KR102466672B1 - Organometallic compound and organic light emitting device including the same - Google Patents

Abstract

Disclosed are an organometallic compound and an organic light emitting device including the organometallic compound.

Description

Organometallic compound and organic light emitting device including the same

An organometallic compound and an organic light emitting device including the same are presented.

An organic light emitting device is a self-luminous device and has a wide viewing angle and excellent contrast, a fast response time, excellent luminance, driving voltage and response speed characteristics, and multi-colorization.

According to one 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 an emission layer. A hole transport region may be provided between the anode and the light emitting layer, and an electron transport region may be provided between the light emitting layer and the cathode. Holes injected from the anode move to the light emitting layer via the hole transport region, and electrons injected from the cathode move to the light emitting layer via the electron transport region. The holes and electrons recombine in the light emitting layer region to generate excitons. As these excitons change from the excited state to the ground state, light is generated.

It is to provide a novel organometallic compound and an organic light emitting device employing the same.

According to one aspect, an organometallic compound represented by Formula 1 is provided:

<Formula 1>

M(L ₁ ) _n1 (L ₂ ) _n2

<Formula 2A>

<Formula 2A>

M in Formula 1 is iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), tholium (Tm) And selected from rhodium (Rh),

In Formula 1, L ₁ is selected from ligands represented by Formula 2A, n1 is 1, 2, or 3, and when n1 is 2 or more, two or more L _1s are the same as or different from each other;

In Formula 1, L ₂ is selected from monovalent organic ligands, divalent organic ligands, trivalent organic ligands, and tetravalent organic ligands, n2 is 0, 1, 2, 3, or 4, and when n2 is 2 or more, 2 or more L ₂ are the same as or different from each other;

In Formula 1, L ₁ and L ₂ are different from each other,

In Formula 2A, R ₁ to R ₃ are each independently a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, or a substituted or unsubstituted C ₂ -C ₆₀ alky group. Nyl 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 ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or An unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and -Si(Q ₅₁ )(Q ₅₂ ) (Q ₅₃ ) selected from,

In Formula 2A, X ₁ is selected from O, S, S(=O) ₂ , N(R ₂₁ ) and Si(R ₂₂ )(R ₂₃ );

In Formula 2A, Y ₁ is a binding site to N, C(R ₄₁ ) or a pyridine ring, Y ₂ is a binding site to N, C(R ₄₂ ) or a pyridine ring, and Y ₃ is N, C(R 41 ) ₄₃ ) or a binding site to a pyridine ring, Y ₄ is a binding site to N, C(R ₄₄ ) or a pyridine ring, Y ₅ is N or C(R ₄₅ ), Y ₆ is N or C(R ₄₆ ), Y ₇ is N or C (R ₄₇ ), Y ₈ is N or C (R ₄₈ ), and one of Y ₁ to Y ₄ is a binding site with a pyridine ring;

In Formula 2A, R ₁₁ , R ₂₁ to R ₂₃ and R ₄₁ to R ₄₈ are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , a hydroxyl group, a cyano group, Nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt thereof, sulfonic acid group or its salt thereof, phosphoric acid group or its salt thereof, 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 Cyclic C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ Aryl group, substituted or unsubstituted C ₆ -C ₆₀ Aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ Arylthio group, substituted or unsubstituted C ₁ -C ₆₀ Heteroaryl group, substituted or unsubstituted A monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), is selected from -B(Q ₆ )(Q ₇ ) and -P(=O)(Q ₈ )(Q ₉ ), and two or more R ₁₁ are optionally bonded to each other to form a saturated or unsaturated C ₄ -C ₆₀ ring. may form, two or more of R ₄₁ to R ₄₄ may be optionally bonded to each other to form a saturated or unsaturated C ₄ -C ₆₀ ring, and two or more of R ₄₅ to R ₄₈ are optionally bonded to each other can form saturated or unsaturated C ₄ -C ₆₀ rings;

In Formula 2A, b1 is selected from an integer of 0 to 3, b4 is selected from an integer of 1 to 4,

* and *' in Formula 2A are binding sites to M in Formula 1,

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 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 Substituents of an aryloxy group, a substituted C ₆ -C ₆₀ arylthio group, a substituted C ₁ -C ₆₀ heteroaryl group, a substituted monovalent non-aromatic condensed polycyclic group, and a substituted monovalent non-aromatic hetero condensed polycyclic group at least one of

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , a hydroxyl group, a cyano group, a nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt thereof, sulfonic acid group or its salt thereof, phosphoric acid group or its salt thereof, C ₁ -C ₆₀ Alkyl group, C ₂ -C ₆₀ Alkenyl group, C ₂ -C ₆₀ an alkynyl group and 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 , a hydroxyl group, a cyano group, a nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt thereof, sulfonic acid group or its salt thereof, phosphoric acid group or its 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 , monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, -N(Q ₁₁ )(Q ₁₂ ), -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ), -B(Q ₁₆ )(Q ₁₇ ) and -P(=O)(Q ₁₈ )(Q ₁₉ ) Substituted with at least one selected from a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and 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 an oxy group, a C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic hetero condensed polycyclic group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , a hydroxyl group, a cyano group, a nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt thereof, sulfonic acid group or its salt thereof, phosphoric acid group or its 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, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic hetero condensed polycyclic group , -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ), -B(Q ₂₆ )(Q ₂₇ ) and -P(=0)(Q ₂₈ )(Q ₂₉ ) substituted with at least one selected from, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a C ₁ -C ₁₀ heterocycloalkenyl group, a C ₆ -C ₆₀ an aryl group, a C ₆ -C ₆₀ aryloxy group, a C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic hetero condensed polycyclic group; and

-N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), -B(Q ₃₆ )(Q ₃₇ ) and -P(=0)(Q ₃₈ )(Q ₃₉ );

is selected from

Wherein Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ , Q ₃₁ to Q ₃₉ and Q ₅₁ to Q ₅₃ 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, 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 ₁ -C ₁₀ heterocycloalkenyl 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 hetero group It is selected from an aryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic hetero condensed 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, including a light emitting layer, and including at least one organometallic compound represented by Chemical Formula 1.

The organometallic compound may be included in the light emitting layer.

The organometallic compound included in the emission layer serves as a dopant, and the emission layer may further include a host.

Since the organometallic compound has excellent electrical properties and thermal stability, an organic light emitting device employing the organometallic compound has excellent driving voltage, efficiency, power, color purity, and lifetime characteristics.

1 is a schematic cross-sectional view of an organic light emitting device according to an embodiment.

The organometallic compound is represented by Formula 1 below:

<Formula 1>

M(L ₁ ) _n1 (L ₂ ) _n2

M in Formula 1 is iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), tholium (Tm) and rhodium (Rh).

For example, M in Formula 1 may be selected from iridium, platinum, osmium, and rhodium.

According to one embodiment, M in Formula 1 may be selected from iridium and platinum, but is not limited thereto.

In Formula 1, L ₁ is selected from ligands represented by Formula 2A, n1 is 1, 2, or 3, and when n1 is 2 or more, two or more L ₁ may be the same as or different from each other.

<Formula 2A>

In Formula 1, L ₂ is selected from monovalent organic ligands, divalent organic ligands, trivalent organic ligands, and tetravalent organic ligands, n2 is 0, 1, 2, 3, or 4, and when n2 is 2 or more, 2 or more L ₂ may be the same as or different from each other.

In Formula 1, L ₁ and L ₂ are different from each other.

For example, n1 in Chemical Formula 1 may be 1.

As another example, the organometallic compound represented by Chemical Formula 1 may not have the form of a salt consisting of ion pairs and may be neutral.

According to one embodiment, M in Formula 1 is Ir, and n1 + n2 is 3; Alternatively, M is Pt, n1 + n2 is 2, and the organometallic compound represented by Chemical Formula 1 may be neutral.

In Formula 2A, R ₁ to R ₃ are each independently a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, or a substituted or unsubstituted C ₂ -C ₆₀ alky group. Nyl 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 ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or An unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and -Si(Q ₅₁ )(Q ₅₂ ) (Q ₅₃ ).

For example, in Formula 2A, R ₁ to R ₃ are independently of each other,

C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group and -Si(Q ₅₁ )(Q ₅₂ )(Q ₅₃ );

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , a hydroxyl group, a cyano group, a nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt thereof, sulfonic acid group or its salt thereof, phosphoric acid group or its salt thereof, C ₁ -C ₁₀ Alkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclo Among the octyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, pyridinyl group and pyrimidinyl group a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group, substituted with at least one selected;

Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, Phenyl 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, pyrazole diary, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl 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, isobenzothia Zolyl group, benzooxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazole Diary, imidazopyridinyl group and imidazopyrimidinyl group; and

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , a hydroxyl group, a cyano group, a nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt thereof, sulfonic acid group or its salt thereof, phosphoric acid group or its salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, cyclopentyl group, cyclo Hexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl 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, purinyl group, quinolinyl group, iso Quinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzooxa Zolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazophy A cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, substituted with at least one selected from a ridinyl group and an imidazopyrimidinyl group ), cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, Pyrroyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, p Ridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazoly Nyl group, cinolinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzooxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazole diyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group and imidazopyrimidinyl group;

is selected from

The Q ₅₁ to Q ₅₃ are independently from each other,

-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 and -CD ₂ CDH ₂ ;

n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group and naph til group; and

Substituted with at least one selected from heavy hydrogen, a C ₁ -C ₁₀ alkyl group and a phenyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group and naphthyl group;

It may be selected from, but is not limited thereto.

As another example, in Formula 2A, R ₁ to R ₃ are independently of each other,

-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 and -CD ₂ CDH ₂ ;

n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group, naph a tyl group and -Si(Q ₅₁ )(Q ₅₂ )(Q ₅₃ ); and

Substituted with at least one selected from heavy hydrogen, a C ₁ -C ₁₀ alkyl group and a phenyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group and naphthyl group;

is selected from

The Q ₅₁ to Q ₅₃ are independently from each other,

-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 and -CD ₂ CDH ₂ ;

n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group and naph til group; and

Substituted with at least one selected from heavy hydrogen, a C ₁ -C ₁₀ alkyl group and a phenyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group and naphthyl group;

can be selected from.

According to one embodiment, the Q ₅₁ to Q ₅₃ may be each independently a methyl group or an ethyl group.

According to one embodiment, in Formula 2A

R ₁ to R ₃ are all the same;

R ₁ and R ₃ are the same and R ₂ is different from R ₁ ; or

All of R ₁ to R ₃ may be different from each other.

In Formula 2A, X ₁ may be selected from O, S, S(=0) ₂ , N(R ₂₁ ), and Si(R ₂₂ )(R ₂₃ ).

For example, X ₁ in Formula 2A is O, S, and N (R ₂₁ ) can be selected from.

According to one embodiment, X ₁ in Formula 2A may be O, but is not limited thereto.

In Formula 2A, R ₁₁ , R ₂₁ to R ₂₃ and R ₄₁ to R ₄₈ are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , a hydroxyl group, a cyano group, Nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt thereof, sulfonic acid group or its salt thereof, phosphoric acid group or its salt thereof, 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 Cyclic C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ Aryl group, substituted or unsubstituted C ₆ -C ₆₀ Aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ Arylthio group, substituted or unsubstituted C ₁ -C ₆₀ Heteroaryl group, substituted or unsubstituted A monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), -B(Q ₆ ) (Q ₇ ) and -P(=0) (Q ₈ ) (Q ₉ ).

For example, in Formula 2A, R ₁₁ , R ₂₁ to R ₂₃ and R ₄₁ to R ₄₈ are each independently

Hydrogen, heavy hydrogen, -F, -Cl, -Br, -I, -SF ₅ , hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid groups or salts thereof, phosphoric acid groups or salts thereof, C ₁ -C ₂₀ alkyl groups and C ₁ -C ₂₀ alkoxy groups;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , a hydroxyl group, a cyano group, a nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt thereof, sulfonic acid group or its salt thereof, phosphoric acid group or its salt thereof, C ₁ -C ₁₀ Alkyl group, C ₁ -C ₁₀ 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 ₁₄ aryl group, C ₁ -C ₁₄ heteroaryl group, monovalent a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group, substituted with at least one selected from a non-aromatic condensed polycyclic group and a monovalent non-aromatic hetero condensed polycyclic 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 ₁₄ aryl group, C ₁ -C ₁₄ hetero an aryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic hetero condensed polycyclic group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , a hydroxyl group, a cyano group, a nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt thereof, sulfonic acid group or its salt thereof, phosphoric acid group or its salt thereof, C ₁ -C ₂₀ Alkyl group, C ₁ -C ₂₀ 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 ₁₄ aryl group, C ₁ -C ₁₄ heteroaryl group, monovalent A C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, C substituted with at least one selected from a non-aromatic condensed polycyclic group and a monovalent non-aromatic heterocondensed polycyclic group; ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₁₄ aryl group, C ₁ -C ₁₄ heteroaryl group, monovalent non-aromatic condensed polycyclic group, and monovalent non-aromatic hetero condensed polycyclic group; and

-N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ) and -P(=0)(Q ₈ )(Q ₉ );

is selected from

Wherein Q ₁ to Q ₉ are each independently a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, or a 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 - It is selected from a C ₁₄ aryl group, a substituted or unsubstituted C ₁ -C ₁₄ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group. can

As another example, in Formula 2A, R ₁₁ , R ₂₁ to R ₂₃ and R ₄₁ to R ₄₈ are independently of each other,

Hydrogen, heavy hydrogen, -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 and 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 , a hydroxyl group, a cyano group, a nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt thereof, sulfonic acid group or its salt thereof, phosphoric acid group or its salt thereof, C ₁ -C ₁₀ Alkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclo Among the octyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, pyridinyl group and pyrimidinyl group a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group, substituted with at least one selected;

Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, Phenyl 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, pyrazole diary, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl 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, isobenzothia Zolyl group, benzooxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazole Diary, imidazopyridinyl group and imidazopyrimidinyl group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , a hydroxyl group, a cyano group, a nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt thereof, sulfonic acid group or its salt thereof, phosphoric acid group or its salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, cyclopentyl group, cyclo Hexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl 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, purinyl group, quinolinyl group, iso Quinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzooxa Zolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazophy A cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, substituted with at least one selected from a ridinyl group and an imidazopyrimidinyl group ), cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, Pyrroyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, p Ridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazoly Nyl group, cinolinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzooxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazole diyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group and imidazopyrimidinyl group; and

-B(Q ₆ )(Q ₇ ) and -P(=0)(Q ₈ )(Q ₉ );

is selected from

Q ₆ to Q ₉ are independently of each other,

-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 and -CD ₂ CDH ₂ ;

n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group and naph til group; and

Substituted with at least one selected from heavy hydrogen, a C ₁ -C ₁₀ alkyl group and a phenyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group and naphthyl group;

It may be selected from, but is not limited thereto.

According to one embodiment, R ₁₁ , R ₂₁ to R ₂₃ and R ₄₁ to R ₄₈ in Formula 2A are independently of each other,

Hydrogen, heavy hydrogen, -F, cyano group, nitro group, -SF ₅ , 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, sec-pentyl group, tert-pentyl group, n-hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, n-heptyl group, isoheptyl group, sec-heptyl group , tert-heptyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl group, n-decyl group, isode Sil group, sec-decyl group, tert-decyl group, methoxy group, ethoxy group, propoxy group, butoxy group, pentoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group , norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, pyridinyl group and pyrimidinyl group;

Heavy hydrogen, -F, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , cyano group, nitro group, C ₁ -C ₁₀ alkyl group, C ₁ -C ₁₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptene A methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-, substituted with at least one selected from the group consisting of a nyl group, a phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group. butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, n-hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, n-heptyl group, isoheptyl group, sec-heptyl group, tert-heptyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl group, n-de Sil group, isodecyl group, sec-decyl group, tert-decyl group, methoxy group, ethoxy group, propoxy group, butoxy group, pentoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamanta an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group; and

-B(Q ₆ )(Q ₇ ) and -P(=0)(Q ₈ )(Q ₉ );

is selected from

Q ₆ to Q ₉ are independently of each other,

-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 and -CD ₂ CDH ₂ ;

n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group and naph til group; and

Substituted with at least one selected from heavy hydrogen, a C ₁ -C ₁₀ alkyl group and a phenyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group and naphthyl group;

can be selected from.

According to another embodiment, R ₁₁ , R ₂₁ to R ₂₃ and R ₄₁ to R ₄₈ in Formula 2A are each independently hydrogen, deuterium, -F, cyano group, nitro group, -SF ₅ , -CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , groups represented by the following formulas 9-1 to 9-17 and the following formulas 10-1 to 10-30 It may be selected from the group represented by, but is not limited to:

In Formulas 9-1 to 9-17 and 10-1 to 10-30, * is a binding site with a neighboring atom.

In Formula 2A, b1 may be selected from an integer of 0 to 3, and b4 may be selected from an integer of 1 to 4.

According to another embodiment, R ₂₁ to R ₂₃ in X ₁ of Formula 2A are independently of each other,

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, phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, A pyridinyl group, a pyrimidinyl group, and a triazinyl group; and

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , 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, and a phosphoric acid group or a salt thereof substituted with at least one C ₁ -C ₂₀ alkyl group, 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 , a hydroxyl group, a cyano group, a nitro group, Among amino groups, amidino groups, hydrazine groups, hydrazone groups, carboxylic acid groups or salts thereof, sulfonic acid groups or salts thereof, phosphoric acid groups or salts thereof, C ₁ -C ₂₀ alkyl groups, C ₁ -C ₂₀ alkoxy groups, phenyl groups and naphthyl groups A cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, and a cyclohexenyl group, substituted with at least one selected from group, cycloheptenyl group, phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrimidinyl group and tria holding;

can be selected from.

In Formula 2A, b1 represents the number of R ₁₁ , when b1 is 2 or more, two or more R ₁₁ are the same as or different from each other, and b4 represents the number of -Si(R ₁ )(R ₂ )(R ₃ ) As such, when b4 is 2 or more, 2 or more -Si(R ₁ )(R ₂ )(R ₃ ) are the same as or different from each other.

For example, in Formula 2A, b1 may be 0, 1 or 2, and b4 may be 1 or 2, but is not limited thereto.

As another example, in Formula 2A, b1 may be 0, 1, or 2, and b4 may be 1, but is not limited thereto.

Two or more R ₁₁ in Formula 2A are optionally bonded to each other to form a saturated or unsaturated C ₄ -C ₆₀ ring (eg, cyclopentane, cyclohexane, adamantane, norbonane, benzene, pyridine, pyrimidine, naphthalene , pyrene, chrysene, etc.), and two or more of R ₄₁ to R ₄₄ are optionally bonded to each other to form a saturated or unsaturated C ₄ -C ₆₀ ring (eg, cyclopentane, cyclohexane, a dathanane, norbonane, benzene, pyridine, pyrimidine, naphthalene, pyrene, chrysene, etc.), and two or more of R ₄₅ to R ₄₈ are optionally bonded to each other to form saturated or unsaturated C ₄ -C ₆₀ rings (eg, cyclopentane, cyclohexane, adamantane, norbonane, benzene, pyridine, pyrimidine, naphthalene, pyrene, chrysene, etc.) can be formed.

For example, two R ₁₁ groups in Formula 2A may combine with each other to form substituted or unsubstituted cyclohexane or substituted or unsubstituted benzene, but is not limited thereto.

According to one embodiment, all of Y ₁ to Y ₈ in Formula 2A may not be N.

According to another embodiment, Y ₁ or Y ₃ in Formula 2A may be N.

According to another embodiment, Y ₅ or Y ₆ in Formula 2A may be N.

According to another embodiment, one or two of Y ₁ , Y ₃ , Y ₅ and Y ₆ in Formula 2A may be N.

According to an embodiment, L ₁ in Formula 1 may be selected from ligands represented by Formulas 2A-1 to 2A-16:

In Formulas 2A-1 to 2A-16, descriptions of R ₁ to R ₃ , X ₁ , Y ₁ to Y ₈ , R ₁₁ , b1 and b4 are the same as described herein, and descriptions of R ₁₅ are R It is the same as the description for ₁₁ , b5 is selected from an integer of 0 to 8, and * and *' are binding sites with M in Formula 1.

According to one embodiment,

In Formulas 2A-1 to 2A-16, Y ₁ is C(R ₄₁ ), Y ₂ is C(R ₄₁ ), Y ₃ is C(R ₄₃ ), Y ₄ is C(R ₄₄ ), Y ₅ is C(R ₄₅ ), Y ₆ is C(R ₄₆ ), Y ₇ is C(R ₄₇ ), and Y ₈ is C(R ₄₈ );

Among Formulas 2A-1, 2A-2, 2A-4, 2A-5, 2A-6, 2A-8, 2A-9, 2A-10, 2A-12, 2A-13, 2A-14 and 2A-16 Y ₁ is N, Y ₄ is C(R ₄₄ ), Y ₅ is C(R ₄₅ ), Y ₆ is C(R ₄₆ ), Y ₇ is C(R ₄₇ ), Y ₈ is C (R ₄₈ );

Among Formulas 2A-1, 2A-2, 2A-4, 2A-5, 2A-6, 2A-8, 2A-9, 2A-10, 2A-12, 2A-13, 2A-14 and 2A-16 Y ₁ is C(R ₄₁ ), Y ₄ is C(R ₄₄ ), Y ₅ is N, Y ₆ is C(R ₄₆ ), Y ₇ is C(R ₄₇ ), Y ₈ is C (R ₄₈ );

Among Formulas 2A-1, 2A-2, 2A-4, 2A-5, 2A-6, 2A-8, 2A-9, 2A-10, 2A-12, 2A-13, 2A-14 and 2A-16 Y ₁ is C(R ₄₁ ), Y ₄ is C(R ₄₄ ), Y ₅ is C(R ₄₅ ), Y ₆ is N, Y ₇ is C(R ₄₇ ), Y ₈ is C (R ₄₈ );

Among Formulas 2A-1, 2A-2, 2A-4, 2A-5, 2A-6, 2A-8, 2A-9, 2A-10, 2A-12, 2A-13, 2A-14 and 2A-16 Y ₁ is N, Y ₄ is C(R ₄₄ ), Y ₅ is N, Y ₆ is C(R ₄₆ ), Y ₇ is C(R ₄₇ ), Y ₈ is C(R ₄₈ ) is;

Among Formulas 2A-1, 2A-2, 2A-4, 2A-5, 2A-6, 2A-8, 2A-9, 2A-10, 2A-12, 2A-13, 2A-14 and 2A-16 Y ₁ is N, Y ₄ is C(R ₄₄ ), Y ₅ is C(R ₄₅ ), Y ₆ is N, Y ₇ is C(R ₄₇ ), Y ₈ is C(R ₄₈ ) is;

In Formulas 2A-3, 2A-7, 2A-11 and 2A-15, Y ₃ is N, Y ₄ is C(R ₄₄ ), Y ₅ is C(R ₄₅ ), and Y ₆ is C(R ₄₆ ), Y ₇ is C(R ₄₇ ), Y ₈ is C(R ₄₈ );

In Formulas 2A-3, 2A-7, 2A-11 and 2A-15, Y ₃ is C(R ₄₃ ), Y ₄ is C(R ₄₄ ), Y ₅ is N, and Y ₆ is C(R ₄₆ ), Y ₇ is C(R ₄₇ ), Y ₈ is C(R ₄₈ );

In Formulas 2A-3, 2A-7, 2A-11 and 2A-15, Y ₃ is C(R ₄₃ ), Y ₄ is C(R ₄₄ ), Y ₅ is C(R ₄₅ ), and Y ₆ is N, Y ₇ is C(R ₄₇ ), Y ₈ is C(R ₄₈ );

In Formulas 2A-3, 2A-7, 2A-11 and 2A-15, Y ₃ is N, Y ₄ is C(R ₄₄ ), Y ₅ is N, Y ₆ is C(R ₄₆ ), Y ₇ is C(R ₄₇ ) and Y ₈ is C(R ₄₈ );

In Formulas 2A-3, 2A-7, 2A-11 and 2A-15, Y ₃ is N, Y ₄ is C(R ₄₄ ), Y ₅ is C(R ₄₅ ), Y ₆ is N, Y ₇ is C(R ₄₇ ), Y ₈ is C(R ₄₈ ); It may be, but is not limited thereto.

Here, i) an organometallic compound employing a ligand represented by Formulas 2A-4, 2A-8, 2A-12 or 2A-16, ii) Formulas 2A-2, 2A-6, 2A-10 or 2A- An organometallic compound employing a ligand represented by 14, iii) an organometallic compound employing a ligand represented by Chemical Formula 2A-3, 2A-7, 2A-11 or 2A-15, and iv) Chemical Formula 2A-1, In the order of organometallic compounds employing ligands represented by 2A-5, 2A-9 or 2A-13, the maximum emission wavelength decreases. That is, the organometallic compound employing the ligand represented by Formulas 2A-1, 2A-5, 2A-9 or 2A-13 in Formulas 2A-1 to 2A-16 has the smallest maximum emission wavelength.

According to another embodiment, L ₁ in Formula 1 may be selected from ligands represented by Formulas 2AA-1, 2AA-2, 2AA-3, 2AA-4, and 2AB. For example, when L ₁ in Formula 1 is selected from ligands represented by Formulas 2AA-1 and 2AB, an organic light-emitting device employing the organometallic compound represented by Formula 1 may have high efficiency and long lifespan. have.

Descriptions of R ₁ to R ₃ , X ₁ , Y ₁ to Y ₈ , R ₁₁ and b1 in Formulas 2AA-1, 2AA-2, 2AA-3, 2AA-4 and 2AB are the same as those described herein, and , Description of R ₁₅ refers to the description of R ₁₁ in the present specification, b5 is an integer selected from 0 to 8, and * and *' are binding sites with M in Formula 1.

For example, among Formulas 2A-1 to 2A-16, 2AA-1, 2AA-2, 2AA-3, 2AA-4 and 2AB

R ₁ to R ₃ are independently of each other,

-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 and -CD ₂ CDH ₂ ;

n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group, naph a tyl group and -Si(Q ₅₁ )(Q ₅₂ )(Q ₅₃ ); and

Substituted with at least one selected from heavy hydrogen, a C ₁ -C ₁₀ alkyl group and a phenyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group and naphthyl group;

is selected from

The Q ₅₁ to Q ₅₃ are independently from each other,

-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 and -CD ₂ CDH ₂ ;

n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group and naph til group; and

Substituted with at least one selected from heavy hydrogen, a C ₁ -C ₁₀ alkyl group and a phenyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group and naphthyl group; is selected from

X ₁ is O, S, S(=0) ₂ , N(R ₂₁ ) and Si(R ₂₂ ) (R ₂₃ ) is selected from

Description of Y ₁ to Y ₈ refers to what is described herein,

R ₁₁ , R ₁₅ , R ₂₁ to R ₂₃ and R ₄₁ to R ₄₈ are independently of each other;

Hydrogen, heavy hydrogen, -F, cyano group, nitro group, -SF ₅ , 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, sec-pentyl group, tert-pentyl group, n-hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, n-heptyl group, isoheptyl group, sec-heptyl group , tert-heptyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl group, n-decyl group, isode Sil group, sec-decyl group, tert-decyl group, methoxy group, ethoxy group, propoxy group, butoxy group, pentoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group , norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, pyridinyl group and pyrimidinyl group;

Heavy hydrogen, -F, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , cyano group, nitro group, C ₁ -C ₁₀ alkyl group, C ₁ -C ₁₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptene A methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-, substituted with at least one selected from the group consisting of a nyl group, a phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group. butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, n-hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, n-heptyl group, isoheptyl group, sec-heptyl group, tert-heptyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl group, n-de Sil group, isodecyl group, sec-decyl group, tert-decyl group, methoxy group, ethoxy group, propoxy group, butoxy group, pentoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamanta an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group; and

-B(Q ₆ )(Q ₇ ) and -P(=0)(Q ₈ )(Q ₉ );

is selected from

Q ₆ to Q ₉ are independently of each other,

-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 and -CD ₂ CDH ₂ ;

n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group and naph til group; and

Substituted with at least one selected from deuterium and C ₁ -C ₁₀ alkyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopen ethyl groups, sec-pentyl groups, tert-pentyl groups, phenyl groups and naphthyl groups; is selected from

b1 is selected from an integer of 0 to 3;

b4 is 1 or 2;

b5 may be selected from an integer of 0 to 8, but is not limited thereto.

According to another embodiment, L ₁ in Formula 1 may be selected from ligands represented by Formulas 2A(1) to 2A(40):

Descriptions of R ₁ to R ₃ , X ₁ , Y ₁ to Y ₈ and R ₁₁ in Formulas 2A(1) to 2A(40) are the same as those described herein, and descriptions of R _11a and R _11b are The description of R ₁₁ in the present specification is the same, and * and *' are binding sites to M in Formula 1, but R ₁₁ , R _11a and R _11b are not hydrogen.

According to one embodiment,

In Chemical Formulas 2A(1) to 2A(40), Y ₁ is C(R ₄₁ ), Y ₂ is C(R ₄₁ ), Y ₃ is C(R ₄₃ ), Y ₄ is C(R ₄₄ ) , Y ₅ is C(R ₄₅ ), Y ₆ is C(R ₄₆ ), Y ₇ is C(R ₄₇ ), Y ₈ is C(R ₄₈ );

Formulas 2A(1) to 2(4), 2A(7) to 2A(12), 2A(15) to 2A(20), 2A(23) to 2A(28) and 2A(31) to 2A(36) ) of which Y ₁ is N, Y ₄ is C(R ₄₄ ), Y ₅ is C(R ₄₅ ), Y ₆ is C(R ₄₆ ), Y ₇ is C(R ₄₇ ), Y ₈ is C(R ₄₈ );

Formulas 2A(1) to 2(4), 2A(7) to 2A(12), 2A(15) to 2A(20), 2A(23) to 2A(28) and 2A(31) to 2A(36) ) of which Y ₁ is C(R ₄₁ ), Y ₄ is C(R ₄₄ ), Y ₅ is N, Y ₆ is C(R ₄₆ ), Y ₇ is C(R ₄₇ ), Y ₈ is C(R ₄₈ );

Formulas 2A(1) to 2(4), 2A(7) to 2A(12), 2A(15) to 2A(20), 2A(23) to 2A(28) and 2A(31) to 2A(36) ) of which Y ₁ is C(R ₄₁ ), Y ₄ is C(R ₄₄ ), Y ₅ is C(R ₄₅ ), Y ₆ is N, Y ₇ is C(R ₄₇ ), Y ₈ is C(R ₄₈ );

Formulas 2A(1) to 2(4), 2A(7) to 2A(12), 2A(15) to 2A(20), 2A(23) to 2A(28) and 2A(31) to 2A(36) ), Y ₁ is N, Y ₄ is C(R ₄₄ ), Y ₅ is N, Y ₆ is C(R ₄₆ ), Y ₇ is C(R ₄₇ ), and Y ₈ is C(R ₄₈ );

Formulas 2A(1) to 2(4), 2A(7) to 2A(12), 2A(15) to 2A(20), 2A(23) to 2A(28) and 2A(31) to 2A(36) ), Y ₁ is N, Y ₄ is C(R ₄₄ ), Y ₅ is C(R ₄₅ ), Y ₆ is N, Y ₇ is C(R ₄₇ ), and Y ₈ is C(R ₄₈ );

Formulas 2A(5), 2A(6), 2A(13), 2A(14), 2A(21), 2A(22), 2A(29), 2A(30), 2A(37) and 2A(38) ) of which Y ₃ is N, Y ₄ is C(R ₄₄ ), Y ₅ is C(R ₄₅ ), Y ₆ is C(R ₄₆ ), Y ₇ is C(R ₄₇ ), Y ₈ is C(R ₄₈ );

Formulas 2A(5), 2A(6), 2A(13), 2A(14), 2A(21), 2A(22), 2A(29), 2A(30), 2A(37) and 2A(38) ) of which Y ₃ is C(R ₄₃ ), Y ₄ is C(R ₄₄ ), Y ₅ is N, Y ₆ is C(R ₄₆ ), Y ₇ is C(R ₄₇ ), Y ₈ is C(R ₄₈ );

Formulas 2A(5), 2A(6), 2A(13), 2A(14), 2A(21), 2A(22), 2A(29), 2A(30), 2A(37) and 2A(38) ) of which Y ₃ is C(R ₄₃ ), Y ₄ is C(R ₄₄ ), Y ₅ is C(R ₄₅ ), Y ₆ is N, Y ₇ is C(R ₄₇ ), and Y ₈ is C(R ₄₈ );

Formulas 2A(5), 2A(6), 2A(13), 2A(14), 2A(21), 2A(22), 2A(29), 2A(30), 2A(37) and 2A(38) ), Y ₃ is N, Y ₄ is C(R ₄₄ ), Y ₅ is N, Y ₆ is C(R ₄₆ ), Y ₇ is C(R ₄₇ ), and Y ₈ is C(R ₄₈ );

Formulas 2A(5), 2A(6), 2A(13), 2A(14), 2A(21), 2A(22), 2A(29), 2A(30), 2A(37) and 2A(38) ) of which Y ₃ is N, Y ₄ is C(R ₄₄ ), Y ₅ is C(R ₄₅ ), Y ₆ is N, Y ₇ is C(R ₄₇ ), and Y ₈ is C(R ₄₈ ); It may be, but is not limited thereto.

For example, in Formulas 2A (1) to 2A (40)

R ₁ to R ₃ are independently of each other,

-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 and -CD ₂ CDH ₂ ;

n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group, naph a tyl group and -Si(Q ₅₁ )(Q ₅₂ )(Q ₅₃ ); and

Substituted with at least one selected from heavy hydrogen, a C ₁ -C ₁₀ alkyl group and a phenyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group and naphthyl group;

is selected from

The Q ₅₁ to Q ₅₃ are independently from each other,

-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 and -CD ₂ CDH ₂ ;

n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group and naph til group; and

Substituted with at least one selected from heavy hydrogen, a C ₁ -C ₁₀ alkyl group and a phenyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group and naphthyl group; is selected from

X ₁ is selected from O, S, S(=0) ₂ , N(R ₂₁ ) and Si(R ₂₂ )(R ₂₃ );

Description of Y ₁ to Y ₈ refers to what is described herein,

R ₁₁ , R _11a , R _11b , R ₂₁ to R ₂₃ and R ₄₁ to R ₄₈ are independently of each other;

Hydrogen, heavy hydrogen, -F, cyano group, nitro group, -SF ₅ , 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, sec-pentyl group, tert-pentyl group, n-hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, n-heptyl group, isoheptyl group, sec-heptyl group , tert-heptyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl group, n-decyl group, isode Sil group, sec-decyl group, tert-decyl group, methoxy group, ethoxy group, propoxy group, butoxy group, pentoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group , norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, pyridinyl group and pyrimidinyl group;

Heavy hydrogen, -F, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , cyano group, nitro group, C ₁ -C ₁₀ alkyl group, C ₁ -C ₁₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptene A methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-, substituted with at least one selected from the group consisting of a nyl group, a phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group. butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, n-hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, n-heptyl group, isoheptyl group, sec-heptyl group, tert-heptyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl group, n-de Sil group, isodecyl group, sec-decyl group, tert-decyl group, methoxy group, ethoxy group, propoxy group, butoxy group, pentoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamanta an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group; and

-B(Q ₆ )(Q ₇ ) and -P(=0)(Q ₈ )(Q ₉ );

selected from (provided that R ₁₁ , R _11a and R _11b in Formulas 2A(1) to 2A(40) are not hydrogen);

Q ₆ to Q ₉ are independently of each other,

-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 and -CD ₂ CDH ₂ ;

n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group and naph til group; and

Substituted with at least one selected from deuterium and C ₁ -C ₁₀ alkyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopen ethyl groups, sec-pentyl groups, tert-pentyl groups, phenyl groups and naphthyl groups; It may be selected from, but is not limited thereto.

According to another embodiment, in Formulas 2A (1) to 2A (40)

R ₁ to R ₃ are independently of each other,

-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 and -CD ₂ CDH ₂ ;

n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group, naph a tyl group and -Si(Q ₅₁ )(Q ₅₂ )(Q ₅₃ ); and

Substituted with at least one selected from heavy hydrogen, a C ₁ -C ₁₀ alkyl group and a phenyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group and naphthyl group;

is selected from

The Q ₅₁ to Q ₅₃ are independently from each other,

-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 and -CD ₂ CDH ₂ ;

n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group and naph til group; and

Substituted with at least one selected from heavy hydrogen, a C ₁ -C ₁₀ alkyl group and a phenyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group and naphthyl group; is selected from

X ₁ is O, S, S(=0) ₂ , N(R ₂₁ ) and Si(R ₂₂ ) (R ₂₃ ) is selected from

Description of Y ₁ to Y ₈ refers to what is described herein,

R ₁₁ , R _11a , R _11b and R ₄₁ to R ₄₈ are deuterium, -F, cyano group, nitro group, -SF ₅ , -CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , selected from the groups represented by Formulas 9-1 to 9-17 and the groups represented by Formulas 10-1 to 10-30,

R ₂₁ to R ₂₃ are independently of each other;

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, phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, A pyridinyl group, a pyrimidinyl group, and a triazinyl group; and

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , 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, and a phosphoric acid group or a salt thereof substituted with at least one C ₁ -C ₂₀ alkyl group, 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 , a hydroxyl group, a cyano group, a nitro group, Among amino groups, amidino groups, hydrazine groups, hydrazone groups, carboxylic acid groups or salts thereof, sulfonic acid groups or salts thereof, phosphoric acid groups or salts thereof, C ₁ -C ₂₀ alkyl groups, C ₁ -C ₂₀ alkoxy groups, phenyl groups and naphthyl groups A cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, and a cyclohexenyl group, substituted with at least one selected from group, cycloheptenyl group, phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrimidinyl group and tria holding;

selected from, but is not limited thereto.

In Formula 1, L ₂ may be selected from ligands represented by Formulas 3A to 3G below:

Among Formulas 3A to 3G

Y ₁₁ to Y ₁₆ are each independently carbon (C) or nitrogen (N), Y ₁₁ and Y ₁₂ are connected to each other by a single bond or a double bond, Y ₁₃ and Y ₁₄ are a single bond or a double bond are connected to each other, Y ₁₅ and Y ₁₆ are connected to each other by a single bond or a double bond;

CY ₃ to CY ₅ are each independently selected from a C ₅ -C ₆₀ cyclic group and a C ₂ -C ₆₀ heterocyclic group (which may be a “monocyclic group” or “polycyclic group”), and CY ₃ and CY ₄ may optionally be further bonded through an organic linking group;

a1 to a3 are independently selected from integers of 1 to 5;

A ₁ is P or As;

X _11a , X _11b , X _12a , X _12b , X _13a and X _13b are, independently of each other, N, O, N(R ₃₄ ), P(R ₃₅ )(R ₃₆ ) and As(R ₃₇ )(R ₃₈ ) (provided that X _12a , X _12b , X _13a and X _13b are not N and O);

R _33" and R _34" are each independently a single bond, a double bond, a substituted or unsubstituted C ₁ -C ₅ alkylene group, a substituted or unsubstituted C ₂ -C ₅ alkenylene group, and a substituted or unsubstituted C 1 -C 5 alkylene group. selected from C ₆ -C ₁₀ arylene groups;

Z ₁ to Z ₃ , R ₃₁ , R _32a , R _32b , R _32c , R _33a , R _33b , R ₃₄ to R ₃₈ and R _35a , R _35b , R _35c and R _35d 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 Salt, 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 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, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, A substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, -N(Q ₁ ) ( Q ₂ ), -Si(Q ₃ ) (Q ₄ ) (Q ₅ ), -B(Q ₆ ) (Q ₇ ) and -P(=0) (Q ₈ ) (Q ₉ ) selected from;

* and *' are binding sites with M in Formula 1,

The above substituted C ₁ -C ₅ alkylene group, substituted C ₂ -C ₅ alkenylene group, substituted C ₆ -C ₁₀ arylene 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 cycloalkyl group Alkenyl 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 At least one of the substituents of the ₁ -C ₆₀ heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed polycyclic group,

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , a hydroxyl group, a cyano group, a nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt thereof, sulfonic acid group or its salt thereof, phosphoric acid group or its salt thereof, C ₁ -C ₆₀ Alkyl group, C ₂ -C ₆₀ Alkenyl group, C ₂ -C ₆₀ an alkynyl group and 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 , a hydroxyl group, a cyano group, a nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt thereof, sulfonic acid group or its salt thereof, phosphoric acid group or its 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 , monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, -N(Q ₁₁ )(Q ₁₂ ), -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ), -B(Q ₁₆ )(Q ₁₇ ) and -P(=O)(Q ₁₈ )(Q ₁₉ ) Substituted with at least one selected from a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and 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 an oxy group, a C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic hetero condensed polycyclic group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , a hydroxyl group, a cyano group, a nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt thereof, sulfonic acid group or its salt thereof, phosphoric acid group or its 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, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic hetero condensed polycyclic group , -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ), -B(Q ₂₆ )(Q ₂₇ ) and -P(=0)(Q ₂₈ )(Q ₂₉ ) substituted with at least one selected from, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a C ₁ -C ₁₀ heterocycloalkenyl group, a C ₆ -C ₆₀ an aryl group, a C ₆ -C ₆₀ aryloxy group, a C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic hetero condensed polycyclic group; and

-N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), -B(Q ₃₆ )(Q ₃₇ ) and -P(=0)(Q ₃₈ )(Q ₃₉ ); is selected from;

Wherein Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano No group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt thereof, sulfonic acid group or its salt thereof, phosphoric acid group or its 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 It is selected from a cyclic monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic hetero condensed polycyclic group.

According to one embodiment, CY ₃ to CY ₅ in Formulas 3A and 3B are each independently selected from benzene, naphthalene, fluorene, spiro-fluorene, indene, pyrrole, thiophene, furan, imidazole, Pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, quinoline, isoquinoline, benzoquinoline, quinoxaline, quinazoline, carbazole, benzoimidazole, benzofuran, benzothiophene, isobenzothiophene, benzoxazole, isobenzoxazole, triazole, tetrazole, oxadiazole, triazine, dibenzofuran, dibenzothiophene and 5 , 6, 7, 8-tetrahydroisoquinoline (5,6,7,8-tetrahydroisoquinoline), but may be selected from, but is not limited thereto.

For example, L ₂ in Formula 1 may be selected from ligands represented by Formulas 3-1 to 3-111, but is not limited thereto:

In Chemical Formulas 3-1 to 3-111,

Z ₁ , Z ₂ , Z _1a , Z _1b , Z _2a , Z _2b , Z _2c , R _34a , R _34b and R _34c are independently of each other,

Hydrogen, heavy hydrogen, -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 and 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 , a hydroxyl group, a cyano group, a nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt thereof, sulfonic acid group or its salt thereof, phosphoric acid group or its salt thereof, C ₁ -C ₁₀ Alkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclo Among the octyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, pyridinyl group and pyrimidinyl group a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group, substituted with at least one selected;

Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, Phenyl 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, pyrazole diary, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl 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, isobenzothia Zolyl group, benzooxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazole Diary, imidazopyridinyl group and imidazopyrimidinyl group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , a hydroxyl group, a cyano group, a nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt thereof, sulfonic acid group or its salt thereof, phosphoric acid group or its salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, cyclopentyl group, cyclo Hexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl 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, purinyl group, quinolinyl group, iso Quinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzooxa Zolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazophy A cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, substituted with at least one selected from a ridinyl group and an imidazopyrimidinyl group ), cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, Pyrroyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, p Ridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazoly Nyl group, cinolinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzooxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazole diyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group and imidazopyrimidinyl group; and

-N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ) and -P(=0)(Q ₈ )(Q ₉ ); is selected from

The Q ₁ to Q ₉ and Q ₄₄ to Q ₄₉ are independently from each other,

-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 and -CD ₂ CDH ₂ ;

n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group and naph til group; and

Substituted with at least one selected from deuterium and C ₁ -C ₁₀ alkyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopen ethyl groups, sec-pentyl groups, tert-pentyl groups, phenyl groups and naphthyl groups;

is selected from

aa2 and ab2 are each independently 1 or 2;

aa3 and ab3 are each independently selected from integers from 1 to 3;

aa4 and ab4 are each independently selected from integers from 1 to 4;

* and *' are binding sites with M in Formula 1.

For example, in Formulas 3-1 to 3-111, Z ₁ , Z ₂ , Z _1a , Z _1b , Z _2a , Z _2b , Z _2c , R _34a , R _34b and R _34c may be independently of each other,

Hydrogen, heavy hydrogen, -F, cyano group, nitro group, -SF ₅ , 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, sec-pentyl group, tert-pentyl group, n-hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, n-heptyl group, isoheptyl group, sec-heptyl group , tert-heptyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl group, n-decyl group, isode Sil group, sec-decyl group, tert-decyl group, methoxy group, ethoxy group, propoxy group, butoxy group, pentoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group , norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, pyridinyl group and pyrimidinyl group;

Heavy hydrogen, -F, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , cyano group, nitro group, C ₁ -C ₁₀ alkyl group, C ₁ -C ₁₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptene A methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-, substituted with at least one selected from the group consisting of a nyl group, a phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group. butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, n-hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, n-heptyl group, isoheptyl group, sec-heptyl group, tert-heptyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl group, n-de Sil group, isodecyl group, sec-decyl group, tert-decyl group, methoxy group, ethoxy group, propoxy group, butoxy group, pentoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamanta an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group; and

-N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ) and -P(=0)(Q ₈ )(Q ₉ );

is selected from

The Q ₁ to Q ₉ are independently from each other,

-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 and -CD ₂ CDH ₂ ;

n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group and naph til group; and

Substituted with at least one selected from deuterium and C ₁ -C ₁₀ alkyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopen ethyl groups, sec-pentyl groups, tert-pentyl groups, phenyl groups and naphthyl groups;

It may be selected from, but is not limited thereto.

According to an embodiment, L ₂ in Formula 1 may be selected from ligands represented by Formulas 3-1(1) to 3-1(59) and Formula 3-111 below:

For example, in Formulas 3-1(1) to 3-1(59) and 3-111

Z ₁ , Z ₂ , Z _1a , Z _1b , Z _1c , Z _1d , Z _2a , Z _2b , Z _2c , Z _2d , R _34a , R _34b and R _34c are, independently of each other, deuterium, -F, cyano group , nitro group, -SF ₅ , -CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , -Si(Q ₃ )(Q ₄ )(Q ₅ ), selected from the groups represented by Chemical Formulas 9-1 to 9-17 and the groups represented by Chemical Formulas 10-1 to 10-30,

The Q ₃ to Q ₅ are independently from each other,

-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 and -CD ₂ CDH ₂ ;

n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group and naph til group; and

Substituted with at least one selected from deuterium and C ₁ -C ₁₀ alkyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopen ethyl groups, sec-pentyl groups, tert-pentyl groups, phenyl groups and naphthyl groups;

is selected from

* and *' are binding sites with M in Formula 1.

According to one embodiment, M in Formula 1 is Ir, and n1 + n2 is 3; or M is Pt, n1 + n2 is 2, the organometallic compound represented by Formula 1 is neutral, and L ₁ in Formula 1 is one of Formulas 2A-1 to 2A-16, 2AA-1, It may be selected from ligands represented by 2AA-2, 2AA-3, 2AA-4 and 2AB, but is not limited thereto.

According to one embodiment, M in Formula 1 is Ir, and n1 + n2 is 3; or M is Pt, n1 + n2 is 2, the organometallic compound represented by Chemical Formula 1 is neutral, and L ₁ in Chemical Formula 1 is represented by Chemical Formulas 2A-1, 2A-5, 2AA-1 and It may be selected from ligands represented by 2AB, but is not limited thereto.

According to another embodiment, M in Formula 1 is Ir, and n1 + n2 is 3; or M is Pt, n1 + n2 is 2, the organometallic compound represented by Chemical Formula 1 is neutral, and L ₁ in Chemical Formula 1 is represented by Chemical Formulas 2A-1, 2A-5, 2AA-1 and It is selected from ligands represented by 2AB, and L ₂ is a ligand represented by Formulas 3-1 to 3-111 (eg, Formulas 3-1(1) to 3-1(59) and 3-111). It may be selected from the displayed ligand), but is not limited thereto.

According to another embodiment, M in Formula 1 is Ir, and n1 + n2 is 3; or M is Pt, n1 + n2 is 2, the organometallic compound represented by Formula 1 is neutral, and L ₁ in Formula 1 is represented by Formulas 2A(1) to 2A(40) It may be selected from ligands, but is not limited thereto.

According to another embodiment, M in Formula 1 is Ir, and n1 + n2 is 3; or M is Pt, n1 + n2 is 2, the organometallic compound represented by Formula 1 is neutral, and L ₁ in Formula 1 is represented by Formulas 2A(1) to 2A(40) is selected from ligands, and L ₂ is a ligand represented by Formulas 3-1 to 3-111 (eg, ligands represented by Formulas 3-1(1) to 3-1(59) and 3-111) It may be selected from, but is not limited thereto.

For example, the organometallic compound represented by Chemical Formula 1 may be one of the following compounds 1 to 481, but is not limited thereto:

<Formula 2A>

Among the organometallic compounds represented by Chemical Formula 1, L ₁ is selected from ligands represented by Chemical Formula 2A, and b4 in Chemical Formula 2A is 1 or more. That is, the substituent of the pyridine-based ring in Formula 2A includes at least one -Si(R ₁ )(R ₂ )(R ₃ ). Since -Si(R ₁ )(R ₂ )(R ₃ ) increases the spin density of metal M of Formula 1, the organometallic compound represented by Formula 1 employing the ligand represented by Formula 2A An organic light emitting device employing may have high efficiency.

In Formula 2A, X ₁ is selected from O, S, S(=O) ₂ , N(R ₂₁ ) and Si(R ₂₂ )(R ₂₃ ). As a result, charge mobility of the organometallic compound employing the ligand represented by Formula 2A is improved, and energy level control becomes easy, so that the efficiency and lifetime of the organic light emitting device employing the organometallic compound can be improved. have.

For example, the HOMO, LUMO, singlet (S ₁ ) and triplet (T ₁ ) energy levels for compounds 1, 2, 8, 22, 139, 146, 304, 305, 321, 323, 327 and 419 above. The results of evaluation using the DFT method of the Gaussian program (structure optimization at the B3LYP, 6-31G (d, p) level) are shown in Table 1 below.

Compound No. HOMO (eV) LUMO (eV) S ₁ energy level (eV) T ₁ energy level (eV) compound 1 -4.842 -1.262 2.887 2.616 compound 2 -4.874 -1.309 2.869 2.591 compound 8 -4.812 -1.249 2.875 2.608 compound 22 -4.812 -1.250 2.889 2.633 compound 139 -4.827 -1.283 2.867 2.589 compound 146 -4.829 -1.261 2.872 2.510 compound 304 -4.781 -1.267 2.837 2.586 compound 305 -4.773 -1.244 2.852 2.600 compound 321 -4.856 -1.369 2.803 2.555 compound 323 -4.820 -1.281 2.849 2.591 compound 327 -4.863 -1.304 2.887 2.614 compound 419 -4.756 -1.331 2.753 2.525

상기 표 1로부터, 상기 화학식 1로 표시되는 유기금속 화합물은 전자 소자, 예를 들면, 유기 발광 소자용 재료로 사용하기에 적합한 전기적 특성을 가짐을 확인할 수 있다.

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

A method for synthesizing the organometallic compound represented by Chemical Formula 1 can be recognized by those skilled in the art by referring to Synthesis Examples to be described later.

Accordingly, the organometallic compound represented by Chemical Formula 1 may be suitable for use as a dopant for an organic layer of an organic light emitting device, for example, a light emitting layer among the organic layers. According to another aspect, the first electrode; a second electrode; and an organic layer interposed 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 may have a low driving voltage, high efficiency, high power, long lifespan, and excellent color purity by including an organic layer including an organometallic compound represented by Chemical Formula 1 as described above.

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

In the present specification, “(the organic layer) contains one or more kinds of organometallic compounds” means “(the organic layer) includes one kind of organometallic compound belonging to the category of Chemical Formula 1 or two different kinds belonging to the category of Chemical Formula 1 above.” It may contain 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 light emitting layer of the organic light emitting device. Alternatively, the organic layer may include Compound 1 and Compound 2 as the organometallic compounds. In this case, Compound 1 and Compound 2 may exist in the same layer (eg, both Compound 1 and Compound 2 may exist in the light emitting 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, the first electrode is an anode, the second electrode is a cathode, and the organic layer includes a hole transport region interposed between the first electrode and the light emitting layer and a hole transport region interposed between the light emitting layer and the second electrode. An electron transport region, wherein the hole transport region includes at least one selected from among a hole injection layer, a hole transport layer, and an electron blocking layer, and the electron transport region comprises at least one selected from a hole blocking layer, an electron transport layer, and an electron injection layer. can include

In this specification, "organic layer" is a term indicating a single layer and/or a plurality of layers interposed between the first electrode and the second electrode in an organic light emitting device. The “organic layer” may include not only organic compounds, but also organic metal complexes including metals.

1 is a schematic cross-sectional view of an organic light emitting diode 10 according to an embodiment of the present invention. Hereinafter, a structure and 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 having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance 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 the 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, metals such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. may be used. .

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

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

The organic layer 15 includes 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 light emitting layer.

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

The hole transport region may include only the hole injection layer or only the 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 a hole injection layer, the hole injection layer (HIL) may be formed on the first electrode 11 using various methods such as a vacuum deposition method, a spin coating method, a cast method, or an LB method. have.

When the hole injection layer is formed 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 hole injection layer, and the like, but, for example, the deposition temperature is from about 100 to about 100 500°C, a degree of vacuum of about 10 ^-8 to about 10 ^-3 torr, and a deposition rate of about 0.01 to about 100 Å/sec, but are not limited thereto.

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

For conditions for forming the hole transport layer and the electron blocking layer, refer to 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)), among the compounds represented by Formula 201 and the compounds represented by Formula 202 below may include at least one:

<Formula 201>

<Formula 202>

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

Phenylene group, pentalenylene group, indenylene group, naphthylene group, azulenylene group, heptalenylene group, acenaphthylene group, fluorenylene group, phenarenylene group, phenanthrenylene group, anthracenylene group, fluoranthenyl a rene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylene group and a pentacenylene group; and

Heavy hydrogen, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt thereof, sulfonic acid group or its salt thereof, phosphoric acid group or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a C ₃ -C ₁₀ cycloalke Nyl 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 A phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, and an azulenylene group, substituted with at least one selected from a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic heterocondensed polycyclic group , Heptalenylene group, acenaphthylene group, fluorenylene group, phenarenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, naphthacenylene group , a picenylene group, a perylene group and a pentacenylene group;

can be selected from.

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

Heavy hydrogen, -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, and a phosphoric acid group or a salt thereof, substituted with at least one selected from a C ₁ -C ₁₀ alkyl group and a C ₁ -C ₁₀ alkoxy group;

a phenyl group, a naphthyl group, anthracenyl group, a fluorenyl group and a pyrenyl group; and

Heavy hydrogen, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt thereof, sulfonic acid group or its salt thereof, phosphoric acid group or a salt thereof, a C ₁ -C ₁₀ alkyl group, and a C ₁ -C ₁₀ alkoxy group, substituted with at least one selected from a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, and a pyrenyl group;

It may be selected from, but is not limited thereto.

In Formula 201, R ₁₀₉ is

phenyl group, naphthyl group, anthracenyl group and pyridinyl group; and

Heavy hydrogen, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt thereof, sulfonic acid group or its salt thereof, phosphoric acid group 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, and a pyridyl group substituted with one or more selected from a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinyl group. Neil group;

can be selected from.

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

<Formula 201A>

For details on R ₁₀₁ , R ₁₁₁ , R ₁₁₂ and R ₁₀₉ in Formula 201A, refer to the above.

For example, the compound represented by Chemical Formula 201 and the compound represented by Chemical 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 hole injection layer has a thickness of about 100 Å to about 10000 Å, for example, about 100 Å to about 1000 Å, and the hole transport layer has a thickness of about 50 Å. to about 2000 Å, for example about 100 Å to about 1500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer satisfy the ranges described above, satisfactory hole transport characteristics 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 material described above. 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 selected from quinone derivatives, metal oxides and cyano group-containing compounds, but is not limited thereto. For example, non-limiting examples of the p-dopant include tetracyanoquinondimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinondimethane quinone derivatives such as phosphorus (F4-TCNQ); metal oxides such as tungsten oxide and molybdenum oxide; and cyano group-containing compounds such as the following compound HT-D1, etc., but are not limited thereto.

<Compound HT-D1> <F4-TCNQ>

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 light emitting layer EML may be formed on the hole transport region using a method such as a vacuum deposition method, a spin coating method, a cast 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 generally can be selected from substantially the same range of conditions as those for forming the hole injection layer.

Meanwhile, when the hole transport region includes an electron blocking layer, the electron blocking layer material may be selected from materials usable in the hole transport region as described above and a host material described later, but is not limited thereto. . For example, when the hole transport region includes an electron blocking layer, mCP described later can 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 Chemical Formula 1.

The host may include at least one of the following TPBi, TBADN, ADN (also referred to as “DNA”), CBP, CDBP, TCP, Mcp, Compound H50 and Compound H51:

<mCP> <Compound H50> <Compound H51>

Alternatively, the host may further include a compound represented by 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 and a pyrenylene group; and

a phenylene group, a naphthylene group, a phenanthrenylene group, and a pyrenylene group substituted with at least one selected from a phenyl group, a naphthyl group, and anthracenyl group;

can be selected from.

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

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

a phenyl group, a naphthyl group, a phenanthrenyl group, and a pyrenyl group substituted with at least one selected from a phenyl group, a naphthyl group, and anthracenyl group;

can be selected from.

In Formula 301, g, h, i, and j may be each independently 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 at least one selected from a phenyl group, a naphthyl group, and an anthracenyl group;

a phenyl group, a naphthyl group, anthracenyl group, a pyrenyl group, a phenanthrenyl group and a fluorenyl group;

Heavy hydrogen, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt thereof, sulfonic acid group or its salt thereof, phosphoric acid group or a 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, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthreate A phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, and a fluorenyl group, substituted with one or more selected from a yl group and a fluorenyl group; and

;

;

It may be selected from, but is not limited thereto.

Alternatively, the host may include a compound represented by 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.

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

In Chemical Formula 302, k and l may be independently integers from 0 to 4. For example, k and l may be 0, 1 or 2.

The compound represented by Chemical Formula 301 and the compound represented by Chemical Formula 302 may include the following compounds H1 to H42, but are not limited thereto.

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 so as to emit white light.

When the light emitting layer includes a host and a dopant, the content of the dopant may be selected in the range of about 0.01 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 aforementioned range, excellent light emitting characteristics may be exhibited without a substantial increase in driving voltage.

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

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

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 structure or a multi-layer structure including two or more different materials.

For conditions for forming the hole blocking layer, the electron transporting layer, and the electron injection layer of the electron transport region, refer to conditions for forming 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 aforementioned range, excellent hole blocking characteristics may 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 and ET2, 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 aforementioned range, satisfactory electron transport characteristics 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 materials described above.

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.

Also, 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 at least one selected from LiF, NaCl, CsF, Li ₂ O, and BaO.

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

A second electrode 19 is provided above 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, or 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), and the like. 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 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.

In the present specification, a C ₁ -C ₆₀ alkyl group refers to a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and specific examples include a methyl group, an ethyl group, a propyl group, an isobutyl group, and a sec-butyl group. , tert-butyl group, pentyl group, iso-amyl group, hexyl group, etc. are included. In the present specification, a C ₁ -C ₆₀ alkylene group means 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 a chemical formula of -OA ₁₀₁ (where A ₁₀₁ is the C ₁ -C ₆₀ alkyl group), and specific examples thereof include a methoxy group, an ethoxy group, An isopropyloxy group and the like are included.

In the present specification, the C ₂ -C ₆₀ alkenyl group has a structure including one or more carbon double bonds at the middle or end of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include an ethenyl group, a propenyl group, a butenyl group, and the like do. In the present specification, a C ₂ -C ₆₀ alkenylene group means 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 triple bonds at the middle or end of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include ethynyl and propynyl groups. , etc. are included. In the present specification, a C ₂ -C ₆₀ alkynylene group means 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 refers to 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. A til group and the like are included. In the present specification, a 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, a 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, a C ₃ -C ₁₀ cycloalkenyl group is a monovalent monocyclic group having 3 to 10 carbon atoms, which has at least one double bond in the ring but does not have aromaticity. Examples include a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group and the like. In the present specification, a 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 heteroatom selected from N, O, P, and S as a ring-forming atom, and in the ring at least has one double bond. Specific examples of the C ₁ -C ₁₀ heterocycloalkenyl group include a 2,3-hydrofuranyl group, a 2,3-hydrothiophenyl 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, a C ₆ -C ₆₀ aryl group refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and a C ₆ -C ₆₀ arylene group refers to a carbocyclic aromatic group having 6 to 60 carbon atoms. Means 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.

In the present specification, the C ₁ -C ₆₀ heteroaryl group is a monovalent group having at least one heteroatom selected from N, O, P, Si and S as a ring-forming atom and having a carbocyclic aromatic system having 1 to 60 carbon atoms. Means, C ₁ -C ₆₀ heteroarylene group is a divalent group containing at least one heteroatom selected from N, O, P and S as a ring-forming atom and having a carbocyclic aromatic system having 1 to 60 carbon atoms. 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.

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

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

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

In the present specification, a substituted C ₁ -C ₆₀ alkyl group, a substituted C ₂ -C ₆₀ alkenyl group, a substituted C ₂ -C ₆₀ alkynyl group, a substituted C ₁ -C ₆₀ alkoxy group, a substituted C ₃ -C ₁₀ cyclo Alkyl 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, substituted monovalent non-aromatic condensed polycyclic group, and substituted monovalent non-aromatic heterocondensed polycyclic group; At least one of the substituents of the group,

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , a hydroxyl group, a cyano group, a nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt thereof, sulfonic acid group or its salt thereof, phosphoric acid group or its salt thereof, C ₁ -C ₆₀ Alkyl group, C ₂ -C ₆₀ Alkenyl group, C ₂ -C ₆₀ an alkynyl group and 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 , a hydroxyl group, a cyano group, a nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt thereof, sulfonic acid group or its salt thereof, phosphoric acid group or its 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 , monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, -N(Q ₁₁ )(Q ₁₂ ), -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ), -B(Q ₁₆ )(Q ₁₇ ) and -P(=O)(Q ₁₈ )(Q ₁₉ ) Substituted with at least one selected from a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and 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 an oxy group, a C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic hetero condensed polycyclic group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , a hydroxyl group, a cyano group, a nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt thereof, sulfonic acid group or its salt thereof, phosphoric acid group or its 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, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic hetero condensed polycyclic group , -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ), -B(Q ₂₆ )(Q ₂₇ ) and -P(=0)(Q ₂₈ )(Q ₂₉ ) substituted with at least one selected from, 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 an aryl group, a C ₆ -C ₆₀ aryloxy group, a C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic hetero condensed polycyclic group; and

-N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), -B(Q ₃₆ )(Q ₃₇ ) and -P(=0)(Q ₃₈ )(Q ₃₉ );

is selected from

Wherein Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano No group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt thereof, sulfonic acid group or its salt thereof, phosphoric acid group or its 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 It is selected from a cyclic monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic hetero condensed polycyclic group.

Hereinafter, for synthesis examples and examples, a compound and an organic light emitting device according to one embodiment of the present invention will be described in more detail, 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' used and the amount of 'A' used were the same based on molar equivalents.

[Example]

Synthesis Example 1: Synthesis of Compound 1

compound Synthesis of A1

2-bromo-5-(trimethylsilyl)pyridine (9 g, 39.09 mmol), 2-(dibenzo[b,d]furan-2-yl)-4,4, 210 mL of 5,5-tetramethyl-1,3,2-dioxaborolane (13.22 g, 44.96 mmol), Pd(PPh ₃ ) ₄ (2.26 g, 1.95 mmol) and K ₂ CO ₃ (16.21 g, 117.27 mmol). After mixing tetrahydrofuran (THF) and 70 mL of distilled water, the mixture was stirred under reflux for 18 hours. After lowering the temperature to room temperature, the organic layer was extracted using methylene chloride (MC), and anhydrous magnesium sulfate ( MgSO ₄ ) was added to remove moisture, and the filtrate obtained by filtration was reduced under reduced pressure. The residue obtained was purified through column chromatography under MC:Hexane = 1:1 condition to obtain 7.4 g (60%) of Compound A1. obtained.

Synthesis of compound M2A

2-phenylpyridine (14.66 g, 94.44 mmol) and iridium chloride (14.80 g, 41.97 mmol) were mixed with 210 mL of ethoxyethanol and 70 mL of distilled water, After the reaction proceeded by stirring under reflux for 24 hours, the temperature was lowered to room temperature. The solid produced therefrom was separated by filtration, thoroughly washed in the order of water/methanol/hexane, and the obtained solid was dried in a vacuum oven to obtain 19.5 g (87%) of compound M2A.

Synthesis of Compound M1A

Compound M2A (6.01 g, 5.60 mmol) was mixed with 45 mL of MC, and then AgOTf (2.88 g, 11.21 mmol) dissolved in 15 mL of methanol was added. Thereafter, the reaction was carried out by stirring at room temperature for 18 hours while blocking light with aluminum foil, followed by celite filtration to remove the generated solid, and further purification of the solid (compound M1A) obtained by depressurizing the filtrate. was used for the next reaction without

Synthesis of Compound 1

Compound M1A (8g, 11.22 mmol) and Compound A1 (4.28 g, 13.47 mmol) were mixed with 100 mL of ethanol, stirred under reflux for 18 hours to proceed with the reaction, and then the temperature was lowered. The mixture obtained therefrom was filtered, and the obtained solid was sufficiently washed with ethanol and hexane, and column chromatography was performed under MC: hexane = 40:60 to obtain 2.54 g (28%) of Compound 1. The material was confirmed through mass and HPLC analysis.

HRMS (MALDI) calcd for C ₄₂ H ₃₄ IrN ₃ OSi: m/z 817.2100, Found: 817.2104

Synthesis Example 2: Synthesis of Compound 3

compound B Synthesis of 1

2-bromo-5-(trimethylsilyl)pyridine (9 g, 39.09 mmol) and 2-(dibenzo[b,d]furan-2-yl)-4,4, 2-bromo-5-(trimethylsilyl)pyridine (9 g, 39.09) instead of 5,5-tetramethyl-1,3,2-dioxaborolane (13.22 g, 44.96 mmol) mmol) and 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (13.47 g, 46.92 mmol) were used. Then, 8.5 g g (55%) of Compound B1 was obtained using the same method as the synthesis method of Compound A1 in Synthesis Example 1.

Synthesis of compound 3

Synthesis above, except that compound M1A (8g, 11.22 mmol) and compound A1 (4.28 g, 13.47 mmol) were used instead of compound M1A (6.00 g, 8.42 mmol) and compound B1 (3.97 g, 10.10 mmol). 2.4 g (32%) of Compound 3 was obtained using the same method as the synthesis method of Compound 1 of Example 1. The material was confirmed through mass and HPLC analysis.

HRMS (MALDI) calcd for C ₄₈ H ₃₉ IrN ₄ Si: m/z 892.2573, Found: 892.2575

Synthesis Example 3: Synthesis of Compound 8

Synthesis of compound C3

2,5-dibromo-4-methylpyridine (18.55 g, 73.92 mmol), dibenzo[b,d]furan-2-ylboronic acid (18.81 g, 88.70 mmol) , Pd(OAc) ₂ (1.66 g, 7.39 mmol), PPh ₃ (3.88 g, 14.78 mmol) and K ₂ CO ₃ (20.43 g, 147.84 mmol) were mixed with 200 mL of acetonitrile and 100 mL of methanol. After mixing, it was stirred at 50° C. for 18 hours, then cooled to room temperature and filtered. From this, the organic layer was extracted using MC, anhydrous magnesium sulfate (MgSO ₄ ) was added to remove moisture, and the obtained filtrate was filtered under reduced pressure, and the obtained residue was subjected to column chromatography under MC:Hx = 60:40 conditions. Purification through the method gave 13.0 g (52%) of compound C3.

Synthesis of Compound C2

300 mL of THF was added to compound C3 (12.24 g, 36.20 mmol), and after cooling to -78 °C, 1.6M n-BuLi (33.94 mL, 54.30 mmol) was slowly added thereto, followed by stirring at -78 °C for 1 hour. Thereafter, TMSCl (6.89 mL, 54.30 mmol) was added, and the reaction was carried out at -78 ° C for 1 hour, followed by heating to room temperature for 12 hours. The organic layer obtained therefrom was extracted using MC, anhydrous magnesium sulfate was added to remove moisture, and the filtrate obtained by filtration was subjected to reduced pressure. Column chromatography was performed on the residue obtained under the conditions of EA: Hexane = 4:96 was performed to give 8.0 g (67%) of compound C2.

Synthesis of compound 8

Synthesis above except that compound M1A (8g, 11.22 mmol) and compound A1 (4.46 g, 13.47 mmol) were replaced with compound M1A (6.00 g, 8.42 mmol) and compound C2 (3.35 g, 10.11 mmol). 2.05 g (29%) of Compound 8 was obtained using the same method as the synthesis method of Compound 1 in Example 1. The material was confirmed through mass and HPLC analysis.

HRMS (MALDI) calcd for C ₄₃ H ₃₆ IrN ₃ OSi: m/z 831.2257, Found: 831.2259

Synthesis Example 4: Synthesis of Compound 22

Synthesis of Compound C1

Compound C2 (7.1 g, 21.42 mmol) was mixed with 100 mL of THF, cooled to -78 ° C, and then lithium diisopropylamide (LDA, 26.8 mL, 53.54 mmol) was slowly added. Thereafter, the reaction was carried out by stirring at -78 ° C. for 1 hour, and then warmed to room temperature, followed by further reaction for 1.5 hours. Subsequently, the temperature was lowered to -78 ° C, 2-bromopropane (5.03 mL, 53.54 mmol) was slowly added, and then the temperature was raised to room temperature, followed by reaction for 12 hours. The organic layer obtained therefrom was extracted using MC, anhydrous magnesium sulfate was added to remove moisture, and the obtained filtrate was filtered under reduced pressure. Column chromatography was performed on the residue obtained under the conditions of EA: Hexane = 4:96 This gave 6.80 g (85%) of compound C1.

Synthesis of compound 22

Synthesis above except that compound M1A (8g, 11.22 mmol) and compound A1 (4.28 g, 13.47 mmol) were replaced with compound M1A (6.00 g, 8.42 mmol) and compound C1 (3.77 g, 10.10 mmol). 2.30 g (31%) of compound 22 was obtained using the same method as the synthesis method of compound 1 of Example 1. The material was confirmed through mass and HPLC analysis.

HRMS (MALDI) calcd for C ₄₆ H ₄₂ IrN ₃ OSi: m/z 873.2726, Found: 873.2720

Synthesis Example 5: Synthesis of Compound 35

Synthesis of compound D3

2,5-dibromo-4-methylpyridine (18.55 g, 73.92 mmol) and dibenzo[b,d]furan-2-ylboronic acid (18.81 g, 88.70 mmol) Synthesis Example above, except that 2,5-dibromo-4-phenylpyridine (15.64 g, 49.97 mmol) and dibenzo[b,d]furan-2-ylboronic acid (12.71 g, 55.96 mmol) were used instead. 13.7 g (69%) of compound D3 was obtained using the same method as the synthesis method of compound C3 in 3.

Synthesis of Compound D2

Compound D2 6.6 g ( 66%) was obtained

Synthesis of compound 35

Synthesis above, except that compound M1A (8g, 11.22 mmol) and compound A1 (4.46 g, 13.47 mmol) were replaced with compound M1A (6.00 g, 8.41 mmol) and compound D2 (3.97 g, 10.09 mmol). 1.8 g (24%) of compound 35 was obtained using the same method as the synthesis method of compound 1 of Example 1. The material was confirmed through mass and HPLC analysis.

HRMS (MALDI) calcd for C ₄₈ H ₃₈ IrN ₃ OSi: m/z 893.2413, Found: 893.2417

Synthesis Example 6: Synthesis of Compound 300

Synthesis of compound M2B

2-phenyl-5-(trimethylsilyl)pyridine (15.05 g, 66.14 mmol) instead of 2-phenylpyridine (14.66 g, 94.44 mmol) and iridium chloride (14.80 g, 41.97 mmol) and 17.2 g (86%) of compound M2B was obtained using the same method as the synthesis method of compound M2A in Synthesis Example 1, except that iridium chloride (4.10 g, 11.62 mmol) was used. .

Synthesis of compound M1B

Compound M1B was obtained by the same method as in the synthesis of compound M1A in Synthesis Example 1, except that compound M2B (4.76 g, 3.5 mmol) was used instead of compound M2A (6.01 g, 5.60 mmol). .

Synthesis of Compound 300

Synthesis above, except that Compound M1B (6.00 g, 6.99 mmol) and Compound A1 (2.66 g, 8.39 mmol) were used instead of Compound M1A (8g, 11.22 mmol) and Compound A1 (4.46 g, 13.47 mmol). 1.3 g (19%) of compound 300 was obtained using the same method as the synthesis method of compound 1 of Example 1. The material was confirmed through mass and HPLC analysis.

HRMS(MALDI) calcd for C ₄₈ H ₅₀ IrN ₃ OSi ₃ : m/z 961.2891, Found: 961.2887

Synthesis Example 7: Synthesis of Compound 305

Synthesis above except that compound M1B (6.00 g, 6.99 mmol) and compound C1 (3.14 g, 8.39 mmol) were used instead of compound M1A (8g, 11.22 mmol) and compound A1 (4.46 g, 13.47 mmol). 1.4 g (20%) of compound 305 was obtained using the same method as the synthesis method of compound 1 of Example 1. The material was confirmed through mass and HPLC analysis.

HRMS(MALDI) calcd for C ₅₂ H ₅₈ IrN ₃ OSi ₃ : m/z 1017.3517, Found: 1017.3512

Synthesis Example 8: Synthesis of Compound 322

Synthesis above except that compound M1B (6.00 g, 6.99 mmol) and compound E1 (2.78 g, 8.74 mmol) were used instead of compound M1A (8g, 11.22 mmol) and compound A1 (4.46 g, 13.47 mmol). 1.1 g (16%) of compound 322 was obtained using the same method as in the synthesis of compound 1 of Example 1. The material was confirmed through mass and HPLC analysis.

HRMS(MALDI) calcd for C ₄₇ H ₄₉ IrN ₄ OSi ₃ : m/z 962.2843, Found: 962.2843

Synthesis Example 9: Synthesis of Compound 327

Synthesis of compound M2C

Compound A1 (8.3 g, 26.15 mmol) and iridium chloride (4.10 g, 11.62 mmol) was used, and 8.3 g (83%) of compound M2C was obtained using the same method as in Synthesis Example 1 for synthesizing compound M2A.

Synthesis of compound M1C

Compound M1C was obtained using the same method as in the synthesis of compound M1A in Synthesis Example 1, except that compound M2C (4.973 g, 2.89 mmol) was used instead of compound M2A (6.01 g, 5.60 mmol). .

Synthesis of Compound 327

Except that compound M1C (6.00 g, 5.78 mmol) and phenylpyridine (1.08 g, 6.94 mmol) were used instead of compound M1A (8g, 11.22 mmol) and compound A1 (4.46 g, 13.47 mmol). , 1.4 g (25%) of compound 327 was obtained using the same method as the synthesis method of compound 1 in Synthesis Example 1. The material was confirmed through mass and HPLC analysis.

HRMS(MALDI) calcd for C ₅₁ H ₄₄ IrN ₃ O ₂ Si ₂ : m/z 979.2601, Found: 979.2603

Example 1

An ITO glass substrate was cut into a size of 50 mm x 50 mm x 0.5 mm, ultrasonically cleaned in acetone, isopropyl alcohol and pure water for 15 minutes each, followed by UV ozone cleaning for 30 minutes.

Subsequently, m-MTDATA was deposited on the ITO electrode (anode) of the glass substrate at a deposition rate of 1 Å/sec to form a 600 Å-thick hole injection layer, and α-NPD was deposited on the hole injection layer at a deposition rate of 1 Å/sec. to form a hole transport layer with a thickness of 250 Å.

Compound 1 (dopant) and CBP (host) were co-deposited on the hole transport layer at a deposition rate of 0.1 Å/sec and 1 Å/sec, respectively, to form a light emitting layer having a thickness of 400 Å.

BAlq was deposited on the light emitting layer at a deposition rate of 1 Å/sec to form a hole blocking layer having a thickness of 50 Å, Alq ₃ was deposited on the hole blocking layer to form an electron transport layer having a thickness of 300 Å, and LiF was formed on the electron transport layer. After depositing a 10 Å thick electron injection layer, vacuum depositing Al on the electron injection layer to form a 1200 Å thick second electrode (cathode), ITO / m-MTDATA (600 Å) / α-NPD (250Å) / CBP + 10% (Compound 1) (400Å) / Balq (50Å) / Alq ₃ (300Å) / LiF (10Å) / Al (1200Å) An organic light emitting device having a structure was manufactured.

Examples 2 to 9 and Comparative Example 1

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

Evaluation Example 1: Characteristic evaluation of organic light emitting device

Driving voltage, efficiency, power, color purity, and lifetime (T ₉₅ ) of each of the organic light emitting diodes prepared in Examples 1 to 9 and Comparative Example 1 were 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, and the life (T ₉₅ ) (at 6000 nit) was evaluated for the time required to reach 95% luminance compared to 100% initial luminance.

dopant Driving
Voltage
(V) efficiency
(cd/A) power
(Im/W) CIEx CIEy life span
(hr)
(T ₉₅ ) Example 1 compound 1 5.0 49.0 30.8 0.339 0.605 210 Example 2 compound 3 4.8 47.5 31.1 0.340 0.602 145 Example 3 compound 8 4.9 48.0 30.8 0.338 0.607 195 Example 4 compound 22 5.0 48.5 30.5 0.336 0.604 200 Example 5 compound 35 5.2 50.5 30.5 0.356 0.605 230 Example 6 compound 300 4.8 51.0 33.4 0.360 0.607 230 Example 7 compound 305 4.9 50.0 32.0 0.345 0.605 210 Example 8 compound 322 4.9 51.5 33.0 0.355 0.604 150 Example 9 compound 327 4.6 50.5 34.5 0.340 0.607 180 Comparative Example 1 Comparative Compound A 5.1 47.5 29.2 0.340 0.607 85

상기 표 2로부터, 실시예 1 내지 9의 유기 발광 소자는 비교예 1의 유기 발광 소자에 비하여 우수한 구동 전압, 효율, 전력, 색순도 및 수명 특성을 가짐을 확인할 수 있다.

From Table 2, it can be seen that the organic light emitting diodes of Examples 1 to 9 have excellent driving voltage, efficiency, power, color purity and lifetime characteristics compared to the organic light emitting diode of Comparative Example 1.

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

Claims (20)

An organometallic compound represented by Formula 1 below:
<Formula 1>
M(L ₁ ) _n1 (L ₂ ) _n2

In Formula 1, M is iridium (Ir),
In Formula 1, L ₁ is selected from ligands represented by Formulas 2A(1) to 2A(8) and 2A(25) to 2A(32), n1 is 1, 2 or 3, and when n1 is 2 or more 2 or more L ₁ are the same as or different from each other;
In Formula 1, L ₂ is selected from ligands represented by 3-1, n2 is 0, 1 or 2, and when n2 is 2 or more, two or more L ₂ are the same as or different from each other;
In Formula 1, L ₁ and L ₂ are different from each other,
In Formula 1, n1 + n2 is 3,
In Formulas 2A(1) to 2A(8) and 2A(25) to 2A(32), R ₁ to R ₃ are independently of each other,
-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 and -CD ₂ CDH ₂ ;
n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group and naph til group; and
Substituted with at least one selected from heavy hydrogen, a C ₁ -C ₁₀ alkyl group and a phenyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group and naphthyl group;
is selected from
In Formulas 2A(1) to 2A(8) and 2A(25) to 2A(32), X ₁ is O, S, S(=0) ₂ , N(R ₂₁ ) and Si(R ₂₂ ) (R ₂₃ ) is selected from,
In Formulas 2A(1) to 2A(8) and 2A(25) to 2A(32), Y ₁ is N or C (R ₄₁ ), Y ₂ is N or C (R ₄₂ ), and Y ₃ is N or C(R ₄₃ ), Y ₄ is N or C(R ₄₄ ), Y ₅ is N or C(R ₄₅ ), Y ₆ is N or C(R ₄₆ ), and Y ₇ is N or C (R ₄₇ ), and Y ₈ is N or C (R ₄₈ );
In Formulas 2A(2), 2A(4), 2A(6) and 2A(8), R ₁₁ is a methyl group (—CH ₃ );
In Formulas 2A(1) to 2A(8), 2A(25) to 2A(32) and 3-1, R _11a , R _11b , R ₂₁ to R ₂₃ , R ₄₁ to R ₄₈ , Z ₁ and Z ₂ are independently of each other, hydrogen, heavy hydrogen, -F, a cyano group, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ - A C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and - It is selected from Si(Q ₃ )(Q ₄ )(Q ₅ ),
In Formulas 2A(25), 2A(27), 2A(29) and 2A(31), R _11a is hydrogen or a methyl group (-CH ₃ ), and Formulas 2A(26), 2A(28), 2A(30) ) And 2A (32), R _11b is hydrogen or a methyl group (-CH ₃ ),
Two or more of R ₄₁ to R ₄₄ in Formulas 2A(1) to 2A(8) and 2A(25) to 2A(32) may optionally combine with each other to form a saturated or unsaturated C ₄ -C ₆₀ ring. And, two or more of R ₄₅ to R ₄₈ may optionally combine with each other to form a saturated or unsaturated C ₄ -C ₆₀ ring,
In Formula 3-1, aa4 and ab4 are each independently selected from integers of 1 to 4;
In Formulas 2A(1) to 2A(8), 2A(25) to 2A(32) and 3-1, * and *' are binding sites to M in Formula 1,
Substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, substituted C ₆ -C ₆₀ aryl group, substituted substituted C ₆ -C ₆₀ aryloxy group, substituted C ₆ -C ₆₀ arylthio group, substituted C ₁ -C ₆₀ heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group and substituted monovalent non-aromatic group The substituent of the heterocondensed polycyclic group is
Deuterium, -F, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , cyano group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group and C ₁ -C ₆₀ alkoxy group;
Heavy hydrogen, -F, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , cyano group, C ₃ -C ₁₀ cycloalkyl 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 heterocondensed polycyclic group and -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ), a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, and a C ₁ -C ₆₀ alkoxy group, substituted with at least one selected from;
C ₃ -C ₁₀ cycloalkyl 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 groups and monovalent non-aromatic condensed heteropolycyclic groups;
Heavy hydrogen, -F, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , cyano group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl 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, A C ₃ -C ₁₀ cycloalkyl group, C ₆ substituted with at least one selected from a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocondensed polycyclic group, and -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ) -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 and monovalent non-aromatic hetero condensed polycyclic group group; and
-Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ );
is selected from
The Q ₃ to Q ₅ , Q ₁₃ to Q ₁₅ , Q ₂₃ to Q ₂₅ and Q ₃₃ to Q ₃₅ are independently of each other,
-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 and -CD ₂ CDH ₂ ;
n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group and naph til group; and
Deuterium, C ₁ -C ₁₀ Substituted with at least one selected from an alkyl group and a phenyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group and naphthyl group;
are selected from According to claim 1,
A neutral, organometallic compound. delete delete According to claim 1,
Wherein R _11a , R _11b , R ₂₁ to R ₂₃ , R ₄₁ to R ₄₈ , Z ₁ and Z ₂ are independently of each other,
hydrogen, heavy hydrogen, -F, a cyano group, a C ₁ -C ₂₀ alkyl group, and a C ₁ -C ₂₀ alkoxy group;
Heavy hydrogen, -F, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , cyano group, C ₁ -C ₁₀ alkyl group, C ₁ -C ₁₀ alkoxy group, C ₃ -C ₁₀ A cycloalkyl group, a C ₆ -C ₁₄ aryl group, a C ₁ -C ₁₄ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic heterocondensed polycyclic group, substituted with at least one selected from, C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group;
a C ₃ -C ₁₀ cycloalkyl group, a C ₆ -C ₁₄ aryl group, a C ₁ -C ₁₄ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic hetero condensed polycyclic group;
Heavy hydrogen, -F, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , cyano group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, C ₃ -C ₁₀ A cycloalkyl group, a C ₆ -C ₁₄ aryl group, a C ₁ -C ₁₄ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic heterocondensed polycyclic group, substituted with at least one selected from, C ₃ -C ₁₀ cycloalkyl group, C ₆ -C ₁₄ aryl group, C ₁ -C ₁₄ heteroaryl group, monovalent non-aromatic condensed polycyclic group, and monovalent non-aromatic hetero condensed polycyclic group; and
-Si(Q ₃ )(Q ₄ )(Q ₅ );
An organometallic compound selected from among. According to claim 1,
Wherein R _11a , R _11b , R ₂₁ to R ₂₃ , R ₄₁ to R ₄₈ , Z ₁ and Z ₂ are independently of each other,
hydrogen, heavy hydrogen, -F, a cyano group, a C ₁ -C ₂₀ alkyl group, and a C ₁ -C ₂₀ alkoxy group;
Heavy hydrogen, -F, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , cyano group, C ₁ -C ₁₀ alkyl group, cyclopentyl group, cyclohexyl group, cyclo A heptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group, substituted with at least one selected from a C ₁ -C ₂₀ alkyl group and C ₁ - C ₂₀ alkoxy group;
Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluorante Nyl 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, pyr Denyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolyl group Nyl group, cinolinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzooxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazole diyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group and imidazopyrimidinyl group; and
Heavy hydrogen, -F, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , cyano group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, cyclo Pentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group , triphenylenyl group, pyrenyl group, chrysenyl group, pyrroyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridi Nyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl 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, benzooxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group , An oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group substituted with at least one selected from the group, cyclo Pentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group , triphenylenyl group, pyrenyl group, chrysenyl group, pyrroyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridi Nyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl 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, benzooxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group , an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group and an imidazopyrimidinyl group;
An organometallic compound selected from among. According to claim 1,
Wherein R _11a , R _11b , R ₂₁ to R ₂₃ , R ₄₁ to R ₄₈ , Z ₁ and Z ₂ are independently of each other,
Hydrogen, heavy hydrogen, -F, cyano group, 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 , sec-pentyl group, tert-pentyl group, n-hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, n-heptyl group, isoheptyl group, sec-heptyl group, tert-heptyl group, n -octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl group, n-decyl group, isodecyl group, sec-decyl group, tert-decyl group, methoxy group, ethoxy group, propoxy group, butoxy group, pentoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group , A phenyl group, a naphthyl group, a pyridinyl group and a pyrimidinyl group; and
Heavy hydrogen, -F, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , cyano group, C ₁ -C ₁₀ alkyl group, C ₁ -C ₁₀ alkoxy group, cyclo A methyl group, substituted with at least one selected from a pentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group, Ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, n -Hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, n-heptyl group, isoheptyl group, sec-heptyl group, tert-heptyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl group, n-decyl group, isodecyl group, sec-decyl group, tert-decyl group, methoxy group, ethoxy group, pro Poxy group, butoxy group, pentoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, phenyl group, naphthyl group, pyridinyl group and pyrimidi Neil group;
An organometallic compound selected from among. According to claim 1,
Wherein R _11a , R _11b , R ₂₁ to R ₂₃ , R ₄₁ to R ₄₈ , Z ₁ and Z ₂ are each independently hydrogen, deuterium, -F, cyano group, -CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , groups represented by the following formulas 9-1 to 9-17 and the following formulas 10-1 to 10-18 and 10-23 to 10-30 An organometallic compound selected from the group represented by:

In Formulas 9-1 to 9-17, 10-1 to 10-18, and 10-23 to 10-30, * is a binding site with a neighboring atom. delete delete According to claim 1,
In Formulas 2A(7), 2A(8), 2A(31) and 2A(32), Y ₁ is C(R ₄₁ ), Y ₂ is C(R ₄₁ ), and Y ₅ is C(R ₄₅ ) , Y ₆ is C(R ₄₆ ), Y ₇ is C(R ₄₇ ) and Y ₈ is C(R ₄₈ );
In Formulas 2A(1) to 2A(4) and 2A(25) to 2A(28), Y ₁ is N, Y ₄ is C(R ₄₄ ), Y ₅ is C(R ₄₅ ), and Y ₆ is C(R ₄₆ ), Y ₇ is C(R ₄₇ ), and Y ₈ is C(R ₄₈ );
In Formulas 2A(1) to 2A(4) and 2A(25) to 2A(28), Y ₁ is C(R ₄₁ ), Y ₄ is C(R ₄₄ ), Y ₅ is N, and Y ₆ is C(R ₄₆ ), Y ₇ is C(R ₄₇ ), and Y ₈ is C(R ₄₈ );
In Formulas 2A(1) to 2A(4) and 2A(25) to 2A(28), Y ₁ is C(R ₄₁ ), Y ₄ is C(R ₄₄ ), and Y ₅ is C(R ₄₅ ) , Y ₆ is N, Y ₇ is C(R ₄₇ ) and Y ₈ is C(R ₄₈ );
In Formulas 2A(1) to 2A(4) and 2A(25) to 2A(28), Y ₁ is N, Y ₄ is C(R ₄₄ ), Y ₅ is N, and Y ₆ is C(R ₄₆ ), Y ₇ is C(R ₄₇ ), Y ₈ is C(R ₄₈ );
In Formulas 2A(1) to 2A(4) and 2A(25) to 2A(28), Y ₁ is N, Y ₄ is C(R ₄₄ ), Y ₅ is C(R ₄₅ ), and Y ₆ is N, Y ₇ is C(R ₄₇ ), Y ₈ is C(R ₄₈ );
In Formulas 2A(5), 2A(6), 2A(29) and 2A(30), Y ₃ is N, Y ₄ is C(R ₄₄ ), Y ₅ is C(R ₄₅ ), and Y ₆ is C(R ₄₆ ), Y ₇ is C(R ₄₇ ), and Y ₈ is C(R ₄₈ );
In Formulas 2A(5), 2A(6), 2A(29) and 2A(30), Y ₃ is C(R ₄₃ ), Y ₄ is C(R ₄₄ ), Y ₅ is N, and Y ₆ is C(R ₄₆ ), Y ₇ is C(R ₄₇ ), and Y ₈ is C(R ₄₈ );
In Formulas 2A(5), 2A(6), 2A(29) and 2A(30), Y ₃ is C(R ₄₃ ), Y ₄ is C(R ₄₄ ), and Y ₅ is C(R ₄₅ ) , Y ₆ is N, Y ₇ is C(R ₄₇ ) and Y ₈ is C(R ₄₈ );
In Formulas 2A(5), 2A(6), 2A(29) and 2A(30), Y ₃ is N, Y ₄ is C(R ₄₄ ), Y ₅ is N, and Y ₆ is C(R ₄₆ ), Y ₇ is C(R ₄₇ ), Y ₈ is C(R ₄₈ );
In Formulas 2A(5), 2A(6), 2A(29) and 2A(30), Y ₃ is N, Y ₄ is C(R ₄₄ ), Y ₅ is C(R ₄₅ ), and Y ₆ is N, Y ₇ is C(R ₄₇ ), and Y ₈ is C(R ₄₈ );
organometallic compounds. delete delete delete delete According to claim 1,
An organometallic compound wherein L ₂ in Formula 1 is selected from ligands represented by Formulas 3-1(1) to 3-1(59):

In Formulas 3-1(1) to 3-1(59)
Z ₁ , Z ₂ , Z _1a , Z _1b , Z _1c , Z _1d , Z _2a , Z _2b , Z _2c and Z _2d are each independently deuterium, -F, cyano group, -CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , -Si(Q ₃ )(Q ₄ )(Q ₅ ), a group represented by the following formulas 9-1 to 9-17 And selected from the group represented by the following formulas 10-1 to 10-18 and 10-23 to 10-30:

In Formulas 9-1 to 9-17, 10-1 to 10-18, and 10-23 to 10-30, * is a binding site with a neighboring atom. According to claim 1,
An organometallic compound, which is one of the following compounds:

a first electrode;
a second electrode; and
an organic layer interposed between the first electrode and the second electrode and including a light emitting layer;
including,
The organic layer includes at least one organometallic compound according to any one of claims 1, 2, 5 to 8, 11, 16 and 17, an organic light emitting device. According to claim 18,
The first electrode is an anode, the second electrode is a cathode,
The organic layer includes a hole transport region interposed between the first electrode and the light emitting layer and an electron transport region interposed between the light emitting layer and the second electrode,
The hole transport region includes at least one selected from a hole injection layer, a hole transport layer, and an electron blocking layer;
Wherein the electron transport region includes at least one selected from a hole blocking layer, an electron transport layer, and an electron injection layer. According to claim 18,
The organometallic compound is included in the light emitting layer, the organic light emitting device.

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