KR20200026119A - Organometallic compound, organic light emitting device including the same and a composition for diagnosing including the same - Google Patents

Abstract

The present invention discloses an organometallic compound represented by following chemical formula 1, an organic light emitting device including the same, and a composition for diagnosis including the same: M(L_1)_n1(L_2)_n2. For the description of M, L_1, L_2, n1 and n2 in chemical formula 1, refer to the present specification. According to the present invention, it is possible to provide the composition for diagnosis having high diagnostic efficiency.

Description

Organometallic compound, organic light emitting device including the same and a composition for diagnosing including the same}

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

An organic light emitting device is a self-luminous device, and is excellent in viewing angle, response time, brightness, driving voltage, and response speed, and may be multicolored.

According to an example, the organic light emitting diode may include an anode, a cathode, and an organic layer disposed between the anode and the cathode and including a light emitting layer. A hole transport region may be disposed between the anode and the light emitting layer, and an electron transport region may be disposed 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 emission layer to generate excitons. The excitons change from excited state to ground state, producing light.

On the other hand, a light emitting compound, for example, a phosphorescent light emitting compound may be used for monitoring, sensing, and detection of biological materials such as various cells, proteins and the like.

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

In Formula 1,

M is iridium (Ir), osmium (Os), titanium (Ti), hafnium (Hf), europium (Eu), rhodium (Rh) or ruthenium (Ru),

L ₁ is a ligand represented by Formula 2,

n1 is 1, 2 or 3, when n1 is 2 or more, two or more L ₁ are the same as or different from each other,

L ₂ is a monodentate ligand, a bidentate ligand, a tridentate ligand or a tetradentate ligand,

n2 is 0, 1, 2, 3 or 4, when n2 is 2 or more, two or more L ₂ are the same as or different from each other,

L ₁ and L ₂ are different from each other,

<Formula 2>

In Formula 2,

X ₁ and X ₂₁ are, independently from each other, C or N,

Ring CY ₁₁ , ring CY ₁₂ and ring CY ₂₁ are independently of each other, a C ₅ -C ₃₀ carbocyclic group or a C ₁ -C ₃₀ heterocyclic group, ring CY ₁₁ and ring CY ₁₂ are condensed with each other,

T ₁ is * -N (R ₂ )-* ', * -B (R ₂ )-*', * -P (R ₂ )-* ', * -C (R ₂ ) (R ₃ )-*' , * -Si (R ₂ ) (R ₃ )-* ', * -Ge (R ₂ ) (R ₃ )-*', * -S- * ', * -Se- *', * -O- * ', * -C (= O)-*', * -S (= O)-* ', * -S (= O) _2- *', * -C (R ₂ ) = * ', * = C (R ₂ )-* ', * -C (R ₂ ) = C (R ₃ )-*', * -C (= S)-* 'or * -C≡C- *', wherein * and * Are each bonding sites with neighboring atoms,

R ₁ to R ₃ and R ₂₁ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine Groups, hydrazone groups, carboxylic acid groups or salts thereof, sulfonic acid groups or salts thereof, phosphoric acid groups or salts thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl groups, substituted or unsubstituted C ₂ -C ₆₀ alkenyl groups, substituted or Unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy 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 heteroaryl group, substituted or unsubstituted 1 A 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 ), Ge (Q ₃ ) (Q ₄ ) (Q ₅ ), -B (Q ₆ ) (Q ₇ ), -P (= O) (Q ₈ ) (Q ₉ ), or -P (Q ₈ ) (Q ₉ ) )ego,

a1 and a21 are each independently an integer of 0 to 20,

At least two of the plurality of R ₁ may optionally, be connected to each other, substituted or unsubstituted with at least one of R _10a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or at least one of R _10a to the ring C ₁ - Can form a C ₃₀ heterocyclic group,

At least two of the plurality of R ₂₁ are optionally, are connected with each other, substituted or unsubstituted with at least one of R _10a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or at least one of R _10a to the ring C ₁ - Can form a C ₃₀ heterocyclic group,

R ₁ to R ₃ and R ₂₁ 2 or more of the selectively, connected to each other, substituted or unsubstituted with at least one of R _10a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or at least one of R _10a to the ring Formed C ₁ -C ₃₀ heterocyclic group,

For a description of R _10a refer to the description for R ₂₁ ,

* And * 'are each a binding site with M in Formula 1,

The substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, Substituted C ₁ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C ₆ -C ₆₀ arylthio group, substituted C ₁ -C ₆₀ heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group and substituted monovalent non-aromatic condensed polycyclic group Substituents independently of one another,

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group Or a C ₁ -C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ heteroaryl group, 1 Valent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group, -N (Q ₁₁ ) (Q ₁₂ ), -Si (Q ₁₃ ) (Q ₁₄ ) (Q ₁₅ ),-Ge (Q ₁₃ ) (Q ₁₄ ) (Q ₁₅ ), -B (Q ₁₆ ) (Q ₁₇ ), -P (= O) (Q ₁₈ ) (Q ₁₉ ), -P (Q ₁₈ ) (Q ₁₉ ), or any thereof C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group or C ₁ -C ₆₀ alkoxy group substituted with a combination;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group , C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic group, - N (Q ₂₁ ) (Q ₂₂ ), -Si (Q ₂₃ ) (Q ₂₄ ) (Q ₂₅ ), -Ge (Q ₂₃ ) (Q ₂₄ ) (Q ₂₅ ), -B (Q ₂₆ ) (Q ₂₇ ) , C ₃ -C ₁₀ cycloalkyl group, C ₁ -unsubstituted or substituted with -P (= 0) (Q ₂₈ ) (Q ₂₉ ), -P (Q ₂₈ ) (Q ₂₉ ), or any combination thereof. C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group , C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ heteroaryl group, a monovalent non- Aromatic condensed polycyclic group or monovalent non-aromatic heterocondensed polycyclic group;

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

Any combination thereof;

ego,

Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ are each independently hydrogen; heavy hydrogen; -F; -Cl; -Br; -I; Hydroxyl group; Cyano group; Nitro group; Amidino groups; Hydrazine group; Hydrazone group; Carboxylic acid groups or salts thereof; Sulfonic acid groups or salts thereof; Phosphoric acid groups or salts thereof; Deuterium, C ₁ -C ₆₀ alkyl, C ₆ -C ₆₀ aryl group, or substituted by any combination thereof or unsubstituted 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; ₆₀ aryl group, heavy hydrogen, C ₁ -C ₆₀ alkyl, C ₆ -C ₆₀ aryl group, or a substituted or unsubstituted in any combination thereof C ₆ -C; C ₆ -C ₆₀ aryloxy group; C ₆ -C ₆₀ arylthio group; C ₁ -C ₆₀ heteroaryl group; Monovalent non-aromatic condensed polycyclic groups; Or a monovalent non-aromatic heterocondensed polycyclic group.

According to another aspect, the first electrode; Second electrode; And an organic layer disposed between the first electrode and the second electrode, the organic layer including a light emitting layer, wherein the organic layer includes one or more kinds of the organometallic compound.

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

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

Since the organometallic compound has excellent electrical properties and thermal stability, an electronic device employing the organometallic compound, for example, an organic light emitting device has improved driving voltage, external quantum efficiency, roll-off ratio and lifetime characteristics. Can have. In addition, since the organometallic compound has excellent phosphorescence properties, using this, it is possible to provide a diagnostic composition having high diagnostic efficiency.

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

The organometallic compound may be represented by Formula 1 below:

<Formula 1>

M (L ₁ ) _n1 (L ₂ ) _n2

M in Formula 1 may be iridium (Ir), osmium (Os), titanium (Ti), hafnium (Hf), europium (Eu), rhodium (Rh) or ruthenium (Ru).

For example, M may be iridium.

L ₁ in Formula 1 may be a ligand represented by Formula 2:

<Formula 2>

For the description of the formula (2) refer to what is described herein.

N1 in Formula 1 represents the number of L ₁ , and 1, 2 or 3, and when n ₁ is 2 or more, two or more L ₁ may be the same or different from each other.

L ₂ in Formula 1 may be a monodentate ligand, a bidentate ligand, a tridentate ligand, or a tetradentate ligand. For a more detailed description of L ₂ refer to what is described herein.

N2 in Formula 1 represents the number of L ₂ , and 0, 1, 2, 3, or 4, and when n ₂ is 2 or more, two or more L ₂ may be identical to or different from each other.

In Formula 1, L ₁ and L ₂ are different from each other. Therefore, when n2 in Formula 1 is not 0, the organometallic compound represented by Formula 1 may be a heteroleptic complex.

According to one embodiment, in Formula 1, i) M is Ir or Os, n1 + n2 is 3 or 4; Or ii) M is Pt and n1 + n2 can be two.

According to another embodiment, n2 in Formula 1 may be 1 or 2.

X ₁ and X ₂₁ in Formula 2 may be independently C or N.

For example, X ₁ may be N and X ₂₁ may be C, but is not limited thereto.

In Formula 2, the bond between X ₁ and M in Formula 1 may be a coordination bond, and the bond between X ₂₁ and M in Formula 1 may be a covalent bond. As a result, the organometallic compound represented by Chemical Formula 1 may be electrically neutral.

In Formula 2, ring CY ₁₁ , ring CY ₁₂ and ring CY ₂₁ may be each independently a C ₅ -C ₃₀ carbocyclic group or a C ₁ -C ₃₀ heterocyclic group. The ring CY ₁₁ and the ring CY ₁₂ are condensed with each other.

For example, the ring CY ₁₁ , ring CY ₁₂ and ring CY ₂₁ may be each independently of one another: i) a first ring, ii) a second ring, iii) a condensed ring of two or more first rings condensed with each other, iv) A condensed ring in which at least two second rings are condensed with each other, or v) a condensed ring in which at least one first ring and at least one second ring are condensed with each other,

The first ring is cyclopentane group, cyclopentadiene group, furan group, thiophene group, pyrrole group, silol group, indene group, benzofuran group, benzothiophene group, indole group, benzosilol group, oxazole group, Isoxazole group, oxadiazole group, isoxadiazole group, oxtriazole group, isoxtriazole group, thiazole group, isothiazole group, thiadiazole group, isothiadiazole group, thiatazole group, Isotiatriazole group, pyrazole group, imidazole group, triazole group, tetrazole group, azasilol group, diazasilol group or triazasilol group,

The second ring is an adamantane group, norbornane group, norbornene group, bicyclo [1.1.1] pentane group, bicyclo [2.1.1] hexane group, bicyclo [2.2 .1] heptane group, bicyclo [2.2.2] octane group, cyclohexane group, cyclohexene group, benzene group, pyridine group, pyrimidine group, pyrazine group, pyridazine group or triazine group.

According to one embodiment, the ring CY ₁₁ , ring CY ₁₂ and ring CY ₂₁ are each independently a cyclopentene group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, Pyrene group, chrysene group, 1,2,3,4-tetrahydronaphthalene (1,2,3,4-tetrahydronaphthalene) group, pyrrole group, borol group, phosphol group, cyclopentadiene group, silol group, Low molar group, thiophene group, selenophene group, furan group, indole group, benzoborol group, benzophosphol group, indene group, benzosilol group, benzo low mole group, benzothiophene group, benzoselenophene group, benzofuran group , Carbazole group, dibenzoborol group, dibenzophosphol group, fluorene group, dibenzosilol group, dibenzozomol group, dibenzothiophene group, dibenzoselenophene group, dibenzofuran group, dibenzoti Offen 5-oxide group, 9H-fluor Ren-9-one group, dibenzothiophene 5,5-dioxide group, azaindole group, azabenzoborol group, azabenzophosphol group, azaindene group, azabenzosilol group, azabenzozomol group, azabenzo Thiophene group, azabenzoselenophene group, azabenzofuran group, azacarbazole group, azadibenzoborol group, azadibenzophosphol group, azafluorene group, azadibenzosilol group, azadibenzozomol group, Azadibenzothiophene group, azadibenzoselenophene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluorene-9-one group, azadibenzothiophene 5,5 -Dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, benzoquinoline group, benzoisoquinoline group, quinoxaline group, quinazoline group, phenanthroline group Pyrazole , Imidazole group, triazole group, azaborol group, azaphosphol group, azacyclopentadiene group, azasilol group, azazomol group, azaselenophene group, oxazole group, isoxazole group, thiazole group, Isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzoimidazole group, benzoxazole group, benzothiazole group, benzoxadiazole group, benzothiadiazole group, 5,6 , 7,8-tetrahydroisoquinoline (5,6,7,8-tetrahydroisoquinoline) group or 5,6,7,8-tetrahydroquinoline (5,6,7,8-tetrahydroquinoline) group.

According to one embodiment, the ring CY ₁₁ is a pyridine group, quinoline group, isoquinoline group, benzoquinoline group or benzoisoquinoline group and / or the ring CY ₁₂ is a benzene group, naphthalene group, phenanthrene group, pyrrole Group, borol group, phosphol group, cyclopentadiene group, silol group, low mole group, thiophene group, selenophene group, furan group, pyrazole group, imidazole group, azaborol group, azaphosphol group, azacyclo Pentadiene group, azasilol group, azazomol group, azaselenophene group, oxazole group, isoxazole group, thiazole group or isothiazole group, and the ring CY ₂₁ is a benzene group, a pyridine group, Pyrimidine group, naphthalene group, fluorene group, carbazole group, dibenzofuran group, dibenzothiophene group or dibenzosilol group.

T ₁ in Formula 2 is * -N (R ₂ )-* ', * -B (R ₂ )-*', * -P (R ₂ )-* ', * -C (R ₂ ) (R ₃ )-* ', * -Si (R ₂ ) (R ₃ )-*', * -Ge (R ₂ ) (R ₃ )-* ', * -S- *', * -Se- * ', * -O- * ', * -C (= O)-*', * -S (= O)-* ', * -S (= O) _2- *', * -C (R ₂ ) = * ' , * = C (R ₂ )-* ', * -C (R ₂ ) = C (R ₃ )-*', * -C (= S)-* 'or * -C≡C- *', * And * 'may each be a binding site with a neighboring atom. For the description of the R ₂ and R ₃ refer to the bar to be described later. R ₂ and R ₃ , optionally, a single bond, a double bond, * -N (R ₄ )-* ', * -B (R ₄ )-*', * -P (R ₄ )-* ', * -C (R ₄ ) (R ₅ )-* ', * -Si (R ₄ ) (R ₅ )-*', * -Ge (R ₄ ) (R ₅ )-* ', * -S- * ', * -Se- *', * -O- * ', * -C (= O)-*', * -S (= O)-* ', * -S (= O) _2- *', * -C (R ₄ ) = * ', * = C (R ₄ )-*', * -C (R ₄ ) = C (R ₅ )-* ', * -C (= S)-*' or * -C≡C- * 'a is connected via a, substituted or unsubstituted with at least one of R _10a C ₅ -C ₃₀ carbocyclic group or at least one of R _10a a substituted or unsubstituted C ₁ -C ₃₀ in Heterocyclic groups can be formed. For the description of R _10a refer to the description of R ₂₁ in the present specification, and the description of the C ₅ -C ₃₀ carbocyclic group and C ₁ -C ₃₀ heterocyclic group is described in ring CY ₂₁ herein. See description for it.

According to one embodiment, T ₁ in Formula 2 may be * -O- * '.

R ₁ to R ₃ and R ₂₁ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , hydroxyl group, cyano group, nitro group, amino group, amidino group, Hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted Or an unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocyclo Alkyl 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, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted 1 is a non-condensed polycyclic aromatic group, a substituted or unsubstituted 1, a non-aromatic heterocyclic condensed polycyclic _{group, -N (Q 1) (Q} 2), -Si (Q 3) (Q 4) (Q 5) , -Ge (Q ₃ ) (Q ₄ ) (Q ₅ ), -B (Q ₆ ) (Q ₇ ), -P (= O) (Q ₈ ) (Q ₉ ), or -P (Q ₈ ) ( Q ₉ ), and the descriptions of Q ₁ to Q ₉ are each referred to herein.

According to one embodiment, R ₁ to R ₃ and R ₂₁ are independently of each other,

Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof , Phosphoric acid groups or salts thereof, -SF ₅ , C ₁ -C ₂₀ alkyl groups or 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 , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₁₀ alkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclo Octyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, bicyclo [1.1.1] pentyl group, bicyclo [2.1.1] hexyl group, bicyclo [2.2.1] heptyl group, bicyclo [2.2.2] octyl group, (C ₁ -C ₂₀ alkyl) cyclopentyl group, (C ₁ -C ₂₀ alkyl) cyclohexyl group, (C ₁ -C ₂₀ alkyl) Cycloheptyl group, (C ₁ -C ₂₀ alkyl) cyclooctyl group, (C ₁ -C ₂₀ alkyl) adamantanyl group, (C ₁ -C ₂₀ alkyl) norbornanyl group, (C ₁ -C ₂₀ alkyl) norbornene group, (C ₁ -C ₂₀ alkyl), cyclopentenyl group, (C ₁ -C ₂₀ alkyl) cyclohexenyl group, (C ₁ -C ₂₀ Kiel) bicyclo heptenyl group, (C ₁ -C ₂₀ alkyl) bicyclo [1.1.1] pentyl, (C ₁ -C ₂₀ alkyl) bicyclo [2.1.1] hexyl group, (C ₁ -C ₂₀ alkyl) Bicyclo [2.2.1] heptyl group, (C ₁ -C ₂₀ alkyl) bicyclo [2.2.2] octyl group, phenyl group, (C ₁ -C ₂₀ alkyl) phenyl group, biphenyl group, terphenyl group, naphthyl group, pyri A C ₁ -C ₂₀ alkyl group or a C ₁ -C ₂₀ alkoxy group substituted with a diyl group, a pyrimidinyl group, or any combination thereof;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino 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, deuterium-containing C ₂ -C ₂₀ alkyl groups (e.g. , * -C (CD ₃ ) _3, etc.), C ₁ -C ₂₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopente Nyl group, cyclohexenyl group, cycloheptenyl group, bicyclo [1.1.1] pentyl group, bicyclo [2.1.1] hexyl group, bicyclo [2.2.1] heptyl group, bicyclo [2.2.2] octyl group , (C ₁ -C ₂₀ alkyl) cyclopentyl group, (C ₁ -C ₂₀ alkyl) cyclohexyl group, (C ₁ -C ₂₀ alkyl) cycloheptyl group, (C ₁ -C ₂₀ alkyl) cyclooctyl group, ( C ₁ -C ₂₀ alkyl) adamantanyl group, (C ₁ -C ₂₀ alkyl) norbornanyl group, (C ₁ -C ₂₀ alkyl) norbornenyl group, (C ₁ -C ₂₀ alkyl) cyclopentenyl group, (C ₁ -C ₂₀ alkyl) cyclohexenyl group, (C ₁ -C ₂₀ alkyl) cycloheptenyl group, (C ₁ -C ₂₀ alkyl) bicyclo [1.1. 1] pentyl group, (C ₁ -C ₂₀ alkyl) bicyclo [2.1.1] hexyl group, (C ₁ -C ₂₀ alkyl) bicyclo [2.2.1] heptyl group, (C ₁ -C ₂₀ alkyl) Cyclo [2.2.2] octyl group, phenyl group, (C ₁ -C ₂₀ alkyl) phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyle Neyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl Group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, furinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, sinolinyl group , Carbazolyl, phenanthrolinyl, Zomidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadizolyl group, triazinyl group, dibenzofura Nilyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group, or any thereof Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantanyl, norbornanyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, unsubstituted or substituted with a combination of bicyclo [1.1.1] pentyl, bicyclo [2.1.1] hexyl, bicyclo [2.2.1] heptyl, bicyclo [2.2.2] octyl group, a phenyl group, (C ₁ -C ₂₀ alkyl) Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthra Senyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl and oxazolyl groups , Isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, furinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, Quinoxalinyl, quinazolinyl, cynolinyl, carbazolyl, phenanthrolinyl, benzoimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzoxazolyl, isobenzooxazolyl, Triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, Azacarbazole group, azadibenzofuranyl group Aza-dibenzo thiophenyl group; or

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

ego,

Q ₁ 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 or -CD ₂ CDH ₂ ; or

N -propyl group, isopropyl group, n -butyl group, sec -butyl group, isobutyl group, tert -butyl group, unsubstituted or substituted with deuterium, a C ₁ -C ₁₀ alkyl group, a phenyl group, or any combination thereof , n -pentyl group, tert -pentyl group, neopentyl group, isopentyl group, sec -pentyl group, 3-pentyl group, sec -isopentyl group, phenyl group, biphenyl group or naphthyl group;

Can be.

According to another embodiment, R ₁ to R ₃ and R ₂₁ are each independently of the other 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 , at least one hydrogen of one of the groups represented by one of formulas 9-1 to 9-66, formulas 9-1 to 9-66 is deuterium A group substituted with a group represented by one of Formulas 10-1 to 10-118, at least one hydrogen of any one of Formulas 10-1 to 10-118 is substituted with deuterium, and the following Formulas 10-201 to 10- A group represented by one of 342, a group in which at least one hydrogen of one of formulas 10-201 to 10-342 is substituted with deuterium, -Si (Q ₃ ) (Q ₄ ) (Q ₅ ) or -Ge (Q ₃ ) (Q ₄ ) (Q ₅ ) (the above descriptions for Q ₃ to Q ₅ may each refer to what is described herein):

In Formulas 9-1 to 9-66, 10-1 to 10-118, and 10-201 to 10-342, * is a binding site with neighboring atoms, Ph is a phenyl group, and TMS is a trimethylsilyl group.

For example, the following Chemical Formula 9-33 is a branched C ₆ alkyl group, which can be seen as a tert-butyl group substituted with two methyl groups.

The "group in which at least one hydrogen of one of Formulas 9-1 to 9-66 is substituted with deuterium" is, for example, a group represented by one of Formulas 9-501 to 9-514 and 9-601 to 9-638 Can be:

The "group in which at least one hydrogen of one of Formulas 10-1 to 10-118 is substituted with deuterium" may be, for example, a group represented by one of Formulas 10-501 to 10-546.

A1 and a21 in Formula 2 indicate the number of R ₁ and R ₂₁ , respectively, and may be each independently an integer of 0 to 20. When a1 is 2 or more, two or more R ₁ may be the same as or different from each other, and when a21 is 2 or more, two or more R ₂₁ may be identical to or different from each other. For example, a1 and a21 may be each independently an integer of 0 to 10.

i) Two or more of the plurality of R ₁ of Formula 2, optionally linked to each other, substituted with at least one R _10a or unsubstituted C ₅ -C ₃₀ carbocyclic group or substituted with at least one R _10a Or an unsubstituted C ₁ -C ₃₀ heterocyclic group, ii) two or more of the plurality of R ₂₁ in Formula 2 are optionally linked to each other, and substituted or unsubstituted with at least one R _10a A substituted C ₅ -C ₃₀ carbocyclic group or a C ₁ -C ₃₀ heterocyclic group unsubstituted or substituted with at least one R _10a , and iii) R ₁ to R ₃ and at least two of R ₂₁ are, optionally, connected to each other, at least one of R _10a to a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or at least one of R _10a to a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic groups can be formed. Here, "at least one of R _10a a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or at least one of R _10a substituted or unsubstituted C ₁ -C ₃₀ with a heterocyclic cyclic group" includes, for example , Adamantane group, norbornane group, norbornene group, bicyclo [1.1.1] pentane group, bicyclo [2.1.1, unsubstituted or substituted with at least one R _10a ] Hexane group, bicyclo [2.2.1] heptane group, bicyclo [2.2.2] octane group, cyclopentane group, cyclohexane group, cycloheptane group, cyclopentene group, cyclohexene group, cycloheptene group, benzene group , Naphthalene group, anthracene group, phenanthrene group, triphenylene group, pyrene group, chrysene group, 1,2,3,4-tetrahydronaphthalene (1,2,3,4-tetrahydronaphthalene) group, pyrrole group , Borol group, phosphol group, cyclopentadiene group, silol group, low mole group, thiophene group, cell Lenophene group, furan group, indole group, benzoborol group, benzophosphol group, indene group, benzosilol group, benzozomolol group, benzothiophene group, benzoselenophene group, benzofuran group, carbazole group, dibenzo Borol group, dibenzophosphol group, fluorene group, dibenzosilol group, dibenzozomol group, dibenzothiophene group, dibenzoselenophene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H -Fluorene-9-one group, dibenzothiophene 5,5-dioxide group, azaindole group, azabenzoborol group, azabenzophosphol group, azaindene group, azabenzosilol group, azabenzo low mole group, Azabenzothiophene group, azabenzoselenophene group, azabenzofuran group, azacarbazole group, azadibenzoborol group, azadibenzophosphol group, azafluorene group, azadibenzosilol group, azadibenzozomol Group, Azadibenzoti Pen groups, azadibenzoselenophene groups, azadibenzofuran groups, azadibenzothiophene 5-oxide groups, aza-9H-fluorene-9-one groups, azadibenzothiophene 5,5-dioxide groups, Pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, benzoquinoline group, benzoisoquinoline group, quinoxaline group, quinazoline group, phenanthroline group, pyrazole group , Imidazole group, triazole group, azaborol group, azaphosphol group, azacyclopentadiene group, azasilol group, azazomol group, azaselenophene group, oxazole group, isoxazole group, thiazole group, Isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzoimidazole group, benzoxazole group, benzothiazole group, benzoxadiazole group, benzothiadiazole group, 5,6 , 7,8-tetra Draw can be isoquinoline (5,6,7,8-tetrahydroisoquinoline) group or a 5,6,7,8-tetrahydroquinoline (5,6,7,8-tetrahydroquinoline) group.

Examples of the C ₁ -C ₆₀ alkyl group, C ₁ -C ₂₀ alkyl group and / or C ₁ -C ₁₀ alkyl group in the present specification include methyl group, ethyl group, n -propyl group, isopropyl group, n -butyl group, sec -butyl group , Isobutyl group, tert -butyl group, n -pentyl group, tert -pentyl group, neopentyl group, isopentyl group, sec -pentyl group, 3-pentyl group, sec -isopentyl group, n -hexyl group, iso hexyl, sec - hexyl group, tert - hexyl, n - heptyl, iso-heptyl, sec - heptyl group, tert - heptyl, n - octyl, yisook group, sec - octyl, tert - octyl group, unsubstituted or substituted with n -nonyl, isononyl, sec -nonyl, tert -nonyl, n -decyl, isodecyl , sec -decyl, tert -decyl, or any combination thereof, Methyl, ethyl, n -propyl, isopropyl, n -butyl, sec -butyl, isobutyl, tert -butyl, n -pentyl, tert -pentyl, neopentyl, isopentyl, sec -pentyl group, 3-pentyl group, sec -isopentyl 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, sec -nonyl, tert -nonyl, n -decyl, isodecyl, sec -decyl or tert -decyl.

Examples of the C ₁ -C ₆₀ alkoxy group, C ₁ -C ₂₀ alkoxy group or C ₁ -C ₁₀ alkoxy group in the present specification may include a methoxy group, ethoxy group, propoxy group, butoxy group or pentoxy group.

Examples of the C ₃ -C ₁₀ cycloalkyl group in the present specification include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group (adamantanyl), and a norbornanyl group (norbornanyl) ), Bicyclo [1.1.1] pentyl, bicyclo [2.1.1] hexyl, bicyclo [2.2.1] heptyl group ( bicyclo [2.2.1] heptyl) and bicyclo [2.2.2] octyl groups.

* And * 'in Formula 2 are each a binding site with M in Formula 1.

로 표시된 그룹은 하기 화학식 CY1-1 내지 CY1-69 중 하나로 표시된 그룹일 수 있다:According to one embodiment, in Formula 2

The group represented by may be a group represented by one of formulas CY1-1 to CY1-69:

In Formulas CY1-1 to CY1-69,

For descriptions of X ₁ and R ₁ , respectively, refer to what is described herein.

X ₁₁ is O, S, Se, N (R ₁₉ ), C (R _19a ) (R _19b ) or Si (R _19a ) (R _19b ),

For the description of R ₁₉ , R _19a , R _19b , R _1a and R _1b , refer to the description of R ₁ in this specification, respectively,

a18 is an integer of 0 to 8,

a16 is an integer of 0 to 6,

a15 is an integer of 0 to 5,

a14 is an integer of 0 to 4,

a13 is an integer of 0 to 3,

* "Is a binding site with T ₁ in Formula 2,

* 'Is a binding site with M in the general formula (1).

로 표시된 그룹은 하기 화학식 CY1(1) 내지 CY1(165) 중 하나로 표시된 그룹일 수 있다:According to another embodiment, in Formula 2

The group represented by may be a group represented by one of the following formulas CY1 (1) to CY1 (165):

In Formulas CY1 (1) to CY1 (165),

For descriptions of X ₁ and X ₁₁ , respectively, refer to what is described herein.

Description of the R ₁₁ to R ₁₆ are, but see the description of the R ₁ of each of the specification, R ₁₁ to R ₁₆ is not hydrogen,

* "Is a binding site with T ₁ in Formula 2,

* 'Is a binding site with M in the general formula (1).

로 표시된 그룹은 하기 화학식 CY21-1 내지 CY21-25 중 하나로 표시된 그룹일 수 있다:According to another embodiment, in Formula 2

The group represented by may be a group represented by one of formulas CY21-1 to CY21-25:

In Formulas CY21-1 to CY21-25,

For descriptions of X ₂₁ and R ₂₁ , refer to what is described herein, respectively,

X ₂₂ is C (R ₂₂ ) (R ₂₃ ), N (R ₂₂ ), O, S or Si (R ₂₂ ) (R ₂₃ ),

For a description of R ₂₂ to R ₂₉ each refer to the description of R ₂₁ in the present specification,

a26 is an integer of 0 to 6,

a24 is an integer of 0 to 4,

a23 is an integer of 0 to 3,

a22 is an integer of 0 to 2,

* "Is a binding site with T ₁ in Formula 2,

* 'Is a binding site with M in the general formula (1).

로 표시된 그룹은 하기 화학식 CY21(1) 내지 CY21(56) 중 하나로 표시된 그룹 또는 상기 화학식 CY21-20 내지 CY21-25 중 하나로 표시된 그룹일 수 있다:According to another embodiment, in Formula 2

The group represented by may be a group represented by one of formulas CY21 (1) to CY21 (56) or a group represented by one of formulas CY21-20 to CY21-25:

In Formulas CY21 (1) to CY21 (56),

For descriptions of X ₂₁ and R ₂₁ , refer to what is described herein, respectively,

For a description of R _21a to R _21d refer to the description of R ₂₁ in this specification, respectively, wherein R ₂₁ and R _21a to R _21d are not hydrogen,

* "Is a binding site with T ₁ in Formula 2,

* Is a binding site with M in formula (1).

L ₂ in Formula 1 may be a bidentate ligand bonded to M of Formula 1 through O, S, Se, N, C, P, Si, or As.

According to one embodiment, L ₂ in Formula 1 may be a bidentate ligand represented by Formula 3 below:

<Formula 3>

In Formula 3,

X ₃₁ and X ₃₂ are independently of each other, O, S, Se, N, C, P, Si or As,

는 X₃₁과 X₃₂를 서로 연결하는 연결기(linking group)를 나타내고,

Represents a linking group connecting X ₃₁ and X ₃₂ to each other,

* And * 'are each a binding site with M in the formula (1).

For example, X ₃₁ and X ₃₂ in Formula 3 may be each independently O, S, Se, or N, but are not limited thereto.

For example, in Formula 3, i) X ₃₁ and X ₃₂ may be O; Or ii) X ₃₁ may be N and X ₃₂ may be C, but is not limited thereto.

According to another embodiment, L ₂ in Chemical Formula 1 is a monodentate ligand, for example, I ⁻ , Br ⁻ , Cl ⁻ , sulfide, nitrate, azide, or hydroxide. (hydroxide), cyanate, isocyanate, thiocyanate, water, acetonitrile, pyridine, ammonia, carbon monoxide, P (Ph) ₃ , P ( Ph) ₂ CH ₃ , PPh (CH ₃ ) ₂ Or P (CH ₃ ) ₃ It may be, but is not limited thereto.

According to another embodiment, L ₂ in Formula 1 is a bidentate ligand such as oxalate, acetylacetonate, picolinic acid, 1,2-bis (di Phenylphosphino) ethene (1,2-bis (diphenylphosphino) ethane), 1,1-bis (diphenylphosphino) methene (1,1-bis (diphenylphosphino) methane), glycinate or ethylenediamine (ethylenediamine), but is not limited thereto.

According to another embodiment, L ₂ in Formula 1 may be a group represented by one of Formulas 3A to 3F:

In Formulas 3A to 3F,

Y ₁₃ is O, N, N (Z ₁ ), P (Z ₁ ) (Z ₂ ) or As (Z ₁ ) (Z ₂ ),

Y ₁₄ is O, N, N (Z ₃ ), P (Z ₃ ) (Z ₄ ) or As (Z ₃ ) (Z ₄ ),

T ₁₁ is a single bond, a double bond, * -C (Z ₁₁ ) (Z ₁₂ )-* ', * -C (Z ₁₁ ) = C (Z ₁₂ )-*', * = C (Z ₁₁ )-* ', * -C (Z ₁₁ ) = *', * = C (Z ₁₁ ) -C (Z ₁₂ ) = C (Z ₁₃ )-* ', * -C (Z ₁₁ ) = C (Z ₁₂ )- C (Z ₁₃ ) = * ', * -N (Z ₁₁ )-*' Or a C ₅ -C ₃₀ carbocyclic group unsubstituted or substituted with at least one Z ₁₁ ,

a11 is an integer of 1 to 10, when a11 is 2 or more, two or more T ₁₁ are the same as or different from each other,

Y ₁₁ and Y ₁₂ are, independently from each other, C or N,

T ₂₁ is a single bond, a double bond, O, S, C (Z ₁₁ ) (Z ₁₂ ), Si (Z ₁₁ ) (Z ₁₂ ) or N (Z ₁₁ ),

Ring CY ₁₁ and ring CY ₁₂ are, independently from each other, a C ₅ -C ₃₀ carbocyclic group or a C ₁ -C ₃₀ heterocyclic group,

A ₁ is P or As,

For the description of Z ₁ to Z ₄ and Z ₁₁ to Z ₁₃ refer to the description of R ₂₁ in the present specification, respectively,

d1 and d2 are each independently an integer of 0 to 10,

* And * 'is a binding site with M in the formula (1).

For the description of the C ₅ -C ₃₀ carbocyclic group and the C ₁ -C ₃₀ heterocyclic group in the above description of Formulas 3A to 3F, refer to the description of the ring CY ₂₁ in the present specification, respectively.

로 표시된 그룹은 하기 화학식 CY11-1 내지 CY11-34 중 하나로 표시된 그룹이고(이거나), For example, of Formula 3D

A group represented by is a group represented by one of formulas CY11-1 to CY11-34, or

로 표시된 그룹은 하기 화학식 CY12-1 내지 CY12-34 중 하나로 표시된 그룹일 수 있다:Formulas 3C and 3D

The group represented by may be a group represented by one of formulas CY12-1 to CY12-34:

In Formulas CY11-1 to CY11-34 and CY12-1 to CY12-34,

X ₃₁ is O, S, N (Z ₁₁ ), C (Z ₁₁ ) (Z ₁₂ ) or Si (Z ₁₁ ) (Z ₁₂ ),

X ₄₁ is O, S, N (Z ₂₁ ), C (Z ₂₁ ) (Z ₂₂ ) or Si (Z ₂₁ ) (Z ₂₂ ),

For descriptions of Y ₁₁ , Y ₁₂ , Z ₁ and Z ₂ , respectively, refer to what is described herein.

For descriptions of Z ₁₁ to Z ₁₈ and Z ₂₁ to Z ₂₈ , refer to the description of R ₂₁ in the present specification, respectively.

d12 and d22 are each independently an integer of 0 to 2,

d13 and d23 are each independently an integer of 0 to 3,

d14 and d24 are each independently an integer of 0 to 4,

d15 and d25 are each independently an integer of 0 to 5,

d16 and d26 are each independently an integer of 0 to 6,

* And * 'in the formulas CY11-1 to CY11-34 and CY12-1 to CY12-34 are each a binding site to M in Formula 1, and * "represents a neighboring atom in Formula 3C or T _{21 in} Formula 3D. Is a combined site.

As another example, L ₂ in Formula 1 may be a group represented by one of the following Formulas 3-1 (1) to 3-1 (66) and 3-1 (301) to 3-1 (309), but It is not limited to:

In Formulas 3-1 (1) to 3-1 (66) and 3-1 (301) to 3-1 (309),

X ₄₁ is O, S, N (Z ₂₁ ), C (Z ₂₁ ) (Z ₂₂ ) or Si (Z ₂₁ ) (Z ₂₂ ),

For the description of Z ₁ to Z ₄ , Z _1a , Z _1b , Z _1c , Z _1d , Z _2a , Z _2b , Z _2c , Z _2d and Z ₁₁ to Z ₁₄ , refer to the description of R ₂₁ in this specification, respectively. and,

d14 is an integer of 0 to 4,

d26 is an integer of 0 to 6,

* And * 'are each a binding site with M in the formula (1).

According to one embodiment, L ₂ may be a ligand represented by Formula 3-1 (301).

According to another embodiment, at least one of Z ₁₁ and Z ₁₃ in Formula 3-1 (301) may not be a methyl group.

According to another embodiment, Z ₁₁ and Z ₁₃ in Formula 3-1 (301) may not be a methyl group at the same time.

According to another embodiment, at least one of Z ₁₁ and Z ₁₃ in Formula 3-1 (301) may be each independently a substituted or unsubstituted C ₃ -C ₆₀ alkyl group, or a substituted or unsubstituted C ₃ − It may be a C ₁₀ cycloalkyl group.

According to another embodiment, Z ₁₁ and Z ₁₃ of Formula 3-1 (301) are each independently a substituted or unsubstituted C ₃ -C ₆₀ alkyl group, or a substituted or unsubstituted C ₃ -C ₁₀ cyclo It may be an alkyl group.

According to another embodiment, at least one of Z ₁₁ and Z ₁₃ in Formula 3-1 (301) may independently be a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group.

According to another embodiment, Z ₁₁ and Z _{13 in} Chemical Formula 3-1 (301), independently of each other, may be a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group.

According to another embodiment, Z ₁₁ and Z ₁₃ of Formula 3-1 (301) are independently of each other,

C ₃ -C ₂₀ alkyl group;

Deuterium, C ₁ -C ₁₀ alkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, bicyclo [1.1.1] pentyl, bicyclo [2.1.1] hexyl, bicyclo [2.2.1] heptyl, bicyclo [2.2.2] octyl group, (C ₁ -C ₂₀ alkyl) cyclopentyl Tyl group, (C ₁ -C ₂₀ alkyl) cyclohexyl group, (C ₁ -C ₂₀ alkyl) cycloheptyl group, (C ₁ -C ₂₀ alkyl) cyclooctyl group, (C ₁ -C ₂₀ alkyl) adamantanyl group, (C ₁ -C ₂₀ alkyl) norbornanyl group, (C ₁ -C ₂₀ alkyl) norbornenyl group, (C ₁ -C ₂₀ alkyl) cyclopentenyl group, (C ₁ -C ₂₀ alkyl) cyclohexenyl group, ( C ₁ -C ₂₀ alkyl) cycloheptenyl group, (C ₁ -C ₂₀ alkyl) bicyclo [1.1.1] pentyl group, (C ₁ -C ₂₀ alkyl) bicyclo [2.1.1] hexyl group, (C ₁ -C ₂₀ alkyl) bicyclo [2.2.1] heptyl, (C ₁ -C ₂₀ alkyl) bicyclo [2.2.2] octyl group, or substituted by any combination thereof C ₃ -C ₂₀ Kilgi; or

Deuterium, C ₁ -C ₂₀ alkyl group, deuterium-containing C ₂ -C ₂₀ alkyl group (eg * -C (CD ₃ ) _3, etc.), cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, Adamantanyl, norbornanyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo [1.1.1] pentyl, bicyclo [2.1.1] hexyl, bicyclo [2.2. 1] heptyl group, bicyclo [2.2.2] octyl group, (C ₁ -C ₂₀ alkyl) cyclopentyl group, (C ₁ -C ₂₀ alkyl) cyclohexyl group, (C ₁ -C ₂₀ alkyl) cycloheptyl group , (C ₁ -C ₂₀ alkyl) cyclooctyl group, (C ₁ -C ₂₀ alkyl) adamantanyl group, (C ₁ -C ₂₀ alkyl) norbornanyl group, (C ₁ -C ₂₀ alkyl) norbornenyl group, ( C ₁ -C ₂₀ alkyl) cyclopentenyl group, (C ₁ -C ₂₀ alkyl) cyclohexenyl group, (C ₁ -C ₂₀ alkyl) cycloheptenyl group, (C ₁ -C ₂₀ alkyl) bicyclo [1.1.1 ] Pentyl group, (C ₁ -C ₂₀ alkyl) bicyclo [2.1.1] hexyl group, (C ₁ -C ₂₀ alkyl) bicyclo [2.2.1] heptyl group, (C ₁ -C ₂₀ alkyl) bicyclo 2.2. 2] cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclosubstituted or unsubstituted with an octyl group or any combination thereof Hexenyl group, cycloheptenyl group, bicyclo [1.1.1] pentyl group, bicyclo [2.1.1] hexyl group, bicyclo [2.2.1] heptyl group, bicyclo [2.2.2] octyl group;

Can be.

As another example, L ₂ in Formula 1 may be a group represented by Formula 3-1-1, but is not limited thereto.

In the above formula 3-1-1,

For a description of Z ₁₂ refer to the description of R ₂₁ in the present specification,

A ₂ and A ₅ are independently of each other hydrogen, deuterium, 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 ₂ -C ₆₀ alky 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 Unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or substituted or unsubstituted monovalent non- Aromatic heterocondensed polycyclic group,

A ₁ , A ₃ , A ₄ and A ₆ are each independently 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 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 heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or substituted or unsubstituted monovalent A non-aromatic heterocondensed polycyclic group,

A ₁ to A ₆ at least two of optionally, be connected to each other, substituted or unsubstituted with at least one of R _1a C ₅ -C ₃₀ carbocyclic group, or a substituted or unsubstituted with at least one of R _1a C ₁ -C ₃₀ heterocyclic group may be formed,

For the description of R _1a refer to the description of Z ₁₂ ,

The substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, Substituted C ₁ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C ₆ -C ₆₀ arylthio group, substituted C ₁ -C ₆₀ heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group and substituted monovalent non-aromatic condensed polycyclic group Substituents independently of one another,

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group Or a C ₁ -C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ heteroaryl group, 1 Valent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group, -N (Q ₁₁ ) (Q ₁₂ ), -Si (Q ₁₃ ) (Q ₁₄ ) (Q ₁₅ ),-Ge (Q ₁₃ ) (Q ₁₄ ) (Q ₁₅ ), -B (Q ₁₆ ) (Q ₁₇ ), -P (= O) (Q ₁₈ ) (Q ₁₉ ), -P (Q ₁₈ ) (Q ₁₉ ), or any thereof C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group or C ₁ -C ₆₀ alkoxy group substituted with a combination;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group , C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic group, - N (Q ₂₁ ) (Q ₂₂ ), -Si (Q ₂₃ ) (Q ₂₄ ) (Q ₂₅ ), -Ge (Q ₂₃ ) (Q ₂₄ ) (Q ₂₅ ), -B (Q ₂₆ ) (Q ₂₇ ) , C ₃ -C ₁₀ cycloalkyl group, C ₁ -unsubstituted or substituted with -P (= 0) (Q ₂₈ ) (Q ₂₉ ), -P (Q ₂₈ ) (Q ₂₉ ), or any combination thereof. C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group , C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ heteroaryl group, a monovalent non- Aromatic condensed polycyclic group or monovalent non-aromatic heterocondensed polycyclic group;

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

Any combination thereof;

ego,

Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ are each independently hydrogen; heavy hydrogen; -F; -Cl; -Br; -I; Hydroxyl group; Cyano group; Nitro group; Amidino groups; Hydrazine group; Hydrazone group; Carboxylic acid groups or salts thereof; Sulfonic acid groups or salts thereof; Phosphoric acid groups or salts thereof; Deuterium, C ₁ -C ₆₀ alkyl, C ₆ -C ₆₀ aryl group, or substituted by any combination thereof or unsubstituted 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; ₆₀ aryl group, heavy hydrogen, C ₁ -C ₆₀ alkyl, C ₆ -C ₆₀ aryl group, or a substituted or unsubstituted in any combination thereof C ₆ -C; C ₆ -C ₆₀ aryloxy group; C ₆ -C ₆₀ arylthio group; C ₁ -C ₆₀ heteroaryl group; Monovalent non-aromatic condensed polycyclic groups; Or a monovalent non-aromatic heterocondensed polycyclic group.

For example, in Formula 3-1-1, A ₁ to A ₆ and Z ₁₂ may be each independently,

Hydrogen, deuterium, -F, cyano group, C ₁ -C ₂₀ alkyl group or C ₁ -C ₂₀ alkoxy group;

Deuterium, -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 Heptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, bicyclo [1.1.1] pentyl group, bicyclo [2.1.1] hex Real group, bicyclo [2.2.1] heptyl group, bicyclo [2.2.2] octyl group, (C ₁ -C ₂₀ alkyl) cyclopentyl group, (C ₁ -C ₂₀ alkyl) cyclohexyl group, (C _1- C ₂₀ alkyl) cycloheptyl group, (C ₁ -C ₂₀ alkyl) cyclooctyl group, (C ₁ -C ₂₀ alkyl) adamantanyl group, (C ₁ -C ₂₀ alkyl) norbornanyl group, (C ₁ -C ₂₀ Alkyl) norbornenyl group, (C ₁ -C ₂₀ alkyl) cyclopentenyl group, (C ₁ -C ₂₀ alkyl) cyclohexenyl group, (C ₁ -C ₂₀ alkyl) cycloheptenyl group, (C ₁ -C ₂₀ alkyl ) Bicyclo [1.1.1] pentyl group, (C ₁ -C ₂₀ alkyl) bicyclo [2.1.1] hexyl group, (C ₁ -C ₂₀ alkyl) bicyclo [2.2.1] heptyl group, (C ₁ -C ₂₀ alkyl) bicyclo [2.2.2 ] Octyl group, a phenyl group, (C ₁ -C ₂₀ alkyl) phenyl group, a biphenyl group, a terphenyl group, or substituted by any combination thereof, C ₁ -C ₂₀ alkyl group or a C ₁ -C ₂₀ alkoxy group; or

Deuterium, -F, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , cyano group, C ₁ -C ₂₀ alkyl group, deuterium-containing C ₂ -C ₂₀ alkyl group (For example, * -C (CD ₃ ) ₃ ) cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group , Cycloheptenyl group, bicyclo [1.1.1] pentyl group, bicyclo [2.1.1] hexyl group, bicyclo [2.2.1] heptyl group, bicyclo [2.2.2] octyl group, (C ₁ -C ₂₀ alkyl) cyclopentyl group, (C ₁ -C ₂₀ alkyl) cyclohexyl group, (C ₁ -C ₂₀ alkyl) cycloheptyl group, (C ₁ -C ₂₀ alkyl) cyclooctyl group, (C ₁ -C ₂₀ alkyl ) Adamantyl, (C ₁ -C ₂₀ alkyl) norbornanyl, (C ₁ -C ₂₀ alkyl) norbornenyl, (C ₁ -C ₂₀ alkyl) cyclopentenyl, (C ₁ -C ₂₀ alkyl) cyclo Hexenyl group, (C ₁ -C ₂₀ alkyl) cycloheptenyl group, (C ₁ -C ₂₀ alkyl) bicyclo [1.1.1] pentyl group, (C ₁ -C ₂₀ alkyl) bicyclo [2.1.1] hex Practical group, (C ₁ -C ₂₀ alkyl ) Bicyclo [2.2.1] heptyl group, (C ₁ -C ₂₀ alkyl) bicyclo [2.2.2] octyl group, phenyl group, (C ₁ -C ₂₀ alkyl) phenyl group, biphenyl group, terphenyl group, or any thereof Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantanyl, norbornanyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, unsubstituted or substituted with a combination of bicyclo [1.1.1] pentyl, bicyclo [2.1.1] hexyl, bicyclo [2.2.1] heptyl, bicyclo [2.2.2] octyl group, a phenyl group, (C ₁ -C ₂₀ alkyl) Phenyl group, biphenyl group, or terphenyl group; wherein A ₁ , A ₃ , A ₄ and A ₆ may not be hydrogen and deuterium.

As another example, A ₁ to A ₆ and Z ₁₂ in Formula 3-1-1 may be each independently

Hydrogen or deuterium;

Deuterium, methyl group, ethyl group, n -propyl group, isopropyl group, n -butyl group, sec -butyl group, isobutyl group, tert -butyl group, n -pentyl group, tert -pentyl group, neopentyl group, isopen group, sec - pentyl, 3-pentyl group, sec - isopentyl group, or in any combination thereof, a substituted or unsubstituted, Methyl, ethyl, n -propyl, isopropyl, n -butyl, sec -butyl, isobutyl, tert -butyl, n -pentyl, tert -pentyl, neopentyl, isopentyl, sec -pentyl group, 3-pentyl group or sec -isopentyl group; or

Deuterium, -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 Heptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, bicyclo [1.1.1] pentyl group, bicyclo [2.1.1] hex Real group, bicyclo [2.2.1] heptyl group, bicyclo [2.2.2] octyl group, (C ₁ -C ₂₀ alkyl) cyclopentyl group, (C ₁ -C ₂₀ alkyl) cyclohexyl group, (C _1- C ₂₀ alkyl) cycloheptyl group, (C ₁ -C ₂₀ alkyl) cyclooctyl group, (C ₁ -C ₂₀ alkyl) adamantanyl group, (C ₁ -C ₂₀ alkyl) norbornanyl group, (C ₁ -C ₂₀ Alkyl) norbornenyl group, (C ₁ -C ₂₀ alkyl) cyclopentenyl group, (C ₁ -C ₂₀ alkyl) cyclohexenyl group, (C ₁ -C ₂₀ alkyl) cycloheptenyl group, (C ₁ -C ₂₀ alkyl ) Bicyclo [1.1.1] pentyl group, (C ₁ -C ₂₀ alkyl) bicyclo [2.1.1] hexyl group, (C ₁ -C ₂₀ alkyl) bicyclo [2.2.1] heptyl group, (C ₁ -C ₂₀ alkyl) bicyclo [2.2.2 ] Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, unsubstituted or substituted with an octyl group, a phenyl group, a (C ₁ -C ₂₀ alkyl) phenyl group, a biphenyl group, a terphenyl group, or any combination thereof, Adamantanyl, norbornanyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo [1.1.1] pentyl, bicyclo [2.1.1] hexyl, bicyclo [2.2. 1] heptyl group, bicyclo [2.2.2] octyl group, phenyl group, (C ₁ -C ₂₀ alkyl) phenyl group, biphenyl group, or terphenyl group; wherein A ₁ , A ₃ , A ₄ and A ₆ are hydrogen and It may not be deuterium.

According to another embodiment, all of A ₁ to A _{6 in} Formula 3-1-1 may not be hydrogen.

According to another embodiment, all of A ₁ to A _{6 in} Formula 3-1-1 may not be hydrogen and deuterium.

According to another embodiment, L ₁ may include at least one deuterium.

According to another embodiment, L ₁ may include at least one fluoro group (-F).

According to another embodiment, a1 in Formula 2 is not 0, and at least one of a1 R ₁ may include at least one deuterium.

According to another embodiment, a1 in Formula 2 is not 0, and at least one of a1 R ₁ may include at least one fluoro group (-F).

According to another embodiment, Formula a1 may be 0, 1, or 2.

According to another embodiment, the condensed ring in which the ring CY ₁₁ and the ring CY ₁₂ are condensed with each other in Formula 2 may be a condensed ring having two, three or four rings condensed with each other.

The organometallic compound represented by Formula 1 may emit visible light, for example, visible light having a maximum emission wavelength in a range of 450 nm or more and 700 nm or less. For example, the visible light may be red light.

As used herein, the term "azaindole group, azabenzoborol group, azabenzophosphol group, azaindene group, azabenzosilol group, azabenzozomol group, azabenzothiophene group, azabenzoselenophene group, azabenzofuran group Azacarbazole group, azadibenzoborol group, azadibenzophosphol group, azafluorene group, azadibenzosilol group, azadibenzo low mole group, azadibenzothiophene group, azadibenzoselenophene group, Azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluorene-9-one group, azadibenzothiophene 5,5-dioxide group "are respectively" indole group, benzoborol group " , Benzophosphol group, indene group, benzosilol group, benzozomol group, benzothiophene group, benzoselenophene group, benzofuran group, carbazole group, dibenzoborol group, dibenzophosphol group, fluorene group, Dibenzosilol group, dibenzo Low mole groups, dibenzothiophene groups, dibenzoselenophene groups, dibenzofuran groups, dibenzothiophene 5-oxide groups, 9H-fluorene-9-one groups, dibenzothiophene 5,5-dioxide groups " It means a heterocyclic ring having the same backbone, wherein at least one of the carbons forming their ring is substituted with nitrogen.

According to one embodiment, the organometallic compound may be selected from Compounds 1 to 366, but is not limited thereto.

L ₁ in the organometallic compound represented by Chemical Formula 1 is selected from ligands represented by Chemical Formula 2, and n1, the number of L ₁ , is 1, 2, or 3. That is, the organometallic compound is a ligand bound to the metal M, and must include at least one ligand represented by the formula (2).

In Formula 2, the ring CY ₁₁ and the ring CY ₁₂ are condensed with each other. As a result, the conjugated length of the LUMO phore among the ligands represented by Formula 2 may be increased, thereby increasing the electron transfer. Therefore, the radiation decay of the organometallic compound employing the ligand represented by Formula 2 may be increased. Can be. Therefore, the luminous efficiency, external quantum efficiency and / or lifetime of an electronic device employing the organometallic compound represented by Formula 1, for example, an organic light emitting device, may be improved.

In addition, in Formula 2, T ₁ is * -N (R ₂ )-* ', * -B (R ₂ )-*', * -P (R ₂ )-* ', * -C (R ₂ ) (R ₃ )-* ', * -Si (R ₂ ) (R ₃ )-*', * -Ge (R ₂ ) (R ₃ )-* ', * -S- *', * -Se- * ', * -O- *', * -C (= O)-* ', * -S (= O)-*', * -S (= O) _2- * ', * -C (R ₂ ) = * ', * = C (R ₂ )-*', * -C (R ₂ ) = C (R ₃ )-* ', * -C (= S)-*' or * -C≡C- * Can be '. That is, T ₁ is not a single bond. As a result, the non-covalent electrons included in T ₁ of the organometallic compound represented by Formula 1 may increase the spin-orbit coupling effect between the metal and the ligand, and the electronic device employing the organometallic compound, for example, The luminous efficiency, external quantum efficiency and / or lifespan of the organic light emitting device can be improved.

Further, the metal M of Formula 1 is iridium (Ir), osmium (Os), titanium (Ti), hafnium (Hf), europium (Eu), rhodium (Rh) or ruthenium (Ru). Although not intended to be limited by a specific theory, the organometallic compound represented by Chemical Formula 1 including M as described above may have a large spin-orbit coupling value compared to platinum (Pt), for example, a triplet state. Since the inter-phase transition between and singlet states can be increased, it can have a relatively large quantum luminous efficiency and relatively short decay time. Therefore, the life of an electronic device employing the organometallic compound, for example, an organic light emitting device can be improved.

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

Compound no. HOMO
(eV) LUMO
(eV) Band gap
(eV) S ₁
(eV) T ₁
(eV) 2 -4.69 -1.59 3.10 2.37 2.46 32 -4.71 -1.94 2.77 2.14 2.10 33 -4.70 -1.94 2.76 2.14 2.10 47 -4.67 -2.20 2.47 2.06 2.03 69 -4.51 -2.01 2.50 1.93 1.90

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

The synthesis method of the organometallic compound represented by the formula (1) can be recognized by those skilled in the art with reference to the synthesis examples described later.

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

The organic light emitting diode may include an organic layer including the organometallic compound represented by Formula 1 as described above, and thus may have a low driving voltage, high external quantum efficiency, long life, and low roll-off ratio.

The organometallic compound represented by Formula 1 may be used between a pair of electrodes of the organic light emitting device. For example, the organometallic compound represented by Formula 1 may be included in the emission layer. In this case, the organometallic compound may serve as a dopant, and the emission layer may further include a host (that is, the content of the organometallic compound represented by Formula 1 is smaller than that of the host). The light emitting layer may emit visible light, for example, visible light having a maximum emission wavelength in a range of 450 nm or more and 700 nm or less.

In the present specification, "(organic layer) contains at least one organometallic compound" means "(organic layer) one organometallic compound belonging to the category of Formula 1 or two different kinds belonging to the category of Formula 1. It may include the above 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 compound. In this case, Compound 1 and Compound 2 may be present in the same layer (for example, both Compound 1 and Compound 2 may be present in the light emitting layer).

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

For example, the first electrode of the organic light emitting diode is an anode, the second electrode is a cathode, the organic layer is a hole transport region disposed between the first electrode and the light emitting layer and the light emitting layer and the second electrode And an electron transport region disposed therebetween, the hole transport region comprising a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof, wherein the electron transport region comprises: a hole blocking layer, an electron Transport layer, electron injection layer, or any combination thereof.

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

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

A substrate may be further 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 waterproofness may be used.

The first electrode 11 may be formed by, for example, providing a first electrode material on the substrate by 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. Indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), or the like may be used as the material for the first electrode. Alternatively, metals such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and the like may be used. .

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

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

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

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

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

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

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

When the hole injection layer is formed by vacuum deposition, 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 as desired, and the deposition temperature is about 100 to about, for example. 500 ° C., a vacuum degree of about 10 ⁻⁸ to about 10 ⁻³ torr, and a deposition rate of about 0.01 to about 100 μs / sec, but is not limited thereto.

When the hole injection layer is formed by spin coating, the coating conditions vary depending on the compound used as the hole injection layer material, the structure and the thermal characteristics of the desired hole injection layer, but the coating speed is 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.

The hole transport layer and the electron blocking layer forming conditions refer to the hole injection layer forming conditions.

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

<Formula 201>

<Formula 202>

In Formula 201, Ar ₁₀₁ and Ar ₁₀₂ independently of each other, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group , Carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl jade Unsubstituted or substituted with a period, a C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed polycyclic group, or any combination thereof , Phenylene group, pentarenylene group, indenylene group, naphthylene group, azulenylene group, heptalylene group, acenaphthylene group, fluorenylene group, phenenalenylene group, phenanthrenylene group, anthylene group It may be a racenylene group, a fluoranthhenylene group, a triphenylenylene group, a pyrenylene group, a chrysenenylene group, a naphthacenylene group, a picenylene group, a perylenenylene group, or a pentacenylene group.

In Formula 201, xa and xb may be each independently an integer of 0 to 5, or 0, 1 or 2. For example, xa may be 1 and xb may be 0.

In Formulas 201 and 202, R ₁₀₁ to R ₁₀₈ , R ₁₁₁ to R _119, and R ₁₂₁ to R ₁₂₄ are each independently,

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

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

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

Can be.

In Formula 201, R ₁₀₉ is deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its Substituted or unsubstituted with a salt, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyridinyl group, or any combination thereof It may be a phenyl group, naphthyl group, anthracenyl group or pyridinyl group.

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

<Formula 201A>

In Formula 201A, for the detailed description of R ₁₀₁ , R ₁₁₁ , R _112, and R ₁₀₉ , refer to the above description.

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

The hole transport region may have a thickness of about 100 kPa to about 10000 kPa, for example, about 100 kPa to about 1000 kPa. If the hole transport region includes at least one of a hole injection layer and a hole transport layer, the thickness of the hole injection layer is about 100 kPa to about 10000 kPa, for example, about 100 kPa to about 1000 kPa, and the thickness of the hole transport layer is about 50 kPa. To about 2000 kPa, for example, about 100 kPa to about 1500 kPa. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer satisfy the above ranges, satisfactory hole transport characteristics can be obtained without a substantial increase in driving voltage.

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

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

The hole transport region may further include a buffer layer.

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

Meanwhile, when the hole transport region includes an electron blocking layer, the electron blocking layer material may include a material that can be used in the hole transport region as described above, a host material described below, or any combination thereof. It is not limited to this. For example, when a hole transport region contains an electron blocking layer, mCP mentioned later can be used as an electron blocking layer material.

The emission layer EML may be formed on the hole transport region by using a method such as vacuum deposition, spin coating, casting, and LB. When the light emitting layer is formed by a vacuum deposition method and a spin coating method, the deposition conditions and the coating conditions vary depending on the compound used, and in general, may be selected from a range of conditions almost the same as the formation of the hole injection layer.

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 comprise TPBi, TBADN, ADN (also called "DNA"), CBP, CDBP, TCP, mCP, Compound H50, Compound H51, or any combination thereof:

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 / or 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 to emit white light.

When the light emitting layer includes a host and a dopant, the content of the dopant may be generally selected from 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 dopant may be an organometallic compound represented by Formula 1 in the present specification. For example, the dopant may be a red phosphorescent dopant.

The light emitting layer may have a thickness of about 100 kPa to about 1000 kPa, for example, about 200 kPa to about 600 kPa. When the thickness of the light emitting layer satisfies the aforementioned range, the light emitting layer may exhibit excellent light emission characteristics without a substantial increase in driving voltage.

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

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

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

Conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer of the electron transport region may be referred to the formation conditions of the hole injection layer.

When the electron transport region includes the hole blocking layer, the hole blocking layer may include, for example, BCP, Bphen, Balq, or any combination thereof, but is not limited thereto.

The hole blocking layer may have a thickness of about 20 kPa to about 1000 kPa, for example, about 30 kPa to about 300 kPa. 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 include BCP, Bphen, Alq ₃ , Balq, TAZ, NTAZ, or any combination thereof.

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

The electron transport layer may have a thickness of about 100 kPa to about 1000 kPa, for example, about 150 kPa to about 500 kPa. When the thickness of the electron transporting layer satisfies the above range, a satisfactory electron transporting characteristic can 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 comprise a Li complex. The Li complex may include, for example, the following compound ET-D1 (LiQ) or ET-D2.

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

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

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

The second electrode 19 is disposed on the organic layer 15. The second electrode 19 may be a cathode. As the material for the second electrode 19, a metal, an alloy, an electrically conductive compound having a relatively low work function, or a combination thereof 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 may be used as a material for forming the second electrode 19. Alternatively, various modifications are possible, such as forming the transmissive second electrode 19 by using ITO or IZO to obtain a front light emitting device.

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

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

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

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

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

In the present specification, a C ₁ -C ₆₀ alkoxy group refers to a monovalent group having a chemical formula of —OA ₁₀₁ (wherein A ₁₀₁ is the C ₁ -C ₆₀ alkyl group), and specific examples thereof include a methoxy group, an ethoxy group, Isopropyloxy group etc. are contained.

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

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

As used herein, a C ₃ -C ₁₀ cycloalkyl group means a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and specific examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cyclohep And a tilt group. As used herein, a C ₃ -C ₁₀ cycloalkylene group refers to a divalent group having the same structure as the C ₃ -C ₁₀ cycloalkyl group.

As used herein, a C ₁ -C ₁₀ heterocycloalkyl group means 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. As used herein, a C ₁ -C ₁₀ heterocycloalkylene group refers to a divalent group having the same structure as the C ₁ -C ₁₀ heterocycloalkyl group.

As used herein, a C ₃ -C ₁₀ cycloalkenyl group is a monovalent monocyclic group having 3 to 10 carbon atoms, and refers to a group having at least one carbon-carbon double bond in the ring, but having no aromaticity. Specific examples thereof include a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, and the like. In the present specification, the C ₃ -C ₁₀ cycloalkenylene group refers to a divalent group having the same structure as the C ₃ -C ₁₀ cycloalkenyl group.

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

As used herein, 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 carbo having 6 to 60 carbon atoms Divalent groups having a cyclic aromatic system. Specific examples of the C ₆ -C ₆₀ aryl group include a phenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, 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, two or more rings may be fused to each other.

The C ₇ -C ₆₀ alkylaryl group herein means a group of the C ₆ -C ₆₀ aryl substituted with at least one C ₁ -C ₆₀ alkyl group.

As used herein, a C ₁ -C ₆₀ heteroaryl group includes a monovalent group having at least one hetero atom selected from N, O, P, Si, and S as a ring-forming atom and having a cyclic aromatic system having 1 to 60 carbon atoms. and means, C ₁ -C ₆₀ hetero arylene group N, O, P, at least one heteroatom selected from the group consisting of Si, and S the ring-forming atoms, and include as a second having a cyclic aromatic system having from 1 to 60 between the carbonyl Means a group. Specific examples of the C ₁ -C ₆₀ heteroaryl group include a pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, 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, two or more rings may be fused to each other.

As used herein, a C ₂ -C ₆₀ alkylheteroaryl group refers to a C ₁ -C ₆₀ heteroaryl group substituted with at least one C ₁ -C ₆₀ alkyl group.

In the specification C ₆ -C ₆₀ aryloxy group -OA, point ₁₀₂ (where, A ₁₀₂ is the C ₆ -C ₆₀ aryl group), a C ₆ -C ₆₀ arylthio group (arylthio) is -SA ₁₀₃ (where , A ₁₀₃ represents the C ₆ -C ₆₀ aryl group.

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

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

As used herein, a C ₅ -C ₃₀ carbocyclic group refers to a saturated or unsaturated cyclic group having only 5 to 30 carbons as ring forming atoms. The C ₅ -C ₃₀ carbocyclic group may be a monocyclic group or a polycyclic group.

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

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

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group Or a C ₁ -C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ Cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₇ -C ₆₀ alkylaryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C _1- C ₆₀ heteroaryl group, C ₂ -C ₆₀ alkylheteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group, -N (Q ₁₁ ) (Q ₁₂ ), -Si (Q ₁₃ ) (Q ₁₄ ) (Q ₁₅ ), -Ge (Q ₁₃ ) (Q ₁₄ ) (Q ₁₅ ), -B (Q ₁₆ ) (Q ₁₇ ), -P (= O) (Q ₁₈ ) ( Q ₁₉ ), C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group or C ₁ -substituted with -P (Q ₁₈ ) (Q ₁₉ ), or any combination thereof. C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group , C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ Aryl group, C ₇ -C ₆₀ alkylaryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, C ₂ -C ₆₀ alkylheteroaryl group, 1 Valent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group, -N (Q ₂₁ ) (Q ₂₂ ), -Si (Q ₂₃ ) (Q ₂₄ ) (Q ₂₅ ),-Ge (Q ₂₃ ) (Q ₂₄ ) (Q ₂₅ ), -B (Q ₂₆ ) (Q ₂₇ ), -P (= O) (Q ₂₈ ) (Q ₂₉ ), -P (Q ₂₈ ) (Q ₂₉ ), or any thereof C ₃ -C ₁₀ cycloalkyl group, C ₁ -C unsubstituted or substituted with a combination ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₇ -C ₆₀ alkylaryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, C ₂ -C ₆₀ alkylheteroaryl group, monovalent non-aromatic condensed polycyclic group, or monovalent non-aromatic condensed polycyclic group;

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

Any combination thereof;

Can be.

In the present specification, Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q _29, and Q ₃₁ to Q ₃₉ are each independently hydrogen; heavy hydrogen; -F; -Cl; -Br; -I; Hydroxyl group; Cyano group; Nitro group; Amidino groups; Hydrazine group; Hydrazone group; Carboxylic acid groups or salts thereof; Sulfonic acid groups or salts thereof; Phosphoric acid groups or salts thereof; Deuterium, C ₁ -C ₆₀ alkyl, C ₆ -C ₆₀ aryl group, or substituted by any combination thereof or unsubstituted 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; ₆₀ aryl group, heavy hydrogen, C ₁ -C ₆₀ alkyl, C ₆ -C ₆₀ aryl group, or a substituted or unsubstituted in any combination thereof C ₆ -C; C ₆ -C ₆₀ aryloxy group; C ₆ -C ₆₀ arylthio group; C ₁ -C ₆₀ heteroaryl group; Monovalent non-aromatic condensed polycyclic groups; Or a monovalent non-aromatic heterocondensed polycyclic group.

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

EXAMPLE

Synthesis Example 1 (Compound 2)

1) Synthesis of Intermediate L2

1-bromo-isoquinoline (6.58 g, 31.64 mmol), phenol (Phenol (3.28 g, 34.80 mmol), CuI (0.603 g, 3.06 mmol) and Cs ₂ CO ₃ (20.62 g, 63.28 mmol) and Pyridine-2-carboxylic Acid (0.78 g, 6.33 mmol) were mixed with 160 mL of dioxane (1,4-Dioxane), and the mixture was stirred under reflux for 18 hours. The resulting filtrate was separated and the filtrate was removed under reduced pressure to remove the solvent, and the residue obtained therefrom was extracted with methylene chloride (MC), and the organic layer was extracted with anhydrous magnesium sulfate (MgSO). ₄ ) was added to remove water, and then the filtrate obtained by filtration was removed under reduced pressure to remove the solvent, and the residue obtained therefrom was purified by column chromatography under EA (ethyl acetate): Hexane = 1:10. This gave 6.46 g (92%) of intermediate L2.

MALDI-TOFMS (m / z): C ₁₅ H ₁₁ NO (M ⁺ ) 222.

2) Synthesis of Intermediate L2-dimer

Intermediate L2 (6.33 g, 28.62 mmol), iridium chloride (4.49 g, 12.72 mmol) was mixed with 60 mL of ethoxyethanol and 20 mL of distilled water, followed by stirring under reflux for 24 hours. After proceeding, the temperature was lowered to room temperature. The resulting solid was isolated by filtration and washed thoroughly with water / methanol / hexanes in order to dry the solid obtained in a vacuum oven to give intermediate L2-dimer (3.69 g, 43%).

3) Synthesis of Compound 2

Intermediate L2-dimer (3.28 g, 2.45 mmol) and 2,2,6,6-tetramethylheptane-3,5-dione (2,2,6,6-tetramethylheptane-3,5-dione) (4.52 g , 24.5 mmol) and Na ₂ CO ₃ (2.59 g, 24.5 mmol) were mixed with 50 mL of ethoxyethanol, and heated and stirred at 90 ° C. for 18 hours to proceed with the reaction. The resulting mixture was filtered and the solid obtained was washed sufficiently with ethanol and subjected to column chromatography under the conditions of dichloromethane: n-hexane = 1: 1 (v / v) to give compound 2 (1.40 g, 35%). ) Was obtained. Mass 2 and Compound 2 were identified by HPLC.

HRMS (MALDI) calcd for C ₄₁ H ₃₉ IrN ₂ O ₄ : m / z 816.2539, Found: 816.2540.

Synthesis Example  2 (compound 3)

3,7-diethylnonane-4,6-dione (5.20 g) instead of 2,2,6,6-tetramethylheptane-3,5-dione (2,2,6,6-tetramethylheptane-3,5-dione) , 24.5 mmol) was used in the same manner as in the synthesis of Compound 2 of Synthesis Example 1, to obtain Compound 3 (1.6 g, 39%). Mass spectrum and HPLC confirmed compound 3

HRMS (MALDI) calcd for C ₄₃ H ₄₃ IrN ₂ O ₄ : m / z 844.2852, Found: 844.2851.

Synthesis Example 3 (Compound 32)

1) Synthesis of Intermediate L32

Intermediate of Synthesis Example 1, except that 3-bromoisoquinoline (5.20 g, 24.5 mmol) was used instead of 1-bromo-isoquinoline Using the same method as the synthesis of L2, intermediate L32 (6.4 g, 91%) was obtained.

MALDI-TOFMS (m / z): C ₁₅ H ₁₁ NO (M ⁺ ) 222

2) Synthesis of Intermediate L32-dimer

Intermediate L32-dimer (4.5 g, 53%) was prepared in the same manner as in the synthesis of Intermediate L2-dimer of Synthesis Example 1, except that Intermediate L32 (5.20 g, 24.5 mmol) was used instead of Intermediate L2. ) Was obtained.

3) Synthesis of Compound 32

Compound 32 (1.3 g, 46) was prepared in the same manner as in the synthesis of Compound 2 of Synthesis Example 1, except that Intermediate L32-dimer (2.29 g, 1.72 mmol) was used instead of Intermediate L2-dimer. %) Was obtained. Mass spectrum and HPLC confirmed compound 32

HRMS (MALDI) calcd for C ₄₁ H ₃₉ IrN ₂ O ₄ : m / z 816.2539, Found: 816.2540.

Synthesis Example 4 (Compound 33)

3,7-diethylnonane-4,6-dione (3.52 g) instead of 2,2,6,6-tetramethylheptane-3,5-dione (2,2,6,6-tetramethylheptane-3,5-dione) , 16.6 mmol) was used in the same manner as in the synthesis of Compound 32 of Synthesis Example 3, to obtain Compound 33 (1.1 g, 39%). Mass spectrum and HPLC confirmed compound 33

HRMS (MALDI) calcd for C ₄₃ H ₄₃ IrN ₂ O ₄ : m / z 844.2852, Found: 844.2851.

Synthesis Example 5 (Compound 47)

1) Synthesis of Intermediate L47

Except for using 3-bromo-6-phenylisoquinoline (3.82 g, 13.5 mmol) instead of 1-bromo-isoquinoline. , Intermediate L47 (3.8 g, 95%) was obtained using the same method as the synthesis method of Intermediate L2 of Synthesis Example 1.

MALDI-TOFMS (m / z): C ₂₁ H ₁₅ NO (M ⁺ ) 298.

2) Synthesis of Intermediate L47-dimer

Intermediate L47-dimer (2.2 g, 47) was used in the same manner as the synthesis of Intermediate L2-dimer of Synthesis Example 1, except that Intermediate L47 (3.8 g, 12.7 mmol) was used instead of Intermediate L2. %) Was obtained.

3) Synthesis of Compound 47

Instead of intermediate L2-dimer, intermediate L47-dimer (2.2 g, 1.72 mmol) was used and 2,2,6,6-tetramethylheptan-3,5-dione (2,2,6,6-tetramethylheptane-3, Using the same method as the synthesis method of Compound 2 of Synthesis Example 1, except that 3,3,7,7-tetramethylnonane-4,6-dione was used instead of 5-dione, Compound 47 ( 1.3 g, 46%) was obtained. Mass spectrum and HPLC confirmed compound 47

HRMS (MALDI) calcd for C ₅₅ H ₅₁ IrN ₂ O ₄ : m / z 996.3478, Found: 996.3477.

Synthesis Example 6 (Compound 69)

1) Synthesis of Intermediate L69

The same method as the synthesis method of Intermediate L47 of Synthesis Example 5 was used except that 3,5-dimethylphenol (1.45 g, 11.83 mmol) was used instead of phenol. To give intermediate L69 (3.2 g, 91%).

MALDI-TOFMS (m / z): C ₂₃ H ₁₉ NO (M ⁺ ) 326.

2) Synthesis of Intermediate L69-dimer

Intermediate L69-dimer (1.9 g, 50) was used in the same manner as the synthesis of Intermediate L47-dimer of Synthesis Example 5, except that Intermediate L69 (3.2 g, 9.76 mmol) was used instead of Intermediate L47. %) Was obtained.

3) Synthesis of Compound 69

Compound 69 (0.98 g, 43) using the same method as the synthesis of Compound 47 of Synthesis Example 5, except that Intermediate L69-dimer (1.9 g, 1.09 mmol) was used instead of Intermediate L47-dimer. %) Was obtained. Mass spectrum and HPLC confirmed compound 69

HRMS (MALDI) calcd for C ₅₉ H ₅₉ IrN ₂ O ₄ : m / z 1052.4104, Found: 1052.4102.

Synthesis Example 7 (Compound 239)

1) Synthesis of Intermediate L239

4-bromobenzo [f] isoquinoline (5.0 g, 19.35 mmol) was used instead of 1-bromo-isoquinoline (5.0 g, 19.35 mmol). Using the same method as the synthesis of Intermediate L2 of Synthesis Example 1, Intermediate L239 (4.4 g, 84%) was obtained.

2) Synthesis of Intermediate L239-dimer

Intermediate L239-dimer (1.8 g, 45) was used in the same manner as the synthesis of Intermediate L2-dimer of Synthesis Example 1, except that Intermediate L239 (3.2 g, 11.71 mmol) was used instead of Intermediate L2. %) Was obtained.

3) Synthesis of Compound 239

Compound 239 (0.54 g, 27) was prepared in the same manner as in the synthesis of Compound 2 of Synthesis Example 1, except that Intermediate L239-dimer (1.6 g, 1.06 mmol) was used instead of Intermediate L2-dimer. %) Was obtained. Mass spectrum and HPLC confirmed Compound 239

HRMS (MALDI) calcd for C ₅₁ H ₄₇ IrN ₂ O ₄ : m / z 944.3165, Found: 944.3161.

Example 1

The glass substrate on which the ITO electrode was formed as an anode was cut into a size of 50 mm x 50 mm x 0.5 mm, ultrasonically cleaned for 5 minutes using isopropyl alcohol and pure water, and then UV ozone cleaned for 30 minutes, and installed in a vacuum deposition apparatus.

2-TNATA was vacuum deposited on the anode (ITO electrode) to form a hole injection layer having a thickness of 600 Å, and 4,4'-bis [N- (1-naphthyl) -N-phenyl was formed on the hole injection layer. Amino] biphenyl (hereinafter NPB) was vacuum deposited to form a hole transport layer having a thickness of 1350 kPa.

Subsequently, CBP (host) and Compound 2 (dopant) were co-deposited on the hole transport layer at a weight ratio of 98: 2 to form a light emitting layer having a thickness of 400 kHz.

Thereafter, BCP is vacuum deposited on the light emitting layer to form a hole blocking layer having a thickness of 50 kV, and Alq _{3 is} then vacuum deposited on the hole blocking layer to form an electron transporting layer having a thickness of 350 kPa. LiF was vacuum deposited to form an electron injection layer having a thickness of 10 kHz, and Al was deposited on the electron injection layer to form a cathode, thereby manufacturing an organic light emitting device.

Examples 2-6 and Comparative Examples A, E and G

An organic light-emitting device was manufactured in the same manner as in Example 1, except that each compound shown in Table 2 was used instead of the compound 2 as a dopant in forming the emission layer.

Evaluation Example 1 Evaluation of Characteristics of Organic Light-Emitting Element

The driving voltage, the maximum value of the external quantum efficiency (Max EQE), the roll-off ratio, and the EL spectrum of each of the organic light emitting diodes manufactured in Examples 1 to 6 and Comparative Examples A, E, and G. The full width at half maximum, maximum emission wavelength, and lifetime (T ₉₇ ) of the main peak were evaluated, and the results are shown in Table 2. As an evaluation device, a current-voltmeter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used, and the life time (LT ₉₇ ) (at 3500 nit) was evaluated for the time taken for the luminance to be 97% compared to the initial luminance of 100%. The roll-off ratio was calculated according to the following equation 20.

(Eq. 20)

Roll-off ratio = {1- (Efficiency (at 3500nit) / Max Luminous Efficiency)} X 100%

Dopant in emitting layer Driving voltage
(V) Max EQE
(%) Roll-Off ratio
(%) LT ₉₇
(hr)
(at 3500nit) Example 1 2 4.7 23.2 10 205 Example 2 69 3.2 31.9 3 557 Example 3 33 4.5 27.8 8 745 Example 4 32 4.3 27.9 7 472 Example 5 47 3.6 29.3 10 580 Example 6 239 4.0 30.2 5 480 Comparative Example A A 8.8 5.5 39 0.2 Comparative Example E E 6.4 16.4 25 52 Comparative Example G G 5.8 22.3 13 175

From Table 2, it can be seen that the organic light emitting diodes of Examples 1 to 6 have improved driving voltage, external quantum efficiency, roll-off ratio, and lifespan characteristics as compared to the organic light emitting diodes of Comparative Examples A, E, and G. .

10: organic light emitting device
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), osmium (Os), titanium (Ti), hafnium (Hf), europium (Eu), rhodium (Rh) or ruthenium (Ru),
L ₁ is a ligand represented by Formula 2,
n1 is 1, 2 or 3, when n1 is 2 or more, two or more L ₁ are the same as or different from each other,
L ₂ is a monodentate ligand, a bidentate ligand, a tridentate ligand or a tetradentate ligand,
n2 is 0, 1, 2, 3 or 4, when n2 is 2 or more, two or more L ₂ are the same as or different from each other,
L ₁ and L ₂ are different from each other,
<Formula 2>

In Formula 2,
X ₁ and X ₂₁ are, independently from each other, C or N,
Ring CY ₁₁ , ring CY ₁₂ and ring CY ₂₁ are independently of each other, a C ₅ -C ₃₀ carbocyclic group or a C ₁ -C ₃₀ heterocyclic group, ring CY ₁₁ and ring CY ₁₂ are condensed with each other,
T ₁ is * -N (R ₂ )-* ', * -B (R ₂ )-*', * -P (R ₂ )-* ', * -C (R ₂ ) (R ₃ )-*' , * -Si (R ₂ ) (R ₃ )-* ', * -Ge (R ₂ ) (R ₃ )-*', * -S- * ', * -Se- *', * -O- * ', * -C (= O)-*', * -S (= O)-* ', * -S (= O) _2- *', * -C (R ₂ ) = * ', * = C (R ₂ )-* ', * -C (R ₂ ) = C (R ₃ )-*', * -C (= S)-* 'or * -C≡C- *', wherein * and * Are each bonding sites with neighboring atoms,
R ₁ to R ₃ and R ₂₁ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine Groups, hydrazone groups, carboxylic acid groups or salts thereof, sulfonic acid groups or salts thereof, phosphoric acid groups or salts thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl groups, substituted or unsubstituted C ₂ -C ₆₀ alkenyl groups, substituted or Unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy 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 heteroaryl group, substituted or unsubstituted 1 A 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 ), Ge (Q ₃ ) (Q ₄ ) (Q ₅ ), -B (Q ₆ ) (Q ₇ ), -P (= O) (Q ₈ ) (Q ₉ ), or -P (Q ₈ ) (Q ₉ ) )ego,
a1 and a21 are each independently an integer of 0 to 20,
At least two of the plurality of R ₁ may optionally, be connected to each other, substituted or unsubstituted with at least one of R _10a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or at least one of R _10a to the ring C ₁ - Can form a C ₃₀ heterocyclic group,
At least two of the plurality of R ₂₁ are optionally, are connected with each other, substituted or unsubstituted with at least one of R _10a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or at least one of R _10a to the ring C ₁ - Can form a C ₃₀ heterocyclic group,
R ₁ to R ₃ and R ₂₁ 2 or more of the selectively, connected to each other, substituted or unsubstituted with at least one of R _10a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or at least one of R _10a to the ring Formed C ₁ -C ₃₀ heterocyclic group,
For a description of R _10a refer to the description for R ₂₁ ,
* And * 'are each a binding site with M in Formula 1,
The substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, Substituted C ₁ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C ₆ -C ₆₀ arylthio group, substituted C ₁ -C ₆₀ heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group and substituted monovalent non-aromatic condensed polycyclic group Substituents independently of one another,
Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group Or a C ₁ -C ₆₀ alkoxy group;
Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ heteroaryl group, 1 Valent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group, -N (Q ₁₁ ) (Q ₁₂ ), -Si (Q ₁₃ ) (Q ₁₄ ) (Q ₁₅ ),-Ge (Q ₁₃ ) (Q ₁₄ ) (Q ₁₅ ), -B (Q ₁₆ ) (Q ₁₇ ), -P (= O) (Q ₁₈ ) (Q ₁₉ ), -P (Q ₁₈ ) (Q ₁₉ ), or any thereof C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group or C ₁ -C ₆₀ alkoxy group substituted with a combination;
Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group , C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic group, - N (Q ₂₁ ) (Q ₂₂ ), -Si (Q ₂₃ ) (Q ₂₄ ) (Q ₂₅ ), -Ge (Q ₂₃ ) (Q ₂₄ ) (Q ₂₅ ), -B (Q ₂₆ ) (Q ₂₇ ) , C ₃ -C ₁₀ cycloalkyl group, C ₁ -unsubstituted or substituted with -P (= 0) (Q ₂₈ ) (Q ₂₉ ), -P (Q ₂₈ ) (Q ₂₉ ), or any combination thereof. C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group , C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ heteroaryl group, a monovalent non- Aromatic condensed polycyclic group or monovalent non-aromatic heterocondensed polycyclic group;
-N (Q ₃₁ ) (Q ₃₂ ), -Si (Q ₃₃ ) (Q ₃₄ ) (Q ₃₅ ), -Ge (Q ₃₃ ) (Q ₃₄ ) (Q ₃₅ ), -B (Q ₃₆ ) (Q ₃₇ ), -P (= 0) (Q ₃₈ ) (Q ₃₉ ), or -P (Q ₃₈ ) (Q ₃₉ ); or
Any combination thereof;
ego,
Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ are each independently hydrogen; heavy hydrogen; -F; -Cl; -Br; -I; Hydroxyl group; Cyano group; Nitro group; Amidino groups; Hydrazine group; Hydrazone group; Carboxylic acid groups or salts thereof; Sulfonic acid groups or salts thereof; Phosphoric acid groups or salts thereof; Deuterium, C ₁ -C ₆₀ alkyl, C ₆ -C ₆₀ aryl group, or substituted by any combination thereof or unsubstituted 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; ₆₀ aryl group, heavy hydrogen, C ₁ -C ₆₀ alkyl, C ₆ -C ₆₀ aryl group, or a substituted or unsubstituted in any combination thereof C ₆ -C; C ₆ -C ₆₀ aryloxy group; C ₆ -C ₆₀ arylthio group; C ₁ -C ₆₀ heteroaryl group; Monovalent non-aromatic condensed polycyclic groups; Or a monovalent non-aromatic heterocondensed polycyclic group. The method of claim 1,
M is Ir or Os, n1 + n2 is 3 or 4, an organometallic compound. The method of claim 1,
X ₁ is N,
X ₂₁ is C, an organometallic compound. The method of claim 1,
The ring CY ₁₁ , the ring CY ₁₂ and the ring CY ₂₁ are each independently a cyclopentene group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene Group, 1,2,3,4-tetrahydronaphthalene (1,2,3,4-tetrahydronaphthalene) group, pyrrole group, borol group, phosphol group, cyclopentadiene group, silol group, low molar group, thiophene group , Selenophene group, furan group, indole group, benzoborol group, benzophosphol group, indene group, benzosilol group, benzozomol group, benzothiophene group, benzoselenophene group, benzofuran group, carbazole group, di Benzoborol group, dibenzophosphol group, fluorene group, dibenzosilol group, dibenzozomol group, dibenzothiophene group, dibenzoselenophene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluorene-9-one group, dibenzo Offen 5,5-dioxide group, azaindole group, azabenzoborol group, azabenzophosphol group, azaindene group, azabenzosilol group, azabenzozomol group, azabenzothiophene group, azabenzoselenophene group, Azabenzofuran group, azacarbazole group, azadibenzoborol group, azadibenzophosphol group, azafluorene group, azadibenzosilol group, azadibenzo low mole group, azadibenzothiophene group, azadibenzo Selenophene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluorene-9-one group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group , Pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, benzoquinoline group, benzoisoquinoline group, quinoxaline group, quinazoline group, phenanthroline group, pyrazole group, imidazole group, trit group Lyazole group, azaborole group, azaphosphol group, azacyclopentadiene group, azasilol group, azazomol group, azaselenophene group, oxazole group, isoxazole group, thiazole group, isothiazole group, Oxadiazole group, thiadiazole group, benzopyrazole group, benzoimidazole group, benzoxazole group, benzothiazole group, benzoxadiazole group, benzothiadiazole group, 5,6,7,8- An organometallic compound, which is a tetrahydroisoquinoline (5,6,7,8-tetrahydroisoquinoline) group or a 5,6,7,8-tetrahydroquinoline (5,6,7,8-tetrahydroquinoline) group. The method of claim 1,
An organometallic compound wherein T ₁ is * -O- * '. The method of claim 1,
R ₁ to R ₃ and R ₂₁ are each independently,
Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof , Phosphoric acid groups or salts thereof, -SF ₅ , C ₁ -C ₂₀ alkyl groups or 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 , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₁₀ alkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclo Octyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, bicyclo [1.1.1] pentyl group, bicyclo [2.1.1] hexyl group, bicyclo [2.2.1] heptyl group, bicyclo [2.2.2] octyl group, (C ₁ -C ₂₀ alkyl) cyclopentyl group, (C ₁ -C ₂₀ alkyl) cyclohexyl group, (C ₁ -C ₂₀ alkyl) Cycloheptyl group, (C ₁ -C ₂₀ alkyl) cyclooctyl group, (C ₁ -C ₂₀ alkyl) adamantanyl group, (C ₁ -C ₂₀ alkyl) norbornanyl group, (C ₁ -C ₂₀ alkyl) norbornene group, (C ₁ -C ₂₀ alkyl), cyclopentenyl group, (C ₁ -C ₂₀ alkyl) cyclohexenyl group, (C ₁ -C ₂₀ Kiel) bicyclo heptenyl group, (C ₁ -C ₂₀ alkyl) bicyclo [1.1.1] pentyl, (C ₁ -C ₂₀ alkyl) bicyclo [2.1.1] hexyl group, (C ₁ -C ₂₀ alkyl) Bicyclo [2.2.1] heptyl group, (C ₁ -C ₂₀ alkyl) bicyclo [2.2.2] octyl group, phenyl group, (C ₁ -C ₂₀ alkyl) phenyl group, biphenyl group, terphenyl group, naphthyl group, pyri A C ₁ -C ₂₀ alkyl group or a C ₁ -C ₂₀ alkoxy group substituted with a diyl group, a pyrimidinyl group, or any combination thereof;
Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino 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, deuterium-containing C ₂ -C ₂₀ alkyl groups (e.g. , * -C (CD ₃ ) _3, etc.), C ₁ -C ₂₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopente Nyl group, cyclohexenyl group, cycloheptenyl group, bicyclo [1.1.1] pentyl group, bicyclo [2.1.1] hexyl group, bicyclo [2.2.1] heptyl group, bicyclo [2.2.2] octyl group , (C ₁ -C ₂₀ alkyl) cyclopentyl group, (C ₁ -C ₂₀ alkyl) cyclohexyl group, (C ₁ -C ₂₀ alkyl) cycloheptyl group, (C ₁ -C ₂₀ alkyl) cyclooctyl group, ( C ₁ -C ₂₀ alkyl) adamantanyl group, (C ₁ -C ₂₀ alkyl) norbornanyl group, (C ₁ -C ₂₀ alkyl) norbornenyl group, (C ₁ -C ₂₀ alkyl) cyclopentenyl group, (C ₁ -C ₂₀ alkyl) cyclohexenyl group, (C ₁ -C ₂₀ alkyl) cycloheptenyl group, (C ₁ -C ₂₀ alkyl) bicyclo [1.1. 1] pentyl group, (C ₁ -C ₂₀ alkyl) bicyclo [2.1.1] hexyl group, (C ₁ -C ₂₀ alkyl) bicyclo [2.2.1] heptyl group, (C ₁ -C ₂₀ alkyl) Cyclo [2.2.2] octyl group, phenyl group, (C ₁ -C ₂₀ alkyl) phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyle Neyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl Group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, furinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, sinolinyl group , Carbazolyl, phenanthrolinyl, Zomidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadizolyl group, triazinyl group, dibenzofura Nilyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group, or any thereof Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantanyl, norbornanyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, unsubstituted or substituted with a combination of bicyclo [1.1.1] pentyl, bicyclo [2.1.1] hexyl, bicyclo [2.2.1] heptyl, bicyclo [2.2.2] octyl group, a phenyl group, (C ₁ -C ₂₀ alkyl) Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthra Senyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl and oxazolyl groups , Isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, furinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, Quinoxalinyl, quinazolinyl, cynolinyl, carbazolyl, phenanthrolinyl, benzoimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzoxazolyl, isobenzooxazolyl, Triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, Azacarbazole group, azadibenzofuranyl group Aza-dibenzo thiophenyl group; or
-N (Q ₁ ) (Q ₂ ), -Si (Q ₃ ) (Q ₄ ) (Q ₅ ), -Ge (Q ₃ ) (Q ₄ ) (Q ₅ ), -B (Q ₆ ) (Q ₇ ), -P (= 0) (Q ₈ ) (Q ₉ ) or -P (Q ₈ ) (Q ₉ );
ego,
Q ₁ 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 or -CD ₂ CDH ₂ ; or
N -propyl group, isopropyl group, n -butyl group, sec -butyl group, isobutyl group, tert -butyl group, unsubstituted or substituted with deuterium, a C ₁ -C ₁₀ alkyl group, a phenyl group, or any combination thereof , n -pentyl group, tert -pentyl group, neopentyl group, isopentyl group, sec -pentyl group, 3-pentyl group, sec -isopentyl group, phenyl group, biphenyl group or naphthyl group;
Phosphorus, organometallic compounds. The method of claim 1,
In Formula 2

An organometallic compound, wherein the group represented by is a group represented by one of formulas CY1-1 to CY1-69:

In Formulas CY1-1 to CY1-69,
For the description of X ₁ and R ₁ , refer to each as described in claim 1,
X ₁₁ is O, S, Se, N (R ₁₉ ), C (R _19a ) (R _19b ) or Si (R _19a ) (R _19b ),
For the description of R ₁₉ , R _19a , R _19b , R _1a and R _1b , refer to the description of R ₁ in claim 1, respectively.
a18 is an integer of 0 to 8,
a16 is an integer of 0 to 6,
a15 is an integer of 0 to 5,
a14 is an integer of 0 to 4,
a13 is an integer of 0 to 3,
* "Is a binding site with T ₁ in Formula 2,
* 'Is a binding site with M in the general formula (1). The method of claim 1,
In Formula 2

An organometallic compound, wherein the group represented by is a group represented by one of formulas CY21-1 to CY21-25:

In Formulas CY21-1 to CY21-25,
For descriptions of X ₂₁ and R ₂₁ , refer to what is described in claim 1, respectively.
X ₂₂ is C (R ₂₂ ) (R ₂₃ ), N (R ₂₂ ), O, S or Si (R ₂₂ ) (R ₂₃ ),
For the description of R ₂₂ to R ₂₉ refer to the description of R ₂₁ in claim 1, respectively.
a26 is an integer of 0 to 6,
a24 is an integer of 0 to 4,
a23 is an integer of 0 to 3,
a22 is an integer of 0 to 2,
* "Is a binding site with T ₁ in Formula 2,
* 'Is a binding site with M in the general formula (1). The method of claim 8,
In Formula 2

An organometallic compound, wherein the group represented by is a group represented by one of formulas CY21 (1) to CY21 (56) or a group represented by one of formulas CY21-20 to CY21-25:

In Formulas CY21 (1) to CY21 (56),
For descriptions of X ₂₁ and R ₂₁ , refer to what is described in claim 1, respectively.
For a description of R _21a to R _21d refer to the description of R ₂₁ in _claim 1, respectively, wherein R ₂₁ and R _21a to R _21d are not hydrogen,
* "Is a binding site with T ₁ in Formula 2,
* Is a binding site with M in formula (1). The method of claim 1,
An organometallic compound of Formula 1, wherein L ₂ is a bidentate ligand each bonded to M of Formula 1 through O, S, Se, N, C, P, Si, or As. The method of claim 1,
In Formula 1, L ₂ is a bidentate ligand represented by Formula 3 below, an organometallic compound.
<Formula 3>

X ₃₁ and X ₃₂ in Formula 3 are each independently O, S, Se, or N,

Represents an arbitrary linker connecting X ₃₁ and X ₃₂ to each other,
* And * 'are each a binding site with M in the formula (1). The method of claim 1,
An organometallic compound wherein L ₂ in Formula 1 is a group represented by one of Formulas 3A to 3F:

In Formulas 3A to 3F,
Y ₁₃ is O, N, N (Z ₁ ), P (Z ₁ ) (Z ₂ ) or As (Z ₁ ) (Z ₂ ),
Y ₁₄ is O, N, N (Z ₃ ), P (Z ₃ ) (Z ₄ ) or As (Z ₃ ) (Z ₄ ),
T ₁₁ is a single bond, a double bond, * -C (Z ₁₁ ) (Z ₁₂ )-* ', * -C (Z ₁₁ ) = C (Z ₁₂ )-*', * = C (Z ₁₁ )-* ', * -C (Z ₁₁ ) = *', * = C (Z ₁₁ ) -C (Z ₁₂ ) = C (Z ₁₃ )-* ', * -C (Z ₁₁ ) = C (Z ₁₂ )- C (Z ₁₃ ) = * ', * -N (Z ₁₁ )-*' Or a C ₅ -C ₃₀ carbocyclic group unsubstituted or substituted with at least one Z ₁₁ ,
a11 is an integer of 1 to 10, when a11 is 2 or more, two or more T ₁₁ are the same as or different from each other,
Y ₁₁ and Y ₁₂ are, independently from each other, C or N,
T ₂₁ is a single bond, a double bond, O, S, C (Z ₁₁ ) (Z ₁₂ ), Si (Z ₁₁ ) (Z ₁₂ ) or N (Z ₁₁ ),
Ring CY ₁₁ and ring CY ₁₂ are, independently from each other, a C ₅ -C ₃₀ carbocyclic group or a C ₁ -C ₃₀ heterocyclic group,
A ₁ is P or As,
For the description of Z ₁ to Z ₄ and Z ₁₁ to Z ₁₃ refer to the description of R ₂₁ in claim 1, respectively.
d1 and d2 are each independently an integer of 0 to 10,
* And * 'is a binding site with M in the formula (1). The method of claim 1,
An organometallic compound of Formula 1, wherein L ₂ is a group represented by one of the following Chemical Formulas 3-1 (1) to 3-1 (66) and 3-1 (301) to 3-1 (309):

In Formulas 3-1 (1) to 3-1 (66) and 3-1 (301) to 3-1 (309),
X ₄₁ is O, S, N (Z ₂₁ ), C (Z ₂₁ ) (Z ₂₂ ) or Si (Z ₂₁ ) (Z ₂₂ ),
The descriptions of Z ₁ to Z ₄ , Z _1a , Z _1b , Z _1c , Z _1d , Z _2a , Z _2b , Z _2c , Z _2d and Z ₁₁ to Z ₁₄ each refer to the description of R ₂₁ in claim 1. See,
d14 is an integer of 0 to 4,
d26 is an integer of 0 to 6,
* And * 'are each a binding site with M in the formula (1). The method of claim 1,
An organometallic compound wherein L ₂ in Formula 1 is a group represented by Formula 3-1-1:

In the above formula 3-1-1,
For a description of Z ₁₂ refer to the description of R ₂₁ in claim 1,
A ₂ and A ₅ are independently of each other hydrogen, deuterium, 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 ₂ -C ₆₀ alky 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 Unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or substituted or unsubstituted monovalent non- Aromatic heterocondensed polycyclic group,
A ₁ , A ₃ , A ₄ and A ₆ are each independently 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 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 heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or substituted or unsubstituted monovalent A non-aromatic heterocondensed polycyclic group,
A ₁ to A ₆ at least two of optionally, be connected to each other, substituted or unsubstituted with at least one of R _1a C ₅ -C ₃₀ carbocyclic group, or a substituted or unsubstituted with at least one of R _1a C ₁ -C ₃₀ heterocyclic group may be formed,
For the description of R _1a refer to the description of Z ₁₂ ,
The substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, Substituted C ₁ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C ₆ -C ₆₀ arylthio group, substituted C ₁ -C ₆₀ heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group and substituted monovalent non-aromatic condensed polycyclic group Substituents independently of one another,
Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group Or a C ₁ -C ₆₀ alkoxy group;
Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ heteroaryl group, 1 Valent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group, -N (Q ₁₁ ) (Q ₁₂ ), -Si (Q ₁₃ ) (Q ₁₄ ) (Q ₁₅ ),-Ge (Q ₁₃ ) (Q ₁₄ ) (Q ₁₅ ), -B (Q ₁₆ ) (Q ₁₇ ), -P (= O) (Q ₁₈ ) (Q ₁₉ ), -P (Q ₁₈ ) (Q ₁₉ ), or any thereof C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group or C ₁ -C ₆₀ alkoxy group substituted with a combination;
Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group , C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic group, - N (Q ₂₁ ) (Q ₂₂ ), -Si (Q ₂₃ ) (Q ₂₄ ) (Q ₂₅ ), -Ge (Q ₂₃ ) (Q ₂₄ ) (Q ₂₅ ), -B (Q ₂₆ ) (Q ₂₇ ) , C ₃ -C ₁₀ cycloalkyl group, C ₁ -unsubstituted or substituted with -P (= 0) (Q ₂₈ ) (Q ₂₉ ), -P (Q ₂₈ ) (Q ₂₉ ), or any combination thereof. C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group , C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ heteroaryl group, a monovalent non- Aromatic condensed polycyclic group or monovalent non-aromatic heterocondensed polycyclic group;
-N (Q ₃₁ ) (Q ₃₂ ), -Si (Q ₃₃ ) (Q ₃₄ ) (Q ₃₅ ), -Ge (Q ₃₃ ) (Q ₃₄ ) (Q ₃₅ ), -B (Q ₃₆ ) (Q ₃₇ ), -P (= 0) (Q ₃₈ ) (Q ₃₉ ), or -P (Q ₃₈ ) (Q ₃₉ ); or
Any combination thereof;
ego,
Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ are each independently hydrogen; heavy hydrogen; -F; -Cl; -Br; -I; Hydroxyl group; Cyano group; Nitro group; Amidino groups; Hydrazine group; Hydrazone group; Carboxylic acid groups or salts thereof; Sulfonic acid groups or salts thereof; Phosphoric acid groups or salts thereof; Deuterium, C ₁ -C ₆₀ alkyl, C ₆ -C ₆₀ aryl group, or substituted by any combination thereof or unsubstituted 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; ₆₀ aryl group, heavy hydrogen, C ₁ -C ₆₀ alkyl, C ₆ -C ₆₀ aryl group, or a substituted or unsubstituted in any combination thereof C ₆ -C; C ₆ -C ₆₀ aryloxy group; C ₆ -C ₆₀ arylthio group; C ₁ -C ₆₀ heteroaryl group; Monovalent non-aromatic condensed polycyclic groups; Or a monovalent non-aromatic heterocondensed polycyclic group. The method of claim 1,
An organometallic compound, which is one of the following compounds 1 to 366:

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

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