, a phenyl group substituted with -F, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group substituted with at least one of a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group,

[0351] However, embodiments of the present disclosure are not limited thereto.

[0352] In one or more than one embodiment, in Formula 202, i) R 201 and R 202 may be linked to each other via a single bond, and / or ii) R 203 and R 204 Can connect via one-touch.

[0353] In one or more than one embodiment, R in Formula 202 201 To R 204 Can be selected from:

[0354] a carbazolyl group; and

[0355] is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C 1 -C 10a carbazolyl group substituted with at least one of a phenyl group substituted with an alkyl group, a phenyl group substituted with -F, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothienyl group,

[0356] However, embodiments of the present disclosure are not limited thereto.

[0357] The compound represented by Formula 201 can be represented by Formula 201A:

[0358] Formula 201A

[0359]

[0360] In one embodiment, the compound represented by Formula 201 may be represented by the following Formula 201A(1), but embodiments of the present disclosure are not limited thereto:

[0361] Formula 201A(1)

[0362]

[0363] In one embodiment, the compound represented by Formula 201 may be represented by the following Formula 201A-1, but embodiments of the present disclosure are not limited thereto:

[0364] Formula 201A-1

[0365]

[0366] The compound represented by Formula 202 can be represented by Formula 202A:

[0367] Formula 202A

[0368]

[0369] In one or more than one embodiments, the compound represented by Formula 202 can be represented by Formula 202A-1:

[0370] Formula 202A-1

[0371]

[0372] In Formula 201A, Formula 201A(1), Formula 201A-1, Formula 202A, and Formula 202A-1,

[0373] L 201 To L 203 , xa1 to xa3, xa5 and R 202 To R 204 Same as described above,

[0374] R211 and R 212 Can be related to R 203 Same as described,

[0375] R 213 To R 217 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C 1 -C 10 a phenyl group substituted with an alkyl group, a phenyl group substituted with -F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenaltenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, The invention also includes but is not limited to: a benzothiophenyl group, a tetraphenyl group, a peryl group, a peryl group, a pentaphenyl group, a hexaphenyl group, a pentacene group, a rubinyl group, a coronet group, an ovaphenyl group, a thienyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilyl group, and a pyridyl group.

[0376] The hole transport region may include at least one compound selected from Compound HT1 to Compound HT39, but the compound included in the hole transport region is not limited thereto:

[0377]

[0378]

[0379]

[0380]

[0381] The thickness of the hole transport region may 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 about to about For example, about to about and the thickness of the hole transport layer may be 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 these ranges, suitable or satisfactory hole transport characteristics may be obtained without a significant increase in driving voltage.

[0382] The emission auxiliary layer may increase light emitting efficiency by compensating the optical resonance distance according to the wavelength of light emitted by the emission layer, and the electron blocking layer may block the flow of electrons from the electron transport region. The emission auxiliary layer and the electron blocking layer may include materials as described above.

[0383] p-dopant

[0384] In addition to these materials, the hole transport region may further contain a charge generating material for improving the conductive property. The charge generating material may be dispersed uniformly or non-uniformly in the hole transport region.

[0385] The charge generating material may be, for example, a p-dopant.

[0386] In one embodiment, the lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant may be -3.5 eV or less.

[0387] The p-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.

[0388] For example, the p-dopant may include at least one selected from the group consisting of: a quinone derivative such as tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ);

[0389] Metal oxides, such as tungsten oxide and molybdenum oxide;

[0390] 1,4,5,8,9,12-Hexaazatriphenylene-hexacarbonitrile (HAT-CN); and

[0391] The compound represented by formula 221,

[0392] However, the embodiments of the present disclosure are not limited thereto:

[0393]

[0394] Formula 221

[0395]

[0396] In formula 221,

[0397] R 221 To R 223 can be independently selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl group, substituted or unsubstituted C 6 -C 60 Aryl group, substituted or unsubstituted C 1 -C 60 heteroaryl group, substituted or unsubstituted monovalent non-aromatic fused polycyclic group and substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, and is selected from R 221 To R 223 At least one of the may have a cyano group, -F, -Cl, -Br, -I, C substituted by -F 1 -C 20 Alkyl groups, C substituted by -Cl 1 -C 20 Alkyl groups, C substituted with -Br 1 -C 20 Alkyl groups and C substituted by -I 1 -C 20 At least one substituent in the alkyl group.

[0398] Emission layer in the organic layer 150

[0399] When the organic light-emitting device 10 is a full-color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, or a blue emission layer; or a red emission layer, a green emission layer, a blue emission layer, and a NIR emission layer. In one or more embodiments, the emission layer may have a stacked structure of two or more layers selected from a red emission layer, a green emission layer, a blue emission layer, and / or a NIR emission layer, wherein the two or more layers are in contact with each other or spaced apart from each other. In one or more embodiments, the emission layer may include two or more materials selected from a red-emitting material, a green-emitting material, a blue-emitting material, and / or a NIR-emitting material, wherein the two or more materials are mixed with each other in a single layer to emit white light.

[0400] The emission layer may include a host and a dopant. The dopant may include an organic metal compound represented by Formula 1. In one or more than one embodiments, the dopant may further include an organic metal compound represented by Formula 1, at least one selected from a phosphorescent dopant and a fluorescent dopant.

[0401] The amount of the dopant in the emission layer may be 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.

[0402] The thickness of the emission layer can be about to about For example, about to about When the thickness of the emission layer is within this range, excellent light emitting characteristics can be obtained without a significant increase in driving voltage.

[0403] Subject in the emission layer

[0404] In one or more than one embodiments, the host may include a compound represented by Formula 301 below.

[0405] Formula 301

[0406] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21

[0407] In formula 301,

[0408] Ar 301 It can be substituted or unsubstituted C 5 -C 60 A carbocyclic group or a substituted or unsubstituted C 1 -C 60 Heterocyclic groups,

[0409] xb11 can be 1, 2 or 3,

[0410] L 301 Can be selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene group, substituted or unsubstituted C 3 -C 10 Cycloalkenylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene group, substituted or unsubstituted C 6 -C60 Arylene group, 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,

[0411] xb1 can be an integer from 0 to 5.

[0412] R 301 It can be selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a substituted or unsubstituted C 1 -C 60 Alkyl groups, substituted or unsubstituted C 2 -C 60 Alkenyl groups, substituted or unsubstituted C 2 -C 60 Alkynyl group, substituted or unsubstituted C 1 -C 60 Alkoxy groups, substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl group, substituted or unsubstituted C 6 -C 60 Aryl group, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio group, substituted or unsubstituted C 1 -C 60 heteroaryl group, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 301 )(Q 302 )(Q 303 )、-N(Q 301 )(Q 302 )、-B(Q 301 )(Q 302 )、-C(=O)(Q 301 )、-S(=O) 2 (Q 301 ) and -P(=O)(Q 301 )(Q 302 ),

[0413] xb21 can be an integer from 1 to 5,

[0414] Q 301 To Q 303 Can be independently selected from C 1 -C 10 Alkyl group, 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.

[0415] In one embodiment, Ar in Formula 301 301 Can be selected from:

[0416] naphthyl group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group, pyrene group, group, a naphthacene group, a phenanthrene group, a perylene group, a pentaphenyl group, an indenoanthracene group, a dibenzofuran group, and a dibenzothiophene group; and

[0417] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ) is at least one substituted naphthyl group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group, pyrene group, group, naphthacene group, phenanthrene group, perylene group, pentaphenyl group, indenoanthracene group, dibenzofuran group and dibenzothiophene group;

[0418] Where Q 31 To Q 33 Can be independently selected from C1 -C 10 Alkyl group, 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.

[0419] When xb11 in formula 301 is two or more, two or more Ar 301 Can connect via one-touch.

[0420] In one or more than one embodiments, the compound represented by Formula 301 can be represented by one of Formula 301-1 or Formula 301-2:

[0421] Formula 301-1

[0422]

[0423] Formula 301-2

[0424]

[0425] In Formula 301-1 and Formula 301-2,

[0426] A 301 To A 304 can be independently selected from a benzene group, a naphthalene group, a phenanthrene group, a fluoranthene group, a triphenylene group, a pyrene group, group, a pyridine group, a pyrimidine group, an indene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, an indole group, a carbazole group, a benzocarbazole group, a dibenzocarbazole group, a furan group, a benzofuran group, a dibenzofuran group, a naphthofuran group, a benzonaphthofuran group, a dinaphthofuran group, a thiophene group, a benzothiophene group, a dibenzothiophene group, a naphthothiophene group, a benzonaphthothiophene group, and a dinaphthothiophene group,

[0427] X 301 Can be O, S or N-[(L 304 ) xb4 -R 304 ],

[0428] R 311 To R 314 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C 1 -C 20 Alkyl group, C 1 -C 20Alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ),

[0429] xb22 and xb23 can each independently be 0, 1 or 2,

[0430] L 301 、xb1、R 301 and Q 31 To Q 33 Same as described above,

[0431] L 302 To L 304 can be independently related to L 301 Same as described,

[0432] xb2 to xb4 may each independently be the same as described with respect to xb1, and

[0433] R 302 To R 304 can be independently compared with R 301 Same as described.

[0434] For example, L in Formula 301, Formula 301-1, and Formula 301-2 301 To L 304 Can be independently selected from:

[0435] a phenylene group, a naphthylene group, a fluorenylene group, a spiro-difluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthrylene group, a fluoranthenylene group, a phenylene group, a pyrenyl ... a phenylene group, a perylene group, a pentphenylene group, a hexaphenylene group, a pentphenylene group, a thienylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranyl group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilylene group, a pyridinylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a thiadiazolylene group, an oxadiazolylene group , pyrazinylene groups, pyrimidinylene groups, pyridazinylene groups, triazinylene groups, quinolinylene groups, isoquinolinylene groups, benzoquinolinylene groups, phthalazinylene groups, naphthyridinylene groups, quinoxalinylene groups, quinazolinylene groups, cinnolinylene groups, phenanthridinylene groups, acridinylene groups, phenanthrolinylene groups, phenazinylene groups, benzimidazolylene groups, isobenzothiazolylene groups, benzoxazolylene groups, isobenzoxazolylene groups, triazolylene groups, tetrazolylene groups, imidazopyridinylene groups, imidazopyrimidinylene groups, and azacarbazolylene groups; and

[0436] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 20 Alkyl group, C 1 -C 20 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthryl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a phenyl group, a peryl group, a pentaphenyl group, a hexaphenyl group, a pentacene group, a thienyl group, a furyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzothioyl group, a pyridyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolyl group, isoquinolyl group, benzoquinolyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group, -Si(Q31 )(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 ) is at least one substituted phenylene group, naphthylene group, fluorenylene group, spiro-bifluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenyl group, anthracenylene group, fluoranthenylene group, phenylphenanthrenyl group, pyrenylene ... a phenylene group, a perylene group, a pentphenylene group, a hexaphenylene group, a pentphenylene group, a thienylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranyl group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilylene group, a pyridinylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a thiadiazolylene group, an oxadiazolylene group a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a triazinylene group, a quinolylene group, an isoquinolylene group, a benzoquinolylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzimidazolylene group, an isobenzothiazolylene group, a benzoxazolylene group, an isobenzoxazolylene group, a triazolylene group, a tetrazolylene group, an imidazopyridylene group, an imidazopyrimidinylene group, and an azacarbazolylene group,

[0437] Where Q 31 To Q 33 Same as described above.

[0438] In one embodiment, R in Formula 301, Formula 301-1 and Formula 301-2 301 To R 304 Can be independently selected from:

[0439] a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthryl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a phenyl group, a peryl group, a pentaphenyl group, a hexaphenyl group, a pentacene group, a thienyl group, a furyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzothioyl group, a pyridyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group , pyrazinyl groups, pyrimidinyl groups, pyridazinyl groups, triazinyl groups, quinolyl groups, isoquinolyl groups, benzoquinolyl groups, phthalazinyl groups, naphthyridinyl groups, quinoxalinyl groups, quinazolinyl groups, cinnolinyl groups, phenanthridinyl groups, acridinyl groups, phenanthrolinyl groups, phenazinyl groups, benzimidazolyl groups, isobenzothiazolyl groups, benzoxazolyl groups, isobenzoxazolyl groups, triazolyl groups, tetrazolyl groups, imidazopyridinyl groups, imidazopyrimidinyl groups, and azacarbazolyl groups; and

[0440] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 20 Alkyl group, C 1 -C 20 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthryl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a phenyl group, a peryl group, a pentaphenyl group, a hexaphenyl group, a pentacene group, a thienyl group, a furyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzothioyl group, a pyridyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolyl group, isoquinolyl group, benzoquinolyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group, -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q31 )(Q 32 )、-B(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ) is at least one substituted phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthryl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, a phenyl group, a peryl group, a pentaphenyl group, a hexaphenyl group, a pentacene group, a thienyl group, a furyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzothioyl group, a pyridyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group a benzoxazolyl group, a benzoxazolyl group, a benzoxazolyl group, a triazine group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group;

[0441] Where Q 31 To Q 33 Same as described above.

[0442] In one or more than one embodiment, the host may comprise 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.

[0443] The host may include 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(carbazol-9-yl)benzene (TCP), bis(4-(9H-carbazol-9-yl)phenyl)diphenylsilane (BCPDS), (4-(1-(4-(diphenylamino)phenyl)cyclohexyl)phenyl)diphenyl-phosphine oxide (POPCPA), and compounds H1 to H55, but embodiments of the present disclosure are not limited thereto:

[0444]

[0445]

[0446]

[0447]

[0448] In one or more embodiments, the host may include at least one selected from a silicon-containing compound (eg, BCPDS used in the following examples) and a phosphine oxide-containing compound (eg, POPCPA used in the following examples).

[0449] The host may include (or consist of) one type of compound, or only two different compounds (eg, the host in the following examples includes (or consists of) BCPDS and POPCPA). However, embodiments of the present disclosure are not limited thereto.

[0450] The dopant contained in the emission layer in the organic layer 150

[0451] The dopant may include an organic metal compound represented by Formula 1. The organic metal compound is the same as described above.

[0452] In one embodiment, the amount of host in the emissive layer may be greater than the amount of the organometallic compound, which is described as a dopant throughout the specification.

[0453] Electron transport region in the organic layer 150

[0454] 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 including a plurality of layers including a plurality of different materials.

[0455] 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.

[0456] For example, the electron transport region may have an electron transport layer / electron injection layer structure, a hole blocking layer / electron transport layer / electron injection layer structure, an electron control layer / electron transport layer / electron injection layer structure, or a buffer layer / electron transport layer / electron injection layer structure, wherein for each structure, the constituent layers are stacked sequentially from the emission layer. However, the embodiment of the structure of the electron transport region is not limited thereto.

[0457] 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 containing at least one π-electron-depleted nitrogen-containing ring.

[0458] 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.

[0459] For example, the “π-electron-depleted nitrogen-containing ring” may be i) a 5- to 7-membered heteromonocyclic group having at least one *-N=*' moiety, ii) a heteropolycyclic group in which two or more 5- to 7-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 of the 5- to 7-membered heteromonocyclic groups, each having at least one *-N=*' moiety, is fused to at least one C 5 -C 60 A carbocyclic group is a fused heteropolycyclic group.

[0460] 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, isobenzothiazole, benzoxazole, isobenzoxazole, triazole, tetrazole, oxadiazole, triazine, thiadiazole, imidazopyridine, imidazopyrimidine, and azacarbazole.

[0461] For example, the electron transport region may include a compound represented by Formula 601:

[0462] Formula 601

[0463] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21

[0464] In formula 601,

[0465] Ar 601 It can be substituted or unsubstituted C 5 -C 60 A carbocyclic group or a substituted or unsubstituted C 1 -C 60 Heterocyclic groups,

[0466] xe11 can be 1, 2 or 3,

[0467] L 601 Can be selected from substituted or unsubstituted C 3 -C 10 Cycloalkylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkylene group, substituted or unsubstituted C 3 -C 10 Cycloalkenylene group, substituted or unsubstituted C 1 -C 10 Heterocycloalkenylene group, substituted or unsubstituted C 6 -C 60 Arylene group, 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,

[0468] xe1 can be an integer from 0 to 5,

[0469] R 601 Can be selected from substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl group, substituted or unsubstituted C 3 -C 10 Cycloalkenyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl group, substituted or unsubstituted C 6 -C 60 Aryl group, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio group, substituted or unsubstituted C 1 -C 60heteroaryl group, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, 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 ),

[0470] Q 601 To Q 603 Can be independently C 1 -C 10 Alkyl group, C 1 -C 10 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group or a naphthyl group,

[0471] xe21 can be an integer from 1 to 5.

[0472] In one embodiment, the number of Ar selected from xe11 601 and xe21 number of R 601 At least one of may comprise the π-electron-depleted nitrogen-containing ring described above.

[0473] In one embodiment, Ar in Formula 601 601 Can be selected from:

[0474] phenyl group, naphthalene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenanthene group, phenanthrenes group, anthracene group, fluoranthene group, triphenylene group, pyrene group, a tetraphenyl group, a phenanthracene group, a perylene group, a pentaphenyl group, an indenoanthracene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, and an azacarbazole group; and

[0475] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C1 -C 20 Alkyl group, C 1 -C 20 Alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, -Si(Q 31 )(Q 32 )(Q 33 )、-S(=O) 2 (Q 31 ) and -P(=O)(Q 31 )(Q 32 ) is at least one substituted phenyl group, naphthyl group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenanthene group, phenanthrenyl group, anthracene group, fluoranthene group, triphenylene group, pyrene group, group, a naphthacene group, a phenanthracene group, a perylene group, a pentaphenyl group, an indenoanthracene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, and an azacarbazole group;

[0476] Where Q 31 To Q 33 Can be independently selected from C 1 -C 10 Alkyl group, C 1 -C 10 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

[0477] When xe11 in formula 601 is two or more, two or more Ar 601 Can connect via one-touch.

[0478] In one or more than one embodiment, Ar in Formula 601 601 It may be an anthracene group.

[0479] In one or more than one embodiments, the compound represented by 601 can be represented by formula 601-1:

[0480] Formula 601-1

[0481]

[0482] In formula 601-1,

[0483] 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 ), selected from X 614 To X 616 At least one of may be N,

[0484] L 611 To L 613 can be independently related to L 601 Same as described,

[0485] xe611 to xe613 can each independently be the same as described with respect to xe1,

[0486] R 611 To R 613 can be independently compared with R 601 Same as described, and

[0487] R 614 To R 616 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C 1 -C 20 Alkyl group, C 1 -C 20 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

[0488] In one embodiment, L in Formula 601 and Formula 601-1 601 and L 611 To L 613 Can be independently selected from:

[0489] a phenylene group, a naphthylene group, a fluorenylene group, a spiro-difluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthrylene group, a fluoranthenylene group, a phenylene group, a pyrenyl ... a phenylene group, a perylene group, a pentphenylene group, a hexaphenylene group, a pentphenylene group, a thienylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranyl group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilylene group, a pyridinylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a thiadiazolylene group, an oxadiazolylene group , pyrazinylene groups, pyrimidinylene groups, pyridazinylene groups, triazinylene groups, quinolinylene groups, isoquinolinylene groups, benzoquinolinylene groups, phthalazinylene groups, naphthyridinylene groups, quinoxalinylene groups, quinazolinylene groups, cinnolinylene groups, phenanthridinylene groups, acridinylene groups, phenanthrolinylene groups, phenazinylene groups, benzimidazolylene groups, isobenzothiazolylene groups, benzoxazolylene groups, isobenzoxazolylene groups, triazolylene groups, tetrazolylene groups, imidazopyridinylene groups, imidazopyrimidinylene groups, and azacarbazolylene groups; and

[0490] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 20 Alkyl group, C 1 -C 20 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthryl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a phenyl group, a peryl group, a pentaphenyl group, a hexaphenyl group, a pentacene group, a thienyl group, a furyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzothioyl group, a pyridyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a benzoquinoline group, a The invention also includes a phenylene group substituted by at least one of a phthalazinyl group, a naphthyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group and an azacarbazolyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracene group, a fluoranthenyl group, a phenylene group, a pyrenyl ... a phenylene group, a perylene group, a pentphenylene group, a hexaphenylene group, a pentphenylene group, a thienylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranyl group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilylene group, a pyridinylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a thiadiazolylene group, an oxadiazolylene group a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a triazinylene group, a quinolylene group, an isoquinolylene group, a benzoquinolylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzimidazolylene group, an isobenzothiazolylene group, a benzoxazolylene group, an isobenzoxazolylene group, a triazolylene group, a tetrazolylene group, an imidazopyridylene group, an imidazopyrimidinylene group, and an azacarbazolylene group;

[0491] However, embodiments of the present disclosure are not limited thereto.

[0492] In one or more than one embodiments, xe1 and xe611 to xe613 in Formula 601 and Formula 601-1 can each independently be 0, 1 or 2.

[0493] In one or more than one embodiments, R in Formula 601 and Formula 601-1 601 and R 611 To R 613 Can be independently selected from:

[0494] a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthryl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a phenyl group, a peryl group, a pentaphenyl group, a hexaphenyl group, a pentacene group, a thienyl group, a furyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzothioyl group, a pyridyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group a benzoxazolyl group, a benzoxazolyl group, a benzoxazolyl group, a triazine group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group;

[0495] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 20 Alkyl group, C 1 -C 20 an alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthryl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a phenyl group, a peryl group, a pentaphenyl group, a hexaphenyl group, a pentacene group, a thienyl group, a furyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzothioyl group, a pyridyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a benzoquinoline group, a a phenyl group substituted by at least one of a benzoimidazole group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group and an azacarbazolyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a phenyl group, a peryl group, a pentaphenyl group, a hexaphenyl group, a pentacene group, a thienyl group, a furyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzothioyl group, a pyridyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group , pyrazinyl groups, pyrimidinyl groups, pyridazinyl groups, triazinyl groups, quinolyl groups, isoquinolyl groups, benzoquinolyl groups, phthalazinyl groups, naphthyridinyl groups, quinoxalinyl groups, quinazolinyl groups, cinnolinyl groups, phenanthridinyl groups, acridinyl groups, phenanthrolinyl groups, phenazinyl groups, benzimidazolyl groups, isobenzothiazolyl groups, benzoxazolyl groups, isobenzoxazolyl groups, triazolyl groups, tetrazolyl groups, imidazopyridinyl groups, imidazopyrimidinyl groups, and azacarbazolyl groups; and

[0496] -S(=O) 2 (Q 601 ) and -P(=O)(Q 601 )(Q 602 );

[0497] Where Q 601 and Q 602 Same as described above.

[0498] The electron transport region may include at least one compound selected from Compound ET1 to Compound ET36, but embodiments of the present disclosure are not limited thereto:

[0499]

[0500]

[0501]

[0502]

[0503] In one or more than one embodiment, the electron transport region may include a 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), NTAZ and diphenyl(4-(triphenylsilyl)phenyl)-phosphine oxide (TSPO1).

[0504]

[0505] The thickness of the buffer layer, the hole blocking layer, and the electron control layer may each be about to about For example, about to about When the thicknesses of the buffer layer, the hole blocking layer, and the electron control layer are within these ranges, the hole blocking layer and the electron control layer may have excellent hole blocking characteristics or electron control characteristics without a significant increase in driving voltage.

[0506] The thickness of the electron transport layer can be about to about For example, 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.

[0507] 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 materials described above.

[0508] 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 Li ions, Na ions, K ions, Rb ions, and Cs ions, and the alkaline earth metal complex may include a metal ion selected from Be ions, Mg ions, Ca ions, Sr ions, and Ba ions. 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.

[0509] 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.

[0510]

[0511] The electron transport region may include an electron injection layer that allows electrons to be easily supplied from the second electrode 190. The electron injection layer may directly contact the second electrode 190.

[0512] 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 multi-layer structure including a plurality of layers including a plurality of different materials.

[0513] 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.

[0514] 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 than one embodiment, the alkali metal may be Li or Cs, but the embodiments of the present disclosure are not limited thereto.

[0515] The alkaline earth metal may be selected from Mg, Ca, Sr and Ba.

[0516] The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb and Gd.

[0517] 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.

[0518] The alkali metal compound can be selected from alkali metal oxides (such as Li 2 O, Cs 2 O or K 2 O) and alkali metal halides (such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI or RbI). In one embodiment, the alkali metal compound can be selected from LiF, Li 2 O, NaF, LiI, NaI, CsI and KI, but the embodiments of the present disclosure are not limited thereto.

[0519] The alkaline earth metal compound can be selected from BaO, SrO, CaO, Ba x Sr 1-x O(0 < x < 1) and Ba x Ca 1-x O(0 < x < 1). In one embodiment, the alkaline earth metal compound can be selected from BaO, SrO and CaO, but the embodiments of the present disclosure are not limited thereto.

[0520] The rare earth metal compound can be selected from YbF 3 、ScF 3 、Sc 2 O 3 、Y 2 O 3 、Ce 2 O 3 、GdF 3 和TbF 3 。 In one embodiment, the rare earth metal compound can be selected from YbF 3 、ScF 3 、TbF 3 、YbI 3 、ScI 3 和TbI 3 , but the embodiments of the present disclosure are not limited thereto.

[0521] The alkali metal complex, alkaline earth metal complex and rare earth metal complex can contain ions of alkali metals, alkaline earth metals and rare earth metals as described above, and the ligands coordinated with the metal ions of the alkali metal complex, alkaline earth metal complex or rare earth metal complex can be selected from hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxyphenyl oxadiazole, hydroxyphenyl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzimidazole, hydroxyphenyl benzothiazole, bipyridine, phenanthroline and cyclopentadiene, but the embodiments of the present disclosure are not limited thereto.

[0522] The electron injection layer may comprise 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 (or consisting thereof) as described above. In one or more than one embodiment, the electron injection layer may further comprise an organic material. When the electron injection layer further comprises 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 comprising an organic material.

[0523] The thickness of the electron injection layer can be about to about For example, 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.

[0524] The second electrode 190

[0525] The second electrode 190 may be located 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 selected from metals, alloys, conductive compounds, and combinations thereof having a relatively low work function.

[0526] 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.

[0527] The second electrode 190 may have a single-layer structure, or a multi-layer structure including two or more layers.

[0528] Figures 2 to 4 Description

[0529] Figure 2 The organic light emitting device 20 includes a first cover layer 210, a first electrode 110, an organic layer 150, and a second electrode 190, which are sequentially stacked in this prescribed order. Figure 3 The organic light emitting device 30 includes a first electrode 110, an organic layer 150, a second electrode 190, and a second cover layer 220, which are sequentially stacked in this prescribed order, and Figure 4The organic light-emitting device 40 includes a first cover layer 210 , a first electrode 110 , an organic layer 150 , a second electrode 190 , and a second cover layer 220 .

[0530] about Figures 2 to 4 , can be combined by reference Figure 1 The description is provided to understand the first electrode 110 , the organic layer 150 , and the second electrode 190 .

[0531] In the organic layer 150 of each of the organic light-emitting devices 20 and 40, light generated in the emission layer can pass through the first electrode 110 and the first covering layer 210 toward the outside, and the first electrode 110 is a semi-transmissive electrode or a transmissive electrode, and in the organic layer 150 of each of the organic light-emitting devices 30 and 40, light generated in the emission layer can pass through the second electrode 190 and the second covering layer 220 toward the outside, and the second electrode 190 is a semi-transmissive electrode or a transmissive electrode.

[0532] The first cover layer 210 and the second cover layer 220 may increase external light emitting efficiency according to the principle of constructive interference.

[0533] The first capping layer 210 and the second capping layer 220 may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or a composite capping layer including an organic material and an inorganic material.

[0534] At least one selected from the first cover layer 210 and the second cover layer 220 may each independently contain at least one material selected from carbocyclic compounds, heterocyclic compounds, amine-based compounds, porphyrin derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, alkali metal complexes, and alkaline earth metal complexes. Carbocyclic compounds, heterocyclic compounds, and amine-based compounds may be optionally substituted with a substituent containing at least one element selected from O, N, S, Se, Si, F, Cl, Br, and I. In one embodiment, at least one selected from the first cover layer 210 and the second cover layer 220 may each independently contain an amine-based compound.

[0535] In one embodiment, at least one selected from the first cover layer 210 and the second cover layer 220 may each independently include the compound represented by Formula 201 or the compound represented by Formula 202.

[0536] In one or more than one embodiments, at least one selected from the first cover layer 210 and the second cover layer 220 may each independently include a compound selected from Compound HT28 to Compound HT33 and Compound CP1 to Compound CP5, but the embodiments of the present disclosure are not limited thereto.

[0537]

[0538] In the above, it has been combined Figures 1 to 4 The organic light emitting device according to the embodiment is described. However, the embodiment of the present disclosure is not limited thereto.

[0539] The layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region can be formed in a specific region by using one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, and laser induced thermal imaging.

[0540] When the layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region are formed by vacuum deposition, the deposition temperature may be about 100° C. to about 500° C., about 10 -8 To about 10 -3 Torr vacuum and approx. to about Deposition is carried out at a deposition rate of .

[0541] When the layer constituting the hole transport region, the emission layer, and the layer constituting the electron transport region are formed by spin coating, the spin coating can be performed at a coating speed of about 2,000 rpm to about 5,000 rpm and at a heat treatment temperature of about 80°C to 200°C by considering the materials contained in the layer to be formed and the structure of the layer to be formed.

[0542] equipment

[0543] The organic light-emitting device as described above may be used in various suitable devices.

[0544] Therefore, another aspect of the embodiment provides an apparatus including the organic light-emitting device.

[0545] The device may be, for example, a light emitting device, a verification device, or an electronic device, but embodiments of the present disclosure are not limited thereto.

[0546] The light emitting device can be used for various suitable displays, light sources, etc.

[0547] The authentication device may be a biometric authentication device for authenticating an individual by using biometric information (eg, information about fingertips, pupils, etc.).

[0548] In addition to the organic light emitting device as described above, the authentication apparatus may further include a biometric information collection unit.

[0549] The electronic device can be a personal computer (e.g., a mobile personal computer), a mobile phone, a digital camera, an electronic notebook, an electronic dictionary, an electronic game console, a medical device (e.g., an electronic thermometer, a blood pressure monitor, a blood glucose meter, a pulse measuring device, a pulse wave measuring device, an electrocardiogram display device, an ultrasonic diagnostic device, an endoscopic display device), a fish finder, various suitable measuring devices, a meter (e.g., a meter for a vehicle, an aircraft, or a ship), a projector, etc., but the implementation scheme is not limited thereto.

[0550] In one or more embodiments, in addition to the organic light-emitting device, the device may further include a thin film transistor. Here, the thin film transistor includes a source electrode and a drain electrode, and the first electrode of the organic light-emitting device may be electrically coupled to at least one of the source electrode and the drain electrode of the thin film transistor.

[0551] General definition of at least some substituents

[0552] As used herein, the term "period 1 transition metal" refers to an element of period 4 in the periodic table and included in the d-block, and examples thereof are scandium (Sc), titanium (Ti), vanadium (V), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu) and zinc (Zn).

[0553] As used herein, the term "period 2 transition metal" refers to an element of the 5th period of the periodic table and included in the d-block, and examples thereof are yttrium (Y), zirconium (Zr), niobium (Nb), molybdenum (Mo), technetium (Tc), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag) and cadmium (Cd).

[0554] As used herein, the term "period 3 transition metal" refers to elements of period 6 of the periodic table and included in the d-block and f-block, and includes lanthanides, which may also be referred to as "inner transition metals." Examples of period 3 transition metals include lanthanum (La), samarium (Sm), europium (Eu), terbium (Yb), thulium (Tm), ytterbium (Yb), lutetium (Lu), hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), gold (Au), and mercury (Hg).

[0555] As used herein, the term “C 1 -C 60 The term “alkyl group” refers to a linear or branched aliphatic saturated hydrocarbon monovalent group having 1 to 60 carbon atoms, and examples thereof include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isopentyl group, and a hexyl group. As used herein, the term “C 1 -C 60"Alkylene group" refers to a group having 1 -C 60 The structure of the alkyl group is substantially the same as that of a divalent group.

[0556] As used herein, the term “C 2 -C 60 "Alkenyl group" means a 2 -C 60 The alkyl group is a hydrocarbon group having at least one carbon-carbon double bond in the main chain (e.g., in the middle) or at the terminal (e.g., at the end), and examples thereof include a vinyl group, a propenyl group, and a butenyl group. As used herein, the term “C 2 -C 60 "Alkenylene group" refers to a 2 -C 60 The structure of the alkenyl group is substantially the same as that of a divalent group.

[0557] As used herein, the term “C 2 -C 60 "Alkynyl group" means a 2 -C 60 The alkyl group is a hydrocarbon group having at least one carbon-carbon triple bond in the main chain (e.g., in the middle) or at the terminal (e.g., at the end), and examples thereof include an ethynyl group and a propynyl group. As used herein, the term “C 2 -C 60 "Alkyne group" refers to a 2 -C 60 The structure of the alkynyl group is essentially the same as that of a divalent group.

[0558] As used herein, the term “C 1 -C 60 "Alkoxy group" refers to a group consisting of -OA 101 (A 101 C 1 -C 60 The invention further comprises a monovalent group represented by an alkyl group (eg, an alkyl group), and examples thereof include a methoxy group, an ethoxy group and an isopropoxy group.

[0559] As used herein, the term “C 3 -C 10 A "cycloalkyl group" refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. As used herein, the term "C 3 -C 10 "Cycloalkylene group" refers to a group having a 3 -C 10 The structure of the cycloalkyl group is substantially the same as that of a divalent group.

[0560] As used herein, the term “C 1 -C 10 The term “heterocycloalkyl group” refers to a monovalent monocyclic group having at least one heteroatom (e.g., 1 to 6 heteroatoms, such as 1, 2, 3, 4, 5 or 6 heteroatoms) selected from N, O, Si, P and S as a ring-forming atom and 1 to 10 carbon atoms, and examples thereof include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group and a tetrahydrothienyl group. As used herein, the term “C 1 -C 10 The term "heterocycloalkylene group" refers to a 1 -C 10 Heterocycloalkyl groups are divalent groups of substantially the same structure.

[0561] As used herein, the term “C 3 -C 10 A "cycloalkenyl group" refers to a monovalent monocyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and having no aromaticity (e.g., the ring and / or the group is not aromatic), and examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. As used herein, the term "C 3 -C 10 "Cycloalkenylene group" refers to a group having a 3 -C 10 Cycloalkenyl groups are divalent groups of substantially the same structure.

[0562] As used herein, the term “C 1 -C 10 The term "heterocycloalkenyl group" refers to a monovalent monocyclic group having at least one heteroatom (e.g., 1 to 6 heteroatoms, such as 1, 2, 3, 4, 5 or 6 heteroatoms) selected from N, O, Si, P and S as a ring atom, 1 to 10 carbon atoms and at least one carbon double bond in its ring. 1 -C 10 Non-limiting examples of heterocycloalkenyl groups include 4,5-dihydro-1,2,3,4-oxatriazolyl groups, 2,3-dihydrofuranyl groups, and 2,3-dihydrothienyl groups. As used herein, the term “C 1 -C 10 The term "heterocycloalkenylene group" refers to a 1 -C 10 Heterocycloalkenyl groups are divalent groups of substantially the same structure.

[0563] As used herein, the term “C 6 -C 60"Aryl group" refers to a monovalent group having a carbocyclic aromatic system containing 6 to 60 carbon atoms, and the C 6 -C 60 Arylene groups refer to divalent groups having a carbocyclic aromatic system containing 6 to 60 carbon atoms. 6 -C 60 Non-limiting examples of aryl groups include phenyl groups, naphthyl groups, anthracenyl groups, phenanthrenyl groups, pyrenyl groups and When C 6 -C 60 Aryl groups 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).

[0564] As used herein, the term “C 1 -C 60 The term "heteroaryl group" refers to a monovalent group of a carbocyclic aromatic system having, in addition to 1 to 60 carbon atoms, at least one heteroatom (e.g., 1-15 heteroatoms, such as 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15 heteroatoms) selected from N, O, Si, P and S as a ring atom. As used herein, the term "C 1 -C 60 The term "heteroarylene group" refers to a divalent group having a carbocyclic aromatic system containing at least one heteroatom (e.g., 1-15 heteroatoms, such as 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15 heteroatoms) 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 are pyridyl groups, pyrimidinyl groups, pyrazinyl groups, pyridazinyl groups, triazinyl groups, quinolyl groups and isoquinolyl groups. 1 -C 60 Heteroaryl groups and C 1 -C 60 When the heteroarylene groups each include two or more rings, the two or more rings may be fused to each other (eg, bonded together).

[0565] As used herein, the term “C 6 -C 60 "Aryloxy group" refers to -OA 102 (A 102 C 6 -C 60 aryl group), and C 6-C 60 Arylthio group represents -SA 103 (A 103 C 6 -C 60 aryl group).

[0566] As used herein, the term “C 1 -C 60 "Heteroaryloxy group" refers to -OA 104 (A 104 It is C 1 -C 60 heteroaryl group), and “C 1 -C 60 "Heteroarylthio group" refers to -SA 105 (A 105 It is C 1 -C 60 heteroaryl group).

[0567] 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), having only carbon atoms as ring-forming atoms, and not having aromaticity in its entire molecular structure (e.g., the entire molecular structure is not aromatic). Examples of monovalent non-aromatic fused polycyclic groups are fluorenyl groups and the like. As used herein, the term "divalent non-aromatic fused polycyclic group" refers to a divalent group having substantially the same structure as a monovalent non-aromatic fused polycyclic group.

[0568] 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 (e.g., 1-15 heteroatoms, such as 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15 heteroatoms) selected from N, O, Si, P and S other than carbon atoms as a ring-forming atom, and having no aromaticity in its entire molecular structure (e.g., the entire molecular structure 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 substantially the same structure as a monovalent non-aromatic fused heteropolycyclic group.

[0569] As used herein, the term “C 5 -C 60 "Carbocyclic group" refers to a monocyclic or polycyclic group that includes only carbon as a ring atom and consists of 5 to 60 carbon atoms. 5 -C60 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 a phenyl group; or a divalent group, such as a phenylene group. In one or more than one embodiment, according to the connection to C 5 -C 60 The number of substituents in a carbocyclic group, C 5 -C 60 The carbocyclic group may be a trivalent group or a tetravalent group.

[0570] As used herein, the term “C 1 -C 60 "Heterocyclic group" refers to a 5 -C 60 The carbocyclic group is a group having substantially the same structure as the carbocyclic group, but in addition to carbon (the number of carbon atoms can be 1 to 60), at least one heteroatom (e.g., 1-15 heteroatoms, such as 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15 heteroatoms) selected from N, O, Si, P and S is used as a ring-forming atom.

[0571] Selected from substituted C 5 -C 60 Carbocyclic groups, substituted C 1 -C 60 Heterocyclic groups, substituted C 3 -C 10 Cycloalkylene groups, substituted C 1 -C 10 Heterocycloalkylene groups, substituted C 3 -C 10 Cycloalkenylene groups, substituted C 1 -C 10 Heterocycloalkenylene groups, substituted C 6 -C 60 Arylene groups, substituted C 1 -C 60 Heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C 1 -C 60 Alkyl groups, substituted C 2 -C 60 Alkenyl groups, substituted C 2 -C 60 Alkynyl groups, substituted C 1 -C 6 Alkoxy groups, substituted C 3 -C 10 Cycloalkyl groups, substituted C1 -C 10 Heterocycloalkyl groups, substituted C 3 -C 10 Cycloalkenyl groups, substituted C 1 -C 10 Heterocycloalkenyl groups, substituted C 6 -C 60 Aryl groups, substituted C 6 -C 60 Aryloxy groups, substituted C 6 -C 60 Arylthio groups, substituted C 1 -C 60 Heteroaryl groups, substituted C 1 -C 60 Heteroaryloxy groups, substituted C 1 -C 60 At least one substituent in the heteroarylthio group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group may be selected from:

[0572] Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl groups and C 1 -C 60 Alkoxy groups;

[0573] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 heteroaryl group, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si(Q 11)(Q 12 )(Q 13 )、-N(Q 11 )(Q 12 )、-B(Q 11 )(Q 12 )、-C(=O)(Q 11 )、-S(=O) 2 (Q 11 ) and -P(=O)(Q 11 )(Q 12 ) at least one substituted C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl groups and C 1 -C 60 Alkoxy groups;

[0574] C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups;

[0575] Each is selected from deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl groups, C 1 -C 60 Heteroaryloxy groups, C 1 -C 60 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-N(Q 21 )(Q 22 )、-B(Q 21 )(Q 22 )、-C(=O)(Q 21 )、-S(=O) 2 (Q 21 ) and -P(=O)(Q 21 )(Q 22 ) at least one substituted C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl groups, C 1 -C 60 Heteroaryloxy groups, C 1 -C 60 a heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group; and

[0576] -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 ),

[0577] Q 1 To Q 3 , Q 21 To Q 23 and Q 31 To Q 33 can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl group, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 1 -C 60 Heteroaryl group, C 1 -C 60 Heteroaryloxy group, C 1 -C 60 heteroarylthio group, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, C substituted by at least one selected from deuterium, -F and cyano group 1 -C 60 An alkyl group, a C substituted by at least one selected from deuterium, -F and a cyano group 6 -C 60 Aryl groups, biphenyl groups and terphenyl groups.

[0578] As used herein, the term "Ph" refers to a phenyl group, as used herein, the term "Me" refers to a methyl group, as used herein, the term "Et" refers to an ethyl group, as used herein, the term "ter-Bu" or "Bu" refers to an ethyl group. t” refers to a tert-butyl group, and as used herein, the term “OMe” refers to a methoxy group.

[0579] As used herein, the term "biphenyl group" refers to a "phenyl group substituted by a phenyl group." In other words, the "biphenyl group" is a group having C 6 -C 60 Aryl group (phenyl group) is a substituted phenyl group as a substituent.

[0580] As used herein, the term "terphenyl group" refers to a "phenyl group substituted by a biphenyl group." In other words, the "terphenyl group" is a phenyl group having a C 6 -C 60 Aryl group (phenyl group) substituted C 6 -C 60 Aryl group (phenyl group) A phenyl group as a substituent.

[0581] As used herein, * and *', unless otherwise defined, each refers to a site of attachment to an adjacent atom in the corresponding formula.

[0582] Hereinafter, the compound according to the embodiment and the organic light-emitting device according to the embodiment will be described in more detail with reference to Synthesis Examples and Examples. As used in describing Synthesis Examples, the phrase "using B instead of A" means using an equimolar equivalent of B instead of A.

[0583] Example

[0584] Synthesis Example 1: Synthesis of Compound 1

[0585] (1) Synthesis of intermediate 1-C

[0586]

[0587] Starting material 1-A (11.8 g, 40 mmol), starting material 1-B (16.7 g, 80 mmol), CuI (3.8 g, 20 mmol), potassium carbonate (11.1 g, 80 mmol) and 1-methyl-1H-imidazole (3.3 g, 40 mmol) were added to 250 ml of toluene, and then, the mixture was refluxed while stirring under a nitrogen atmosphere for 7 days. Then, the reaction mixture was cooled to room temperature, 300 ml of water was added to separate the organic layer, and the aqueous layer was extracted twice with 250 ml of dichloromethane. The extracted organic layer was mixed with MgSO 4 The mixture was stirred together to remove water therefrom, and the organic layer was filtered and evaporated under reduced pressure. The obtained solid was subjected to column chromatography using dichloromethane and n-hexane as eluents to obtain 5.6 g of Intermediate 1-C in a yield of 33%.

[0588] MS (MALDI-TOF) m / z: 424[M]+

[0589] (2) Synthesis of intermediate 1-F

[0590]

[0591] Starting material 1-D (6.0 g, 17.4 mmol), starting material 1-E (2.8 g, 17.4 mmol), tetrakistriphenylphosphine palladium (0.6 g, 0.5 mmol) and potassium carbonate (7.2 g, 52.1 mmol) were loaded into a 250 ml flask, and then, 100 ml of toluene, 20 ml of ethanol and 20 ml of water were added thereto. The resulting mixture was stirred at room temperature for 30 minutes while heating with N 2 The mixture was bubbling, and then the temperature was raised and then stirred for 12 hours while refluxed. The reaction mixture was cooled to room temperature, and 100 ml of water and 100 ml of ethyl acetate were added to separate the organic layer. The aqueous layer was extracted twice with 50 ml of dichloromethane. The extracted organic layer was mixed with MgSO 4 The mixture was stirred together to remove water therefrom, and the organic layer was filtered and evaporated under reduced pressure. The obtained solid was subjected to column chromatography using dichloromethane and n-hexane as eluents to obtain 3.8 g of Intermediate 1-F in a yield of 75%.

[0592] MS (MALDI-TOF) m / z: 295[M]+

[0593] (3) Synthesis of intermediate 1-G

[0594]

[0595] Intermediate 1-C (5.5 g, 13.0 mmol) and Intermediate 1-F (3.8 g, 13.0 mmol) were added to 100 ml of toluene, and then tris(dibenzylideneacetone)dipalladium(0) (0.4 g, 0.4 mmol), tri-tert-butylphosphine (0.2 g, 0.8 mmol, 50% solution in toluene) and sodium tert-butoxide (3.7 g, 39.0 mmol) were added thereto. The resulting mixture was stirred at room temperature for 30 minutes while heating with N 2 Bubble, and then, raise the temperature, and then stir for 24 hours while reflux. The reaction mixture is cooled to room temperature, and 100 ml of water and 100 ml of ethyl acetate are added to separate the organic layer. The aqueous layer is extracted twice with 500 ml of dichloromethane. The extracted organic layer is mixed with MgSO 4The mixture was stirred together to remove water therefrom, and the organic layer was filtered and evaporated under reduced pressure. The obtained solid was subjected to column chromatography using dichloromethane as an eluent to obtain 4.6 g of Intermediate 1-G in a yield of 55%.

[0596] MS (MALDI-TOF) m / z: 638[M]+

[0597] (4) Synthesis of Compound 1

[0598]

[0599] The starting material 1-G (4.6 g, 7.2 mmol) and potassium tetrachloroplatinate (II) (3.1 g, 7.6 mmol) were added to a sealed tube, and 500 ml of glacial acetic acid and n-tetrabutylammonium bromide (0.2 g, 0.7 mmol) were added thereto. The resulting mixture was stirred at room temperature for 30 minutes while heating with N 2 The mixture was stirred for 96 hours and then refluxed. The reaction mixture was cooled to room temperature, 500 ml of water was added thereto and stirred. The resulting precipitate was filtered, washed three times with water, and then the solid obtained was dried. The dry solid was subjected to column chromatography using dichloromethane and normal hexane as eluents, and 1.4 g of compound 1 was obtained, with a yield of 23%.

[0600] MS (MALDI-TOF) m / z: 831[M]+

[0601] Synthesis Example 2: Synthesis of Compound 2

[0602] (1) Synthesis of intermediate 2-C

[0603]

[0604] The starting material 2-A (10.0 g, 28.9 mmol), the starting material 2-B (6.2 g, 28.9 mmol), tetrakistriphenylphosphine palladium (1.0 g, 0.9 mmol) and potassium carbonate (12.0 g, 86.8 mmol) were loaded into a 250 ml flask, and then, 200 ml of toluene, 40 ml of ethanol and 40 ml of water were added thereto. The resulting mixture was stirred at room temperature for 30 minutes while heating with N 2 Bubble, and then, raise the temperature, and then stir for 12 hours while reflux. The reaction mixture is cooled to room temperature, and 200 ml of water and 200 ml of ethyl acetate are added to separate the organic layer. 100 ml of dichloromethane is added to the aqueous layer to extract the organic layer. This extraction process is performed twice. The extracted organic layer is mixed with MgSO 4The mixture was stirred together to remove water therefrom, and the organic layer was filtered and evaporated under reduced pressure. The obtained solid was subjected to column chromatography using dichloromethane and n-hexane as eluents to obtain 4.4 g of Intermediate 2-C in a yield of 38%.

[0605] MS (MALDI-TOF) m / z: 395[M]+

[0606] (2) Synthesis of intermediate 2-E

[0607]

[0608] Starting material 2-C (4.4 g, 11.0 mmol) and starting material 2-D (4.2 g, 11.0 mmol) were added to 100 ml of toluene, and then tris(dibenzylideneacetone)dipalladium(0) (0.3 g, 0.3 mmol), tri-tert-butylphosphine (0.15 g, 0.7 mmol, 50% solution in toluene) and sodium tert-butoxide (3.2 g, 33.0 mmol) were added thereto. The resulting mixture was stirred at room temperature for 30 minutes while heating with N 2 Bubble, and then, raise the temperature, and then stir for 24 hours while reflux. The reaction mixture is cooled to room temperature, and 100 ml of water and 100 ml of ethyl acetate are added to separate the organic layer. The aqueous layer is extracted twice with 500 ml of dichloromethane to obtain an organic layer. The extracted organic layer is mixed with MgSO 4 The mixture was stirred together to remove water therefrom, and the organic layer was filtered and evaporated under reduced pressure. The obtained solid was subjected to column chromatography using dichloromethane as an eluent to obtain 3.4 g of Intermediate 2-E in a yield of 45%.

[0609] MS (MALDI-TOF) m / z: 694[M]+

[0610] (3) Synthesis of Compound 2

[0611]

[0612] The starting material 2-E (3.4 g, 5.0 mmol) and potassium tetrachloroplatinate (II) (2.2 g, 5.3 mmol) were added to a sealed tube, and 300 ml of glacial acetic acid and n-tetrabutylammonium bromide (0.1 g, 0.5 mmol) were added thereto. The resulting mixture was stirred at room temperature for 30 minutes while heating with N 2The mixture was stirred for 96 hours and then refluxed. The reaction mixture was cooled to room temperature, 300 ml of water was added thereto and stirred. The resulting precipitate was filtered, washed three times with water, and then the solid obtained was dried. The dry solid was subjected to column chromatography using dichloromethane and normal hexane as eluents, and 0.8 g of compound 2 was obtained, with a yield of 18%.

[0613] MS (MALDI-TOF) m / z: 886[M]+

[0614] Synthesis Example 3: Synthesis of Compound 3

[0615] (1) Synthesis of intermediate 3-C

[0616]

[0617] Starting material 3-A (9.9 g, 40 mmol), starting material 3-B (18.7 g, 80 mmol), CuI (3.8 g, 20 mmol), potassium carbonate (11.3 g, 80 mmol) and 1-methyl-1H-imidazole (3.3 g, 40 mmol) were added to 250 ml of toluene, and then, the mixture was refluxed while stirring under a nitrogen atmosphere for 7 days. The reaction mixture was cooled to room temperature, and 300 ml of water was added to separate the organic layer. The aqueous layer was extracted twice with 250 ml of dichloromethane to obtain an organic layer. The extracted organic layer was mixed with MgSO 4 The mixture was stirred together to remove water therefrom, and the organic layer was filtered and evaporated under reduced pressure. The obtained solid was subjected to column chromatography using dichloromethane and n-hexane as eluents to obtain 4.3 g of Intermediate 3-C in a yield of 27%.

[0618] MS (MALDI-TOF) m / z: 400[M]+

[0619] (2) Synthesis of intermediate 3-F

[0620]

[0621] The starting material 3-D (6.9 g, 20.0 mmol), the starting material 3-E (4.2 g, 20.0 mmol), tetrakistriphenylphosphine palladium (0.7 g, 0.6 mmol) and potassium carbonate (8.3 g, 59.9 mmol) were loaded into a 250 ml flask, and then, 200 ml of toluene, 40 ml of ethanol and 40 ml of water were added thereto. The resulting mixture was stirred at room temperature for 30 minutes while heating with N 2Bubble, and then, raise the temperature, and then stir for 12 hours while reflux. The reaction mixture is cooled to room temperature, and 200 ml of water and 200 ml of ethyl acetate are added to separate the organic layer. The aqueous layer is extracted twice with 100 ml of dichloromethane to obtain an organic layer. The extracted organic layer is mixed with MgSO 4 The mixture was stirred together to remove water therefrom, and the organic layer was filtered and evaporated under reduced pressure. The obtained solid was subjected to column chromatography using dichloromethane and n-hexane as eluents to obtain 4.8 g of Intermediate 3-F in a yield of 70%.

[0622] MS (MALDI-TOF) m / z: 345[M]+

[0623] (3) Synthesis of intermediate 3-G

[0624]

[0625] Starting material 3-C (4.3 g, 10.8 mmol) and starting material 3-F (3.7 g, 10.8 mmol) were added to 100 ml of toluene, and then tris(dibenzylideneacetone)dipalladium(0) (0.3 g, 0.3 mmol), tri-tert-butylphosphine (0.15 g, 0.7 mmol, 50% solution in toluene) and sodium tert-butoxide (3.1 g, 32.4 mmol) were added thereto. The resulting mixture was stirred at room temperature for 30 minutes while heating with N 2 Bubble, and then, raise the temperature, and then stir for 24 hours while reflux. The reaction mixture is cooled to room temperature, and 100 ml of water and 100 ml of ethyl acetate are added to separate the organic layer. The aqueous layer is extracted twice with 500 ml of dichloromethane to obtain an organic layer. The extracted organic layer is mixed with MgSO 4 The mixture was stirred together to remove water therefrom, and the organic layer was filtered and evaporated under reduced pressure. The obtained solid was subjected to column chromatography using dichloromethane as an eluent to obtain 3.5 g of Intermediate 3-G in a yield of 49%.

[0626] MS (MALDI-TOF) m / z: 664[M]+

[0627] (4) Synthesis of Compound 3

[0628]

[0629] The starting material 3-G (3.5 g, 5.3 mmol) and potassium tetrachloroplatinate (II) (2.3 g, 5.6 mmol) were added to a sealed tube, and 300 ml of glacial acetic acid and n-tetrabutylammonium bromide (0.1 g, 0.5 mmol) were added thereto. The resulting mixture was stirred at room temperature for 30 minutes while heating with N2 Bubbling, and then, raising the temperature while sealing the tube with its lid closed, then stirring 96 hours while reflux. The reaction mixture is cooled to room temperature, 300ml of water is added thereto and stirred. The precipitate obtained is filtered, washed with water three times, and then the solid obtained is dried. Using dichloromethane and normal hexane as eluents, the dry solid is subjected to column chromatography, 0.9g of compound 3 is obtained, and the yield is 20%.

[0630] MS (MALDI-TOF) m / z: 857[M]+

[0631] Example 1

[0632] As the anode, a glass substrate on which 120 nm thick ITO was deposited was subjected to ultrasonic cleaning and pretreatment (with ultraviolet (UV) and O 3 treatment, and heat treatment).

[0633] Compound HT6 and HAT-CN were co-deposited on the anode to form a hole transport layer having a thickness of 120 nm.

[0634] Compound H56 as a host and Compound 1 as a dopant were co-deposited on the hole transport layer at a weight ratio of 98:2 to form an emission layer having a thickness of 30 nm.

[0635] BAlq is deposited on the emission layer to form a hole blocking layer having a thickness of 5 nm, and then, Alq3 is deposited on the hole blocking layer to form an electron transport layer having a thickness of 25 nm, and then, LiF is deposited on the electron transport layer to form an electron injection layer having a thickness of 0.5 nm, and then, Al is deposited on the electron injection layer to form a cathode having a thickness of 150 nm, thereby completing the manufacture of an organic light-emitting device having a structure of ITO (120 nm) / HT6: HAT-CN (120 nm) / H56: 1 (2 wt %) (30 nm) / BAlq (5 nm) / Alq (25 nm) / LiF (0.5 nm) / Al (150 nm).

[0636] Example 2

[0637] An organic light-emitting device was manufactured in substantially the same manner as in Example 1, except that Compound 2 was used instead of Compound 1 as a dopant.

[0638] Example 3

[0639] An organic light-emitting device was manufactured in substantially the same manner as in Example 1, except that Compound 3 was used instead of Compound 1 as a dopant.

[0640] Evaluation Example 1

[0641] The driving voltage, current density, external quantum luminescence efficiency, and maximum emission wavelength of the organic light-emitting devices manufactured according to Examples 1 to 3 were measured by using a Keithley SMU 236 and a luminance meter PR650.

[0642] It was found that the organic light-emitting devices of Examples 1 to 3 had lower driving voltage and higher external quantum luminescence efficiency than other organic light-emitting devices in the related art while emitting near-infrared light having a maximum emission wavelength of 720 nm or more.

[0643] An organic light-emitting device including the organometallic compound may emit red light or near-infrared light having a maximum emission wavelength of 720 nm or more and 2,500 nm or less while having low driving voltage and high external quantum luminescence efficiency.

[0644] 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 be considered as available for other similar features or aspects in other embodiments.

[0645] It should be understood that although the terms "first", "second", "third", etc. can be used to describe various elements, components, areas, layers and / or parts in this article, these elements, components, areas, layers and / or parts should not be limited by these terms. These terms are used to distinguish one element, component, area, layer or part from another element, component, area, layer or part. Therefore, without departing from the spirit and scope of the present disclosure, the first element, component, area, layer or part described above can be referred to as the second element, component, area, layer or part.

[0646] For ease of explanation, spatial relative terms, such as "under", "lower", "below", "below", "above", "upper", etc., can be used in this article to describe the relationship between one element or feature and another element or feature, as illustrated in the accompanying drawings. It should be understood that, in addition to the directions described in the accompanying drawings, spatial relative terms are intended to cover different directions of the device in use or operation. For example, if the device in the accompanying drawings is turned over, the elements described as "under" or "under" or "below" other elements or features will be positioned "above" other elements or features. Therefore, the exemplary terms "under" and "below" can cover both the upper and lower directions. The device can be oriented in other ways (for example, rotated 90 degrees or in other directions), and the spatial relative descriptors used in this article should be interpreted accordingly. As used herein, the term "and / or" includes any combination and all combinations of one or more than one of the related listed items. When a statement such as "at least one / at least one" is before a column of elements, the elements of the entire column are modified and the individual elements of the column are not modified.

[0647] As used herein, the terms "substantially", "about" and similar terms are used as terms of approximation rather than as terms of degree, and are intended to account for inherent deviations in measured or calculated values, which those of ordinary skill in the art will recognize. In addition, when describing embodiments of the present disclosure, the use of "may" refers to "one or more than one embodiment 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.

[0648] In addition, any numerical range listed herein is intended to include all sub-ranges of the same numerical precision within the scope of the listing. For example, the range of "1.0 to 10.0" is intended to include all sub-ranges between the listed minimum value 1.0 and the listed maximum value 10.0 (and including the end value), that is, having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, for example, such as 2.4 to 7.6. Any maximum numerical value listed herein is intended to include all lower numerical limits included therein, and any minimum numerical value listed in this specification is intended to include all higher numerical limits included therein. Therefore, the applicant reserves the right to modify this specification (including claims) to explicitly list any sub-ranges included in the scope explicitly listed herein.

[0649] Although one or more embodiments have been described with reference to the accompanying drawings, it will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope as defined by the claims and their equivalents.

Claims

1. An organic light-emitting device, comprising: a first electrode; a second electrode; as well as an organic layer between the first electrode and the second electrode and including an emission layer, wherein: The organic layer includes an organometallic compound represented by Formula 1: Formula 1 <h2 style=";text-align:left;direction:ltr">M1(L1)<h2 style=";text-align:left;direction:ltr"> n1 <h2 style=";text-align:left;direction:ltr"> (L2)<h2 style=";text-align:left;direction:ltr"> n2 Formula 1-21 Formula 2-1 Formula 3-1 Among them, in Formula 1, Formula 1-21, Formula 2-1 and Formula 3-1, M1 is selected from platinum, palladium, ruthenium and osmium; *1 to *4 each represent a binding site with M1; L1 is a ligand represented by formula 1-21; L2 is selected from a monodentate ligand and a bidentate ligand; n1 is 1, n2 is 0; A 11 To A 14 Each independently selected from the group represented by formula 2-1, the group represented by formula 3-1, C5-C 60 Carbocyclic groups and C1-C 60 Heterocyclic groups; Selected from A 11 To A 14 At least one of the groups is selected from the group represented by formula 2-1; and Selected from A 11 To A 14 One of the following is selected from the group represented by formula 3-1; Y 11 To Y 14 are each independently selected from N and C; L 11 To L 13 Each independently selected from a single bond, *-O-*', *-S-*', *-C(R 17 )(R 18 )-*'、*-C(R 17 )=*'、*=C(R 17 )-*'、*-C(R 17 )=C(R 18 )-*', *-C(=O)-*', *-C(=S)-*' and *-C≡C-*'; R 11 To R 14 , R 17 and R 18 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, a substituted or unsubstituted C1-C 60 Alkyl groups and substituted or unsubstituted C6-C 60 Aryl groups; When A 11 is a group represented by Formula 2-1 or a group represented by Formula 3-1, R 11 is hydrogen; When A 12 is a group represented by Formula 2-1 or a group represented by Formula 3-1, R 12 is hydrogen; When A 13 is a group represented by Formula 2-1 or a group represented by Formula 3-1, R 13 is hydrogen; When A 14 is a group represented by Formula 2-1 or a group represented by Formula 3-1, R 14 is hydrogen; b11 to b14 are each independently 1; X 21 Selected from O, S, N (R 24 ) and C(R 24 )(R 25 ); X 22 To X 25 are each independently selected from N and C, A 21 and A 22 Each independently selected from C5-C 60 Carbocyclic groups and C1-C 60 A heterocyclic group, and 21 and A 22 At least one of them is C 10 -C 60 Carbocyclic groups; X 31 N, N-* or C(R 31 ), X 32 N, N-* or C(R 32 ), X 33 N, N-* or C(R 33 ), X 34 N, N-* or C(R 34 ), Selected from X 31 To X 34 Two of them are independently N or N-*, In formula 3-1, i)X 31 N-*, X 32 C(R 32 ), and R 32 is the attachment site; ii) X 31 C(R 31 ), X 32 is N-*, and R 31 is the attachment site; iii) X 32 N-*, X 33 C(R 33 ), and R 33 is the attachment site; or iv) X 32 C(R 32 ), X 33 is N-*, and R 32 is the connection site; A 31 is selected from a phenyl group and a naphthyl group; R 24 , R 25 and R 31 To R 34 are each independently selected from a linking site, hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, a substituted or unsubstituted C1-C 60 Alkyl groups and substituted or unsubstituted C6-C 60 Aryl groups; R 21 and R 22 Each is independently a binding site or hydrogen; b21R 21 、b22 R 22 , R 24 and R 25 Two or three of them are linking sites, b21 is 0 or 2, b22 is 0 or 2, * and *' each represent a connection site with an adjacent atom, wherein the substituted C1-C 60 The alkyl group and the substituted C6-C 60 At least one substituent in the aryl group is selected from: Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl groups and C1-C 60 Alkoxy groups; and C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups and monovalent non-aromatic fused heteropolycyclic groups.

2. The organic light emitting device according to claim 1, wherein: A 11 To A 14 Each independently selected from the group represented by formula 2-1, the group represented by formula 3-1, a phenyl group, a naphthalene group, an anthracene group, a phenanthrene group, a phenanthrenene group, a triphenylene group, a pyrene group, group, a cyclopentadiene group, a 1,2,3,4-tetralinyl group, a furan group, a thiophene group, a silole group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzosilole group, a dibenzosilole group, an indenopyridine group, an indolopyridine group, a benzofuranopyridine group, a benzothienopyridine group, a benzothienopyridine group, a benzothienopyridine group, an indenopyrimidine group, an indolopyrimidine group, a benzofuranopyrimidine group, a benzothienopyrimidine group, a benzothienopyrimidine group, a benzothienopyrimidine group, a dihydropyridine group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazolinyl group, a phenanthroline group, a benzoquinoline group group, a benzoisoquinoline group, a benzoquinoxaline group, a benzoquinazoline group, a pyrrole group, a pyrazole group, an imidazole group, a 2,3-dihydroimidazole group, a triazole group, a 2,3-dihydrotriazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a 2,3-dihydrobenzimidazole group, an imidazopyridine group, a 2,3-dihydroimidazopyridine group, an imidazopyrimidine group, a 2,3-dihydroimidazopyrimidine group, an imidazopyrazine group, a 2,3-dihydroimidazopyrazine group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, and a 5,6,7,8-tetrahydroquinoline group.

3. The organic light emitting device according to claim 1, wherein: A 11 To A 14 Each is independently selected from the group represented by Formula 2-1, the group represented by Formula 3-1, a phenyl group, a naphthyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group and an isoquinoline group.

4. The organic light emitting device according to claim 1, wherein: Selected from Y 11 To Y 14 Two of them are C, and the remaining two are N.

5. The organic light emitting device according to claim 1, wherein: L 11 To L 13 are each independently selected from a single bond, *-O-*' and *-S-*'.

6. The organic light emitting device according to claim 1, wherein: A 21 and A 22 are each independently selected from a phenyl group, a naphthyl group, a phenanthrene group, a phenalene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group and a quinazoline group, and A 21 and A 22 At least one of them is independently selected from a naphthyl group, a phenanthrene group and a phenalene group.

7. The organic light emitting device according to claim 1, wherein: The group represented by Formula 2-1 is represented by one of Formulas 2-12 to 2-25: Among them, in Formula 2-12 to Formula 2-25, X 21 Selected from O, S, N (R 24 ) and C(R 24 )(R 25 ); X 26a N or C (R 26a ), X 26b N or C (R 26b ), X 26c N or C (R 26c ), X 26d N or C (R 26d ), X 26e N or C (R 26e ), X 26f N or C (R 26f ), X 26g N or C (R 26g ), X 26h N or C (R 26h ), X 26i N or C (R 26i ), X 26j N or C (R 26j ), X 26k N or C (R 26k ), and X 26l N or C (R 26l ), R 24 and R 25 As defined in claim 1; R 26a To R 26l As claimed in claim 1, regarding R in formula 2-1 21 and R 22 definition; R is selected from Formula 2-12 to Formula 2-14 24 , R 25 and R 26a To R 26j Two or three of them are linking sites, R is selected from Formula 2-15 to Formula 2-23 24 , R 25 and R 26a To R 26l Two or three of them are linking sites, R selected from Formula 2-24 and Formula 2-25 24 , R 25 and R 26a To R 26k Two or three of them are attachment sites, and * indicates the connection site with the adjacent atom.

8. The organic light emitting device according to claim 1, wherein: The group represented by Formula 2-1 is represented by one of Formulas 2-32 to 2-37 and 2-39 to 2-44: Among them, in Formula 2-32 to Formula 2-37 and Formula 2-39 to Formula 2-44, R 24 As defined in claim 1, X 26a N or C (R 26a ), X 26b N or C (R 26b ), X 26c N or C (R 26c ), X 26d N or C (R 26d ), X 26e N or C (R 26e ), X 26f N or C (R 26f ), X 26g N or C (R 26g ), X 26h N or C (R 26h ), X 26i N or C (R 26i ), X 26j N or C (R 26j ), X 26k N or C (R 26k ), and X 26l N or C (R 26l ), R 26a To R 26l are each independently hydrogen; and *, *' and *" each represent a site of attachment to an adjacent atom.

9. The organic light emitting device according to claim 1, wherein: In formula 3-1, X 31 and X 32 Each independently is N or N-*; X 31 and X 33 Each independently is N or N-*; X 31 and X 34 Each independently is N or N-*; X 32 and X 33 Each independently is N or N-*; X 32 and X 34 are each independently N or N-*; or X 33 and X 34 Each is independently N or N-*.

10. An organic light-emitting device, comprising: a first electrode; a second electrode; as well as an organic layer between the first electrode and the second electrode and including an emission layer, wherein: The organic layer comprises an organic metal compound selected from Compound 1 to Compound 26, Compound 31 to Compound 38, and Compound 45 to Compound 50:

11. The organic light emitting device according to claim 1, wherein: The organometallic compound emits near infrared light having a maximum emission wavelength of 720 nm or more and 2,500 nm or less.

12. The organic light emitting device according to claim 1, wherein: 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 emission layer and / or an electron transport region between the emission layer and the second electrode, The hole transport region includes a hole injection layer, a hole transport layer, an emission 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.

13. The organic light emitting device according to claim 1, wherein: The organometallic compound is included in the emission layer.

14. A device comprising the organic light-emitting device according to claim 1.

15. The apparatus of claim 14, wherein: The device is a light emitting device or a verification device.

16. An electronic device comprising the organic light-emitting device according to claim 1.

17. An organometallic compound represented by Formula 1: Formula 1 <h2 style=";text-align:left;direction:ltr">M1(L1)<h2 style=";text-align:left;direction:ltr"> n1 <h2 style=";text-align:left;direction:ltr"> (L2)<h2 style=";text-align:left;direction:ltr"> n2 Formula 1-21 Formula 2-1 Formula 3-1 in, In Formula 1, Formula 1-21, Formula 2-1 and Formula 3-1, M1 is selected from platinum, palladium, ruthenium and osmium; *1 to *4 each represent a binding site with M1; L1 is a ligand represented by formula 1-21; L2 is selected from a monodentate ligand and a bidentate ligand; n1 is 1, n2 is 0; A 11 To A 14 Each independently selected from the group represented by formula 2-1, the group represented by formula 3-1, C5-C 60 Carbocyclic groups and C1-C 60 Heterocyclic groups; Selected from A 11 To A 14 At least one of the groups is selected from the group represented by formula 2-1; and Selected from A 11 To A 14 One of the following is selected from the group represented by formula 3-1; Y 11 To Y 14 are each independently selected from N and C; L 11 To L 13 Each independently selected from a single bond, *-O-*', *-S-*', *-C(R 17 )(R 18 )-*'、*-C(R 17 )=*'、*=C(R 17 )-*'、*-C(R 17 )=C(R 18 )-*', *-C(=O)-*', *-C(=S)-*' and *-C≡C-*'; R 11 To R 14 , R 17 and R 18 are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, a substituted or unsubstituted C1-C 60 Alkyl groups and substituted or unsubstituted C6-C 60 Aryl groups; When A 11 is a group represented by Formula 2-1 or a group represented by Formula 3-1, R 11 is hydrogen; When A 12 is a group represented by Formula 2-1 or a group represented by Formula 3-1, R 12 is hydrogen; When A 13 is a group represented by Formula 2-1 or a group represented by Formula 3-1, R 13 is hydrogen; When A 14 is a group represented by Formula 2-1 or a group represented by Formula 3-1, R 14 is hydrogen; b11 to b14 are each independently 1; X 21 Selected from O, S, N (R 24 ) and C(R 24 )(R 25 ); X 22 To X 25 are each independently selected from N and C, A 21 and A 22 Each independently selected from C5-C 60 Carbocyclic groups and C1-C 60 A heterocyclic group, and 21 and A 22 At least one of them is C 10 -C 60 Carbocyclic groups; X 31 N, N-* or C(R 31 ), X 32 N, N-* or C(R 32 ), X 33 N, N-* or C(R 33 ), X 34 N, N-* or C(R 34 ), Selected from X 31 To X 34 Two of them are independently N or N-*, In formula 3-1, i)X 31 N-*, X 32 C(R 32 ), and R 32 is the attachment site; ii) X 31 C(R 31 ), X 32 is N-*, and R 31 is the attachment site; iii) X 32 N-*, X 33 C(R 33 ), and R 33 is the attachment site; or iv) X 32 C(R 32 ), X 33 is N-*, and R 32 is the connection site; A 31 is selected from a phenyl group and a naphthyl group; R 24 , R 25 and R 31 To R 34 are each independently selected from a linking site, hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, a substituted or unsubstituted C1-C 60 Alkyl groups and substituted or unsubstituted C6-C 60 Aryl groups; R 21 , R 22 and R 39 are each independently selected from the attachment site and hydrogen; Select from b21 R 21 、b22 R 22 , R 24 and R 25 Two or three of them are linking sites, b21 is 0 or 2, b22 is 0 or 2, and * and *' each represent a connection site with an adjacent atom, wherein the substituted C1-C 60 The alkyl group and the substituted C6-C 60 At least one substituent in the aryl group is selected from: Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl groups and C1-C 60 Alkoxy groups; and C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy groups, C6-C 60 Arylthio group, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups and monovalent non-aromatic fused heteropolycyclic groups.

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