KR20220113256A - Organometallic compound, organic light emitting device including the same and electronic apparatus comprising organic light emitting device - Google Patents

Abstract

Disclosed are an organometallic compound represented by chemical formula 1, an organic light-emitting device including the organometallic compound, and a diagnostic composition including the organometallic compound. The chemical formula 1 is M_1(Ln_1)_(n1)(Ln_2)_(n2), wherein Ln1 is a ligand represented by chemical formula 1-1, and for descriptions of other substituents, refer to the description of the invention.

Description

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

An organometallic compound, an organic light emitting device including the same, and an electronic device including the organic light emitting device are provided.

An organic light emitting device is a self-luminous device, and has excellent viewing angle, response time, luminance, driving voltage, response speed, and the like, and can be multicolored.

According to an example, the organic light emitting device may include an anode, a cathode, and an organic layer interposed between the anode and the cathode and including a light emitting layer. A hole transport region may be provided between the anode and the emission layer, and an electron transport region may be provided between the emission layer and the cathode. Holes injected from the anode move to the emission layer via the hole transport region, and electrons injected from the cathode move to the emission layer via the electron transport region. The holes and electrons recombine in the emission layer region to generate excitons. Light is generated as this exciton changes from an excited state to a ground state.

A novel organometallic compound, an organic light emitting device employing the same, and an electronic device including the organic light emitting device are provided.

According to one aspect, there is provided an organometallic compound represented by the following Chemical Formula 1:

<Formula 1>

M ₁ (Ln ₁ ) _n1 (Ln ₂ ) _n2

In Formula 1,

M ₁ is a transition metal,

Ln ₁ is a ligand represented by the following formula 1-1,

Ln ₂ is a bidentate ligand,

n1 is 1, 2 or 3,

n2 is 0, 1 or 2,

<Formula 1-1>

In Formula 1-1,

X ₁ is C or N, X ₂ is C or N,

X ₁₁ is C(R ₁ ) or N, X ₁₂ is C(R ₂ ) or N, X ₁₃ is C(R ₃ ) or N, X ₁₄ is C(R ₄ ) or N,

Y ₁ is O, S, Se, C(R ₅ )(R ₆ ) or N(R ₅ ),

CY ₂ is a C ₅ -C ₃₀ carbocyclic group or a C ₁ -C ₃₀ heterocyclic group,

R ₁ to R ₆ , R ₁₀ and R ₂₀ are each independently a group represented by Formula 2-1, a group represented by Formula 2-2, 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 substituted or unsubstituted C ₁ -C ₆₀ Alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted A substituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, 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 a monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ) or -P(=O)(Q ₈ )(Q ₉ ),

In Formulas 2-1 and 2-2,

L ₁ is a single bond; a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group; Or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group;

a1 is 0, 1, 2, 3, 4 or 5;

When CY ₂ is a benzene group,

(i) at least one of R ₁ to R ₄ is a group represented by Formula 2-1 or a group represented by Formula 2-2,

(ii) at least one of R ₁₀ and R ₂₀ is a group represented by Formula 2-2,

when CY ₂ is not a benzene group, at least one of R ₁ to R ₄ and R ₁₀ and R ₂₀ is a group represented by Formula 2-1 or a group represented by Formula 2-2,

two R ₁₀ are optionally bonded to each other, a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group; Or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group; may form,

two or more of the plurality of R ₂₀ may be optionally bonded to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group; Or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group; may form,

two or more of R ₅ , R ₆ R ₁₀ and R ₂₀ are optionally bonded to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group; Or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group; may form,

b10 is 1 or 2,

b20 is 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;

*, *' and *" are each a binding site with a neighboring atom,

Said substituted C ₅ -C ₃₀ carbocyclic group, substituted C ₁ -C ₃₀ heterocyclic group, substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, substituted C ₁ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C ₆ -C ₆₀ arylthio group, substituted C ₁ -C ₆₀ heteroaryl group , among the substituents of a substituted C ₁ -C ₆₀ heteroaryloxy group, a substituted C ₁ -C ₆₀ heteroarylthio group, a substituted monovalent non-aromatic condensed polycyclic group and a substituted monovalent non-aromatic condensed polycyclic group at least one,

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 salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ an alkynyl group or a C ₁ -C ₆₀ alkoxy group;

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 salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₃ -C ₁₀ cycloalkyl group, 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 , C ₁ -C ₆₀ heteroaryloxy group, C ₁ -C ₆₀ heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q ₁₁ )(Q ₁₂ ) (Q ₁₃ ), -Ge(Q ₁₁ )(Q ₁₂ )(Q ₁₃ ), -N(Q ₁₄ )(Q ₁₅ ), -B(Q ₁₆ )(Q ₁₇ ), -P(=O)(Q ₁₈ )(Q ₁₉ ) or any combination thereof, substituted with a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, or a C ₁ -C ₆₀ alkoxy group;

C ₃ -C ₁₀ cycloalkyl group, 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 aryl Oxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, C ₁ -C ₆₀ heteroaryloxy group, C ₁ -C ₆₀ heteroarylthio group, monovalent non-aromatic condensed polycyclic group or a monovalent non-aromatic condensed heteropolycyclic group;

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 salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, 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 group, 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, C ₁ -C ₆₀ heteroaryloxy group, C ₁ -C ₆₀ heteroarylthi Group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q ₂₁ )(Q ₂₂ )(Q ₂₃ ), -Ge(Q ₂₁ )(Q ₂₂ )(Q ₂₃ ) , -N(Q ₂₄ )(Q ₂₅ ), -B(Q ₂₆ )(Q ₂₇ ), -P(=O)(Q ₂₈ )(Q ₂₉ ), C ₃ - C ₁₀ cycloalkyl group, 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 condensed polycyclic group or monovalent non-aromatic condensed heteropolycyclic group; or

-Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -Ge(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₄ )(Q ₃₅ ), -B(Q ₃₆ )(Q ₃₇ ) ) or -P(=O)(Q ₃₈ )(Q ₃₉ );

The Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cya No group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted substituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or an unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ - C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted A substituted C ₁ -C ₆₀ heteroaryloxy group, a substituted or unsubstituted C ₁ -C ₆₀ heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent ratio -Aromatic heterocondensed polycyclic group.

According to another aspect, the first electrode; a second electrode; and an organic layer interposed between the first electrode and the second electrode and including a light emitting layer, wherein the organic layer includes at least one of the organometallic compounds.

The organometallic compound may be included in the emission layer of the organic layer, and the organometallic compound included in the emission layer may serve as a dopant.

According to another aspect, an electronic device including the organic light emitting device is provided.

The organometallic compound has excellent electrical properties and stability, and an electronic device employing the organometallic compound, for example, an organic light emitting device, has a low driving voltage, high efficiency, long lifespan, reduced roll-off ratio, and relatively A narrow EL spectrum may have a full width at half maximum (FWHM) of the emission peak. Therefore, by using the organometallic compound, a high-quality organic light emitting device can be implemented.

1 is a cross-sectional view schematically illustrating an organic light emitting device according to an exemplary embodiment.

The organometallic compound is represented by the following formula (1):

<Formula 1>

M ₁ (Ln ₁ ) _n1 (Ln ₂ ) _n2

In Formula 1, M ₁ is a transition metal.

According to one embodiment, in Formula 1, M ₁ may be a 1-period transition metal, a 2-period transition metal, or a 3-period transition metal.

According to one embodiment, M ₁ is iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm) or rhodium (Rh).

For example, M ₁ may be Ir, Os, Pt, Pd, or Au.

According to one embodiment, M ₁ may be Ir.

In Formula 1, Ln ₁ is a ligand represented by Formula 1-1.

<Formula 1-1>

In Formula 1-1, X ₁ is C or N, and X ₂ is C or N.

In Formula 1-1, X ₁₁ is C(R ₁ ) or N, X ₁₂ is C(R ₂ ) or N, X ₁₃ is C(R ₃ ) or N, and X ₁₄ is C(R ₄ ) ) or N.

According to one embodiment, any one of X ₁₁ to X ₁₄ may not be N.

According to one embodiment, at least one of X ₁₁ to X ₁₄ may not be N.

According to one embodiment, each of X ₁₁ to X ₁₄ may not be N. For example, X ₁₁ may be C(R ₁ ), X ₁₂ may be C(R ₂ ), X ₁₃ may be C(R ₃ ), and X ₁₄ may be C(R ₄ ).

The bond between M ₁ and X ₁ may be a covalent bond or a coordination bond.

The bond between M ₁ and X ₂ may be a covalent bond or a coordination bond.

According to one embodiment, X ₁ may be N, X ₂ may be C, the bond between X ₁ and M ₁ may be a coordination bond, and the bond between X ₂ and M ₁ may be a covalent bond.

In Formula 1-1, Y ₁ is O, S, Se, C(R ₅ )(R ₆ ), or N(R ₅ ).

In Formula 1-1, CY ₂ is a C ₅ -C ₃₀ carbocyclic group or a C ₁ -C ₃₀ heterocyclic group.

According to one embodiment, CY ₂ is i) a first ring, ii) a second ring, iii) a condensed ring in which two or more first rings are condensed with each other, iv) a condensed ring in which two or more second rings are condensed with each other, or v) at least one first ring and at least one second ring are condensed rings condensed with each other,

The first ring is a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a silol group, an indene group, a benzofuran group, a benzothiophene group, an indole group, a benzosilol group, an oxazole group, isoxazole group, oxadiazole group, isoxadiazole group, oxatriazole group, isoxatriazole group, thiazole group, isothiazole group, thiadiazole group, isothiadiazole group, thiatriazole group, an isothiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azacilol group, a diazasilol group or a triazasilol group,

The second ring is an adamantane group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.1]heptane group (norbor norbornane group), bicyclo[2.2.2]octane group, cyclohexane group, cyclohexene group, benzene group, pyridine group, pyrimidine group, pyrazine group, pyridazine group or triazine group.

According to one embodiment, the CY ₂ are each independently, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, 1,2,3,4-tetrahydro Naphthalene (1,2,3,4-tetrahydronaphthalene) group, thiophene group, furan group, pyrrole group, cyclopentadiene group, silol group, borol group, phosphol group, selenophene group, low mole group, benzothiophene group , benzofuran group, indole group, indene group, benzosilol group, benzoborol group, benzophosphole group, benzoselenophene group, benzozermol group, dibenzothiophene group, dibenzofuran group, carbazole group, fluorene Group, dibenzosilol group, dibenzoborol group, dibenzophosphole group, dibenzoselenophene group, dibenzozermol group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzo Thiophene 5,5-dioxide group, azabenzothiophene group, azabenzofuran group, azaindole group, azaindene group, azabenzosilol group, azabenzoborol group, azabenzophosphole group, azabenzoselenophene group , azabenzolowmol group, azadibenzothiophene group, azadibenzofuran group, azacarbazole group, azafluorene group, azadibenzosilol group, azadibenzoborol group, azadibenzophosphole group, azadi Benzoselenophene group, azadibenzozermol group, azadibenzothiophene 5-oxide group, aza-9H-fluoren-9-one group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, phenanthroline group, pyrazole group, imidazole group, triazole group, oxazole group, iso Oxazole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzoimidazole group, benzoxazole group, benzothiazole group, benzoxadiazole group, benzo Thiadiazole group, 5,6,7,8-tetrahydroisoquinoline (5,6,7,8-tetrahydroisoquino line) group, 5,6,7,8-tetrahydroquinoline (5,6,7,8-tetrahydroquinoline) group, adamantane group, norbornane group or norbornene group; or

A group represented by the following formula 8-1 or 8-2; may be:

<Formula 8-1>

<Formula 8-2>

In Formulas 8-1 and 8-2,

Y ₈₁ to Y ₈₄ are each independently a single bond, O, S, N(R ₈₁ ), C(R ₈₁ )(R ₈₂ ), Si(R ₈₁ )(R ₈₂ ), C(=O), S (=O), S(=O) ₂ , B(R ₈₁ ), P(R ₈₁ ) or P(=O)(R ₈₁ ),

CY ₈₁ to CY ₈₃ are each independently, a benzene group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a triazine group, a quinoline group, Isoquinoline group, quinoxaline group, quinazoline group, phenanthroline group, benzofuran group, benzothiophene group, fluorene group, carbazole group, dibenzofuran group, dibenzothiophene group, dibenzosilol group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, or an azadibenzosilol group;

For the description of R ₈₁ and R ₈₂ independently of each other, refer to the description of R ₁₀ and R ₂₀ above.

According to one embodiment, in Formulas 8-1 to 8-2, Y ₈₁ to Y ₈₄ may be each independently selected from a single bond, O, S, N(R ₈₁ ), C(R ₈₁ )(R ₈₂ ), or Si(R ₈₁ )(R ₈₂ ).

According to one embodiment, each of Y ₈₁ and Y ₈₂ may not be a single bond at the same time, and Y ₈₃ and Y ₈₄ may not each be a single bond at the same time. That is, at least one of Y ₈₁ and Y ₈₂ may not be a single bond, and at least one of Y ₈₃ and Y ₈₄ may not be a single bond.

According to one embodiment, CY ₈₁ to CY ₈₃ may each independently be a benzene group, a naphthalene group, a pyridine group, or a pyrimidine group.

According to one embodiment, CY ₈₁ to CY ₈₃ may each independently be a benzene group or a naphthalene group.

According to one embodiment, CY ₂ is a benzene group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a triazine group, a quinoline group, Isoquinoline group, quinoxaline group, quinazoline group, phenanthroline group, benzofuran group, benzothiophene group, fluorene group, carbazole group, dibenzofuran group, dibenzothiophene group, dibenzosilol group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group or an azadibenzosilol group; or

It may be a group represented by Formula 8-1 or 8-2.

According to one embodiment, CY ₂ may be represented by any one of the following Chemical Formulas CY2-1 to CY2-22:

In Formulas CY2-1 to CY2-22,

X ₂₁ and X ₂₂ are each independently O, S, N(R _29a ), C(R _29a )(R _29b ) or Si(R _29a )(R _29b ),

The descriptions of R ₂₁ to R ₂₈ , R _29a and R _29b are each independently refer to the description of R ₂₀ ,

R ₂₁ to R ₂₈ , R _29a and R _29b may be optionally bonded to two or more adjacent to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group; or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group;

* and *' are binding sites with neighboring atoms, respectively.

For example, a cyclopentane group, a cyclopentene group, or a cyclopentane group, which is unsubstituted or substituted with at least one R _10a by combining adjacent two or more of R ₂₁ to R ₂₈ , R _29a and R _29b Diene group, furan group, thiophene group, pyrrole group, silol group, adamantane group, norbornane group, norbornene group, cyclohexane group, cyclohexene group, benzene group, naphthalene group , an indene group, an indole group, a benzofuran group, a benzothiophene group, a benzosilol group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group or a dibenzosilol group.

In Formula 1-1, R ₁ to R _{6 ,} R ₁₀ and R ₂₀ may each independently represent a group represented by Formula 2-1, a group represented by Formula 2-2, 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, substituted or unsubstituted A substituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₂ -C ₁₀ hetero Cycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryloxy group, substituted or unsubstituted C ₁ -C ₆₀ heteroarylthio group, substituted or unsubstituted monovalent non-aromatic condensation polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heterocyclic polycyclic group, -N(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ) or -P(=O)(Q ₈ ) (Q ₉ ).

<Formula 2-1> <Formula 2-2>

In Formulas 2-1 and 2-2, L ₁ is a single bond; a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group; Or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group;

In Formulas 2-1 and 2-2, a1 is 0, 1, 2, 3, 4 or 5.

According to one embodiment, L ₁ is a single bond, a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, phenanthrenyl Ren group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, perylenylene group, pentaphenylene group, hexacenylene group, pentacenylene group, thiophenylene group, furanylene group, carba Zolylene group, indolylene group, isoindolylene group, benzofuranylene group, benzothiophenylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosilolylene group , pyridinylene group, imidazolylene group, pyrazolylene group, thiazolylene group, isothiazolylene group, oxazolylene group, isoxazolylene group, thiadiazolylene group, oxadiazolylene group, pyrazinylene group, pyrimidinylene group , pyridazinylene group, triazinylene group, quinolinylene group, isoquinolinylene group, benzoquinolinylene group, phthalazinylene group, naphthyridinylene group, quinoxalinylene group, quinazolinylene group, cinolinyl group Ren group, phenanthridinylene group, acridinylene group, phenanthrolinylene group, phenazinylene group, benzoimidazolylene group, isobenzothiazolylene group, benzoxazolylene group, isobenzoxazolylene group, triazolylene group, tetrazolyl a rene group, an imidazopyridinylene group, an imidazopyrimidinylene group, or an azacarbazolylene group; or

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl Renyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindoleyl group, benzofuranyl group, benzothiophenyl group , dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazole Diary, isoxazolyl group, thiadiazolyl group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, isobenzothiazolyl group, benzoxazolyl group , isobenzoxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group or any combination thereof substituted with, phenylene group, naphthylene group, fluorine group Nylene group, spiro-bifluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenyl group Rene group, perylenylene group, pentaphenylene group, hexacenylene group, pentacenylene group, thiophenylene group, furanylene group, carbazolylene group, indolylene group, isoindolylene group, benzofuranylene group, benzothiophenylene group, Dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosilolylene group, pyridinylene group, imidazolylene group, pyrazolylene group, thiazolylene group, isothiazolylene group , oxazolylene group, isoxazolylene group, thiadiazolylene group, oxadiazolylene group, pyrazinylene group, pyrimidinylene group, Pyridazinylene group, triazinylene group, quinolinylene group, isoquinolinylene group, benzoquinolinylene group, phthalazinylene group, naphthyridinylene group, quinoxalinylene group, quinazolinylene group, cinolinylene group , phenanthridinylene group, acridinylene group, phenanthrolinylene group, phenazinylene group, benzoimidazolylene group, isobenzothiazolylene group, benzoxazolylene group, isobenzoxazolylene group, triazolylene group, tetrazolylene group , an imidazopyridinylene group, an imidazopyrimidinylene group, or an azacarbazolylene group; may be.

In Formula 1-1, when CY ₂ is a benzene group, at least one of R ₁ to R ₄ is a group represented by Formula 2-1 or 2-2, or at least one of R ₁₀ and R ₂₀ One is a group represented by Formula 2-2.

For example, when CY ₂ in Formula 1-1 is a group represented by Formula CY2-1, at least one of R ₁ to R ₄ is a group represented by Formula 2-1 or Formula 2-2 or at least one of R ₁₀ and R ₂₀ is a group represented by Formula 2-2.

In Formula 1-1, when CY ₂ is not a benzene group, at least one of R ₁ to R ₄ and R ₁₀ and R ₂₀ may be a group represented by Formula 2-1 or a group represented by Formula 2-2. have.

For example, when CY ₂ in Formula 1-1 is a group represented by any one of Formulas CY2-2 to CY2-22, at least one of R ₁ to R ₄ and R ₁₀ and R ₂₀ is represented by Formula 2-1 It may be a group represented by or a group represented by Formula 2-2.

According to one embodiment, at least one of R ₁ to R ₄ may be a group represented by Formula 2-1 or a group represented by Formula 2-2.

According to one embodiment, at least one of R ₁ to R ₄ , R ₁₀ and R ₂₀ may be a group represented by Formula 2-2.

According to one embodiment, R ₁ to R ₆ , R ₁₀ and R ₂₀ are independently of each other,

A group represented by Formula 2-1, a group represented by Formula 2-2, 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, -SF ₅ , a C ₁ -C ₂₀ alkyl group, a C ₂ -C ₂₀ alkenyl group, a C ₁ -C ₂₀ alkoxy group or a C ₁ -C ₂₀ alkylthio group;

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 salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₁₀ alkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclo Octyl group, adamantanyl group, norbornanyl group (bicyclo[2.2.1]heptyl group), norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, bicyclo[1.1.1]pentyl group, bi Cyclo[2.1.1]hexyl group, bicyclo[2.2.2]octyl group, (C ₁ -C ₂₀ alkyl)cyclopentyl group, (C ₁ -C ₂₀ alkyl)cyclohexyl group, (C ₁ -C ₂₀ alkyl ) cycloheptyl group, (C ₁ -C ₂₀ alkyl) cyclooctyl group, (C ₁ -C ₂₀ alkyl) adamantanyl group, (C ₁ -C ₂₀ alkyl) norbonanyl group, (C ₁ -C ₂₀ alkyl) nor Bornenyl group, (C ₁ -C ₂₀ alkyl)cyclopentenyl group, (C ₁ -C ₂₀ alkyl)cyclohexenyl group, (C ₁ -C ₂₀ alkyl)cycloheptenyl group, (C ₁ -C ₂₀ alkyl)bicyclo [1.1.1]pentyl group, (C ₁ -C ₂₀ alkyl)bicyclo[2.1.1]hexyl group, (C ₁ -C ₂₀ alkyl)bicyclo[2.2.2]octyl group, phenyl group, (C ₁ - C ₂₀ alkyl) phenyl group, biphenyl group, terphenyl group, naphthyl group, pyridinyl group, pyrimidinyl group or any combination thereof substituted with, C ₁ -C ₂₀ alkyl group, C ₂ -C ₂₀ alkenyl group, C ₁ - C ₂₀ alkoxy group or C ₁ -C ₂₀ alkylthio group;

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 salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₂₀ alkyl group, deuterated C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, bicyclo[1.1. 1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo[2.2.2]octyl group, (C ₁ -C ₂₀ alkyl) cyclopentyl group, (C ₁ -C ₂₀ alkyl) cyclohexyl group, ( C ₁ -C ₂₀ alkyl)cycloheptyl group, (C ₁ -C ₂₀ alkyl)cyclooctyl group, (C ₁ -C ₂₀ alkyl)adamantanyl group, (C ₁ -C ₂₀ alkyl)norbonanyl group, (C ₁ -C ₂₀ alkyl) norbornenyl group, (C ₁ -C ₂₀ alkyl) cyclopentenyl group, (C ₁ -C ₂₀ alkyl) cyclohexenyl group, (C ₁ -C ₂₀ alkyl) cycloheptenyl group, (C ₁ - C ₂₀ alkyl)bicyclo[1.1.1]pentyl group, (C ₁ -C ₂₀ alkyl)bicyclo[2.1.1]hexyl group, (C ₁ -C ₂₀ alkyl)bicyclo[2.2.2]octyl group, Phenyl group, (C ₁ -C ₂₀ alkyl) phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group , pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthrolinyl group, Benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group , triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group , azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group or any combination thereof unsubstituted or substituted, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, bicyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo[2.2.2]octyl group , phenyl group, (C ₁ -C ₂₀ alkyl) phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyrida Zinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthrolinyl group , benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzo furanyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group, azadibenzofuranyl group or azadibenzothiophenyl group; or

-N(Q ₄ )(Q ₅ ) or -B(Q ₁ )(Q ₂ );

Q ₁ to Q ₅ are each independently,

Deuterium, -F, -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, -CD ₂ CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , -CH ₂ CF ₃ , -CH ₂ CF ₂ H, -CH ₂ CFH ₂ , -CHFCH ₃ , -CHFCF ₂ H, -CHFCFH ₂ , -CHFCF ₃ , -CF ₂ CF ₃ , -CF ₂ CF ₂ H or -CF ₂ CFH ₂ ; or

Deuterium, -F, C ₁ -C ₁₀ alkyl group, phenyl group or any combination thereof unsubstituted or substituted, n -propyl group, isopropyl group, n -butyl group, sec -butyl group, isobutyl group, tert -butyl group, n -pentyl group, tert -pentyl group, neopentyl group, isopentyl group, sec -pentyl group, 3-pentyl group, sec -isopentyl group, phenyl group, biphenyl group or naphthyl group; may be.

According to one embodiment, R ₁ to R ₆ , R ₁₀ and R ₂₀ are independently of each other,

A group represented by Formula 2-1, a group represented by Formula 2-2, hydrogen, deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group or C ₁ -C ₆₀ alkoxy group; or

It may be a group represented by any one of Formulas 9-1 to 9-43, 9-201 to 9-237, 10-1 to 10-129, and 10-201 to 10-350:

In Formulas 9-1 to 9-43, 9-201 to 9-237, 10-1 to 10-129, and 10-201 to 10-350, * is a bonding site with an adjacent atom, Ph is a phenyl group, TMS is a trimethylsilyl group, and TMG is a trimethylgermyl group.

According to one embodiment, the R ₁ to R ₄ are each independently a group represented by Formula 2-1, a group represented by Formula 2-2, hydrogen, deuterium, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, 2-methylbutyl group, sec-pentyl group, tert-pentyl group, neo- pentyl group, 3-pentyl group, 3-methyl-2-butyl group, phenyl group, biphenyl group, C ₁ -C ₂₀ alkylphenyl group or naphthyl group,

At least one of R ₁ to R ₄ may be a group represented by Formula 2-1 or a group represented by Formula 2-2.

According to one embodiment, at least one of R ₁ to R ₄ is —Si(Q ₁ )(Q ₂ )(Q ₃ ) or —Ge(Q ₁ )(Q ₂ )(Q ₃ );

-Si(Q ₁ )(Q ₂ )(Q ₃ ), -Ge(Q ₁ )(Q ₂ )(Q ₃ ) or a combination thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alke Nyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ hetero Cycloalkenyl 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, C ₁ -C ₆₀ heteroaryloxy group, C ₁ -C ₆₀ heteroarylthio group, monovalent non-aromatic condensed polycyclic group, or monovalent non-aromatic condensed heteropolycyclic group; may be.

According to one embodiment, any one of R ₁ to R ₄ may be a group represented by Formula 2-1 or a group represented by Formula 2-2, and the remainder may be hydrogen.

According to one embodiment, any one of R ₁ to R ₄ , R ₁₀ and R ₂₀ may be a group represented by Formula 2-2.

In Formula 1-1, b10 is 1 or 2, and b20 is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

When b10 is 2, two or more R ₁₀ are the same as or different from each other, and when b20 is 2 or more, two or more R ₂₀ are the same or different from each other.

In Formula 1-1, two R ₁₀ ; two or more of the plurality of R ₂₀ ; or two or more of R ₅ , R ₆ R ₁₀ and R ₂₀ ; these are optionally combined with each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group; Or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group; may form.

According to one embodiment, the two R ₁₀ ; two or more of the plurality of R ₂₀ ; or two or more of R ₅ , R ₆ R ₁₀ and R ₂₀ ; is optionally bonded to each other through a single bond, a double bond, or a first linking group, and is optionally substituted with at least one R _10a C ₅ - A C ₃₀ carbocyclic group or a C ₁ -C ₃₀ heterocyclic group unsubstituted or substituted with at least one R _10a (eg, a fluorene group, carbazole, substituted or unsubstituted with at least one R _10a ) group, dibenzothiophene group, dibenzofuran group, dibenzosilol group, xanthene group, acridine group, etc.). For the description of R _10a , refer to the description of R ₁ in the present specification.

For example, the two R ₁₀ ; two or more of the plurality of R ₂₀ ; or two or more adjacent R ₅ , R ₆ R ₁₀ and R ₂₀ ; optionally bonded to each other, substituted or unsubstituted with at least one R _10a , a cyclopentane group, a cyclopentene group, a cyclopentadiene group, and a furan group, thiophene group, pyrrole group, silol group, adamantane group, norbornane group, norbornene group, cyclohexane group, cyclohexene group, benzene group, naphthalene group, indene group, It may form an indole group, a benzofuran group, a benzothiophene group, a benzosilol group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group or a dibenzosilol group.

The first linking group is *-N(R ₈ )-*', *-B(R ₈ )-*', *-P(R ₈ )-*', *-C(R ₈ )(R ₉ )- *', *-Si(R ₈ )(R ₉ )-*', *-Ge(R ₈ )(R ₉ )-*', *-S-*', *-Se-*', *-O -*', *-C(=O)-*', *-S(=O)-*', *-S(=O) ₂ -*', *-C(R ₈ )=*', * =C(R ₈ )-*', *-C(R ₈ )=C(R ₉ )-*', *-C(=S)-*' and *-C≡C-*' and, for the description of R ₈ and R ₉ , refer to the description of R ₁₀ in the present specification, respectively, and * and *' are binding sites with neighboring atoms, respectively.

According to one embodiment, Ln ₁ may be represented by any one of Formulas 3-1 to 3-4 below:

in Formulas 3-1 to 3-4

For descriptions of X ₁ , X ₂ , Y ₁ , CY ₂ , X ₁₁ to X ₁₄ , R ₂₀ and b20, refer to the description described herein,

For the description of R ₁₁ , R ₁₂ and R ₁₄ independently of each other, refer to the description of R ₁₀ ,

* and *' are binding sites with neighboring atoms, respectively.

In Formula 1, n1 is 1, 2, or 3.

In Formula 1, Ln ₂ is a bidentate ligand.

According to one embodiment, Ln ₂ may be represented by any one of Formulas 5, 6, and 8-1 to 8-11:

<Formula 5>

<Formula 6>

In Formulas 5, 6 and 8-1 to 8-11,

X ₃ is C or N, X ₄ is C or N,

X ₅ and X ₆ are each independently O or S,

CY ₃ and CY ₄ are each independently a C ₅ -C ₃₀ carbocyclic group or a C ₁ -C ₃₀ heterocyclic group,

R ₃₀ , R ₄₀ and A ₁ to A ₇ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group , hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted A substituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, A substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ - C ₆₀ aryloxy group, 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, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q ₁ )(Q ₂ )(Q ₃ ), -Ge(Q ₁ )(Q ₂ )(Q ₃ ) or -B(Q ₁ )(Q ₂ ),

b30 and b40 are, independently of each other, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10,

Ph is a phenyl group,

* and *' are binding sites with neighboring atoms, respectively.

According to one embodiment, CY ₃ and CY ₄ in Formula 5 may be each independently of each other, and the description of CY ₂ may be referred to.

According to one embodiment, the CY ₃ is a pyridine group, a pyrimidine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrazole group, a tria It may be a azole group, an imidazole group, an indole group, a benzopyrazole group, a benzimidazole group, an azadibenzothiophene group, an azadibenzofuran group, an azacarbazole group, an azafluorene group or an azadibenzosilol group. have.

According to one embodiment, CY ₃ may be represented by any one of the following Chemical Formulas CY3-1 to CY3-13:

In Formulas CY3-1 to CY3-13,

X ₃₁ is O, S, N(R _39a ), C(R _39a )(R _39b ) or Si(R _39a )(R _39b ),

For the description of R ₃₁ to R ₃₈ , R _39a and R _39b independently of each other, refer to the description of R ₃₀ ,

R ₃₁ to R ₃₈ , R _39a and R _39b may be optionally bonded to two or more adjacent to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group; or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group;

* and *' are binding sites with neighboring atoms, respectively.

For example, a cyclopentane group, a cyclopentene group, or a cyclopentane group, which is unsubstituted or substituted with at least one R _10a by combining adjacent two or more of R ₃₁ to R ₃₈ , R _39a and R _39b Diene group, furan group, thiophene group, pyrrole group, silol group, adamantane group, norbornane group, norbornene group, cyclohexane group, cyclohexene group, benzene group, naphthalene group , an indene group, an indole group, a benzofuran group, a benzothiophene group, a benzosilol group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group or a dibenzosilol group.

According to one embodiment, CY ₄ is a benzene group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a benzothiophene group, a benzofuran group, and an indole group. Group, indene group, benzosilol group, dibenzothiophene group, dibenzofuran group, carbazole group, fluorene group, dibenzosilol group, azadibenzothiophene group, azadibenzofuran group, azacarbazole group , an azafluorene group or an azadibenzosilol group.

According to one embodiment, CY ₄ may be represented by any one of the following Chemical Formulas CY4-1 to CY4-13:

In Formulas CY4-1 to CY4-13,

X ₄₁ is O, S, N(R _49a ), C(R _49a )(R _49b ) or Si(R _49a )(R _49b ),

For the description of R ₄₁ to R ₄₈ , R _49a and R _49b independently of each other, refer to the description of R ₄₀ ,

two or more of R ₄₁ to R ₄₈ , R _49a and R _49b are optionally bonded to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group; or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group;

* and *' are binding sites with neighboring atoms, respectively.

For example, a cyclopentane group, a cyclopentene group, or a cyclopentane group, which is unsubstituted or substituted with at least one R _10a by combining adjacent two or more of R ₄₁ to R ₄₈ , R _49a and R _49b Diene group, furan group, thiophene group, pyrrole group, silol group, adamantane group, norbornane group, norbornene group, cyclohexane group, cyclohexene group, benzene group, naphthalene group , an indene group, an indole group, a benzofuran group, a benzothiophene group, a benzosilol group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group or a dibenzosilol group.

According to one embodiment, X ₃ is N, X ₄ is C,

The bond between M ₁ and X ₃ is a coordination bond,

The bond between M ₁ and X ₄ may be a covalent bond.

According to one embodiment, X ₅ and X ₆ are each O,

The bond between M ₁ and X ₅ is a coordination bond,

The bond between M ₁ and X ₆ may be a covalent bond.

R ₃₀ and R ₄₀ are each independently of each other, and the description of R ₅ , R ₆ , R ₁₀ or R ₂₀ may be referred to.

When b30 is 2 or more, two or more R ₃₀ are the same or different from each other, and when b40 is 2 or more, two or more R ₄₀ are the same or different from each other.

According to one embodiment, Ln ₂ may be selected from the following Chemical Formulas 5-1 to 5-129:

In Formulas 5-1 to 5-129,

X ₅₁ is O, S, N(R ₅₄ ), C(R ₅₄ )(R ₅₅ ) or Si(R ₅₄ )(R ₅₅ ),

R ₅₁ to R ₅₅ and R ₆₁ to R ₆₇ are each independently 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, -SF ₅ , a C ₁ -C ₂₀ alkyl group or a C ₁ -C ₂₀ alkoxy group;

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 salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₁₀ alkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclo Octyl group, bicyclo [2.2.1] heptanyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, C ₁ -C ₂₀ alkylphenyl group , a C ₁ -C ₂₀ alkyl group or a C ₁ -C ₂₀ alkoxy group substituted with a naphthyl group, a pyridinyl group, a pyrimidinyl group, or any combination thereof;

Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, bicyclo[2.2.1]heptanyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group , phenyl group, biphenyl group, C ₁ -C ₂₀ alkylphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, Thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindole Diary, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthrolinyl group, benzimidazolyl group , benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzo a thiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, or an imidazopyrimidinyl group;

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 salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, cyclopentyl group, cyclo Hexyl group, cycloheptyl group, cyclooctyl group, bicyclo[2.2.1]heptanyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group , C ₁ -C ₂₀ Alkylphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group , imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, Indazolyl group, furinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, Benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzo Silolyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, -Si(Q ₁₁ )(Q ₁₂ )(Q ₁₃ ), -B(Q ₁₁ )(Q ₁₂ ) ), -N(Q ₁₁ )(Q ₁₂ ) or any combination thereof, substituted with a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a bicyclo[2.2.1]heptanyl group, adamanta Nyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, C ₁ -C ₂₀ alkylphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group , fluoranthenyl group, triphenylenyl group, pyrenyl group, Chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, Pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenane Trollinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, or an imidazopyrimidinyl group; or

-Si(Q ₁ )(Q ₂ )(Q ₃ ), -B(Q ₁ )(Q ₂ ) or -N(Q ₁ )(Q ₂ );

Q ₁ to Q ₃ and Q ₁₁ to Q ₁₃ are each independently,

Methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, 2-methylbutyl group, sec-pen tyl group, tert-pentyl group, neo-pentyl group, 3-pentyl group, 3-methyl-2-butyl group, phenyl group, biphenyl group, C ₁ -C ₂₀ alkylphenyl group or naphthyl group; or

methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, iso pentyl group, 2-methylbutyl group, sec-pentyl group, tert-pentyl group, neo-pentyl group, 3-pentyl group, 3-methyl-2-butyl group, phenyl group or naphthyl group;

b51 and b54 are each independently 1 or 2,

b53 and b55 are, independently of each other, 1, 2 or 3,

b52 and b56 are, independently of each other, 1, 2, 3 or 4,

Ph is a phenyl group;

Ph-d5 is a phenyl group in which all hydrogens are substituted with deuterium;

* and *' are binding sites with neighboring atoms.

In Formula 1-1, n2 is 0, 1, or 2.

According to one embodiment, the organometallic compound may be a compound represented by any one of the following Chemical Formulas 11-1 to 11-8:

In Formulas 11-1 to 11-8,

For descriptions of M ₁ , X ₁ , X ₂ , Y ₁ , CY ₂ , X ₁₁ to X ₁₄ , R ₂₀ and b20, respectively, refer to the description described herein,

For the description of R ₁₁ , R ₁₂ and R ₁₄ independently of each other, refer to the description of R ₁₀ ,

X ₃ is C or N, X ₄ is C or N,

X ₅ and X ₆ are each independently O or S,

CY ₃ and CY ₄ are each independently a C ₅ -C ₃₀ carbocyclic group or a C ₁ -C ₃₀ heterocyclic group,

R ₃₀ , R ₄₀ and A ₁ to A ₇ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group , hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted A substituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, A substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ - C ₆₀ aryloxy group, 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, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q ₁ )(Q ₂ )(Q ₃ ), -Ge(Q ₁ )(Q ₂ )(Q ₃ ) or -B(Q ₁ )(Q ₂ ),

b30 and b40 are, independently of each other, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

According to one embodiment, the organometallic compound may be electrically neutral.

According to one embodiment, the M ₁ may be Ir, and the sum of n1 + n2 may be 3.

According to one embodiment, the organometallic compound may be selected from the following compounds 1 to 322:

.

.

The organometallic compound represented by Formula 1 satisfies the structure of Formula 1 described above. Specifically, the ligand represented by Formula 1-1 has a structure in which a heterocycle including a heteroatom Y ₁ is condensed, and when CY ₂ is a benzene group, R ₁ to At least one of R ₄ is a group represented by Formula 2-1 or Formula 2-2, that is, a substituent including a Si or Ge atom, or at least one of R ₁₀ and R ₂₀ is a group represented by Formula 2-2, that is, Ge When it is a substituent including an atom, and CY ₂ is not a benzene group, at least one of R ₁ to R ₄ , R ₁₀ and R ₂₀ is a group represented by Formula 2-1 or Formula 2-2, that is, including a Si or Ge atom. is a substituent. Due to this structure, an electronic device including the organometallic compound represented by Formula 1, for example, an organic light emitting device, may exhibit a low driving voltage, high efficiency, and long lifespan, and a roll-off phenomenon may be reduced.

The HOMO energy level, LUMO energy level, energy gap, T ₁ energy level, and S ₁ energy level of some of the organometallic compounds represented by Formula 1 above are accompanied by molecular structure optimization by density functional theory (DFT) based on B3LYP The evaluation results using a Gaussian 09 program are shown in Table 1 below.

Compound No. HOMO
(eV) LUMO
(eV) energy gap
(eV) S1
(eV) T1
(eV) compound 1 -4.840 -1.417 3.423 2.830 2.520 compound 2 -4.800 -1.400 3.400 2.800 2.507 compound 3 -4.829 -1.418 3.411 2.843 2.454

From Table 1, it can be confirmed that the organometallic compound represented by Chemical Formula 1 has electrical properties suitable for use as a dopant in an electronic device, for example, an organic light emitting device.

According to one embodiment, the full width at half maximum (FWHM) of the emission peak of the emission spectrum or the electroluminescence spectrum of the organometallic compound may be 75 nm or less. For example, the half maximum width (FWHM) of the emission peak of the emission spectrum or the electroluminescence spectrum of the organometallic compound may be in the range of 30 nm to 75 nm, 40 nm to 70 nm, or 45 nm to 68 nm.

Meanwhile, according to another embodiment, the maximum emission wavelength (emission peak wavelength, λ _max ) of the emission spectrum of the emission spectrum or the electroluminescence spectrum of the organometallic compound may be in the range of 500 nm to 750 nm.

A method of synthesizing the organometallic compound represented by Chemical Formula 1 may be recognized by those skilled in the art with reference to Synthesis Examples to be described later.

Accordingly, the organometallic compound represented by Chemical Formula 1 may be suitable for use as a dopant in an organic layer of an organic light emitting device, for example, a light emitting layer among the organic layers. According to another aspect, the organometallic compound; a second electrode; and an organic layer disposed between the first electrode and the second electrode, including a light emitting layer, and including at least one organometallic compound represented by Chemical Formula 1;

The organic light emitting device includes an organic layer including the organometallic compound represented by Chemical Formula 1 as described above, and thus has excellent driving voltage, excellent current efficiency, external quantum efficiency, excellent roll-off ratio, and relatively narrow EL spectrum emission peak. It may have a full width at half maximum (FWHM) and excellent lifetime characteristics.

The organometallic compound represented by Formula 1 may be used between a pair of electrodes of the organic light emitting device. For example, the organometallic compound represented by Formula 1 may be included in the emission layer. In this case, the organometallic compound acts as a dopant, and the light emitting layer may further include a host (that is, the content of the organometallic compound represented by Formula 1 in the light emitting layer is less than the content of the host) .

According to one embodiment, the light emitting layer may emit green light. For example, the emission layer may emit green light having a maximum emission wavelength of 500 nm to 600 nm.

According to one embodiment, the light emitting layer may emit red light. For example, the emission layer may emit red light having a maximum emission wavelength of 600 nm to 750 nm.

In the present specification, "(organic layer) includes one or more organometallic compounds" means "(organic layer) one organometallic compound belonging to the category of Formula 1 or two different types belonging to the category of Formula 1 above. It may include more than one organometallic compound".

For example, the organic layer may include only Compound 1 as the organometallic compound. In this case, the compound 1 may be present in the emission layer of the organic light emitting device. Alternatively, the organic layer may include the compound 1 and the compound 2 as the organometallic compound. In this case, the compound 1 and the compound 2 may be present in the same layer (for example, both the compound 1 and the compound 2 may be present in the emission layer).

The first electrode is an anode that is a hole injection electrode and the second electrode is a cathode that is an electron injection electrode, or the first electrode is a cathode that is an electron injection electrode and the second electrode is an anode that is a hole injection electrode.

For example, in the organic light emitting device, the first electrode is an anode, the second electrode is a cathode, and the organic layer is a hole transport region disposed between the first electrode and the light emitting layer, and the light emitting layer and the second electrode It further comprises an electron transport region disposed therebetween, wherein the hole transport region comprises a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof, wherein the electron transport region is a hole blocking layer, an electron a transport layer, an electron injection layer, or any combination thereof.

As used herein, the term “organic layer” refers to a single and/or a plurality of layers disposed between the first electrode and the second electrode among the organic light emitting diodes. The "organic layer" may include not only an organic compound, but also an organometallic complex including a metal.

1 is a schematic cross-sectional view of an organic light emitting device 10 according to an embodiment of the present invention. Hereinafter, a structure and a manufacturing method of an organic light emitting device according to an embodiment of the present invention will be described with reference to FIG. 1 . The organic light emitting device 10 has a structure in which a first electrode 11 , an organic layer 15 , and a second electrode 19 are sequentially stacked.

A substrate may be additionally disposed below the first electrode 11 or above the second electrode 19 . As the substrate, a substrate used in a conventional organic light emitting device may be used, and a glass substrate or a transparent plastic substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, handling easiness and waterproofness may be used.

The first electrode 11 may be formed, for example, by providing a material for the first electrode on a substrate using a deposition method or a sputtering method. The first electrode 11 may be an anode. The material for the first electrode may be selected from materials having a high work function to facilitate hole injection. The first electrode 11 may be a reflective electrode, a transflective electrode, or a transmissive electrode. As a material for the first electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), or the like may be used. Alternatively, a metal such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag) may be used. .

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

An organic layer 15 is disposed on the first electrode 11 .

The organic layer 15 may include a hole transport region; an emission layer; and an electron transport region.

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

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

The hole transport region may include only a hole injection layer or only a hole transport layer. Alternatively, the hole transport region may have a structure of a hole injection layer/hole transport layer or a hole injection layer/hole transport layer/electron blocking layer sequentially stacked from the first electrode 11 .

When the hole transport region includes the hole injection layer, the hole injection layer (HIL) may be formed on the first electrode 11 by using various methods such as vacuum deposition, spin coating, casting, LB, and the like. have.

In the case of forming the hole injection layer by the vacuum deposition method, the deposition conditions vary depending on the compound used as the hole injection layer material, the structure and thermal characteristics of the target hole injection layer, etc., but, for example, the deposition temperature is about 100 to about 500° C., a vacuum degree of about 10 ⁻⁸ to about 10 ⁻³ torr, and a deposition rate of about 0.01 to about 100 Å/sec may be selected in the range, but not limited thereto.

In the case of forming the hole injection layer by spin coating, the coating conditions are different depending on the compound used as the hole injection layer material, the structure and thermal properties of the desired hole injection layer, but a coating speed of about 2000 rpm to about 5000 rpm, The heat treatment temperature for removing the solvent after coating may be selected from a temperature range of about 80° C. to 200° C., but is not limited thereto.

For the conditions for forming the hole transport layer and the electron blocking layer, refer to the conditions for forming the hole injection layer.

The hole transport region is, for example, m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated NPB, TAPC, HMTPD, TCTA (4,4', 4"-tris(N-carbazolyl)triphenylamine (4,4',4"-tris(N-carbazolyl)triphenylamine)), PANI/DBSA (Polyaniline/Dodecylbenzenesulfonic acid: polyaniline/dodecylbenzenesulfonic acid), PEDOT /PSS(Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate):poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate)), PANI/CSA (Polyaniline/Camphor sulfonicacid: polyaniline/camphorsulfonic acid), PANI/PSS (Polyaniline)/Poly(4-styrenesulfonate):polyaniline)/poly(4-styrenesulfonate)), a compound represented by the following formula 201 and a compound represented by the following formula 202 It may contain one:

<Formula 201>

<Formula 202>

In Formula 201, Ar ₁₀₁ and Ar ₁₀₂ are each independently

Phenylene group, pentarenylene group, indenylene group, naphthylene group, azulenylene group, heptalenylene group, acenaphthylene group, fluorenylene group, phenarenylene group, phenanthrenylene group, anthracenylene group, fluoranthenyl a ren group, a triphenylenylene group, a pyrenylene group, a chrysenylenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, or a pentacenylene group; or

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, 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 group, C ₃ -C ₁₀ cycloalkenyl group , C ₁ -C ₁₀ heterocycloalkyl 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 condensed polycyclic group, monovalent non-aromatic condensed heterocondensed polycyclic group or any combination thereof, substituted with phenylene group, pentarenylene group, indenylene group, naphthylene group, azule Nylene group, heptalenylene group, acenaphthylene group, fluorenylene group, phenarenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylenylene group, naphtha It may be a cenylene group, a picenylene group, a perylenylene group, or a pentacenylene group.

In Formula 201, xa and xb may be each independently an integer of 0 to 5, or 0, 1, or 2. For example, xa may be 1 and xb may be 0, but is not limited thereto.

In Formulas 201 and 202, R ₁₀₁ to R ₁₀₈ , R ₁₁₁ to R ₁₁₉ and R ₁₂₁ to R ₁₂₄ are each independently

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, Phosphoric acid or a salt thereof, a C ₁ -C ₁₀ alkyl group (eg, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, etc.) or a C ₁ -C ₁₀ alkoxy group (eg, a methoxy group, an ethoxy group) period, propoxy group, butoxy group, pentoxy group, etc.);

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its a C ₁ -C ₁₀ alkyl group or a C ₁ -C ₁₀ alkoxy group, substituted with a salt, or any combination thereof;

a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, or a pyrenyl group; or

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or A salt thereof, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, or any combination thereof, substituted with a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, or a pyrenyl group; may be, but limited thereto it's not going to be

In Formula 201, R ₁₀₉ is,

a phenyl group, a naphthyl group, an anthracenyl group, or a pyridinyl group; or

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or A salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyridinyl group, or any combination thereof substituted with a phenyl group, a naphthyl group, an anthracenyl group, or pyri It may be a denyl group;

According to one embodiment, the compound represented by Formula 201 may be represented by Formula 201A, but is not limited thereto:

<Formula 201A>

For a detailed description of R ₁₀₁ , R ₁₁₁ , R ₁₁₂ and R ₁₀₉ in Formula 201A, refer to the above description.

For example, the compound represented by Formula 201 and the compound represented by Formula 202 may include the following compounds HT1 to HT20, but are not limited thereto:

The hole transport region may have a thickness of about 100 Å to about 10000 Å, for example, about 100 Å to about 1000 Å. If 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 is about 100 Å to about 10000 Å, for example, about 100 Å to about 1000 Å, and the thickness of the hole transport layer is about 50 Å to about 2000 Angstroms, for example from about 100 Angstroms to about 1500 Angstroms. When the thickness of the hole transport region, the hole injection layer, and the hole transport layer satisfies the above-described ranges, a satisfactory hole transport characteristic may be obtained without a substantial increase in driving voltage.

The hole transport region may further include a charge-generating material to improve conductivity in addition to the above-described material. The charge-generating material may be uniformly or non-uniformly dispersed in the hole transport region.

The charge-generating material may be, for example, a p-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, and a cyano group-containing compound, but is not limited thereto. For example, non-limiting examples of the p-dopant include tetracyanoquinonedimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane quinone derivatives such as phosphorus (F4-TCNQ), F6-TCNNQ and the like; metal oxides such as tungsten oxide and molybdenum oxide; and cyano group-containing compounds such as the following compounds HT-D1 and F12, but are not limited thereto.

The hole transport region may further include a buffer layer.

The buffer layer may serve to increase efficiency by compensating for an optical resonance distance according to a wavelength of light emitted from the light emitting layer.

The emission layer EML may be formed on the hole transport region by using a method such as a vacuum deposition method, a spin coating method, a casting method, or an LB method. In the case of forming the light emitting layer by vacuum deposition or spin coating, the deposition conditions and coating conditions vary depending on the compound used, but in general, they may be selected from within the same range of conditions as those for forming the hole injection layer.

Meanwhile, when the hole transport region includes the electron blocking layer, the electron blocking layer material may be selected from materials that can be used for the hole transport region as described above and a host material to be described later, but is not limited thereto. . For example, when the hole transport region includes an electron blocking layer, mCP, which will be described later, may be used as the electron blocking layer material.

The emission layer may include a host and a dopant, and the dopant includes an organometallic compound represented by Formula 1 above.

The host may comprise at least one of the following TPBi, TBADN, ADN (also referred to as "DNA"), CBP, CDBP, TCP, mCP, compound H50 and compound H51:

Alternatively, the host may include a compound represented by the following Chemical Formula 301:

<Formula 301>

In Formula 301, Ar ₁₁₁ and Ar ₁₁₂ are each independently

a phenylene group, a naphthylene group, a phenanthrenylene group, or a pyrenylene group; or

It may be a phenylene group, a naphthylene group, a phenanthrenylene group, or a pyrenylene group, substituted with a phenyl group, a naphthyl group, an anthracenyl group, or any combination thereof.

In Formula 301, Ar ₁₁₃ to Ar ₁₁₆ are each independently

C ₁ -C ₁₀ alkyl group, phenyl group, naphthyl group, phenanthrenyl group or pyrenyl group; or

It may be a phenyl group, a naphthyl group, a phenanthrenyl group or a pyrenyl group, substituted with a phenyl group, a naphthyl group, an anthracenyl group, or any combination thereof.

In Formula 301, g, h, i, and j may each independently represent an integer of 0 to 4, for example, 0, 1, or 2.

In Formula 301, Ar ₁₁₃ to Ar ₁₁₆ are each independently

a C ₁ -C ₁₀ alkyl group substituted with a phenyl group, a naphthyl group, an anthracenyl group, or any combination thereof;

a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, or a fluorenyl group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group , a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group or a fluorenyl group substituted with a fluorenyl group or any combination thereof; or

;

;

may be, but is not limited thereto.

Alternatively, the host may include a compound represented by the following Chemical Formula 302:

<Formula 302>

For a detailed description of Ar ₁₂₂ to Ar ₁₂₅ in Formula 302, refer to the description of Ar ₁₁₃ in Formula 301.

Ar ₁₂₆ and Ar ₁₂₇ in Formula 302 may each independently represent a C ₁ -C ₁₀ alkyl group (eg, a methyl group, an ethyl group, or a propyl group).

In Formula 302, k and l may be each independently an integer of 0 to 4. For example, k and l may be 0, 1, or 2.

When the organic light emitting device is a full color organic light emitting device, the light emitting layer may be patterned into a red light emitting layer, a green light emitting layer, and a blue light emitting layer. Alternatively, the light emitting layer may have a structure in which a red light emitting layer, a green light emitting layer, and/or a blue light emitting layer are stacked, and thus various modifications such as emitting white light are possible.

When the light emitting layer includes a host and a dopant, the content of the dopant may be generally selected from about 0.01 parts by weight to about 15 parts by weight based on about 100 parts by weight of the host, but is not limited thereto.

The light emitting layer may have a thickness of about 100 Å to about 1000 Å, for example, about 200 Å to about 600 Å. When the thickness of the light emitting layer satisfies the above-described range, excellent light emitting characteristics may be exhibited without a substantial increase in driving voltage.

Next, an electron transport region is disposed on the emission layer.

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

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

For the conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer in the electron transport region, refer to the formation conditions of the hole injection layer.

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 is not limited thereto.

The hole blocking layer may have a thickness of about 20 Å to about 1000 Å, for example, about 30 Å to about 300 Å. When the thickness of the hole blocking layer satisfies the above range, excellent hole blocking characteristics can be obtained without a substantial increase in driving voltage.

The electron transport layer may further include at least one of BCP, Bphen, and Alq ₃ , BAlq, TAZ, and NTAZ.

Alternatively, the electron transport layer may include at least one of the following compounds ET1 to ET25, but is not limited thereto.

The electron transport layer may have a thickness of about 100 Å to about 1000 Å, for example, about 150 Å to about 500 Å. When the thickness of the electron transport layer satisfies the above range, a satisfactory electron transport characteristic may be obtained without a substantial increase in driving voltage.

The electron transport layer may further include a metal-containing material in addition to the above-described material.

The metal-containing material may include a Li complex. The Li complex may include, for example, the following compound ET-D1 (lithium quinolate, LiQ) or ET-D2.

In addition, the electron transport region may include an electron injection layer (EIL) that facilitates injection of electrons from the second electrode 19 .

The electron injection layer may include LiF, NaCl, CsF, Li ₂ O, BaO, or any combination thereof.

The electron injection layer may have a thickness of about 1 Å to about 100 Å, for example, about 3 Å to about 90 Å. When the thickness of the electron injection layer satisfies the above range, a satisfactory level of electron injection characteristics may be obtained without a substantial increase in driving voltage.

A second electrode 19 is provided on the organic layer 15 . The second electrode 19 may be a cathode. As the material for the second electrode 19 , a metal, an alloy, an electrically conductive compound, and a combination thereof having a relatively low work function may be used. Specific examples include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. It can be used as a material for forming the second electrode 19 . Alternatively, various modifications are possible, such as forming the transmissive second electrode 19 using ITO or IZO in order to obtain a top light emitting device.

In the above, the organic light emitting device has been described with reference to FIG. 1, but is not limited thereto.

According to another aspect, there is provided a diagnostic composition comprising at least one organometallic compound represented by Formula 1 above.

Since the organometallic compound represented by Formula 1 may provide high luminous efficiency, the diagnostic composition including the organometallic compound may have high diagnostic efficiency.

The diagnostic composition may be variously applied to various diagnostic kits, diagnostic reagents, biosensors, biomarkers, and the like.

In the present specification, the C ₁ -C ₆₀ alkyl group refers to a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and specific examples thereof include a methyl group, an ethyl group, a propyl group, an isobutyl group, and a sec-butyl group. group, tert-butyl group, pentyl group, iso-amyl group, hexyl group and the like. In the present specification, the C ₁ -C ₆₀ alkylene group refers to a divalent group having the same structure as the C ₁ -C ₆₀ alkyl group.

In the present specification, the C ₁ -C ₆₀ alkoxy group refers to a monovalent group having the formula of -OA ₁₀₁ (here, A ₁₀₁ is the C ₁ -C ₆₀ alkyl group), and specific examples thereof include a methoxy group, an ethoxy group, isopropyloxy group and the like.

In the present specification, the C ₂ -C ₆₀ alkenyl group has a structure including one or more carbon-carbon double bonds in the middle or at the terminal of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include an ethenyl group, a propenyl group, a butenyl group, etc. This is included. In the present specification, the C ₂ -C ₆₀ alkenylene group refers to a divalent group having the same structure as the C ₂ -C ₆₀ alkenyl group.

In the present specification, the C ₂ -C ₆₀ alkynyl group has a structure including one or more carbon-carbon triple bonds in the middle or at the terminal of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include an ethynyl group, a propynyl group ( propynyl) and the like. In the present specification, the C ₂ -C ₆₀ alkynylene group refers to a divalent group having the same structure as the C ₂ -C ₆₀ alkynyl group.

In the present specification, the C ₃ -C ₁₀ cycloalkyl group means a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and specific examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cyclohep group. til groups, and the like. In the present specification, the C ₃ -C ₁₀ cycloalkylene group refers to a divalent group having the same structure as the C ₃ -C ₁₀ cycloalkyl group.

In the present specification, the C ₁ -C ₁₀ heterocycloalkyl group refers to a monovalent monocyclic group having 1 to 10 carbon atoms including at least one hetero atom selected from N, O, P, Si and S as a ring-forming atom, Specific examples thereof include a tetrahydrofuranyl group, a tetrahydrothiophenyl group, and the like. In the present specification, the C ₁ -C ₁₀ heterocycloalkylene group refers to a divalent group having the same structure as the C ₁ -C ₁₀ heterocycloalkyl group.

In the present specification, the C ₃ -C ₁₀ cycloalkenyl group is a monovalent monocyclic group having 3 to 10 carbon atoms, and has at least one carbon-carbon double bond in the ring, but refers to a group that does not have aromaticity, , and specific examples thereof include a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, and the like. In the present specification, the C ₃ -C ₁₀ cycloalkenylene group refers to a divalent group having the same structure as the C ₃ -C ₁₀ cycloalkenyl group.

In the present specification, the C ₁ -C ₁₀ heterocycloalkenyl group is a monovalent monocyclic group having 1 to 10 carbon atoms including at least one hetero atom selected from N, O, P, Si and S as a ring-forming atom, has at least one double bond in it. Specific examples of the C ₁ -C ₁₀ heterocycloalkenyl group include a 2,3-dihydrofuranyl group, a 2,3-dihydrothiophenyl group, and the like. In the present specification, the C ₁ -C ₁₀ heterocycloalkenylene group refers to a divalent group having the same structure as the C ₁ -C ₁₀ heterocycloalkenyl group.

In the present specification, the C ₆ -C ₆₀ aryl group refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and the C ₆ -C ₆₀ arylene group is a carbo group having 6 to 60 carbon atoms. It refers to a divalent group having a cyclic aromatic system. Specific examples of the C ₆ -C ₆₀ aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a chrysenyl group, and the like. When the C ₆ -C ₆₀ aryl group and the C ₆ -C ₆₀ arylene group include two or more rings, the two or more rings may be fused to each other. The C ₇ -C ₆₀ alkylaryl group refers to a C ₆ -C ₆₀ aryl group substituted with at least one C ₁ -C ₆₀ alkyl group.

In the present specification, the C ₁ -C ₆₀ heteroaryl group comprises at least one hetero atom selected from N, O, P, Si and S as a ring-forming atom and a monovalent group having a cyclic aromatic system having 1 to 60 carbon atoms. means, and the C ₁ -C ₆₀ heteroarylene group comprises at least one hetero atom selected from N, O, P and S as a ring-forming atom and is a divalent group having a carbocyclic aromatic system having 1 to 60 carbon atoms. it means. Specific examples of the C ₁ -C ₆₀ heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and the like. When the C ₁ -C ₆₀ heteroaryl group and the C ₁ -C ₆₀ heteroarylene group include two or more rings, the two or more rings may be fused to each other. The C ₂ -C ₆₀ alkylheteroaryl group refers to a C ₁ -C ₆₀ heteroaryl group substituted with at least one C ₁ -C ₆₀ alkyl group.

In the present specification, the C ₆ -C ₆₀ aryloxy group refers to -OA ₁₀₂ (here, A ₁₀₂ is the C ₆ -C ₆₀ aryl group), and the C ₆ -C ₆₀ arylthio group is -SA ₁₀₃ (here , A ₁₀₃ represents the above C ₆ -C ₆₀ aryl group).

In the present specification, the C ₁ -C ₆₀ heteroaryloxy group refers to -OA ₁₀₄ (wherein A ₁₀₄ is the C ₁ -C ₆₀ heteroaryl group), and the C ₁ -C ₆₀ heteroarylthio group (heteroarylthio) is -SA ₁₀₅ (herein, A ₁₀₅ is the C ₁ -C ₆₀ heteroaryl group).

In the present specification, a monovalent non-aromatic condensed polycyclic group has two or more rings condensed with each other, contains only carbon as a ring-forming atom, and the entire molecule is non-aromatic. means a monovalent group having (eg, having 8 to 60 carbon atoms). Specific examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group and the like. In the present specification, the divalent non-aromatic condensed polycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.

In the present specification, the monovalent non-aromatic condensed heteropolycyclic group includes two or more rings condensed with each other, and a hetero atom selected from N, O, P, Si and S in addition to carbon as a ring forming atom. and means a monovalent group (eg, having 1 to 60 carbon atoms) having non-aromaticity in the entire molecule. The monovalent non-aromatic condensed heteropolycyclic group includes a carbazolyl group and the like. In the present specification, the condensed divalent non-aromatic heteropolycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.

In the present specification, a C ₅ -C ₃₀ carbocyclic group refers to a saturated or unsaturated cyclic group having only 5 to 30 carbon atoms as ring forming atoms. The C ₅ -C ₃₀ carbocyclic group may be a monocyclic group or a polycyclic group.

In the present specification, the C ₁ -C ₃₀ heterocyclic group refers to a saturated or unsaturated cyclic group having at least one hetero atom selected from N, O, P, Si and S in addition to 1 to 30 carbon atoms as ring forming atoms. The C ₁ -C ₃₀ heterocyclic group may be a monocyclic group or a polycyclic group.

Said substituted C ₅ -C ₃₀ carbocyclic group, substituted C ₁ -C ₃₀ heterocyclic group, substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, substituted C ₁ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₇ -C ₆₀ alkylaryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C ₆ -C ₆₀ arylthio group , at least a substituent of a substituted C ₁ -C ₆₀ heteroaryl group, a substituted C ₂ -C ₆₀ alkylheteroaryl group, a substituted monovalent non-aromatic condensed polycyclic group, and a substituted monovalent non-aromatic condensed polycyclic group The one is,

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, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group or a C ₁ -C ₆₀ alkoxy group;

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, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₃ -C ₁₀ cycloalkyl group, 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 ₇ -C ₆₀ alkylaryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, C ₂ -C ₆₀ alkylheteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₁₁ )(Q ₁₂ ), -Si C ₁ substituted with (Q ₁₃ )(Q ₁₄ )(Q ₁₅ ), -B(Q ₁₆ )(Q ₁₇ ), -P(=O)(Q ₁₈ )(Q ₁₉ ), or any combination thereof -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group or C ₁ -C ₆₀ alkoxy group;

C ₃ -C ₁₀ cycloalkyl group, 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 ₇ -C ₆₀ alkyl Aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, C ₂ -C ₆₀ alkylheteroaryl group, monovalent non-aromatic condensed polycyclic group or 1 is a non-aromatic condensed heteropolycyclic group;

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, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, 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 group, 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 ₇ -C ₆₀ alkylaryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, C ₂ -C ₆₀ alkylheteroaryl group, 1 Condensed non-aromatic polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ), -B(Q ₂₆ ) C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C substituted with (Q ₂₇ ), —P(=O)(Q ₂₈ )(Q ₂₉ ), or any combination thereof ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₇ -C ₆₀ alkylaryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, C ₂ -C ₆₀ alkylheteroaryl group, monovalent non-aromatic condensed polycyclic group or monovalent non-aromatic condensed heteropolycyclic group; or

-N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), -B(Q ₃₆ )(Q ₃₇ ) or -P(=O)(Q ₃₈ )(Q ₃₉ ) );ego,

The Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cya No group, nitro group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, C ₁ -C ₆₀ alkyl group, deuterium, C ₁ -C ₆₀ alkyl group, C ₆ -C ₆₀ aryl group or any combination thereof substituted 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 group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, deuterium, C ₁ -C ₆₀ alkyl group and C C ₆ -C ₆₀ aryl group substituted with at least one of ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, C ₂ -C ₆₀ may be an alkylheteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group.

Hereinafter, a compound and an organic light emitting device according to an embodiment of the present invention will be described in more detail with reference to Synthesis Examples and Examples, but the present invention is not limited to the following Synthesis Examples and Examples. In the following Synthesis Example, in the expression "'B' was used instead of 'A'", the amount of 'B' and the amount of 'A' used were the same on a molar equivalent basis.

[Example]

Synthesis Example 1: Synthesis of Compound 1

(1) Synthesis of compound 1A(1)

2-phenylpyridine (7.5 g, 33.1 mmol) and iridium chloride (5.2 g, 14.7 mmol) were mixed with 120 mL of ethoxyethanol and 40 mL of distilled water, and then After stirring under reflux for 24 hours, the temperature was lowered to room temperature. The resulting solid was separated by filtration, washed sufficiently in the order of water/methanol/hexane, and the obtained solid was dried in a vacuum oven to obtain 8.2 g (yield of 82%) of Compound 1A(1).

(2) Synthesis of compound 1A

Compound 1A (1.6 g, 1.2 mmol) and 45 mL of methylene chloride were mixed, and then AgOTf (0.6 g, 2.3 mmol) was mixed with 15 mL of methanol and then added. After that, the mixture was stirred at room temperature for 18 hours in a state of blocking light with aluminum foil, filtered through celite to remove the produced solid, and the filtrate was reduced pressure to obtain a solid (Compound 1B) without further purification. It was used in the next reaction.

(3) Synthesis of compound 1B

In a nitrogen environment, phenyl boronic acid (0.5 g, 3.75 mmol) and 3-chloro-6- (trimethyl lowyl) benzofuro [3,2-c] pyridine (1.0 g, 3.1 mmol) were mixed with 1,4-dioxane 75 ml then melted in. Potassium carbonate (K ₂ CO ₃ ) (1.0 g, 9.37 mmol) was dissolved in 25 mL of distilled water (DI water), and then added to the reaction mixture, and a palladium catalyst (Pd(PPh ₃ ) ₄ ) (0.18 g, 0.16 mmol) was added. added. Then, the reaction mixture was stirred under reflux at 100 °C . After extraction, the obtained solid was subjected to column chromatography (eluent: MC (methylene chloride) and hexane) to conduct compound 3-phenyl-6-(trimethyllowyl)benzofuro[3,2-c]pyridine 1.0g ( yield of 88%). The material was identified through mass and HPLC analysis.

HRMS(MALDI) calcd for C ₂₀ H ₁₉ GeNO: m/z: 362.01 Found: 364.08

(4) Synthesis of compound 1

35 mL of 2-ethoxyethanol and 35 mL of N,N-dimethylformimide were mixed with Compound 1A (1.3 g, 1.8 mmol) and Compound 1B (0.7 g, 2.0 mmol), and the temperature was lowered after stirring under reflux for 24 hours. lowered The mixture was extracted with methylene chloride and water, and the water layer was removed. After treatment with anhydrous magnesium sulfate, the mixture was filtered and concentrated under reduced pressure. After extraction, the obtained solid was subjected to column chromatography (eluent: MC (methylene chloride) and hexane) to obtain 0.66 g (yield of 40%) of Compound 1. The material was identified through mass and HPLC analysis.

HRMS(MALDI) calcd for C ₄₃ H ₃₄ GeIrN ₂ O: m/z: 859.61 Found: 862.13

Synthesis Example 2: Synthesis of compound 2

In the synthesis of compound 2A(1), the above synthesis example, except that 2-phenyl-5-(trimethylsilyl)pyridine (8.7g, 38.3mmol) was used instead of 2-phenylpyridine By using the same method as for the synthesis of compound 1 of 1, 0.65 g (yield of 46%) of compound 2 was obtained. The material was identified through mass and HPLC analysis.

HRMS(MALDI) calcd for C ₄₉ H ₅₀ GeIrN ₂ OSi ₂ : m/z: 1003.97 Found: 1006.33

Synthesis Example 3: Synthesis of compound 3

(3) Synthesis of compound 3B

Under nitrogen environment, dibenzo[b,d]furan-4-ylboronic acid (1.0g, 4.9mmol) and 3-chloro-6-(trimethyllowyl)benzofuro[3,2-c]pyridine (1.3g , 4.0 mmol) was dissolved in 90 ml of 1,4-dioxane. Potassium carbonate (K ₂ CO ₃ ) (1.3 g, 12.2 mmol) was dissolved in 30 mL of distilled water (DI water), and then added to the reaction mixture, and a palladium catalyst (Pd(PPh ₃ ) ₄ ) (0.23 g, 0.2 mmol) was added. added. Then, the reaction mixture was stirred under reflux at 100 °C . After extraction, the obtained solid was subjected to column chromatography (eluent: MC (methylene chloride) and hexane) to perform compound 3-(dibenzo[b,d]furan-4-yl)-6-(trimethyllowmyl)benzo 1.5 g (yield of 82%) of puro[3,2-c]pyridine was obtained. The material was identified through mass and HPLC analysis.

HRMS(MALDI) calcd for C ₂₁ H ₂₅ GeNO ₂ : m/z: 452.09 Found: 454.08

(4) Synthesis of compound 3

40 mL of 2-ethoxyethanol and 40 mL of N,N-dimethylformimide were mixed with Compound 1A (1.4 g, 2.0 mmol) and Compound 1B (1.0 g, 2.2 mmol), stirred under reflux for 24 hours, and then the temperature was lowered. lowered The mixture was extracted with methylene chloride and water, and the water layer was removed. After treatment with anhydrous magnesium sulfate, the mixture was filtered and concentrated under reduced pressure. After extraction, column chromatography (eluent: MC (methylene chloride) and hexane) was performed on the obtained solid to obtain 0.72 g of compound 3 (yield of 38%). The material was identified through mass and HPLC analysis.

HRMS(MALDI) calcd for C ₄₅ H ₃₆ GeIrN ₃ O ₂ : m/z: 951.68 Found: 954.18

Synthesis Example 4: Synthesis of compound 64

(1) Synthesis of compound 64A

Under nitrogen environment, 1-bromo-7-(trimethyllowyl)benzofuro[2,3-c]pyridine (1.5g, 4.1mmol) and 2-(3,5-dimethylphenyl)-4,4,5 ,5-Tetramethyl-1,3,2-dioxoborolein (1.1 g, 4.5 mmol) was dissolved in 90 ml of 1,4-dioxane. Potassium carbonate (K ₂ CO ₃ ) (1.3 g, 12.3 mmol) was dissolved in 30 mL of distilled water (DI water), and then added to the reaction mixture, and a palladium catalyst (Pd(PPh3)4) (0.24 g, 0.21 mmol) was added. did. Then, the reaction mixture was stirred at reflux at 110 °C . After extraction, the obtained solid was subjected to column chromatography (eluent: MC (methylene chloride) and hexane) to perform compound 64A 1-(3,5-dimethylphenyl)-7-(trimethyllowyl)benzofuro[2, 1.4 g of 3-c]pyridine (yield of 87%) was obtained. The material was identified through mass and HPLC analysis.

HRMS(MALDI) calcd for C ₂₂ H ₂₃ GeNO: m/z: 390.06 Found: 392.04

(2) Synthesis of compound 64B

Compound 64A (1.4 g, 3.57 mmol) and iridium chloride (0.6 g, 1.70 mmol) were mixed with 15 mL of 2-ethoxyethanol and 5 mL of distilled water (DI water), and then After stirring under reflux for 24 hours, the temperature was lowered to room temperature. The resulting solid was separated by filtration, washed sufficiently in the order of water/methanol/hexane, and the obtained solid was dried in a vacuum oven to obtain 1.5 g of Compound 64B (yield of 83%). The obtained compound 64B was used in the next reaction without further purification.

(3) Synthesis of compound 64

Pentane-2,4-dione (0.19 g, 1.86 mmol) and potassium carbonate (K ₂ CO ₃ ) (0.26 g, 1.86 mmol) were added to compound 64B (1.50 g, 0.75 mmol), and 2-ethoxyethanol 15 mL were mixed and stirred at room temperature for 18 hours. After extraction, column chromatography (eluent: MC (methylene chloride) and hexane) was performed on the obtained solid. 0.68 g (85% yield) of compound 64 was obtained. The material was identified through mass and HPLC analysis.

HRMS(MALDI) calcd for C ₄₉ H ₅₂ Ge ₂ IrN ₂ O ₄ : m/z: 1070.44 Found: 1072.83

Synthesis Example 5: Synthesis of compound 66

In the synthesis of compound 66A, 8-bromo-2-(trimethyllowyl)furo[2,3-b:5,4 instead of 1-bromo-7-(trimethyllowyl)benzofuro[2,3-c]pyridine -c'] Using the same method as for the synthesis of compound 64 of Synthesis Example 4, except that -c']dipyridine (1.5 g, 4.10 mmol) was used, 0.55 g of compound 66 (80% yield) ) was obtained. The material was identified through mass and HPLC analysis.

HRMS(MALDI) calcd for C ₄₇ H ₅₀ Ge ₂ IrN ₄ O ₄ : m/z: 1072.42 Found: 1074.92

Synthesis Example 6: Synthesis of compound 145

2-(4-(t-butyl)naphthalene-2 instead of 2-(3,5-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxoborolane in the synthesis of compound 145A -yl) -4,4,5,5-tetramethyl-1,3,2-dioxoborolein (1.4 g, 4.52 mmol) was used, except that the synthesis of compound 64 of Synthesis Example 4 Using the same method as the method, 0.62 g (yield of 90%) of compound 145 was obtained. The material was identified through mass and HPLC analysis.

HRMS(MALDI) calcd for C ₆₁ H ₆₄ Ge ₂ IrN ₂ O ₄ : m/z: 1226.67 Found: 1229.31

Synthesis Example 7: Synthesis of compound 155

In the synthesis of compound 155A, 1-bromo-6-(trimethyllowyl)benzofuro[2,3-c] instead of 1-bromo-7-(trimethyllowyl)benzofuro[2,3-c]pyridine 0.60 g (87% yield) of Compound 155 was obtained by using the same method as for the synthesis of Compound 64 of Synthesis Example 4, except that pyridine (1.5 g, 4.1 mmol) was used. The material was identified through mass and HPLC analysis.

HRMS(MALDI) calcd for C ₆₁ H ₆₄ Ge ₂ IrN ₂ O ₄ : m/z: 1226.67 Found: 1228.99

Synthesis Example 8: Synthesis of compound 159

In the synthesis of compound 159A, 1-bromo-8-(trimethyllowyl)benzofuro[2,3-c]pyridine instead of 1-bromo-7-(trimethyllowyl)benzofuro[2,3-c]pyridine (1.5 g, 4.11 mmol) was used, and 3,7-diethylnonane-4,6-dione (0.3 g, 1.40 mmol) was used instead of pentane-2,4-dione in the synthesis of compound 159. Except for, by using the same method as for the synthesis of compound 64 of Synthesis Example 4, 0.6 g (yield of 80%) of compound 159 was obtained. The material was identified through mass and HPLC analysis.

HRMS(MALDI) calcd for C ₆₉ H ₈₀ Ge ₂ IrN ₂ O ₄ : m/z: 1338.89 Found: 1341.30

Example 1

A glass substrate patterned with ITO as an anode was cut into a size of 50 mm x 50 mm x 0.5 mm and ultrasonically cleaned for 5 minutes each using isopropyl alcohol and pure water, then irradiated with ultraviolet rays for 30 minutes and cleaned by exposure to ozone and vacuum deposition installed in the device.

Compound HT3 and F12 (p-dopant) were vacuum co-deposited on the anode at a weight ratio of 98:2 to form a hole injection layer with a thickness of 100 Å, and on the hole injection layer, compound HT3 was vacuum deposited to form a hole having a thickness of 1650 Å. A transport layer was formed.

Then, compound GH3 (host) and compound 1 (dopant) were co-deposited on the hole transport layer in a weight ratio of 92:8 to form a light emitting layer having a thickness of 400 Å.

Thereafter, the compound ET3 and LiQ (n-dopant) were co-deposited on the light emitting layer in a 50:50 volume ratio to form an electron transport layer having a thickness of 350 Å, and LiQ (n-dopant) was vacuum deposited on the electron transport layer to 10 Å An organic light-emitting device was manufactured by forming an electron injection layer with a thickness of 1000 Å and vacuum-depositing Al on the electron injection layer to form a cathode with a thickness of 1000 Å.

Examples 2-3, Comparative Examples 1 and 2

An organic light emitting diode was manufactured in the same manner as in Example 1, except that the compounds shown in Table 2 were used instead of Compound 1 as a dopant when the light emitting layer was formed.

For each organic light emitting device manufactured in Examples 1 to 3 and Comparative Examples 1 and 2, the maximum value of external quantum efficiency (Max EQE), the driving voltage, the maximum emission wavelength (λ _max ) of the emission spectrum, and the full width at half maximum width at half maximum, FWHM) was evaluated and the results are shown in Table 2. A current-voltmeter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used as evaluation devices.

of the light emitting layer
dopant Max EQE
(%) drive voltage
(V) Maximum emission wavelength (nm) half width
(nm) Example 1 compound 1 20.5 4.1 522 68 Example 2 compound 2 21 4.1 524 68 Example 3 compound 3 22.5 4.0 527 60 Comparative Example 1 compound A 20 4.2 544 80 Comparative Example 2 compound B 20 4.3 585 72

From Table 2, it can be seen that the organic light-emitting devices of Examples 1 to 3 have higher external quantum efficiency, lower driving voltage, and narrower half-width than the organic light-emitting devices of Comparative Examples 1 and 2.

Example 4

A glass substrate patterned with ITO as an anode was cut into a size of 50 mm x 50 mm x 0.5 mm and ultrasonically cleaned for 5 minutes each using isopropyl alcohol and pure water, then irradiated with ultraviolet rays for 30 minutes and cleaned by exposure to ozone and vacuum deposition installed in the device.

Compounds HT3 and F12 (p-dopant) were vacuum co-deposited on the anode at a weight ratio of 98:2 to form a hole injection layer having a thickness of 100 Å, and the compound HT3 was vacuum-deposited on the hole injection layer to form holes having a thickness of 1600 Å. A transport layer was formed.

Then, compound RH3 (host) and compound 64 (dopant) were co-deposited on the hole transport layer in a weight ratio of 97:3 to form a light emitting layer having a thickness of 400 Å.

Thereafter, the compound ET3 and LiQ (n-dopant) were co-deposited on the light emitting layer in a 50:50 volume ratio to form an electron transport layer with a thickness of 350 Å, and LiQ was vacuum deposited on the electron transport layer to form an electron injection layer with a thickness of 10 Å. was formed, and Al was vacuum-deposited on the electron injection layer to form a cathode having a thickness of 1000 Å, thereby manufacturing an organic light emitting device.

Examples 5 to 6 and Comparative Example 3

An organic light emitting diode was manufactured in the same manner as in Example 4, except that the compound shown in Table 3 was used instead of Compound 64 as a dopant when the light emitting layer was formed.

For each organic light emitting device manufactured in Examples 4 to 6 and Comparative Example 3, the maximum value of external quantum efficiency (Max EQE), the driving voltage, the maximum emission wavelength (λ _max ) of the emission spectrum, and the full width at full width at half maximum, FWHM) and the results are shown in Table 3. A current-voltmeter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used as evaluation devices.

of the light emitting layer
dopant Max EQE
(%) drive voltage
(V) Maximum emission wavelength (nm) life span
(relative value, %) Example 4 compound 64 23 4.9 610 100% Example 5 compound 66 23 4.9 624 105% Example 6 compound 145 24 4.8 634 110% Comparative Example 3 compound C 23 5.1 595 100%

From Table 3, it can be seen that the organic light emitting devices of Examples 4 to 6 have excellent external quantum efficiency and lifespan characteristics, and have low driving voltages.

In addition, it was found that the organic light emitting devices of Examples 4 to 6 had equal or higher external quantum efficiencies, lower driving voltages, and equal or superior lifetimes compared to the organic light emitting diodes of Comparative Example 3.

10: organic light emitting device
11: first electrode
15: organic layer
19: second electrode

Claims (20)

An organometallic compound represented by the following formula (1):
<Formula 1>
M ₁ (Ln ₁ ) _n1 (Ln ₂ ) _n2
In Formula 1,
M ₁ is a transition metal,
Ln ₁ is a ligand represented by the following formula 1-1,
Ln ₂ is a bidentate ligand,
n1 is 1, 2 or 3,
n2 is 0, 1 or 2,
<Formula 1-1>

In Formula 1-1,
X ₁ is C or N, X ₂ is C or N,
X ₁₁ is C(R ₁ ) or N, X ₁₂ is C(R ₂ ) or N, X ₁₃ is C(R ₃ ) or N, X ₁₄ is C(R ₄ ) or N,
Y ₁ is O, S, Se, C(R ₅ )(R ₆ ) or N(R ₅ ),
CY ₂ is a C ₅ -C ₃₀ carbocyclic group or a C ₁ -C ₃₀ heterocyclic group,
R ₁ to R ₆ , R ₁₀ and R ₂₀ are each independently a group represented by Formula 2-1, a group represented by Formula 2-2, 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 substituted or unsubstituted C ₁ -C ₆₀ Alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted A substituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, 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 a monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ) or -P(=O)(Q ₈ )(Q ₉ ),

In Formulas 2-1 and 2-2,
L ₁ is a single bond; a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group; Or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group;
a1 is 0, 1, 2, 3, 4 or 5;
When CY ₂ is a benzene group,
(i) at least one of R ₁ to R ₄ is a group represented by Formula 2-1 or a group represented by Formula 2-2,
(ii) at least one of R ₁₀ and R ₂₀ is a group represented by Formula 2-2,
when CY ₂ is not a benzene group, at least one of R ₁ to R ₄ and R ₁₀ and R ₂₀ is a group represented by Formula 2-1 or a group represented by Formula 2-2,
two R ₁₀ are optionally bonded to each other, a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group; Or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group; may form,
two or more of the plurality of R ₂₀ may be optionally bonded to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group; Or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group; may form,
two or more of R ₅ , R ₆ R ₁₀ and R ₂₀ are optionally bonded to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group; Or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group; may form,
b10 is 1 or 2,
b20 is 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;
*, *' and *" are each a binding site with a neighboring atom,
Said substituted C ₅ -C ₃₀ carbocyclic group, substituted C ₁ -C ₃₀ heterocyclic group, substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, substituted C ₁ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C ₆ -C ₆₀ arylthio group, substituted C ₁ -C ₆₀ heteroaryl group , among the substituents of a substituted C ₁ -C ₆₀ heteroaryloxy group, a substituted C ₁ -C ₆₀ heteroarylthio group, a substituted monovalent non-aromatic condensed polycyclic group and a substituted monovalent non-aromatic condensed polycyclic group at least one,
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 salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ an alkynyl group or a C ₁ -C ₆₀ alkoxy group;
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 salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₃ -C ₁₀ cycloalkyl group, 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 , C ₁ -C ₆₀ heteroaryloxy group, C ₁ -C ₆₀ heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q ₁₁ )(Q ₁₂ ) (Q ₁₃ ), -Ge(Q ₁₁ )(Q ₁₂ )(Q ₁₃ ), -N(Q ₁₄ )(Q ₁₅ ), -B(Q ₁₆ )(Q ₁₇ ), -P(=O)(Q ₁₈ )(Q ₁₉ ) or any combination thereof, substituted with a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, or a C ₁ -C ₆₀ alkoxy group;
C ₃ -C ₁₀ cycloalkyl group, 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 aryl Oxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, C ₁ -C ₆₀ heteroaryloxy group, C ₁ -C ₆₀ heteroarylthio group, monovalent non-aromatic condensed polycyclic group or monovalent non-aromatic condensed heteropolycyclic group;
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 salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, 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 group, 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, C ₁ -C ₆₀ heteroaryloxy group, C ₁ -C ₆₀ heteroarylthi Group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q ₂₁ )(Q ₂₂ )(Q ₂₃ ), -Ge(Q ₂₁ )(Q ₂₂ )(Q ₂₃ ) , -N(Q ₂₄ )(Q ₂₅ ), -B(Q ₂₆ )(Q ₂₇ ), -P(=O)(Q ₂₈ )(Q ₂₉ ), C ₃ - C ₁₀ cycloalkyl group, 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 condensed polycyclic group or monovalent non-aromatic condensed heteropolycyclic group; or
-Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -Ge(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₄ )(Q ₃₅ ), -B(Q ₃₆ )(Q ₃₇ ) ) or -P(=O)(Q ₃₈ )(Q ₃₉ );
The Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cya No group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted substituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or an unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ - C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted a substituted C ₁ -C ₆₀ heteroaryloxy group, a substituted or unsubstituted C ₁ -C ₆₀ heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group; or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group; According to claim 1,
M ₁ is iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm) or rhodium ( Rh), an organometallic compound. According to claim 1,
M ₁ is Ir,
An organometallic compound, wherein the sum of n1 + n2 is 3. According to claim 1,
CY ₂ is a benzene group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group , quinazoline group, phenanthroline group, benzofuran group, benzothiophene group, fluorene group, carbazole group, dibenzofuran group, dibenzothiophene group, dibenzosilol group, azafluorene group, azacarba a zole group, an azadibenzofuran group, an azadibenzothiophene group or an azadibenzosilol group; or
A group represented by the following formula 8-1 or 8-2; phosphorus, an organometallic compound:
<Formula 8-1>

<Formula 8-2>

In Formulas 8-1 and 8-2,
Y ₈₁ to Y ₈₄ are each independently a single bond, O, S, N(R ₈₁ ), C(R ₈₁ )(R ₈₂ ), Si(R ₈₁ )(R ₈₂ ), C(=O), S (=O), S(=O) ₂ , B(R ₈₁ ), P(R ₈₁ ) or P(=O)(R ₈₁ ),
CY ₈₁ to CY ₈₃ are each independently, a benzene group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a triazine group, a quinoline group, Isoquinoline group, quinoxaline group, quinazoline group, phenanthroline group, benzofuran group, benzothiophene group, fluorene group, carbazole group, dibenzofuran group, dibenzothiophene group, dibenzosilol group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, or an azadibenzosilol group;
For the description of R ₈₁ and R ₈₂ independently of each other, refer to the description of R ₁₀ and R ₂₀ in claim 1 . According to claim 1,
CY ₂ is an organometallic compound represented by any one of the following Chemical Formulas 2-1 to 2-22:

In Formulas 2-1 to 2-22,
X ₂₁ and X ₂₂ are each independently O, S, N(R _29a ), C(R _29a )(R _29b ) or Si(R _29a )(R _29b ),
For the description of R ₂₁ to R ₂₈ , R _29a and R _29b independently of each other, refer to the description of R ₂₀ in claim 1 ,
R ₂₁ to R ₂₈ , R _29a and R _29b may be optionally bonded to two or more adjacent to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group; or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group;
* and *' are binding sites with neighboring atoms, respectively. According to claim 1,
L ₁ is a single bond, a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, fluorine lanthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, perylenylene group, pentaphenylene group, hexacenylene group, pentacenylene group, thiophenylene group, furanylene group, carbazolylene group, indolylene group, Isoindolylene group, benzofuranylene group, benzothiophenylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosilolylene group, pyridinylene group, imida Zolylene group, pyrazolylene group, thiazolylene group, isothiazolylene group, oxazolylene group, isoxazolylene group, thiadiazolylene group, oxadiazolylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, tria Zinylene group, quinolinylene group, isoquinolinylene group, benzoquinolinylene group, phthalazinylene group, naphthyridinylene group, quinoxalinylene group, quinazolinylene group, cinolinylene group, phenanthridinylene group, Acridinylene group, phenanthrolinenylene group, phenazinylene group, benzoimidazolylene group, isobenzothiazolylene group, benzoxazolylene group, isobenzoxazolylene group, triazolylene group, tetrazolylene group, imidazopyridinyl a ren group, an imidazopyrimidinylene group, or an azacarbazolylene group; or
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl Renyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindoleyl group, benzofuranyl group, benzothiophenyl group , dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazole Diary, isoxazolyl group, thiadiazolyl group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, isobenzothiazolyl group, benzoxazolyl group , isobenzoxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group or any combination thereof substituted with, phenylene group, naphthylene group, fluorine group Nylene group, spiro-bifluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenyl group Rene group, perylenylene group, pentaphenylene group, hexacenylene group, pentacenylene group, thiophenylene group, furanylene group, carbazolylene group, indolylene group, isoindolylene group, benzofuranylene group, benzothiophenylene group, Dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosilolylene group, pyridinylene group, imidazolylene group, pyrazolylene group, thiazolylene group, isothiazolylene group , oxazolylene group, isoxazolylene group, thiadiazolylene group, oxadiazolylene group, pyrazinylene group, pyrimidinylene group, Pyridazinylene group, triazinylene group, quinolinylene group, isoquinolinylene group, benzoquinolinylene group, phthalazinylene group, naphthyridinylene group, quinoxalinylene group, quinazolinylene group, cinolinylene group , phenanthridinylene group, acridinylene group, phenanthrolinylene group, phenazinylene group, benzoimidazolylene group, isobenzothiazolylene group, benzoxazolylene group, isobenzoxazolylene group, triazolylene group, tetrazolylene group , an imidazopyridinylene group, an imidazopyrimidinylene group, or an azacarbazolylene group; phosphorus, an organometallic compound. According to claim 1,
Any one of R ₁ to R ₄ is a group represented by Formula 2-1 or a group represented by Formula 2-2, and the remainder is hydrogen, respectively. According to claim 1,
Any one of R ₁ to R ₄ , R ₁₀ and R ₂₀ is a group represented by Formula 2-2, an organometallic compound. According to claim 1,
R ₁ to R ₆ , R ₁₀ and R ₂₀ are each independently a group represented by Formula 2-1, a group represented by Formula 2-2, hydrogen, deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group or C ₁ -C ₆₀ alkoxy group; or
An organometallic compound, which is a group represented by any one of Formulas 9-1 to 9-43, 9-201 to 9-237, 10-1 to 10-129, and 10-201 to 10-350:

In Formulas 9-1 to 9-43, 9-201 to 9-237, 10-1 to 10-129, and 10-201 to 10-350, * is a bonding site with an adjacent atom, Ph is a phenyl group, TMS is a trimethylsilyl group, and TMG is a trimethylgermyl group. According to claim 1,
Ln ₁ is an organometallic compound represented by any one of the following formulas 3-1 to 3-4:

in Formulas 3-1 to 3-4
For a description of X ₁ , X ₂ , Y ₁ , CY ₂ , X ₁₁ to X ₁₄ , R ₂₀ and b20, see paragraph 1,
For the description of R ₁₁ , R ₁₂ and R ₁₄ independently of each other, refer to the description of R ₁₀ in claim 1,
* and *' are binding sites with neighboring atoms, respectively. According to claim 1,
Ln ₂ is an organometallic compound represented by any one of the following formulas 5, 6, and 8-1 to 8-11:
<Formula 5>

<Formula 6>

In Formulas 5, 6 and 8-1 to 8-11,
X ₃ is C or N, X ₄ is C or N,
X ₅ and X ₆ are each independently O or S,
CY ₃ and CY ₄ are each independently a C ₅ -C ₃₀ carbocyclic group or a C ₁ -C ₃₀ heterocyclic group,
R ₃₀ , R ₄₀ and A ₁ to A ₇ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group , hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted A substituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, A substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ - C ₆₀ aryloxy group, 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, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q ₁ )(Q ₂ )(Q ₃ ), -Ge(Q ₁ )(Q ₂ )(Q ₃ ) or -B(Q ₁ )(Q ₂ ),
b30 and b40 are, independently of each other, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10,
Ph is a phenyl group,
* and *' are binding sites with neighboring atoms, respectively. According to claim 1,
Ln ₂ is an organometallic compound selected from the following formulas 5-1 to 5-129:

In Formulas 5-1 to 5-129,
X ₅₁ is O, S, N(R ₅₄ ), C(R ₅₄ )(R ₅₅ ) or Si(R ₅₄ )(R ₅₅ ),
R ₅₁ to R ₅₅ and R ₆₁ to R ₆₇ are each independently 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, -SF ₅ , a C ₁ -C ₂₀ alkyl group or a C ₁ -C ₂₀ alkoxy group;
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 salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₁₀ alkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclo Octyl group, bicyclo [2.2.1] heptanyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, C ₁ -C ₂₀ alkylphenyl group , a C ₁ -C ₂₀ alkyl group or a C ₁ -C ₂₀ alkoxy group substituted with a naphthyl group, a pyridinyl group, a pyrimidinyl group, or any combination thereof;
Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, bicyclo[2.2.1]heptanyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group , phenyl group, biphenyl group, C ₁ -C ₂₀ alkylphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, Thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindole Diary, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthrolinyl group, benzimidazolyl group , benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzo a thiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, or an imidazopyrimidinyl group;
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 salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, cyclopentyl group, cyclo Hexyl group, cycloheptyl group, cyclooctyl group, bicyclo[2.2.1]heptanyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group , C ₁ -C ₂₀ Alkylphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group , imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, Indazolyl group, furinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, Benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, dibenzo Silolyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, -Si(Q ₁₁ )(Q ₁₂ )(Q ₁₃ ), -B(Q ₁₁ )(Q ₁₂ ) ), -N(Q ₁₁ )(Q ₁₂ ) or any combination thereof, substituted with a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a bicyclo[2.2.1]heptanyl group, adamanta Nyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, C ₁ -C ₂₀ alkylphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group , fluoranthenyl group, triphenylenyl group, pyrenyl group, Chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, Pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenane Trollinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, or an imidazopyrimidinyl group; or
-Si(Q ₁ )(Q ₂ )(Q ₃ ), -Ge(Q ₁ )(Q ₂ )(Q ₃ ), -B(Q ₁ )(Q ₂ ) or -N(Q ₁ )(Q ₂ ) );ego,
Q ₁ to Q ₃ and Q ₁₁ to Q ₁₃ are each independently,
Methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, 2-methylbutyl group, sec-pen tyl group, tert-pentyl group, neo-pentyl group, 3-pentyl group, 3-methyl-2-butyl group, phenyl group, biphenyl group, C ₁ -C ₂₀ alkylphenyl group or naphthyl group; or
methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, iso pentyl group, 2-methylbutyl group, sec-pentyl group, tert-pentyl group, neo-pentyl group, 3-pentyl group, 3-methyl-2-butyl group, phenyl group or naphthyl group;
b51 and b54 are each independently 1 or 2,
b53 and b55 are, independently of each other, 1, 2 or 3,
b52 and b56 are, independently of each other, 1, 2, 3 or 4,
Ph is a phenyl group,
Ph-d5 is a phenyl group in which all hydrogens are substituted with deuterium,
* and *' are binding sites with neighboring atoms. According to claim 1,
The organometallic compound is a compound represented by any one of the following formulas 11-1 to 11-8, an organometallic compound:

In Formulas 11-1 to 11-8,
For a description of M ₁ , X ₁ , X ₂ , Y ₁ , CY ₂ , X ₁₁ to X ₁₄ , R ₂₀ and b20, see claim 1,
For the description of R ₁₁ , R ₁₂ and R ₁₄ independently of each other, refer to the description of R ₁₀ in claim 1,
X ₃ is C or N, X ₄ is C or N,
X ₅ and X ₆ are each independently O or S,
CY ₃ and CY ₄ are each independently a C ₅ -C ₃₀ carbocyclic group or a C ₁ -C ₃₀ heterocyclic group,
R ₃₀ , R ₄₀ and A ₁ to A ₇ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group , hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted A substituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, A substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ - C ₆₀ aryloxy group, 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, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q ₁ )(Q ₂ )(Q ₃ ), -Ge(Q ₁ )(Q ₂ )(Q ₃ ) or -B(Q ₁ )(Q ₂ ),
b30 and b40 are, independently of each other, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10. According to claim 1,
The organometallic compound is electrically neutral, the organometallic compound. According to claim 1,
Any one of the following compounds 1 to 322, an organometallic compound:

. a first electrode;
a second electrode; and
an organic layer disposed between the first electrode and the second electrode and including a light emitting layer;
The organic layer comprises at least one organometallic compound of any one of claims 1 to 15, an organic light emitting device. 17. The method of claim 16,
The organometallic compound is included in the light emitting layer, an organic light emitting device. 18. The method of claim 17,
The light emitting layer further comprises a host, and the content of the host is greater than the content of the organometallic compound, the organic light emitting device. 17. The method of claim 16,
The first electrode is an anode,
The second electrode is a cathode,
The organic layer further includes a hole transport region disposed between the first electrode and the light emitting layer and an electron transport region disposed between the light emitting layer and the second electrode,
The hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof,
The electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof. An electronic device comprising the organic light emitting device of claim 16 .

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