Organic metal compound and organic light-emitting device comprising the same

Abstract

Provided are an organic metal compound and an organic light-emitting device comprising the same. The organic metal compound is represented by Formula 1, wherein in Formula 1, M, X 11 , X 12 , X 13 , X 14 , A 11 , R 11 , R 14 ,b11,n,L 11 and m are described in the specification. Formula 1#imgabs0#

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to and the benefits of Korean Patent Application No. 10-2019-0089219 filed in the Korean Intellectual Property Office on July 23, 2019, and all rights arising therefrom, the contents of which are incorporated herein in their entirety by reference Technical Field

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

[0004] Compared with other types of devices, organic light emitting devices are self-emissive devices that produce full-color images and have wide viewing angles, high contrast, short response times, and excellent characteristics in terms of brightness, driving voltage, and response speed.

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

[0006] One or more embodiments include novel organometallic compounds and organic light-emitting devices including the same.

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

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

[0009] Formula 1

[0010]

[0011] In formula 1,

[0012] M may be a first row transition metal, a second row transition metal, or a third row transition metal of the periodic table,

[0013] X 11 Can be N or C, and in X 11 The bond between and M can be a coordination bond,

[0014] X12 Can be N or C(R 12 ),

[0015] X 13 Can be N or C(R 13 ), where X 12 and X 13 Not N at the same time,

[0016] X 14 Can be N or C,

[0017] A 11 Can be C 5 -C 60 Carbocyclic group or C 1 -C 60 Heterocyclic groups,

[0018] R with quantity b11 11 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 7 -C 60 Alkaryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 Alkyl heteroaryl, substituted or unsubstituted C 1 -C 60Heteroaryloxy, substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused 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 ), or -P(=S)(Q 1 )(Q 2 ), where two adjacent R 11 may be optionally linked to each other to form a substituted or unsubstituted C 5 -C 30 A carbocyclic group or a substituted or unsubstituted C 1 -C 30 Heterocyclic groups,

[0019] R 12 and R 13 Can be independently:

[0020] -F, -Cl, -Br, -I, cyano, or nitro; or

[0021] C substituted by at least one selected from -F, -Cl, -Br, -I, cyano and nitro 1 -C 60 alkyl,

[0022] R 14 Can be substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 1 -C 60 a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,

[0023] b11 can be 1, 2, 3, 4, 5, 6, 7 or 8,

[0024] Q 1 -Q 3can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, selected from deuterium, -F, cyano, C 1 -C 60 Alkyl and C 6 -C 60 At least one substituted C 1 -C 60 Alkyl, or is selected from deuterium, -F, cyano, C 1 -C 60 Alkyl and C 6 -C 60 At least one substituted C 6 -C 60 Aryl,

[0025] n can be 1, 2 or 3,

[0026] L 11 may be a monodentate ligand, a bidentate ligand, or a tridentate ligand, and

[0027] m can be 0, 1, 2, 3, 4 or 5.

[0028] Another aspect of the present disclosure provides an organic light emitting device including: a first electrode; a second electrode; an organic layer between the first electrode and the second electrode and including an emission layer,

[0029] The organic layer comprises the above-described organometallic compound.

[0030] The organometallic compound may be included in the emission layer. The organometallic compound in the emission layer may serve as a dopant. BRIEF DESCRIPTION OF THE DRAWINGS

[0031] By combining Figure 1 These and / or other aspects will become clear and more readily understood from the following description of the embodiments contemplated herein. Figure 1 is a schematic diagram of an organic light emitting device according to an embodiment. DETAILED DESCRIPTION

[0032] Embodiments will now be described in detail, examples of which are illustrated in the accompanying drawings, wherein the same reference numerals refer to the same elements throughout. In this regard, the present embodiment may have different forms and should not be construed as being limited to the description set forth herein. Therefore, the following only describes the embodiments with reference to the accompanying drawings to illustrate aspects of the present description. As used herein, the term "and / or" includes any and all combinations of one or more of the related enumerated items. Expressions such as "at least one (kind)" when before or after a list of elements modify the entire list of elements and do not modify the individual elements of the list.

[0033] It will be understood that although the terms "first", "second", "third", etc. may be used herein to describe various elements, components, regions, layers and / or parts, these elements, components, regions, layers and / or parts should not be limited by these terms. These terms are only used to distinguish one element, component, region, layer or part from another element, component, region, layer or part. Therefore, without departing from the teachings herein, the first element, component, region, layer or part discussed below may be referred to as a second element, component, region, layer or part.

[0034] The terms used herein are only for the purpose of describing specific embodiments and are not intended to be limiting. As used herein, "one", "a", "the", and "at least one" do not represent a limit on quantity and are intended to cover both the singular and the plural, unless the context clearly indicates otherwise. For example, "(an) element" has the same meaning as "at least one element", unless the context clearly indicates otherwise.

[0035] "Or" means "and / or". As used herein, the term "and / or" includes any and all combinations of one or more of the relevant listed items. It will be further understood that the terms "comprise" or "include" when used in this specification indicate the presence of the stated features, regions, integers, steps, operations, elements, and / or components, but do not exclude the presence or addition of one or more additional features, regions, integers, steps, operations, elements, components, and / or their collections.

[0036] In addition, relative terms such as "lower" or "bottom" and "upper" or "top" may be used herein to describe the relationship of one element to another element as shown in the figure. It will be understood that in addition to the orientation depicted in the figure, relative terms are also intended to include different orientations of the device. For example, if the device in one of the figures is turned over, the element described as "on the "lower" side of the other element will be oriented on the "upper" side of the other element. Therefore, depending on the specific orientation of the figure, the exemplary term "lower" may include both "lower" and "upper" orientations. Similarly, if the device in one of the figures is turned over, the element described as "below" or "below" the other element will be oriented "above" the other element. Therefore, the exemplary terms "below..." or "below..." may include both "above..." and "below..." orientations.

[0037] As used herein, "about" or "approximately" includes the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art taking into account the measurement in question and the errors associated with the measurement of the particular quantity (i.e., the limitations of the measurement system). For example, "about" can mean that the deviation from the stated value is within one or more standard deviations, or within a range of ±10% or 5%.

[0038] Unless otherwise defined, all terms (including technical and scientific terms) used in this article have the same meaning as commonly understood by ordinary technicians in the field to which the present disclosure belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as their meanings consistent with their meanings in the context of the relevant art and the present disclosure, and will not be interpreted in an idealized or overly formal sense unless clearly defined in this article.

[0039] Exemplary embodiments are described herein with reference to cross-sectional views as schematic diagrams of idealized embodiments. Thus, deviations from the shapes of the figures as a result of, for example, manufacturing techniques and / or tolerances are expected. Therefore, the embodiments described herein should not be construed as being limited to the specific shapes of the regions as shown herein, but rather include deviations in shape caused by, for example, manufacturing. For example, a region illustrated or described as flat may typically have rough and / or nonlinear features. In addition, the illustrated sharp corners may be rounded. Therefore, the regions shown in the figures are schematic in nature, and their shapes are not intended to illustrate the precise shapes of the regions, and are not intended to limit the scope of the claims.

[0040] One aspect of the present disclosure provides an organometallic compound represented by the following Formula 1:

[0041] Formula 1

[0042]

[0043] M in Formula 1 may be a first row transition metal, a second row transition metal, or a third row transition metal of the periodic table.

[0044] In one or more embodiments, M in Formula 1 may be 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) or thulium (Tm), but the embodiments of the present disclosure are not limited thereto.

[0045] In one or more embodiments, M in Formula 1 may be Pt, Pd, Cu, Ag, Au, Rh, Ir, Ru, or Os, but embodiments of the present disclosure are not limited thereto.

[0046] In one or more embodiments, M in Formula 1 may be Ru or Os, but embodiments of the present disclosure are not limited thereto.

[0047] In formula 1, X 11 Can be N or C, and in X 11 The bond between X and M can be a coordination bond. 11 Donates an electron pair to M, so in X 11 and M. Therefore, the organometallic compound represented by Formula 1 is different from the one in which X 11 The bond between X and M is a covalent bond. 11 The bond between A and M is limited to coordination bonds, so 11 Not a phenyl group.

[0048] In formula 1, X 12Can be N or C(R 12 ), and R 12 May be the same as described below.

[0049] In formula 1, X 13 Can be N or C(R 13 ), and R 13 May be the same as described below.

[0050] However, in Formula 1, excluding X 12 and X 13 The case where it is N at the same time.

[0051] For example, in Formula 1, X 12 Can be N, and X 13 Can be C(R 13 ); or X 12 Can be C(R 12 ), and X 13 It may be N, but the embodiments of the present disclosure are not limited thereto.

[0052] In one or more embodiments, in Formula 1, X 12 Can be N, and X 13 Can be C(R 13 ), but the implementation of the present disclosure is not limited thereto.

[0053] In formula 1, X 14 may be N or C, and optionally, in X 11 and X 14 The bond between can be a single bond or a double bond.

[0054] For example, in Formula 1, X 14 It may be C, but the embodiments of the present disclosure are not limited thereto.

[0055] In one or more embodiments, X 11 Can be N, X 14 Can be C, and optionally, in X 11 and X 14 The bond between may be a single bond or a double bond, but embodiments of the present disclosure are not limited thereto.

[0056] In one or more embodiments, X 11 Can be C, X 14 may be N, and optionally, in X 11 and X 14 The bond between may be a single bond or a double bond, but embodiments of the present disclosure are not limited thereto.

[0057] In formula 1, A 11 Can be C 5 -C 60Carbocyclic group or C 1 -C 60 In one or more embodiments, A 11 Can include X 11 and X 14 C as a ring member 5 -C 60 Carbocyclic group or C 1 -C 60 Heterocyclic groups. For example, A 11 Can be saturated or unsaturated C 5 -C 60 Carbocyclic groups or saturated or unsaturated C 1 -C 60 Heterocyclic groups. For example, A 11 Can be C 5 -C 60 Saturated or unsaturated alicyclic carbocyclic group or C 6 -C 60 Aromatic groups, or C 1 -C 60 Saturated or unsaturated alicyclic heterocyclic group or C 1 -C 60 (For example, C 5 -C 60 ) heteroaromatic group.

[0058] For example, A in Formula 1 11 It may be i) a 6-membered ring, ii) a condensed ring in which two 6-membered rings are condensed to each other, or iii) a condensed ring in which one 6-membered ring and one 5-membered ring are condensed to each other, but embodiments of the present disclosure are not limited thereto.

[0059] The 6-membered ring may be a cyclohexane group, a cyclohexene group, a cyclohexadiene group, an adamantane group, a norbornane group, a norbornene group, a phenyl group, a pyridine group, a dihydropyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

[0060] The 5-membered ring may be a cyclopentane group, a cyclopentene group, a cyclopentadiene group, a furan group, a thiophene group, a silole group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, a 2,3-dihydroimidazole group, a 2,3-dihydrotriazole group, Azole group, iso azole group, thiazole group, isothiazole group, an oxadiazole group, or a thiadiazole group.

[0061] In one or more embodiments, in Formula 1, The moiety represented by (wherein *' represents a binding site with M, and * represents a binding site with a carbon atom) may be represented by one of Formulae 2-1 to 2-17, but the embodiments of the present disclosure are not limited thereto:

[0062]

[0063]

[0064] In formulas 2-1 to 2-17,

[0065] X 21 Can be N or C(R 21 ), X 22 Can be N or C(R 22 ), X 23 Can be N or C(R 23 ), X 24 Can be N or C(R 24 ), X 25 Can be N or C(R 25 ), and X 26 Can be N or C(R 26 ),

[0066] X 27 and X 28 Can be C,

[0067] X 29 Can be O, S, N (R 29 ) or C(R 29 )(R 30 ),

[0068] R 21 -R 26 , R 29 and R 30 Can be independently related to R 11 Same as described,

[0069] * indicates the binding site to the carbon atom, and

[0070] *' indicates the binding site with M.

[0071] In one or more embodiments, in Formula 1, (wherein *' represents a binding site with M, and * represents a binding site with a carbon atom) The moiety represented by may be represented by one of Formulae 3-1 to 3-54, but the embodiments of the present disclosure are not limited thereto:

[0072]

[0073]

[0074]

[0075] In formulas 3-1 to 3-54,

[0076] R 21 -R 26 and R 29 Each can be referred to by referring to R described below 11 And understand,

[0077] * indicates the binding site to the carbon atom, and

[0078] *' indicates the binding site with M.

[0079] The number b11 in formula 1 is R 11 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 7 -C 60 Alkaryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 Alkyl heteroaryl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused 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 ), or -P(=S)(Q 1 )(Q 2 ), where two adjacent R 11 may be optionally linked to each other to form a substituted or unsubstituted C 5 -C 30 A carbocyclic group or a substituted or unsubstituted C 1 -C 30 Heterocyclic groups, and

[0080] Q 1 -Q 3 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60Alkyl heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, selected from deuterium, -F, cyano, C 1 -C 60 Alkyl and C 6 -C 60 At least one substituted C 1 -C 60 Alkyl, or is selected from deuterium, -F, cyano, C 1 -C 60 Alkyl and C 6 -C 60 At least one substituted C 6 -C 60 Aryl.

[0081] For example, the number R in formula 1 is b11 11 Can be independently:

[0082] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, -SF 5 , C 1 -C 20 Alkyl, or C 1 -C 20 Alkoxy;

[0083] Each of the following is substituted by at least one C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 10 alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridinyl, and pyrimidinyl;

[0084] Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazolyl, triazineyl, dibenzofuranyl, dibenzothiophenyl, dibenzothioyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, or imidazopyrimidinyl;

[0085] Each of which is selected from at least one substituted cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, Oxazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, dibenzothioyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, or imidazopyrimidinyl: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, C 1 -C20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, dibenzothioyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, and -Si(Q) 33 )(Q 34 )(Q 35 );or

[0086] -N(Q 1 )(Q 2 )、-Si(Q 3 )(Q 4 )(Q 5 )、-B(Q 6 )(Q 7 ), or -P(=O)(Q 8 )(Q 9 ),and

[0087] Q 1 -Q 9 and Q 33 -Q 35 Can be independently:

[0088] -CH 3 、-CD 3 、-CD 2 H.-CDH 2 、-CH 2 CH 3 、-CH 2 CD 3 、-CH 2 CD 2 H, -CH 2 CDH 2 、-CHDCH 3 、-CHDCD 2 H, -CHDCDH2 、-CHDCD 3 、-CD 2 CD 3 、-CD 2 CD 2 H, or -CD 2 CDH 2 ;

[0089] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or

[0090] Each is selected from deuterium, C 1 -C 10 At least one of the alkyl and phenyl groups is substituted with n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl,

[0091] However, the implementation of the present disclosure is not limited thereto.

[0092] In one or more embodiments, the number of R in Formula 1 is b11 11 can be independently hydrogen, deuterium, -F, cyano, nitro, -SF 5 、-CH 3 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , groups represented by formulae 9-1 to 9-21, groups represented by formulae 10-1 to 10-253, -N(Q 1 )(Q 2 )、-Si(Q 3 )(Q 4 )(Q 5 )、-B(Q 6 )(Q 7 ), or -P(=O)(Q 8 )(Q 9 ), but the implementation of the present disclosure is not limited thereto:

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102] In one or more embodiments, Q 1 -Q 9 Can be independently:

[0103] -CH 3 、-CD 3 、-CD 2 H.-CDH 2 、-CH 2 CH 3 、-CH 2 CD 3 、-CH 2 CD 2 H, -CH 2 CDH 2 、-CHDCH 3 、-CHDCD 2 H, -CHDCDH 2 、-CHDCD 3 、-CD 2 CD 3 、-CD 2 CD 2 H, or -CD 2 CDH 2 ;

[0104] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or

[0105] Each is selected from deuterium, C 1 -C 10 At least one of the alkyl and phenyl groups may be substituted with n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl.

[0106] In formulas 9-1 to 9-21 and 10-1 to 10-253,

[0107] * indicates the binding site with the adjacent atom,

[0108] i-Pr represents isopropyl, t-Bu represents tert-butyl,

[0109] Ph means phenyl,

[0110] 1-Nph represents 1-naphthyl, 2-Nph represents 2-naphthyl,

[0111] 2-Pyr represents 2-pyridyl, 3-Pyr represents 3-pyridyl, 4-Pyr represents 4-pyridyl, and

[0112] TMS stands for trimethylsilyl.

[0113] R in Formula 1 12 and R 13 Can be independently:

[0114] -F, -Cl, -Br, -I, cyano, or nitro; or

[0115] C substituted by at least one selected from the following 1 -C 60 Alkyl: -F, -Cl, -Br, -I, cyano, and nitro.

[0116] For example, R in Formula 1 12 and R 13 Can be independently:

[0117] -F, -Cl, or cyano; or

[0118] Methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl, or tert-decyl, each substituted by at least one selected from -F, -Cl and cyano, but embodiments of the present disclosure are not limited thereto.

[0119] In one or more embodiments, R in Formula 1 12 and R 13 Can be independently:

[0120] -F or cyano; or

[0121] a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, or a tert-butyl group, each of which is substituted with at least one selected from -F and a cyano group, but embodiments of the present disclosure are not limited thereto.

[0122] In one or more embodiments, R in Formula 1 12 and R 13 can be independently -F, cyano, or -CF 3 , but the implementation of the present disclosure is not limited thereto.

[0123] R in Formula 1 14 Can be substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 1 -C 60 A heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, but embodiments of the present disclosure are not limited thereto.

[0124] For example, R 14 Can be:

[0125] Phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, oxazolyl, pyridyl, pyrazinyl, pyrimidinyl, indolyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzo oxazolyl, triazolyl, tetrazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, dibenzothioyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, or imidazopyrimidinyl; or

[0126] Each of which is selected from at least one substituted phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, oxazolyl, pyridyl, pyrazinyl, pyrimidinyl, indolyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, benzo Azolyl, triazolyl, tetrazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, dibenzothioyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, or imidazopyrimidinyl: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, C 1 -C 20Alkoxy, cyclopentyl, cyclopentyl substituted by deuterium, cyclohexyl, cyclohexyl substituted by deuterium, cycloheptyl, cycloheptyl substituted by deuterium, cyclooctyl, cyclooctyl substituted by deuterium, bicyclo[2.2.1]heptyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, dibenzothioyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, and -Si(Q33)(Q 34 )(Q35), and

[0127] Q 33 -Q 35 Can be independently:

[0128] -CH 3 、-CD 3 、-CD 2 H.-CDH 2 、-CH 2 CH 3 、-CH 2 CD 3 、-CH 2 CD 2 H, -CH 2 CDH 2 、-CHDCH 3 、-CHDCD 2 H, -CHDCDH 2 、-CHDCD 3 、-CD 2 CD 3 、-CD 2 CD 2 H, or -CD 2 CDH 2 ;

[0129] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or

[0130] Each is selected from deuterium, C 1 -C 10 At least one of the alkyl and phenyl groups may be substituted with n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl, but embodiments of the present disclosure are not limited thereto.

[0131] In one or more embodiments, R in Formula 1 14 Can be:

[0132] Phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, benzofuranyl, benzothiophenyl, benzo oxazolyl, dibenzofuranyl, dibenzothiophenyl, or dibenzothioyl; or

[0133] Each of which is selected from at least one substituted phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, benzofuranyl, benzothiophenyl, benzo Azolyl, dibenzofuranyl, dibenzothiophenyl, or dibenzothioyl: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, methoxy, ethoxy, propoxy, butoxy, cyclopentyl, cyclohexyl, phenyl, naphthyl, and -Si(Q) 33 )(Q34)(Q35), and

[0134] Q 33 -Q 35 Can be independently:

[0135] -CH 3 、-CD 3 、-CD 2 H.-CDH 2 、-CH 2 CH 3 、-CH 2 CD 3 、-CH 2 CD 2 H, -CH 2 CDH 2 、-CHDCH 3 、-CHDCD 2 H, -CHDCDH 2 、-CHDCD 3 、-CD 2 CD3 、-CD 2 CD 2 H, or -CD 2 CDH 2 ;

[0136] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl; or

[0137] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl, each of which is substituted with deuterium, but the embodiments of the present disclosure are not limited thereto.

[0138] In one embodiment, R in Formula 1 14 It may be one of formulas 10-17 to 10-100, 10-175 to 10-222, 10-247 and 10-248, but the embodiments of the present disclosure are not limited thereto:

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145] In formulas 10-17 to 10-100, 10-175 to 10-222, 10-247 and 10-248,

[0146] * indicates the binding site with the adjacent atom,

[0147] i-Pr represents isopropyl, and t-Bu represents tert-butyl,

[0148] Ph means phenyl,

[0149] 1-Nph represents 1-naphthyl, and 2-Nph represents 2-naphthyl, and

[0150] TMS stands for trimethylsilyl.

[0151] In formula 1, b11 represents R 11 The number of substitutions is , wherein b11 can be 1, 2, 3, 4, 5, 6, 7 or 8.

[0152] The symbol n in formula 1 represents represents the number of ligands, where n can be 1, 2 or 3.

[0153] For example, n in Formula 1 may be 2, but embodiments of the present disclosure are not limited thereto.

[0154] L in Formula 1 11 It can be a monodentate ligand, a bidentate ligand, or a tridentate ligand.

[0155] For example, L in Formula 1 11 It can be a monodentate ligand, for example, I - Br - , Cl - , sulfide (sulfur), nitrate, azide (azide), hydroxide, cyanate, isocyanate, thiocyanate, water, acetonitrile, pyridine, ammonia, carbon monoxide, P(Ph) 3 、P(Ph) 2 CH 3 PPh(CH 3 ) 2 , P(CH 3 ) 3 PPh(CH 2 CH 3 ) 2 , or PPh(C(CH 3 ) 2 ) 2 , but the implementation of the present disclosure is not limited thereto.

[0156] In one or more embodiments, L in Formula 1 11 The bidentate ligand may be, for example, oxalate, acetylacetonate, picolinic acid, 1,2-bis(diphenylphosphino)ethane, 1,1-bis(diphenylphosphino)methane, glycinate, or ethylenediamine, but embodiments of the present disclosure are not limited thereto.

[0157] In one or more embodiments, L in Formula 1 11 It may be a ligand represented by one of Formulae 7-1 to 7-11, but the embodiments of the present disclosure are not limited thereto:

[0158]

[0159] In formulas 7-1 to 7-11,

[0160] A 71 and A 72 Can be independently C 5 -C 20 Carbocyclic group or C 1 -C 20 Heterocyclic groups,

[0161] X 71 and X 72 are each independently C or N,

[0162] 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 ), and X 77 Can be N or C (Q 77 ),

[0163] X 78 Can be O, S or N (Q 78 ), and X 79 Can be O, S or N (Q 79 ),

[0164] Y 71 and Y 72 can be independently a single bond, a double bond, a substituted or unsubstituted C 1 -C 5 Alkylene, substituted or unsubstituted C 2 -C 5 Alkenylene, or substituted or unsubstituted C 6 -C 10 Arylene,

[0165] Z 71 and Z 72 can be independently N, O, N(R 75 )、P(R 75 )(R 76 ), or As(R 75 )(R 76 ),

[0166] Z 73 Can be P or As,

[0167] Z 74 Can be C(=O) or CH 2 ,

[0168] R 71 -R 80 and Q 73 -Q 79 Each of them may be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 heteroaryl, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, wherein R 71 and R 72 may be optionally linked to each other to form a ring, R 77 and R 78 may be optionally linked to each other to form a ring, R 78 and R 79 may be optionally linked to each other to form a ring, and R 79 and R 80 may be optionally linked to each other to form a ring,

[0169] b71 and b72 may each independently be 1, 2 or 3, and

[0170] * and *' each independently represent a binding site with an adjacent atom.

[0171] For example, A in formula 7-11 71 and A 72 Each may independently be a phenyl group, a naphthyl group, an imidazole group, a benzimidazole group, a pyridine group, a pyrimidine group, a triazine group, a quinoline group, or an isoquinoline group, but embodiments of the present disclosure are not limited thereto.

[0172] For example, X in formula 7-11 72 and X 79 Each may be N, but the embodiments of the present disclosure are not limited thereto.

[0173] For example, in Formula 7-7, X 73 Can be C(Q 73);X 74 Can be C(Q 74 );X 75 Can be C(Q 75 );X 76 Can be C(Q 76 ); and X 77 Can be C(Q 77 ), but the implementation of the present disclosure is not limited thereto.

[0174] For example, in formula 7-8, X 78 Can be N(Q 78 ); and X 79 Can be N(Q 79 ), but the implementation of the present disclosure is not limited thereto.

[0175] For example, Y in Formulas 7-2, 7-3, and 7-8 71 and Y 72 The groups may each independently be a substituted or unsubstituted methylene group, or a substituted or unsubstituted phenylene group, but the embodiments of the present disclosure are not limited thereto.

[0176] For example, Z in equations 7-1 and 7-2 71 and Z 72 Each may be 0, but the embodiments of the present disclosure are not limited thereto.

[0177] For example, Z in formula 7-4 73 It may be P, but the embodiments of the present disclosure are not limited thereto.

[0178] For example, R in Formulas 7-1 to 7-8 71 -R 80 and Q 73 -Q 79 Can be independently:

[0179] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C 1 -C 20 Alkyl, or C 1 -C 20 Alkoxy;

[0180] Each of the following is substituted by at least one C 1 -C 20 Alkyl or C 1 -C 20 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, phenyl, naphthyl, pyridyl, and pyrimidyl;

[0181] Phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazolyl, triazineyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, or imidazopyridinyl; or

[0182] Each of which is selected from at least one substituted phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, Oxazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, or imidazopyridinyl: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthryl, pyrenyl, yl, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, Azolyl, iso oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzo Azolyl, isobenzo Azolyl, triazolyl, tetrazolyl, oxadiazolyl, triazineyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, and imidazopyridinyl, but embodiments of the present disclosure are not limited thereto.

[0183] In one or more embodiments, L in Formula 1 11 It may be a ligand represented by one of Formulae 5-1 to 5-116 and 8-1 to 8-29, but the embodiments of the present disclosure are not limited thereto:

[0184]

[0185]

[0186]

[0187]

[0188] In formulas 5-1 to 5-116 and 8-1 to 8-29,

[0189] R 51 -R 53 may each independently be hydrogen, -F, cyano, nitro, methyl, ethyl, propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl, tert-decyl, methoxy, ethoxy, propoxy, butoxy, pentyloxy, phenyl, naphthyl, pyridyl, pyrimidinyl, triazine, dibenzofuranyl, or dibenzothiophenyl; or

[0190] methyl, ethyl, propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl, tert-decyl, methoxy, ethoxy, propoxy, butoxy, pentyloxy, phenyl, naphthyl, pyridyl, pyrimidinyl, triazinyl, dibenzofuranyl, or dibenzothiophenyl, each substituted with at least one selected from -F, cyano, and nitro,

[0191] b51 and b54 can each independently be 1 or 2,

[0192] b53 and b55 can each independently be 1, 2 or 3,

[0193] b52 can be 1, 2, 3 or 4,

[0194] Ph means phenyl,

[0195] Ph-d5 represents a phenyl group in which all hydrogen atoms are replaced by deuterium.

[0196] Et represents ethyl,

[0197] i-Pr represents isopropyl, and

[0198] * and *' each represent a binding site with an adjacent atom.

[0199] The symbol m in formula 1 represents L 11 , where m can be 0, 1, 2, 3, 4 or 5.

[0200] For example, in Formula 1, L 11 It may be a monodentate ligand, and m may be 2, but embodiments of the present disclosure are not limited thereto.

[0201] In one or more embodiments, the organometallic compound represented by Formula 1 may be represented by Formula 1-1, but embodiments of the present disclosure are not limited thereto:

[0202] Formula 1-1

[0203]

[0204] In formula 1-1,

[0205] M.A 11 , X 11 , X 14 , R 11 , R 13 , R 14 ,b11,L 11, n and m may each independently be the same as described with respect to Formula 1.

[0206] For example, in Formula 1-1, M may be Ru or Os, n may be 2, and L may be 11 It may be a monodentate ligand, and m may be 2, but embodiments of the present disclosure are not limited thereto.

[0207] In one or more embodiments, the organometallic compound represented by Formula 1 may be represented by one of Formulas 1-11 to 1-24, but embodiments of the present disclosure are not limited thereto:

[0208]

[0209]

[0210]

[0211] In formulas 1-11 to 1-24,

[0212] M.R 13 , R 14 , L 11 , n and m may each independently be the same as described with respect to Formula 1, and R 21 -R 26 can be independently related to R in Formula 1 11 Same as described.

[0213] For example, in Formulas 1-11 to 1-24, M may be Ru or Os, n may be 2, and L may be 11 It may be a monodentate ligand, and m may be 2, but embodiments of the present disclosure are not limited thereto.

[0214] In one or more embodiments, the organometallic compound may be one of compounds 1 to 11, but embodiments of the present disclosure are not limited thereto:

[0215]

[0216]

[0217] In compounds 1 to 11,

[0218] Ph represents a phenyl group, Me represents a methyl group, i-Pr represents an isopropyl group, i-Bu represents an isobutyl group, and t-Bu represents a tert-butyl group.

[0219] The maximum emission wavelength (actually measured value) of the organometallic compound represented by Formula 1 may be about 550 nm or more and about 700 nm or less, for example, about 600 nm to about 650 nm.

[0220] When the organometallic compound represented by Formula 1 includes Os or Ru, the organometallic compound may emit light (eg, green or red light) at a long wavelength while having a molecular weight small enough to be deposited.

[0221] Since the organic metal compound represented by Formula 1 must (substantially) include a substituent capable of donating electrons, such as an aryl group, at the 4-position of the 5-membered ring, the electrical stability of the organic metal compound can be improved. Therefore, the life span of an organic light-emitting device including the organic metal compound can be improved.

[0222] Since the organic metal compound represented by Formula 1 must include a substituent having a planar shape and having a large steric hindrance, such as an aryl group, at the 4-position of the 5-membered ring, the transition dipole moment of the organic metal compound can be arranged in a predetermined direction. Therefore, the efficiency of an organic light-emitting device including the organic metal compound can be improved.

[0223] Since the organometallic compound represented by Formula 1 must include a structure capable of attracting electrons, such as N or C(CF) at the 2- or 3-position of the 5-membered ring, 3 ), so the thermal stability of the organic metal compound can be improved. Therefore, the life span of the organic light emitting device including the organic metal compound can be improved.

[0224] The highest occupied molecular orbital (HOMO) energy level, the lowest unoccupied molecular orbital (LUMO) energy level, and the triplet state (T) energy level of some compounds of the organometallic compound represented by Formula 1 were evaluated by density functional theory (DFT) with molecular structure optimization using Gaussian 09 program (structure optimization was performed based on B3LYP, 6-31G (d, p) level). 1 ) levels, and the results are shown in Table 1.

[0225] Table 1

[0226] Compound No. HOMO(eV) LUMO(eV) <![CDATA[T 1 (eV)]]> 1 -4.551 -1.368 2.313 2 -4.598 -1.427 2.301 3 -4.639 -1.442 2.321 4 -4.761 -2.160 1.762 5 -4.480 -1.815 1.932 6 -4.676 -2.099 1.826 7 -4.402 -1.915 1.647 8 -4.724 -2.172 1.710 9 -4.721 -2.143 1.741

[0227]

[0228]

[0229] It is confirmed from Table 1 that the organometallic compound represented by Formula 1 has such electrical characteristics as to be suitable for use in an electric device, for example, suitable for use as a dopant for an organic light-emitting device.

[0230] The synthesis method of the organometallic compound represented by Formula 1 can be understood by those of ordinary skill in the art by referring to the synthesis examples provided below.

[0231] Therefore, the organometallic compound represented by Formula 1 is suitable for use as an organic layer of an organic light-emitting device, for example, suitable for use as a dopant in an emission layer of the organic layer. Therefore, another aspect of the present disclosure provides an organic light-emitting device, comprising: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode and comprising an emission layer, wherein the organic layer comprises at least one organometallic compound represented by Formula 1.

[0232] Due to including the organic layer including the organometallic compound represented by Formula 1, the organic light emitting device may have low driving voltage, high efficiency, high power, high quantum efficiency, long lifespan, low roll-off ratio, and excellent color purity.

[0233] The organic metal compound represented by Formula 1 can be used between the electrode pairs of the organic light-emitting device. For example, the organic metal compound represented by Formula 1 can be included in the emission layer. In this regard, the organic metal compound can act as a dopant, and the emission layer can further include a host (i.e., the amount of the organic metal compound represented by Formula 1 is less than the amount of the host). In this regard, the dopant can emit blue light.

[0234] As used herein, the expression “(the organic layer) includes at least one organic metal compound” may include the case where “(the organic layer) includes the same organic metal compound represented by Formula 1” and the case where “(the organic layer) includes two or more different organic metal compounds represented by Formula 1”.

[0235] For example, the organic layer may include only Compound 1 as the organometallic compound. In this regard, Compound 1 may be present only in the emission layer of the organic light-emitting device. In one or more embodiments, the organic layer may include Compound 1 and Compound 2 as the organometallic compound. In this regard, Compound 1 and Compound 2 may be present in the same layer (for example, Compound 1 and Compound 2 may all be present in the emission layer).

[0236] The first electrode may be an anode as a hole injection electrode, and the second electrode may be a cathode as an electron injection electrode; or the first electrode may be a cathode as an electron injection electrode, and the second electrode may be an anode as a hole injection electrode.

[0237] In one or more embodiments, in the organic light-emitting device, the first electrode is an anode, and the second electrode is a cathode, and the organic layer further includes a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode, and the hole transport region includes at least one selected from a hole injection layer, a hole transport layer, and an electron blocking layer, and the electron transport region includes at least one selected from a hole blocking layer, an electron transport layer, and an electron injection layer.

[0238] The term "organic layer" as used herein refers to a single layer or a plurality of layers between the first electrode and the second electrode of the organic light emitting device. The "organic layer" may further include an organic metal compound including a metal in addition to an organic compound.

[0239] Figure 1 FIG. 1 is a schematic cross-sectional view of an organic light-emitting device 10 according to an embodiment. Figure 1 The structure of an organic light emitting device according to an embodiment and a method of manufacturing the organic light emitting device according to an embodiment are described. The organic light emitting device 10 includes a first electrode 11 , an organic layer 15 , and a second electrode 19 , which are sequentially stacked.

[0240] A substrate may be additionally provided below the first electrode 11 or above the second electrode 19. For use as the substrate, any substrate used in a general organic light-emitting device may be used, and the substrate may be a glass substrate or a transparent plastic substrate each having excellent mechanical strength, thermal stability, transparency, surface smoothness, easy handling, and water resistance.

[0241] The first electrode 11 may be formed by depositing or sputtering a material for forming the first electrode 11 on the substrate. The first electrode 11 may be an anode. The material for forming the first electrode 11 may be a material having a high work function to facilitate hole injection. The first electrode 11 may be a reflective electrode, a semi-reflective electrode, or a transmissive electrode. The material for forming the first electrode 11 may be, for example, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), and zinc oxide (ZnO). In one or more embodiments, the material used to form the first electrode 11 may be a metal such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag).

[0242] The first electrode 11 may have a single-layer structure or a multi-layer structure including two or more layers. For example, the first electrode 11 may have a three-layer structure of ITO / Ag / ITO, but the structure of the first electrode 11 is not limited thereto.

[0243] The organic layer 15 is disposed on the first electrode 11 .

[0244] The organic layer 15 may include a hole transport region, an emission layer, and an electron transport region.

[0245] The hole transport region may be disposed between the first electrode 11 and the emission layer.

[0246] The hole transport region may include at least one of a hole injection layer, a hole transport layer, an electron blocking layer, and a buffer layer.

[0247] The hole transport region may include only a hole injection layer or a hole transport layer. In one or more embodiments, the hole transport region may have a hole injection layer / hole transport layer structure or a hole injection layer / hole transport layer / electron blocking layer structure, which are sequentially stacked in the order stated starting from the first electrode 11.

[0248] When the hole transport region includes a hole injection layer (HIL), the HIL may be formed on the first electrode 11 by using one or more suitable methods such as vacuum deposition, spin coating, casting, and / or Langmuir-Blodgett (LB) deposition.

[0249] When the hole injection layer is formed by vacuum deposition, the deposition conditions may vary depending on the material used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the deposition conditions may include a deposition temperature of about 100° C. to about 500° C., a ... -8 Torr - about 10 -3 Torr vacuum pressure, and However, the deposition conditions are not limited thereto.

[0250] When the hole injection layer is formed using spin coating, the coating conditions may vary according to the material used to form the hole injection layer, and the structure and thermal properties of the hole injection layer. For example, the coating speed may be about 2,000 rpm to about 5,000 rpm, and the temperature of heat treatment to remove the solvent after coating may be about 80° C. to about 200° C. However, the coating conditions are not limited thereto.

[0251] By referring to the conditions for forming the hole injection layer, the conditions for forming the hole transport layer and the electron blocking layer can be understood.

[0252] The hole transport region may include at least one selected from the group consisting of m-MTDATA, TDATA, 2-TNATA, NPB, 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 the following Formula 201, and a compound represented by the following Formula 202:

[0253]

[0254] Formula 201

[0255]

[0256] Formula 202

[0257]

[0258] Ar in Formula 201 101 -Ar 102 Can be independently:

[0259] Phenylene, cyclopentadienylene, indenylene, naphthylene, 1-Heptalenyl, 1-Heptalenyl, 1-Acenaphthenylidene, 1-Fluorenyl, 1-Phenanthrenyl, 1-Anthracenyl, 1-Fluoranthenyl, 1-Benzo[9,10]phenanthrenyl, 1-Pyrenyl, 1-Phenanth ... phenylene, tetraphenylene, phenylene, perylene, or pentacene; or

[0260] Each of which is selected from at least one substituted phenylene, pentalene, indenylene, naphthylene, 1-Heptalenyl, 1-Heptalenyl, 1-Acenaphthenylidene, 1-Fluorenyl, 1-Phenanthrenyl, 1-Anthracenyl, 1-Fluoranthenyl, 1-Benzo[9,10]phenanthrenyl, 1-Pyrenyl, 1-Phenanth ... phenylene, tetraphenylene, a phenylene group, a perylene group, or a pentacene group: a deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidine 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 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1-C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, a monovalent non-aromatic fused polycyclic group, and a monovalent non-aromatic fused heteropolycyclic group.

[0261] Symbols xa and xb in Formula 201 may each independently be an integer of 0 to 5, or 0, 1, or 2. For example, xa may be 1 and xb may be 0, but xa and xb are not limited thereto.

[0262] R in formula 201 and 202 101 -R 108 , R 111 -R 119 , and R 121 -R 124 Can be independently:

[0263] hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C 1 -C 10 Alkyl (e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl, etc.), or C 1 -C 10 Alkoxy (e.g., methoxy, ethoxy, propoxy, butoxy, pentoxy, etc.);

[0264] Each of the following is substituted by at least one C 1 -C 10 Alkyl or C 1 -C 10 Alkoxy: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, and phosphoric acid group or its salt;

[0265] Phenyl, naphthyl, anthracenyl, fluorenyl, or pyrenyl; or

[0266] each being selected from at least one substituted phenyl, naphthyl, anthracenyl, fluorenyl, or pyrenyl group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C 1 -C 10 Alkyl, and C 1 -C 10 Alkoxy group, but the embodiments of the present disclosure are not limited thereto.

[0267] R in Formula 201 109 Can be:

[0268] phenyl, naphthyl, anthracenyl, or pyridyl; or

[0269] each being selected from at least one substituted phenyl, naphthyl, anthracenyl, or pyridyl group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C 1 -C 20 Alkyl, C 1 -C 20 alkoxy, phenyl, naphthyl, anthracenyl, and pyridyl.

[0270] In one or more embodiments, the compound represented by Formula 201 may be represented by the following Formula 201A, but embodiments of the present disclosure are not limited thereto:

[0271] Formula 201A

[0272]

[0273] About R in Formula 201A 101 , R 111 , R 112 and R 109 The detailed description has been described above.

[0274] For example, the compound represented by Formula 201 and the compound represented by Formula 202 may include compounds HT1 to HT20 shown below, but are not limited thereto:

[0275]

[0276]

[0277]

[0278] The thickness of the hole transport region may be For example When the hole transport region includes both a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be For example In the range of, and the thickness of the hole transport layer can be For example When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transport characteristics may be obtained without a significant increase in driving voltage.

[0279] In addition to these materials, the hole transport region may further include a charge generating material for improving conductive properties. The charge generating material may be uniformly or non-uniformly dispersed in the hole transport region.

[0280] The charge generating material may be, for example, a p-dopant. The p-dopant may be a quinone derivative, a metal oxide, or a compound containing a cyano group, but the embodiments of the present disclosure are not limited thereto. Non-limiting examples of the p-dopant are quinone derivatives such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ); metal oxides such as tungsten oxide or molybdenum oxide; and compounds containing a cyano group such as the following compound HT-D1 or compound HT-D2, but are not limited thereto:

[0281]

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

[0283] Also, the buffer layer may compensate for an optical resonance distance according to a wavelength of light emitted from the emission layer, and thus, efficiency of the formed organic light emitting device may be improved.

[0284] Then, an emission layer may be formed on the hole transport region by vacuum deposition, spin coating, casting, LB deposition, etc. When the emission layer is formed by vacuum deposition or spin coating, although the deposition or coating conditions may vary depending on the compound used to form the emission layer, the deposition or coating conditions may be similar to those applied when forming the hole injection layer.

[0285] Meanwhile, when the hole transport region includes an electron blocking layer, the material for the electron blocking layer may be the material for the hole transport region described above and / or the material for the host to be described later. However, the material for the electron blocking layer is not limited thereto. For example, when the hole transport region includes an electron blocking layer, the material for the electron blocking layer may be mCP to be described later.

[0286] The emission layer may include a host and a dopant, and the dopant may include an organic metal compound represented by Formula 1.

[0287] The host may include at least one selected from TPBi, TBADN, ADN (also referred to as "DNA"), CBP, CDBP, TCP, mCP, Compound H50 to Compound H52:

[0288]

[0289] In one or more embodiments, the host may further include a compound represented by the following formula 301:

[0290] Formula 301

[0291]

[0292] Ar in Formula 301 111 -Ar 112 Can be independently:

[0293] Phenylene, naphthylene, phenanthrenyl, or pyrenylene; or

[0294] Phenylene, naphthylene, phenanthrenylene, or pyrenylene, each of which is substituted with at least one selected from phenyl, naphthyl, and anthracenyl.

[0295] Ar in Formula 301 113 -Ar 116 Can be independently:

[0296] C 1 -C 10 alkyl, phenyl, naphthyl, phenanthrenyl, or pyrenyl; or

[0297] Phenyl, naphthyl, phenanthrenyl, or pyrenyl, each of which is substituted with at least one selected from the group consisting of phenyl, naphthyl, and anthracenyl.

[0298] The symbols g, h, i, and j in formula 301 may each independently be an integer from 0 to 4, and may be 0, 1, or 2, for example.

[0299] Ar in Formula 301 113 -Ar 116 Can be independently:

[0300] C substituted by at least one selected from phenyl, naphthyl and anthracenyl 1 -C 10 alkyl;

[0301] Phenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl, or fluorenyl; or

[0302] each being selected from at least one substituted phenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl, or fluorenyl group: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, phenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl, fluorenyl, and

[0303]

[0304] However, the implementation of the present disclosure is not limited thereto.

[0305] In one or more embodiments, the host may include a compound represented by the following formula 302:

[0306] Formula 302

[0307]

[0308] Ar in formula 302 122 -Ar 125 With respect to Ar in Formula 301 113 Same as described in detail.

[0309] Ar in formula 302 126 and Ar 127 Can be independently C 1 -C 10 Alkyl (eg, methyl, ethyl, or propyl).

[0310] The symbols k and l in formula 302 may each independently be an integer from 0 to 4. For example, k and l may be 0, 1, or 2.

[0311] The compound represented by Formula 301 and the compound represented by Formula 302 may include the following compounds H1 to H42, but are not limited thereto:

[0312]

[0313]

[0314]

[0315] When the organic light emitting device is a full-color organic light emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and a blue emission layer. In one or more embodiments, due to the stacked structure including the red emission layer, the green emission layer, and / or the blue emission layer, the emission layer may emit white light.

[0316] When the emission layer includes a host and a dopant, the amount of the dopant may generally range from 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.

[0317] The dopant may include at least one organic metal compound represented by Formula 1.

[0318] The thickness of the emission layer may be For example 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.

[0319] Then, an electron transport region may be disposed on the emission layer.

[0320] The electron transport region may include at least one selected from a hole blocking layer, an electron transport layer, and an electron injection layer.

[0321] For example, the electron transport region may have a hole blocking layer / electron transport layer / electron injection layer structure or an electron transport layer / electron injection layer structure, but the structure of the electron transport region is not limited thereto. The electron transport layer may have a multilayer structure or a single layer structure including two or more different materials.

[0322] The conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer constituting the electron transport region can be understood by referring to the conditions for forming the hole injection layer.

[0323] When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, at least one of BCP, Bphen, and BAlq, but embodiments of the present disclosure are not limited thereto:

[0324]

[0325] The thickness of the hole blocking layer may be For example When the thickness of the hole blocking layer is within these ranges, the hole blocking layer may have excellent hole blocking characteristics without a significant increase in driving voltage.

[0326] The electron transport layer may further include BCP, Bphen, Alq 3, BAlq, TAZ and NTAZ:

[0327]

[0328] In one or more embodiments, the electron transport layer may include at least one of ET1 to ET25, but is not limited thereto:

[0329]

[0330]

[0331] The thickness of the electron transport layer may be For example When the thickness of the electron transport layer is within the above range, the electron transport layer may have satisfactory electron transport characteristics without a significant increase in driving voltage.

[0332] Also, the electron transport layer may further include a material including a metal in addition to the above-mentioned materials.

[0333] 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:

[0334]

[0335] The electron transport region may include an electron injection layer that facilitates the flow of electrons from the second electrode 19 thereinto.

[0336] The electron injection layer may include a material selected from LiF, NaCl, CsF, Li 2 At least one of O and BaO.

[0337] The thickness of the electron injection layer can be For example When the thickness of the electron injection layer is within these ranges, satisfactory electron injection characteristics can be obtained without a significant increase in driving voltage.

[0338] The second electrode 19 is disposed on the organic layer 15. The second electrode 19 may be a cathode. The material for forming the second electrode 19 may be a metal, an alloy, a conductive compound, and a combination thereof having a relatively low work function. For example, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag) may be used as a material for forming the second electrode 19. In order to manufacture a top-emitting light-emitting device, a transmissive electrode formed using ITO or IZO may be used as the second electrode 19.

[0339] In the above, reference has been made to Figure 1 An organic light emitting device according to an embodiment is described.

[0340] As used herein, the term "first row transition metal of the periodic table" refers to a 4th period element of the periodic table that is also included in the d-block. Examples of the first row transition metal of the periodic table may include scandium (Sc), titanium (Ti), vanadium (V), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), or zinc (Zn).

[0341] As used herein, the term "second row transition metal of the periodic table" refers to a 5th period element of the periodic table that is also included in the d block. Examples of the second row transition metal of the periodic table may include yttrium (Y), zirconium (Zr), niobium (Nb), molybdenum (Mo), technetium (Tc), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), or cadmium (Cd).

[0342] As used herein, the term "third row transition metal of the periodic table" refers to a 6th period element of the periodic table that is included in both the d-block and the f-block. Examples of the third row transition metal of the periodic table may include lanthanum (La), samarium (Sm), europium (Eu), terbium (Tb), thulium (Tm), ytterbium (Yb), lutetium (Lu), hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), gold (Au), or mercury (Hg).

[0343] As used herein, the term "C 1 -C 60 "Alkyl" refers to a linear or branched aliphatic saturated hydrocarbon monovalent group having 1 to 60 carbon atoms, and examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl. As used herein, the term "C 1 -C 60 "Alkylene" refers to a group having a C 1 -C 60 Alkyl is a divalent group of the same structure.

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

[0345] As used herein, the term "C 2 -C 60"Alkenyl" refers to 2 -C 60 The term "C" as used herein refers to a hydrocarbon group having at least one carbon-carbon double bond in the middle or at the terminal of the alkyl group, and examples thereof include ethenyl, propenyl, and butenyl. 2 -C 60 "Alkenylene" refers to a 2 -C 60 Alkenyl is a divalent group of the same structure.

[0346] As used herein, the term "C 2 -C 60 "Alkynyl" refers to a C 2 -C 60 The term "C" as used herein refers to a hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the terminal of the alkyl group, and examples thereof include ethynyl and propynyl. 2 -C 60 "Alkyne" refers to a group having a C 2 -C 60 Alkynyl is a divalent group of the same structure.

[0347] As used herein, the term "C 3 -C 10 "Cycloalkyl" refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. As used herein, the term "Cycloalkyl" refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. 3 -C 10 "Cycloalkylene" refers to a cycloalkylene having a 3 -C 10 Cycloalkyl is a divalent group of the same structure.

[0348] As used herein, the term "C 1 -C 10 "Heterocycloalkyl" refers to a monovalent saturated monocyclic group having at least one selected from N, O, P, Si, B, Se, Ge and S as a ring-forming atom and 1 to 10 carbon atoms, and non-limiting examples thereof include tetrahydrofuranyl and tetrahydrothienyl. As used herein, the term "C 1 -C 10 "Heterocycloalkylene" refers to a 1 -C 10 Heterocycloalkyl is a divalent group of the same structure.

[0349] As used herein, the term "C 3 -C 10"Cycloalkenyl" refers to a monovalent monocyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and not having aromaticity, and non-limiting examples thereof include cyclopentenyl, cyclohexenyl, and cycloheptenyl. As used herein, the term "C 3 -C 10 "Cycloalkenylene" refers to a 3 -C 10 Cycloalkenyl is a divalent group of the same structure.

[0350] As used herein, the term "C 1 -C 10 The term "heterocycloalkenyl" refers to a monovalent monocyclic group having at least one atom selected from N, O, P, Si, B, Se, Ge and S as a ring atom, 1 to 10 carbon atoms, and at least one carbon-carbon double bond in its ring. 1 -C 10 Examples of heterocycloalkenyl are 2,3-dihydrofuranyl and 2,3-dihydrothienyl. 1 -C 10 "Heterocycloalkenylene" refers to a 1 -C 10 Heterocycloalkenyl is a divalent group of the same structure.

[0351] As used herein, the term "C 6 -C 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and as used herein, the term "C 6 -C 60 "Arylene" refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. 6 -C 60 Non-limiting examples of aryl groups include phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, and When C 6 -C 60 Aryl and C 6 -C 60 When the arylene groups each include two or more rings, the rings may be fused to each other.

[0352] As used herein, the term "C 7 -C 60 "Alkaryl" refers to an arylene group substituted by an alkyl group. A non-limiting example is a benzene ring substituted by a methyl group.

[0353] As used herein, the term "C 1 -C 60The term "heteroaryl" as used herein refers to a monovalent group having a heterocyclic aromatic system having, in addition to 1 to 60 carbon atoms, at least one atom selected from N, O, P, Si, B, Se, Ge and S as a ring-forming atom. 1 -C 60 The term "heteroarylene" refers to a divalent group having a heterocyclic aromatic system having, in addition to 1 to 60 carbon atoms, at least one heteroatom selected from N, O, P, B, Se, Ge and S as a ring-forming atom. 1 -C 60 Non-limiting examples of heteroaryl groups include pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. 1 -C 60 Heteroaryl and C 1 -C 60 When the heteroarylene groups each include two or more rings, the rings may be fused to each other.

[0354] As used herein, the term "C 2 -C 60 "Alkylheteroaryl" refers to a heteroarylene group substituted by an alkyl group. A non-limiting example is a pyridine ring substituted by a methyl group.

[0355] The term "C 6 -C 60 "Aryloxy" means -OA 102 (A 102 C 6 -C 60 Aryl), and C 6 -C 60 Arylthio represents -SA 103 (A 103 C 6 -C 60 aryl).

[0356] The term "monovalent non-aromatic fused polycyclic group" as used herein refers to a monovalent group (e.g., having 8-60 carbon atoms) having two or more rings fused to each other, having only carbon atoms as ring-forming atoms, and not having aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic fused polycyclic group include fluorenyl. The term "divalent non-aromatic fused polycyclic group" as used herein refers to a divalent group having the same structure as the monovalent non-aromatic fused polycyclic group.

[0357] The term "monovalent non-aromatic fused heteropolycyclic group" as used herein refers to a monovalent group (e.g., having 2-60 carbon atoms) having two or more rings fused to each other, having at least one heteroatom selected from N, O, P, Si, B, Se, Ge and S as a ring-forming atom in addition to carbon atoms, and having no aromaticity in its entire molecular structure. Non-limiting examples of the monovalent non-aromatic fused heteropolycyclic group include carbazolyl. The term "divalent non-aromatic fused heteropolycyclic group" as used herein refers to a divalent group having the same structure as the monovalent non-aromatic fused heteropolycyclic group.

[0358] As used herein, the term "C 5 -C 30 A "carbocyclic group" refers to a saturated or unsaturated cyclic group having only 5 to 30 carbon atoms as ring atoms. As used herein, the term "C 5 -C 30 The "carbocyclic group" refers to a monocyclic group or a polycyclic group, and refers to a monovalent, divalent, trivalent, tetravalent, pentavalent, or hexavalent group according to its chemical structure.

[0359] As used herein, the term "C 1 -C 30 A "heterocyclic group" refers to a saturated or unsaturated cyclic group having, in addition to 1 to 30 carbon atoms, at least one heteroatom selected from N, O, Si, P, B, Se, Ge and S as a ring atom. As used herein, the term "C 1 -C 30 The "heterocyclic group" refers to a monocyclic group or a polycyclic group, and refers to a monovalent, divalent, trivalent, tetravalent, pentavalent, or hexavalent group according to its chemical structure.

[0360] In this specification, substituted C 5 -C 30 Carbocyclic groups, substituted C 1 -C 30 Heterocyclic groups, substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 1-C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 7 -C 60 Alkaryl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 Heteroaryl, substituted C 2 -C 60 Alkyl heteroaryl, substituted C 1 -C 60 Heteroaryloxy, substituted C 1 -C 60 At least one substituent of the heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be:

[0361] Deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, or C 1 -C 60 Alkoxy;

[0362] Each of the following is substituted by at least one C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, or C 1 -C 60 Alkoxy: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 11 )(Q 12 )、-Si(Q 13 )(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 ), and -P(=O)(Q 18 )(Q 19 );

[0363] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 a heteroaryl group, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group;

[0364] Each of the following is substituted by at least one C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 heteroaryl, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -N(Q 21 )(Q 22 )、-Si(Q 23 )(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 ), and -P(=O)(Q 28 )(Q 29 );or

[0365] -N(Q 31 )(Q 32 )、-Si(Q 33 )(Q 34 )(Q35 )、-B(Q 36 )(Q 37 ), or -P(=O)(Q 38 )(Q 39 ),and

[0366] Q 1 -Q 9 , Q 11 -Q 19 , Q 21 -Q 29 , and Q 31 -Q 39 may be each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, selected from C 1 -C 60 Alkyl and C 6 -C 60 At least one substituted C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group.

[0367] Hereinafter, the compound and the organic light-emitting device according to the embodiment are described in detail with reference to the synthesis examples and the examples. However, the organic light-emitting device is not limited thereto. The phrase "using 'B' instead of 'A'" used in describing the synthesis examples means that the molar equivalent of 'B' is the same as the molar equivalent of 'A'.

[0368] Example

[0369] Synthesis Example 1: Synthesis of Compound 1

[0370] Compound 1 was synthesized according to the following Scheme 1.

[0371] Solution 1

[0372]

[0373] Synthesis Example 2: Synthesis of Compound 8

[0374] Compound 8 was synthesized according to the following Scheme 2.

[0375] Solution 2

[0376]

[0377] Example 1

[0378] Formed thereon The glass substrate of thick ITO electrode (first electrode, anode) is subjected to ultrasonic treatment with distilled water. After completing the distilled water cleaning, the glass substrate is subjected to ultrasonic treatment by sequentially using isopropanol, acetone and methanol, dried, and then transferred to a plasma cleaner. The glass substrate is cleaned for 5 minutes using oxygen plasma, and then provided to a vacuum deposition device.

[0379] Compound HT3 was vacuum deposited on the ITO electrode of the glass substrate to form The first hole injection layer is vacuum deposited on the first hole injection layer to form a A second hole injection layer having a thickness of , and TAPC is vacuum deposited on the second hole injection layer to form a An electron blocking layer with a thickness of , thereby forming a hole transport region.

[0380] Compound H52 (host) and Compound 1 (dopant, 2 wt %, based on the total weight of the emissive layer) were co-deposited on the hole transport region to form a The thickness of the emission layer.

[0381] Compound ET3 is vacuum deposited on the emission layer to form a An electron transport layer having a thickness of , ET-D1(LiQ) is deposited on the electron transport layer to form a An electron injection layer having a thickness of , and Al is deposited on the electron injection layer to form A second electrode (cathode) with a thickness of is formed, thereby completing the manufacture of the organic light-emitting device.

[0382]

[0383] Comparative Examples 1 to 3

[0384] An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compounds shown in Table 2 were each used as a dopant instead of Compound 1 when forming the emission layer.

[0385] Evaluation Example: Evaluation of Characteristics of Organic Light-Emitting Device

[0386] The EL spectra, the change of current density according to voltage, the change of brightness according to voltage, the current efficiency, the conversion efficiency, the external quantum efficiency, the roll-off ratio, and the CIE color coordinates of the organic light emitting devices manufactured according to Example 1 and Comparative Examples 1 to 3 were measured. The detailed measurement method is as follows, and the results are shown in Table 2.

[0387] (1) Measurement of EL spectrum

[0388] The organic light-emitting devices were measured by using a luminance meter (Minolta CS-1000A) at 500 cd / m 2 The EL spectrum was measured at a brightness of and the result was obtained.

[0389] (2) Measurement of changes in current density according to voltage

[0390] With respect to the manufactured organic light emitting device, a current value flowing therethrough was measured by using a current-voltage meter (Keithley 2400) while increasing a voltage from 0 V to 10 V, and the result was obtained by dividing the measured current value by an area.

[0391] (3) Measurement of changes in brightness according to voltage

[0392] With respect to the manufactured organic light emitting device, luminance was measured by using a luminance meter (Minolta Cs-1000A) while increasing voltage from 0 V to 10 V, and the result thereof was obtained.

[0393] (4) Measurement of conversion efficiency

[0394] The same current density (10 mA / cm2) was measured by using the current density and luminance and voltage measured in (2) and (3). 2 ) is measured. Then, the conversion efficiency is calculated by dividing the current efficiency by the x value of the CIE color coordinates measured in (6).

[0395] (5) Measurement of CIE color coordinates

[0396] For the manufactured organic light-emitting device, the CIE color coordinates were obtained as follows: by measuring the brightness of 500 cd / m by using a luminance meter (Minolta Cs-1000A). 2 EL spectrum when .

[0397] (6) Measurement of roll-off ratio

[0398] For the fabricated organic light-emitting device, calculate 1-(EQE / EQE 最大 ) to obtain the roll-off ratio value. EQE max is the maximum EQE. EQE is the external quantum efficiency.

[0399] Table 2

[0400]

[0401]

[0402]

[0403] It is confirmed from Table 2 that the organic light emitting device of Example 1 has improved characteristics compared with the organic light emitting devices of Comparative Examples 1 to 3.

[0404] Since the organometallic compound has improved electrical characteristics and / or thermal stability, an organic light emitting device including the organometallic compound may simultaneously have improved current density, current efficiency, conversion efficiency, EQE, roll-off ratio, and color purity.

[0405] 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 in each embodiment should typically be considered as available for other similar features or aspects in other embodiments.

[0406] Although one or more embodiments have been described with reference to the drawings, it will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope as defined by the following claims.

Claims

1. An organic metal compound represented by formula 1-11: in, In formula 1-11, M is osmium, The bond between N and M in the pyridine ring is a coordination bond. R 21 and R 24 are each independently hydrogen or deuterium, R 22 is phenyl or phenyl substituted by at least one selected from the group consisting of deuterium, -CD3, -CD2H, -CDH2, or C1-C 20 alkyl, R 23 C1-C 20 Alkyl or C1-C 20 Alkyl: deuterium, -CD3, -CD2H, -CDH2, or C1-C 10 alkyl, R 13 is -F, cyano, or -CF3, R 14 is phenyl or phenyl substituted by at least one selected from the group consisting of deuterium, -CD3, -CD2H, -CDH2, and C1-C 20 alkyl, n is 2, L 11 is a ligand represented by formula 7-4: In formula 7-4, Z 73 For P, R 71 C1-C 20 Alkyl or deuterated C1-C 20 alkyl, R 72 is phenyl or phenyl substituted by at least one selected from the group consisting of deuterium, -CD3, -CD2H, -CDH2, or C1-C 20 alkyl, R 73 For: C1-C 20 Alkyl; C1-C substituted by deuterium 20 Alkyl; phenyl; or phenyl substituted by at least one selected from the group consisting of deuterium, -CD3, -CD2H, -CDH2, or C1-C 20 alkyl, m is 2, and * indicates the binding site with the adjacent atom.

2. The organometallic compound according to claim 1, wherein R 13 It is -F or cyano.

3. The organometallic compound according to claim 1, wherein R 14 for: phenyl; or A phenyl group substituted with at least one selected from the group consisting of deuterium, -CD3, -CD2H, -CDH2, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, and tert-butyl.

4. The organometallic compound according to claim 1, wherein R 14 It is one of formulas 10-17 to 10-24, and 10-53 to 10-66: in, In formulas 10-17 to 10-24, and 10-53 to 10-66, * indicates the binding site with the adjacent atom, i-Pr represents isopropyl, and t-Bu represents tert-butyl.

5. The organometallic compound according to claim 1, wherein L 11 is a ligand represented by one of formulas 8-3, 8-4, 8-7, 8-8, 8-10, 8-11, 8-13, 8-14, 8-16 and 8-17: Wherein Ph represents phenyl, Ph-d5 represents a phenyl group in which all hydrogen atoms are replaced by deuterium. Et represents ethyl, i-Pr represents isopropyl, and * indicates the binding site with the adjacent atom.

6. The organometallic compound according to claim 1, wherein The organometallic compound is one of compounds 1 and 2: in, In compounds 1 and 2, Ph represents a phenyl group, Me represents a methyl group, i-Pr represents an isopropyl group, and i-Bu represents an isobutyl group.

7. 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, The organic layer comprises at least one organic metal compound as claimed in any one of claims 1 to 6.

8. The organic light emitting device according to claim 7, wherein The organometallic compound is included in the emission layer.

9. The organic light emitting device according to claim 8, wherein The emission layer further includes a host, and an amount of the host in the emission layer is greater than an amount of the organometallic compound in the emission layer.

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