KR102606341B1 - Organometallic compound, organic light emitting device including the same and a composition for diagnosing including the same - Google Patents

Abstract

Disclosed are an organometallic compound, an organic light-emitting device containing the organometallic compound, and a diagnostic composition containing the organometallic compound.

Description

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

Organometallic compounds, organic light-emitting devices containing the same, and diagnostic compositions containing the same are presented.

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

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

Meanwhile, light-emitting compounds, for example, phosphorescent compounds, can be used for monitoring, sensing, and detection of biological substances such as various cells and proteins.

The aim is to provide new organometallic compounds, organic light-emitting devices employing them, and diagnostic compositions employing them.

According to one aspect, an organometallic compound represented by the following formula (1) is provided:

<Formula 1>

<Formula 71>

*-(L ₇₁ ) _b71 -(T ₇₁ ) _c71

<Formula 72>

*-(L ₇₂ ) _b72 -(T ₇₂ ) _c72

Of formulas 1, 71 and 72

M is a 1st period transition metal, 2nd period transition metal, or 3rd period transition metal,

X ₁ is N,

X ₂ to X ₄ are each independently C or N,

Among the bonds between X ₁ and M, _the bond between X ₂ and M, the bond between X ₃ and M, and the bond between

Y ₁ to Y ₆ are each independently C or N,

Y ₇ and Y ₈ are independently of each other C, N, O, Si, or S,

X ₁ and Y ₇ , X ₁ and Y _{1 ,} X ₂ and Y _{2 ,} X ₂ and Y ₃ , X ₃ and _{Y 4 ,} X ₃ and _{Y 5} , are connected through bonding,

CY ₁ is selected from C ₁ -C ₃₀ heterocyclic group,

CY ₂ to CY ₄ are independently selected from C ₅ -C ₃₀ carbocyclic group and C ₁ -C ₃₀ heterocyclic group,

T ₁ to T ₃ are independently of each other, *-N[(L ₅ ) _b5 -(R ₅ )]-*', *-B(R ₅ )-*', *-P(R ₅ )-*' , *-C(R ₅ )(R ₆ )-*', *-Si(R ₅ )(R ₆ )-*', *-Ge(R ₅ )(R ₆ )-*', *-S- *', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) ₂ -*' , *-C(R ₅ )=*', *=C(R ₅ )-*', *-C(R ₅ )=C(R ₆ )-*', *-C(=S)-*' and *-C≡C-*',

L ₅ is selected from a single bond, a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group and a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,

b5 is selected from 1 to 3, and when b5 is 2 or more, 2 or more L _5s are the same or different from each other,

R ₅ and R ₆ are optionally bonded to each other through a first linking group, forming a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group. can form,

n1 to n3 are independently of each other and are 0, 1, 2 or 3. When n1 is 0, *-(T ₁ ) _n1 -*' becomes a single bond, and when n2 is 0, *-(T ₂ ) _n2 -*' becomes a single bond, and when n3 is 0, *-(T ₃ ) _n3 -*' becomes a single bond,

R ₇₁ is a group represented by formula 71 above,

L ₇₁ is,

C ₂ -C ₆₀ alkylene group; and

A C ₂ -C ₆₀ alkylene group substituted _with at least one selected from deuterium, deuterated C 1 _-C 60 alkyl group, C ₃ -C ₁₀ cycloalkyl group, and C ₃ -C ₁₀ cycloalkenyl group;

is selected from,

b71 is 0, 1, or 2,

T ₇₁ is,

C ₁ -C ₆₀ alkyl group; and

C ₁ -C ₆₀ alkyl group substituted with at least one selected from deuterated, deuterated C 1 -C 60 alkyl group, C ₃ -C ₁₀ cycloalkyl group, and _{C 3} -C _{10 cycloalkenyl} group;

is selected from,

c71 is an integer selected from 1 to 10,

R ₇₂ is a group represented by Formula 72 above,

L ₇₂ is,

C ₆ -C ₆₀ arylene group, C ₁ -C ₆₀ heteroarylene group, divalent non-aromatic condensed polycyclic group and divalent non-aromatic condensed heteropolycyclic group; and

Deuterium, C ₁ -C ₆₀ alkyl group, deuterated C ₁ -C ₆₀ alkyl group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ hetero C ₆ -C substituted with at least one selected from cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group. ₆₀ arylene group, C ₁ -C ₆₀ heteroarylene group, divalent non-aromatic condensed polycyclic group and divalent non-aromatic condensed heteropolycyclic group;

is selected from,

b72 is 0, 1, or 2,

T ₇₂ is,

C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group; and

Deuterium, C ₁ -C ₆₀ alkyl group, deuterated C ₁ -C ₆₀ alkyl group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ hetero C ₆ -C substituted with _at least one selected from cycloalkenyl group, C 6 -C ₆₀ aryl group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group. ₆₀ aryl group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group;

is selected from,

c72 is an integer selected from 1 to 10,

a71 and a72 are independently selected from integers from 1 to 5,

R ₁ to R ₆ are each independently hydrogen, deuterium, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or a salt thereof, Sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted 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 cyclo Alkenyl 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, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group groups, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ) and -P(=O)(Q ₈ )( Q ₉ ) is selected,

a1 to a4 are independently of each other 0, 1, 2, 3, 4 or 5,

Formula 1 does not include fluorine (-F),

Two of a1 R ₁ may optionally be combined with each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,

Two of a2 R ₂ may optionally be combined with each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,

Two of a3 R ₃ may optionally be combined with each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,

Two of a4 R ₄ may optionally be combined with each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,

Two or more adjacent R ₁ to R ₄ may optionally be combined with each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group. can,

One of R ₅ and R ₆ and one of R ₁ to R ₄ are optionally combined with each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group. can form a cyclic group,

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

Deuterium, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH 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 and C ₁ -C ₆₀ alkoxy group;

Deuterium, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH 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 ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group groups, -N(Q ₁₁ )(Q ₁₂ ), -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ), -B(Q ₁₆ )(Q ₁₇ ), and -P(=O)(Q ₁₈ )( Q ₁₉ ) substituted with at least one selected from C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group and C ₁ -C ₆₀ alkoxy group;

C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl Oxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group;

Deuterium, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH 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 group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ ) (Q ₂₄ ) (Q ₂₅ ), -B (Q ₂₆ ) (Q ₂₇ ), and -P (=O) (Q ₂₈ ) (Q ₂₉ ), substituted with at least one selected from C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ aryl Thio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group; and

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

is selected from,

Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ are independently selected from hydrogen, deuterium, -Cl, -Br, -I, 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 ₁ -C ₆₀ alkyl group and C ₆ -C ₆₀ aryl group substituted with at least one of C 6 -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C _{6 -C 60} arylthio group, C ₁ -C ₆₀ is selected from heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed polycyclic group.

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

An organometallic compound in the organic layer may serve as a dopant.

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

The organometallic compound has excellent electrical properties and thermal stability, and organic light-emitting devices employing the organometallic compound have excellent driving voltage, efficiency, power, color purity, and lifespan characteristics. Additionally, since the organometallic compound has excellent phosphorescent properties, using it can provide a diagnostic composition with high diagnostic efficiency.

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

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

<Formula 1>

In Formula 1, M may be a 1-period transition metal, a 2-period transition metal, or a 3-period transition metal.

For example, in Formula 1, M may be platinum (Pt) or palladium (Pd), but is not limited thereto.

The organometallic compound represented by Formula 1 may be neutral, not consisting of ion pairs of cations and anions.

In Formula 1, X ₁ is N, and X ₂ to X ₄ may be independently C or N.

In Formula 1, two of the bonds between X ₁ and M, the _bond between X ₂ and M, the bond between X ₃ and M, and the bond between It can be.

According to one embodiment, in Formula 1, X ₂ and X ₃ are carbon, X ₄ is nitrogen, the bond between X ₂ and M and the bond between _{X 3} and M are covalent bonds, and between The bond between and X ₄ and M may be a coordination bond, but is not limited thereto.

In Formula 1, Y ₁ to Y ₆ may be independently C or N, and Y ₇ and Y ₈ may be independently C, N, O, Si, or S.

According to one embodiment, in Formula 1, Y ₁ to Y ₅ are C, and Y ₆ to Y ₈ may each independently be C or N, but are not limited thereto.

_In Formula ₁ , _{X 1} and Y ₇ , _{X 1 and} Y _{1 ,} X _{2 and} Y ₂ , X ₂ and Y ₃ , ₈ can each be connected through chemical bonds.

In Formula 1, CY ₁ is selected from a C ₁ -C ₃₀ heterocyclic group, and CY ₂ to CY ₄ are independently selected from a C ₅ -C ₃₀ carbocyclic group and a C ₁ -C ₃₀ heterocyclic group. can be selected

For example, in Formula 1, CY ₁ is a pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, phenanthroline group, pyrrole. group, pyrazole group, imidazole group, triazole group, tetrazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group , benzoimidazole group, benzoxazole group, benzothiazole group, benzooxadiazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline (5,6,7,8-tetrahydroisoquinoline ) group and 5,6,7,8-tetrahydroquinoline (5,6,7,8-tetrahydroquinoline) group, and CY ₂ to CY ₄ are independently of each other, benzene group, naphthalene group, anthracene group, phenane Trene group, triphenylene group, pyrene group, chrysen group, cyclopentadiene group, 1,2,3,4-tetrahydronaphthalene group, pyrrole group, thiophene group, furan group, indole group, benzoborole group, benzophosphole group, indene group, benzosilol group, benzogermole group, benzothiophene group, benzoselenophene group, benzofuran group, carbazole group, dibenzoborole group , dibenzophosphole group, fluorene group, dibenzosilol group, dibenzogermol group, dibenzothiophene group, dibenzoselenophene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-flu. Orene-9-one group, dibenzothiophene 5,5-dioxide group, azacarbazole group, azadibenzoborole group, azadibenzophosphole group, azafluorene group, azadibenzosilol group, azadibenzo low mole group, azadibenzothiophene group, azadibenzoselenophene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluoren-9-one group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, phenanthroline group, pyrazole group, Dazole group, triazole group, tetrazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzo Oxazole group, benzothiazole group, benzooxadiazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group and 5,6, It may be selected from the 7,8-tetrahydroquinoline (5,6,7,8-tetrahydroquinoline) group.

According to one embodiment, CY ₁ and CY ₄ in Formula 1 are independently selected from a pyridine group, a pyrimidine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a pyrazole group, is selected from the imidazole group and the triazole group, and CY ₂ and CY ₃ are independently of each other, benzene group, naphthalene group, 1,2,3,4-tetrahydronaphthalene group, carbazole group, fluorene group, dibenzo It may be selected from a thiophene group and a dibenzofuran group, but is not limited thereto.

In the present specification, "azacabazole group, azadibenzoborole group, azadibenzophosphole group, azafluorene group, azadibenzosilol group, azadibenzogermol group, azadibenzothiophene group, azadibenzosele “nophene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluoren-9-one group and azadibenzothiophene 5,5-dioxide group” are, respectively, “carbazole group” , dibenzoborole group, dibenzophosphole group, fluorene group, dibenzosilol group, dibenzogermole group, dibenzothiophene group, dibenzoselenophene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group and dibenzothiophene 5,5-dioxide group", but refers to a heterocycle in which at least one of the carbons forming the ring is substituted with nitrogen. do.

In Formula 1, CY ₁ and CY ₄ may be the same, but are not limited thereto.

As another example, CY ₂ and CY ₃ in Formula 1 may be the same, but are not limited thereto.

로 표시되는 모이어티와

로 표시되는 모이어티가 서로 동일하고,

로 표시되는 모이어티와

로 표시되는 모이어티가 서로 동일할 수 있다.According to one embodiment, in Formula 1,

The moiety represented by

The moieties indicated by are identical to each other,

The moiety represented by

The moieties indicated by may be identical to each other.

According to another embodiment, the organometallic compound may have a structure that is symmetrical about the axis of symmetry connecting M and T ₁ in Chemical Formula 1.

In Formula 1, T ₁ to T ₃ are independently of each other, *-N[(L ₅ ) _b5 -(R ₅ )]-*', *-B(R ₅ )-*', *-P(R ₅ )-*', *-C(R ₅ )(R ₆ )-*', *-Si(R ₅ )(R ₆ )-*', *-Ge(R ₅ )(R ₆ )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) ₂ -*', *-C(R ₅ )=*', *=C(R ₅ )-*', *-C(R ₅ )=C(R ₆ )-*', *-C(=S )-*' and *-C≡C-*'. For a description of R ₅ and R ₆ , refer to what will be described later.

The L ₅ is selected from a single bond, a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group and a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group, and b5 is selected from 1 to 3 (e.g. For example, b5 may be 1), and if b5 is 2 or more, 2 or more L ₅ may be the same or different from each other.

According to one embodiment, L ₅ is,

single bond, phenylene group, naphthylene group, fluorenylene group, pyridinylene group, pyrimidinylene group and carbazonylene group; and

Deuterium, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or A phenylene group, naph substituted with at least one selected from the group consisting of a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a biphenyl group and a terphenyl group. tylene group, fluorenylene group, pyridinylene group, pyrimidinylene group and carbazonylene group;

It may be selected from among, but is not limited to.

R ₅ and R ₆ are optionally bonded to each other through a first linking group, forming a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group. A group (e.g., a 5- to 7-membered cyclic group with 5 or 6 carbon atoms; or a 5- or 6-carbon group substituted with at least one of deuterium, cyano group, C ₁ -C ₁₀ alkyl group, and C ₆ -C ₁₄ aryl group) 5- to 7-membered cyclic group) can be formed.

According to one embodiment, in Formula 1, T ₁ to T ₃ are each independently selected from *-N[(L ₅ ) _b5 -(R ₅ )]-*', *-B(R ₅ )-*', *-C(R ₅ )(R ₆ )-*', *-Si(R ₅ )(R ₆ )-*', *-S-*', *-O-*' and *-C(=O )-*', but is not limited thereto.

According to another embodiment, T ₁ to T ₃ in Chemical Formula 1 are independently of each other, *-C(R ₅ )(R ₆ )-*', *-Si(R ₅ )(R ₆ )-*' and *-Ge(R ₅ )(R ₆ )-*',

The R ₅ and R ₆ are connected to each other through a first connector,

The first linking group is a single bond, *-N[(L ₉ ) _b9 -(R ₉ )]-*', *-B(R ₉ )-*', *-P(R ₉ )-*', *-C(R ₉ )(R ₁₀ )-*', *-Si(R ₉ )(R ₁₀ )-*', *-Ge(R ₉ )(R ₁₀ )-*', *-S-* ', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) ₂ -*', selected from *-C(R ₉ )=C(R ₁₀ )-*', *-C(=S)-*' and *-C≡C-*',

For the description of L ₉ and b9, refer to the description of L ₅ and b5 in this specification, respectively,

For the description of R ₉ and R ₁₀ , refer to the description of R ₅ in the present specification, respectively,

* and *' may be independently bonding sites with neighboring atoms, but are not limited thereto.

In Formula 1, n1 to n3 are independently 0, 1, 2, or 3. When n1 is 0, *-(T ₁ ) _n1 -*' becomes a single bond, and when n2 is 0, *-( T ₂ ) _n2 -*' can be a single bond, and if n3 is 0, *-(T ₃ ) _n3 -*' can be a single bond. When n1 is 2 or more, two or more T ₁ 's may be the same or different from each other, when n2 is 2 or more, two or more T ₂ 's may be the same or different from each other, and when n3 is 2 or more, two or more T ₃ 's may be the same or different from each other.

According to one embodiment, n1 to n3 in Formula 1 may be independently 0 or 1.

According to another embodiment, n1 + n2 + n3 in Formula 1 may be 0 or 1.

According to another embodiment, in Formula 1, n1 may be 1, and n2 and n3 may be 0 or 1.

In Formula 1, R ₇₁ is a group represented by Formula 71:

<Formula 71>

*-(L ₇₁ ) _b71 -(T ₇₁ ) _c71

In Formula 71,

L ₇₁ is,

C ₂ -C ₆₀ alkylene group; and

A C ₂ -C ₆₀ alkylene group substituted _with at least one selected from deuterium, deuterated C 1 _-C 60 alkyl group, C ₃ -C ₁₀ cycloalkyl group, and C ₃ -C ₁₀ cycloalkenyl group;

is selected from,

b71 is 0, 1, or 2,

T ₇₁ is,

C ₁ -C ₆₀ alkyl group; and

C ₁ -C ₆₀ alkyl group substituted with at least one selected from deuterated, deuterated C 1 -C 60 alkyl group, C ₃ -C ₁₀ cycloalkyl group, and _{C 3} -C _{10 cycloalkenyl} group;

is selected from,

c71 may be an integer selected from 1 to 10.

For example, in Formula 71 above,

L ₇₁ is,

C ₂ -C ₁₀ alkylene group; and

Deuterated, deuterated C ₁ -C ₂₀ alkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbonanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group and cyclohepte. A C ₂ -C ₁₀ alkylene group substituted with at least one selected from among nyl groups;

is selected from,

b71 is 0 or 1,

T ₇₁ is,

C ₁ -C ₁₀ alkyl group; and

Deuterated, deuterated C ₁ -C ₂₀ alkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbonanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group and cyclohepte. A C ₁ -C ₁₀ alkyl group substituted with at least one selected from among nyl groups;

is selected from,

c71 may be 1 or 2, but is not limited thereto.

In Formula 1, R ₇₂ is a group represented by the following Formula 72:

<Formula 72>

*-(L ₇₂ ) _b72 -(T ₇₂ ) _c72

In Formula 72,

L ₇₂ is,

C ₆ -C ₆₀ arylene group, C ₁ -C ₆₀ heteroarylene group, divalent non-aromatic condensed polycyclic group and divalent non-aromatic condensed heteropolycyclic group; and

Deuterium, C ₁ -C ₆₀ alkyl group, deuterated C ₁ -C ₆₀ alkyl group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ hetero C ₆ -C substituted with _at least one selected from cycloalkenyl group, C 6 -C ₆₀ aryl group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group. ₆₀ arylene group, C ₁ -C ₆₀ heteroarylene group, divalent non-aromatic condensed polycyclic group and divalent non-aromatic condensed heteropolycyclic group;

is selected from,

b72 is 0, 1, or 2,

T ₇₂ is,

C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group; and

Deuterium, C ₁ -C ₆₀ alkyl group, deuterated C ₁ -C ₆₀ alkyl group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ hetero C ₆ -C substituted with at least one selected from cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group. ₆₀ aryl group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group;

is selected from,

c72 may be an integer selected from 1 to 10.

For example, in Formula 72 above,

L ₇₂ is,

Phenylene group, naphthylene group, pyridinylene group, pyrimidinylene group, triazinylene group, quinolinylene group, isoquinolinylene group, quinoxalinylene group, quinazolinylene group, fluorenylene group, carbazonylene group, Dibenzofuranylene group and dibenzothiophenylene group; and

Deuterium, C ₁ -C ₂₀ alkyl group, deuterated C ₁ -C ₂₀ alkyl group, phenyl group, naphthyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazoly A phenylene group, a naphthylene group, a pyridinylene group, a pyrimidinylene group, a triazinylene group, and a quinolinylene group substituted with at least one selected from a nyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group. , isoquinolinenylene group, quinoxalinylene group, quinazolinylene group, fluorenylene group, carbazonylene group, dibenzofuranylene group and dibenzothiophenylene group;

is selected from,

b72 is 0 or 1,

T ₇₂ is,

Phenyl group, naphthyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, fluorenyl group, carbazolyl group, dibenzofuranyl group and dibenzothio phenyl group; and

Deuterium, C ₁ -C ₂₀ alkyl group, deuterated C ₁ -C ₂₀ alkyl group, phenyl group, naphthyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazoly Phenyl group, naphthyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolyl group, substituted with at least one selected from the group consisting of nyl group, fluorenyl group, carbazolyl group, dibenzofuranyl group and dibenzothiophenyl group. Nyl group, quinoxalinyl group, quinazolinyl group, fluorenyl group, carbazolyl group, dibenzofuranyl group and dibenzothiophenyl group;

is selected from,

c72 may be 1 or 2, but is not limited thereto.

In Formula 1, a71 and a72 represent the numbers of R ₇₁ and R ₇₂ , respectively, and may be selected from integers of 1 to 5. That is, in Formula 1, CY ₁ is necessarily substituted with at least one R ₇₁ and at least one R ₇₂ . a71 and a72 may be independently 1 or 2. For example, a71 and a72 may be 1, but are not limited thereto.

In Formula 1, R ₁ to R ₆ are independently selected from hydrogen, deuterium, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, carboxylic acid group. or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, 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, substituted or unsubstituted monovalent non- Aromatic heterocondensed polycyclic groups, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ) and -P(=O)( It can be selected from Q ₈ )(Q ₉ ). Here, Q ₁ to Q ₉ refer to what is described in the present specification.

For example, R ₁ to R ₆ are independently of each other,

Hydrogen, deuterium, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salts thereof, C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group;

Deuterium, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or Its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C ₁ -C ₁₀ alkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group. , a C ₁ -C ₂₀ alkyl group substituted with at least one of norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridinyl and pyrimidinyl groups, and C ₁ -C ₂₀ alkoxy group;

Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, Phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazole Diary group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, Quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothia Zolyl group, benzooxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazole diary group, imidazopyridinyl group and imidazopyrimidinyl group;

Deuterium, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or Its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group ), norbornanyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl. , triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridi Nyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group , cinolinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group. , oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, -N(Q ₃₁ )( Q ₃₂ ) and -Si (Q ₃₃ ) (Q ₃₄ ) (Q ₃₅ ) substituted with at least one selected from cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbona Nyl group (norbornanyl), norbornenyl group (norbornenyl), cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl group Nyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cynolinyl group , carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazole diyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group and imidazopyrimidinyl group; and

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

is selected from,

Q ₁ to Q ₉ and Q ₃₁ to Q ₃₅ are independently of each other,

-CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CH 2 CH ₃ , -CH ₂ CD ₃ , -CH ₂ CD ₂ H, -CH _{2 CDH 2} , -CHDCH ₃ , -CHDCD ₂ H , -CHDCDH ₂ , -CHDCD ₃ , -CD ₂ CD ₃ , -CD ₂ CD ₂ H and -CD ₂ CDH ₂ ;

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

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

can be selected from among.

According to one embodiment, in Formula 1,

R ₁ to R ₆ are independently of each other hydrogen, deuterium, cyano group, nitro group, -CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -OCH ₃ , of the following formulas 9-1 to 9-19 A group represented by a group represented by the following formulas 10-1 to 10-168, -N(Q ₁ )(Q ₂ ) and -Si(Q ₃ )(Q ₄ )(Q ₅ ),

R ₇₁ is -CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , a group represented by the following formulas 9-1 to 9-19 and formulas 10-5 to 10-8, 10-11 and 10-12 is selected from the group indicated by,

R ₇₂ may be selected from the group represented by formulas 10-13 to 10-152 and 10-159 to 10-168, but is not limited thereto:

In Formulas 9-1 to 9-19 and 10-1 to 10-168, * is a bonding site with an adjacent atom, Ph is a phenyl group, Cz is a carbazolyl group, and TMS is a trimethylsilyl group.

In Formula 1, a1 to a4 each represent the number of R ₁ to R ₄ and may be independently 0, 1, 2, 3, 4, or 5. When a1 is 2 or more, two or more R _1s may be the same or different from each other, when a2 is 2 or more, two or more R _2s may be the same or different from each other, and when a3 is 2 or more, 2 or more R ₃ may be the same or different from each other, and when a4 is 2 or more, 2 or more R ₄ may be the same or different from each other, but is not limited thereto.

In Formula 1, two of a1 R ₁ are optionally bonded to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group. It can be formed, and two of a2 R ₂ are optionally bonded to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group. It can be formed, and two of a3 R ₃ are optionally bonded to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group. It can be formed, and two of a4 R ₄ are optionally bonded to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group. It can be formed, and two or more adjacent R ₁ to R ₄ are optionally bonded to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group. Can form a click group, and one of R ₅ and R ₆ and one of R ₁ to R ₄ are optionally combined with each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted It can form a ringed C ₁ -C ₃₀ heterocyclic group.

For example, in Formula 1, i) a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group formed by two of a1 R ₁ bonded to each other. group, ii) a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group, formed by two of a2 R _2s bonded to each other, iii) a3 a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group formed by two of R ₃ being bonded to each other, iv) two of a4 R ₄ are bonded to each other; A substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group, v) formed by combining two adjacent R ₁ to R ₄ groups. , a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group and vi) one of R ₅ and R ₆ and one of R ₁ to R ₄ , The substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or the substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group formed by combining each other, independently of one another,

Pentadiene group, cyclohexane group, cycloheptane group, adamantane group, bicyclo-heptanes group, bicyclo-octane group, benzene group, pyridine group, pyrimidine group, pyrazine group, pyridazine group. , naphthalene group, anthracene group, tetracene group, phenanthrene group, dihydronaphthalene group, phenalene group, benzothiophene group, benzofuran group, indene group, indole group, benzosilol group, azabenzothiophene group, aza benzofuran group, azaindene group, azaindole group and azabenzosilol group;

substituted with at least one R ₁₀ , a pentadiene group, a cyclohexane group, a cycloheptane group, an adamantane group, a bicyclo-heptanes group, a bicyclo-octane group, a benzene group, a pyridine group, a pyridine group. Mydine group, pyrazine group, pyridazine group, naphthalene group, anthracene group, tetracene group, phenanthrene group, dihydronaphthalene group, phenalene group, benzothiophene group, benzofuran group, indene group, indole group, benzosilol groups, azabenzothiophene group, azabenzofuran group, azaindene group, azaindole group and azabenzosilol group;

It may be selected from among, but is not limited to.

For the description of R ₁₀ , refer to the description of R ₁ in this specification.

The organometallic compound represented by Formula 1 defined as described above does not contain fluorine (F).

으로 표시되는 모이어티가 하기 화학식 CY1-1 내지 CY1-6으로 표시되는 그룹 중에서 선택될 수 있다:According to one embodiment, in Formula 1,

The moiety represented by may be selected from the group represented by the formulas CY1-1 to CY1-6:

Among the formulas CY1-1 to CY1-6

_{For descriptions of _}

c2 is selected from an integer of 0 to 2,

* and *' are each binding sites with neighboring atoms.

로 표시되는 모이어티가 하기 화학식 CY2-1 내지 CY2-25로 표시되는 그룹 중에서 선택될 수 있다:According to another embodiment, in Formula 1,

The moiety represented by may be selected from the group represented by the following formulas CY2-1 to CY2-25:

Of the formulas CY2-1 to CY2-25

For _{descriptions of}

X ₂₁ is O, S, N(R ₂₁ ) or C(R ₂₁ )(R ₂₂ ),

For descriptions of R ₂₁ to R ₂₈ , refer to the description of R ₂ in the present specification, respectively,

c5 is selected from an integer from 0 to 5,

c4 is selected from an integer from 0 to 4,

c3 is selected from an integer of 0 to 3,

c2 is selected from an integer of 0 to 2,

*, *' and *" are each binding sites with neighboring atoms.

로 표시되는 모이어티가 하기 화학식 CY3-1 내지 CY3-25로 표시되는 그룹 중에서 선택될 수 있다:According to another embodiment, in Formula 1,

The moiety represented by may be selected from the group represented by the formulas CY3-1 to CY3-25:

Of the formulas CY3-1 to CY3-25

For _{descriptions of}

X ₃₁ is O, S, N(R ₃₁ ) or C(R ₃₁ )(R ₃₂ ),

For descriptions of R ₃₁ to R ₃₈ , refer to the description of R ₃ in the specification, respectively,

c5 is selected from an integer from 0 to 5,

c4 is selected from an integer from 0 to 4,

c3 is selected from an integer of 0 to 3,

c2 is selected from an integer of 0 to 2,

*, *' and *" are each binding sites with neighboring atoms.

로 표시되는 모이어티가 하기 화학식 CY4-1 내지 CY4-35로 표시되는 그룹 중에서 선택될 수 있다:According to another embodiment, in Formula 1,

The moiety represented by may be selected from the group represented by the formulas CY4-1 to CY4-35:

Among the formulas CY4-1 to CY4-35

For _{descriptions of}

X ₄₁ is O, S, N(R ₄₁ ) or C(R ₄₁ )(R ₄₂ ),

R _71a refers to the description of R ₇₁ in this specification,

R _72a refers to the description of R ₇₂ in this specification,

For descriptions of R ₄₁ to R ₄₈ , refer to the description of R ₄ in the specification, respectively,

c6 is selected from integers from 0 to 6,

c5 is selected from an integer from 0 to 5,

c4 is selected from an integer from 0 to 4,

c3 is selected from an integer of 0 to 3,

c2 is selected from an integer of 0 to 2,

* and *' are each binding sites with neighboring atoms.

According to another implementation:

로 표시되는 모이어티가 하기 화학식 CY1(1) 및 CY1(2)로 표시되는 그룹 중에서 선택되고 (선택되거나),In Formula 1 above,

The moiety represented by is selected (or selected) from the group represented by the formulas CY1(1) and CY1(2),

로 표시되는 모이어티가 하기 화학식 CY2(1) 내지 CY2(4)로 표시되는 그룹 중에서 선택되고 (선택되거나),In Formula 1 above,

The moiety represented by is selected (or selected) from the group represented by the formulas CY2(1) to CY2(4),

로 표시되는 모이어티가 하기 화학식 CY3(1) 내지 CY3(4)로 표시되는 그룹 중에서 선택되고 (선택되거나),In Formula 1 above,

The moiety represented by is selected (or selected) from the group represented by the formulas CY3(1) to CY3(4),

로 표시되는 모이어티가 하기 화학식 CY4(1) 내지 CY4(19)로 표시되는 그룹 중에서 선택될 수 있으나, 이에 한정되는 것은 아니다:In Formula 1 above,

The moiety represented by may be selected from the group represented by the following formulas CY4(1) to CY4(19), but is not limited thereto:

Among the formulas CY1(1), CY1(2), CY2(1) to CY2(4), CY3(1) to CY3(4), and CY4(1) to CY4(19),

For descriptions of X ₁ , R ₁ , _{R 71} , R ₇₂ , X ₂ , _{R 2} , X ₃ , R ₃ ,

X ₄₁ is O, S, N(R ₄₁ ) or C(R ₄₁ )(R ₄₂ ),

For descriptions of R _4a , R _4b , R ₄₁ and R ₄₂ , refer to the description of R ₄ in the specification, respectively,

R _71a refers to the description of R ₇₁ in this specification,

R _72a refers to the description of R ₇₂ in this specification,

*, *' and *" are each binding sites with neighboring atoms.

According to another embodiment, the organometallic compound may be represented by the following formula 1(1):

<Formula 1(1)>

In the above formula 1(1)

_{M , _ _ _ _ _ _ _ _ _ _} For description, refer to what is described in the specification, respectively,

CY ₅ and CY ₆ are, independently of each other, a C ₅ -C ₃₀ carbocyclic group or a C ₁ -C ₃₀ heterocyclic group,

For descriptions of R ₅₁ and R ₆₁ , independently of each other, refer to the description of R ₁ in the specification,

a51 and a61 are independently of each other 0, 1, 2 or 3,

T ₄ is C, Si or Ge,

T ₅ is a single bond, *-N[(L ₇ ) _b7 -(R ₇ )]-*', *-C(R ₇ )(R ₈ )-*', *-Si(R ₇ )(R ₈ )-*', *-Ge(R ₇ )(R ₈ )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-* ', *-S(=O)-*', *-S(=O) ₂ -*', *-C(R ₇ )=C(R ₈ )-*', *-C(=S)- is selected from *' and *-C≡C-*',

For the description of L ₇ and b7, refer to the description of L ₅ and b5 in this specification, respectively,

For descriptions of R ₇ and R ₈ , refer to the description of R ₅ in the specification, respectively.

* and *' are, independently of each other, binding sites with neighboring atoms.

For example, T ₅ is a single bond, *-N[(L ₇ ) _b7 -(R ₇ )]-*', *-C(R ₇ )(R ₈ )-*', *-Si(R ₇ )(R ₈ )-*', *-S-*', *-O-*' and *-C(=O)-*'.

The organometallic compound represented by Formula 1 may be selected from the following compounds 1 to 201, but is not limited thereto:

The organometallic compound represented by Formula 1 does not contain fluorine. Accordingly, the organometallic compound represented by Formula 1 has relatively excellent metal-to-ligand charge-transfer (MLCT) and can have a short decay rate.

In addition, since a71 and a72 in Formula 1 are not 0, CY ₁ in Formula 1 is “simultaneously” substituted with R ₇₁ and R ₇₂ as described herein. Accordingly, an electronic device employing the organometallic compound represented by Formula 1, for example, an organic light emitting device, can achieve improved efficiency and lifespan “at the same time.”

For example, the HOMO, LUMO, singlet (S ₁ ) and triplet (T ₁ ) energy levels for some of the above compounds and compound A were calculated using the DFT method of the Gaussian program (B3LYP, 6-31G(d , The structural optimization at the p) level) evaluation results are shown in Table 1 below.

Compound No. HOMO(eV) LUMO(eV) S ₁ energy level (eV) T ₁ energy level (eV) One -4.321 -1.591 2.165 1.951 2 -4.349 -1.675 2.121 1.915 4 -4.275 -1.566 2.144 1.932 5 -4.352 -1.618 2.176 1.956 7 -4.317 -1.672 2.122 1.924 9 -4.395 -1.674 2.153 1.939 17 -4.416 -1.687 2.175 1.956 18 -4.408 -1.682 2.726 1.951 21 -4.333 -1.603 2.156 1.931 26 -4.392 -1.731 2.119 1.921 55 -4.348 -1.734 2.093 1.899 59 -4.320 -1.657 2.131 1.933 78 -4.395 -1.725 2.128 1.938 79 -4.431 -1.671 2.191 1.976 87 -4.493 -1.744 2.177 1.960 92 -4.360 -1.699 2.100 1.885 101 -4.525 -1.826 2.140 1.914 102 -4.368 -1.708 2.099 1.886 103 -4.326 -1.671 2.095 1.886 104 -4.406 -1.788 2.095 1.906 127 -4.448 -1.683 2.194 1.977 128 -4.478 -1.768 2.151 1.941 148 -4.465 -1.677 2.206 1.982 155 -4.310 -1.672 2.113 1.916 A -4.419 -1.589 2.236 1.985

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

The method for synthesizing the organometallic compound represented by Formula 1 can be recognized by those skilled in the art by referring to the synthesis examples described later.

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

The organic light-emitting device may have a low driving voltage, high efficiency, high power, high quantum efficiency, long lifespan, low roll-off ratio, and excellent color purity by providing an organic layer containing the organometallic compound represented by Chemical Formula 1 as described above. .

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

In this specification, “(the organic layer) includes one or more types of organometallic compounds” means “(the organic layer) includes one type of organometallic compound belonging to the category of Formula 1 above or two different types of organometallic compounds belonging to the category of Formula 1 above. It can be interpreted as “may include the above organometallic compounds.”

For example, the organic layer may include only Compound 1 as the organometallic compound. At this time, 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. At this time, Compound 1 and Compound 2 may exist in the same layer (for example, Compound 1 and Compound 2 may both exist in the emission 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, in the organic light-emitting device, the first electrode is an anode, the second electrode is a cathode, and the organic layer includes a hole transport region interposed between the first electrode and the light-emitting layer and the light-emitting layer and the second electrode. It further includes an electron transport region interposed therebetween, wherein the hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, and the electron transport region includes a hole blocking layer, an electron transport layer, It may include an electron injection layer or any combination thereof.

As used herein, “organic layer” is a term referring to a single and/or multiple layers interposed between a first electrode and a second electrode in an organic light emitting device. The “organic layer” may include not only organic compounds but also organometallic complexes containing metals.

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

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

The first electrode 11 may be formed, for example, by providing a first electrode material on the upper part of the substrate using a deposition method or sputtering method. The first electrode 11 may be an anode. The material for the first electrode may be selected from materials with 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), etc. can be used as materials 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), etc. can be used. .

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

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

The organic layer 15 includes a hole transport region; 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 a hole injection layer, the hole injection layer (HIL) can be formed on the first electrode 11 using various methods such as vacuum deposition, spin coating, casting, and LB method. there is.

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

When forming a hole injection layer by spin coating, the coating conditions vary depending on the compound used as the hole injection layer material, the structure and thermal properties 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 in the temperature range of about 80°C to 200°C, but is not limited thereto.

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

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

<Formula 201>

<Formula 202>

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

Phenylene group, pentarenylene group, indenylene group, naphthylene group, azulenylene group, hepthalenylene group, acenaphthylene group, fluorenylene group, phenarenylene group, phenanthrenylene group, anthracenylene group, fluoranthenyl lene group, triphenylenylene group, pyrenylene group, chrycenylenylene group, naphthacenylene group, picenylene group, perylenylene group and pentacenylene group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or Salts thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group , C ₁ -C ₁₀ heterocycloalkyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ Substituted with at least one of heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed polycyclic group, phenylene group, pentalenylene group, indenylene group, naphthylene group, azulenylene group, heptal Lenylene group, acenaphthylene group, fluorenylene group, phenarenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrycenylenylene group, naphthacenylene group, p cenylene group, perylenylene group and pentacenylene group;

can be selected from among.

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

In Formulas 201 and 202, R ₁₀₁ to R ₁₀₈ , R ₁₁₁ to R ₁₁₉ and R ₁₂₁ to R ₁₂₄ are 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 or salt thereof, sulfonic acid or salt thereof, Phosphoric acid or its salt, C ₁ -C ₁₀ alkyl group (for example, methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, etc.) and C ₁ -C ₁₀ alkoxy group (for example, methoxy group, ethoxy group, etc.) group, 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 its salt, sulfonic acid or its salt and phosphoric acid or C ₁ -C ₁₀ alkyl group and C ₁ -C ₁₀ alkoxy group substituted with one or more of its salts;

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

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or salts thereof, phenyl group, naphthyl group, anthracenyl group, fluorenyl group and pyrenyl group substituted with one or more of C ₁ -C ₁₀ alkyl group and C ₁ -C ₁₀ alkoxy group;

It may be selected from among, but is not limited to.

In Formula 201, R ₁₀₉ is,

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

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or Salts thereof, phenyl group, naphthyl group, anthracenyl group and pyridinyl group substituted with one or more of C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group and pyridinyl group;

can be selected from among.

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>

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

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

The thickness of the hole transport region may be about 100Å to about 10000Å, for example, about 100Å to about 1000Å. If the hole transport region includes at least one of a hole injection layer and a hole transport layer, the thickness of the hole injection layer is about 100 Å to about 10000 Å, for example, about 100 Å to about 1000 Å, and the thickness of the hole transport layer is about 50 Å. It may be from about 2000 Å, for example from about 100 Å to about 1500 Å. When the thickness of the hole transport region, hole injection layer, and hole transport layer satisfies the above-mentioned 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 non-uniformly dispersed within the hole transport region.

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

The hole transport region may further include a buffer layer.

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

An emission layer (EML) can be formed on the hole transport region using a method such as vacuum deposition, spin coating, casting, or LB method. When forming a light-emitting layer by vacuum deposition or spin coating, the deposition and coating conditions vary depending on the compound used, but can generally be selected from a range of conditions that are almost the same as those for forming the hole injection layer.

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

The light-emitting layer may include a host and a dopant, and the dopant includes an organometallic compound represented by Chemical Formula 1.

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

Alternatively, the host may further include a compound represented by the following formula 301:

<Formula 301>

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

phenylene group, naphthylene group, phenanthrenylene group and pyrenylene group; and

A phenylene group, a naphthylene group, a phenanthrenylene group, and a pyrenylene group substituted with one or more of a phenyl group, a naphthyl group, and an anthracenyl group;

can be selected from among.

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

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

phenyl group, naphthyl group, phenanthrenyl group and pyrenyl group substituted with one or more of phenyl group, naphthyl group and anthracenyl group;

can be selected from among.

In Formula 301, g, h, i, and j may independently be integers from 0 to 4, for example, 0, 1, or 2.

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

C ₁ -C ₁₀ alkyl group substituted with one or more of a phenyl group, naphthyl group, and anthracenyl group;

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

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

;

;

It may be selected from among, but is not limited to.

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

<Formula 302>

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

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

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

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

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

When the light-emitting layer includes a host and a dopant, the content of the dopant can typically be selected in the range of about 0.01 to about 15 parts by weight based on about 100 parts by weight of the host, but is not limited thereto.

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

Next, an electron transport region is placed on top of the light emitting 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 hole blocking layer/electron transport layer/electron injection layer or electron transport layer/electron injection layer, but is not limited thereto. The electron transport layer may have a single-layer structure or a multi-layer structure including two or more different materials.

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

When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, at least one of the following BCP, Bphen, and Balq, but is not limited thereto.

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

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

Alternatively, the electron transport layer may include at least one of the following compounds ET1 and ET2, but is not limited thereto.

The thickness of the electron transport layer may be about 100Å to about 1000Å, for example, about 150Å to about 500Å. When the thickness of the electron transport layer satisfies the range described above, satisfactory electron transport characteristics 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 include a Li complex. The Li complex may include, for example, the following compound ET-D1 (lithium quinolate, LiQ) or ET-D2.

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

The electron injection layer may include at least one selected from LiF, NaCl, CsF, Li ₂ O, and BaO.

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

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

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

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

Since the organometallic compound represented by Formula 1 can provide high luminous efficiency, a diagnostic composition containing the organometallic compound can have high diagnostic efficiency.

The diagnostic composition can be applied to various diagnostic kits, diagnostic reagents, biosensors, biomarkers, etc.

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

As used herein, C ₁ -C ₆₀ alkoxy group refers to a monovalent group having the chemical formula -OA ₁₀₁ (where A ₁₀₁ is the C ₁ -C ₆₀ alkyl group), and specific examples thereof include methoxy group, ethoxy group, Isopropyloxy group, etc. are included.

As used herein, the C ₂ -C ₆₀ alkenyl group has a structure containing one or more carbon-carbon double bonds in the middle or end of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include ethenyl group, propenyl group, butenyl group, etc. This is included. As used herein, 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 containing one or more carbon-carbon triple bonds in the middle or end of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include ethynyl group, propynyl group ( propynyl), etc. As used herein, 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, C ₃ -C ₁₀ cycloalkyl group refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and specific examples thereof include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, and cyclohepyl group. Includes til group, etc. As used herein, the 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, C ₁ -C ₁₀ heterocycloalkyl group refers to a monovalent monocyclic group having 1 to 10 carbon atoms containing at least one hetero atom selected from N, O, P, Si and S as a ring-forming atom, Specific examples thereof include tetrahydrofuranyl, tetrahydrothiophenyl, etc. As used herein, the 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, the C ₃ -C ₁₀ cycloalkenyl group refers to a monovalent monocyclic group having 3 to 10 carbon atoms, which has at least one carbon-carbon double bond in the ring, but does not have aromaticity. , specific examples thereof include cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, etc. As used herein, 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 containing at least one hetero atom selected from N, O, P, Si, and S as a ring-forming atom, forming a ring. It has at least one double bond within it. Specific examples of the C ₁ -C ₁₀ heterocycloalkenyl group include 2,3-dihydrofuranyl group, 2,3-dihydrothiophenyl group, and the like. As used herein, 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, the C ₆ -C ₆₀ aryl group refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and the C ₆ -C ₆₀ arylene group refers to a carbocyclic aromatic system having 6 to 60 carbon atoms. It refers to a divalent group with a cyclic aromatic system. Specific examples of the C ₆ -C ₆₀ aryl group include phenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, chrysenyl group, etc. When the C ₆ -C ₆₀ aryl group and the C ₆ -C ₆₀ arylene group include two or more rings, the two or more rings may be fused to each other.

As used herein, the C ₁ -C ₆₀ heteroaryl group is a monovalent group containing 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. Meaning, the C ₁ -C ₆₀ heteroarylene group is a divalent group containing at least one hetero atom selected from N, O, P and S as a ring-forming atom and having a carbocyclic aromatic system of 1 to 60 carbon atoms. it means. Specific examples of the C ₁ -C ₆₀ heteroaryl group include pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, etc. When the C ₁ -C ₆₀ heteroaryl group and the C ₁ -C ₆₀ heteroarylene group include two or more rings, the two or more rings may be fused to each other.

As used herein, the C ₆ -C ₆₀ aryloxy group refers to -OA ₁₀₂ (where A ₁₀₂ is the C ₆ -C ₆₀ aryl group), and the C ₆ -C ₆₀ arylthio group refers to -SA ₁₀₃ (where A 102 is the C 6 -C 60 aryl group). , A ₁₀₃ refers to the C ₆ -C ₆₀ aryl group.

As used herein, a monovalent non-aromatic condensed polycyclic group has two or more rings condensed with each other, contains only carbon as a ring forming atom, and the entire molecule is non-aromatic. It means a monovalent group having (for example, having 8 to 60 carbon atoms). Specific examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group and the like. As used herein, a 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 has two or more rings condensed with each other, and contains a hetero atom selected from N, O, P, Si, and S in addition to carbon as a ring-forming atom. It refers to a monovalent group (for example, having 1 to 60 carbon atoms) in which the entire molecule has non-aromaticity. The monovalent non-aromatic condensed heteropolycyclic group includes a carbazolyl group and the like. As used herein, a divalent non-aromatic condensed heteropolycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.

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

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

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 ₆ -C ₆₀ aryloxy group, substituted C ₆ -C ₆₀ arylthio group, substituted C ₁ -C ₆₀ heteroaryl group , at least one of the substituents of the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic heterocondensed 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, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ Alkynyl group and C ₁ -C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ - C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group , monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, -N(Q ₁₁ )(Q ₁₂ ), -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ), -B(Q ₁₆ ) (Q ₁₇ ) and -P (=O) (Q ₁₈ ) (Q ₁₉ ), substituted with at least one selected from C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group and C ₁ -C ₆₀ alkoxy group;

C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl Oxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group;

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

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

is selected from,

Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, No group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, 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 heterocycloalke Nyl group, C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ alkyl group and C ₆ -C ₆₀ aryl group substituted with at least one of C 6 -C _{60 aryl group, C 6 -C 60} aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group.

Hereinafter, a compound and an organic light-emitting device according to an embodiment of the present invention will be described in more detail through synthesis examples and examples, but the present invention is not limited to the following synthesis examples and examples. In the following synthesis example, in the expression "'B' was used instead of 'A'", the amount of 'B' used and the amount of 'A' used are the same on a molar equivalent basis.

[Example]

Synthesis Example 1: Synthesis of Compound 1

Synthesis of intermediates 1-2

4.03 g (20.1 mmol) of 2-bromo-5-methyl-4-phenylpyridine (Intermediate 1-3) was mixed with 100 mL of toluene, 30 mL of ethanol, and water. Mix with 30 mL, add 7.20 g (20.1 mmol) of 3-bromophenylboronic acid, 1.62 g (1.40 mmol) of palladium catalyst, and 5.28 g (50.1 mmol) of sodium carbonate. It was heated and refluxed at 120°C for 18 hours. The result obtained from this was concentrated under reduced pressure, mixed with 400 ml of dichloromethane, and filtered through diatomaceous earth. The obtained organic layer was dried over magnesium sulfate, distilled under reduced pressure, and purified by liquid chromatography to obtain 4.55 g of Intermediate 1-2 ( Yield 70%) was obtained.

LC-MS m/z = 314 (M+H) ⁺

Synthesis of Intermediate 1-1

Mix 6.58 g (20.3 mmol) of Intermediate 1-2 with 100 mL of toluene, 1.43 g (8.45 mmol) of [1,1'-biphenyl]-2-amine, 0.49 g (0.85 mmol) of Pd(dba) ₂ , and P 1.1 g (2.54 mmol) of (tBu) ₃ and 2.03 g (21.1 mmol) of sodium butoxide were added and heated to reflux at 130°C for 24 hours. The result obtained from this was concentrated under reduced pressure, mixed with 200 ml of dichloromethane, dried over magnesium sulfate, distilled under reduced pressure, and then purified by liquid chromatography to obtain 5.0 g of Intermediate 1-1 (yield 90%). did. LC-MS m/z = 656 (M+H) ⁺ .

Synthesis of Compound 1

At room temperature, 2.10 g (3.2 mmol) of Intermediate 1-1 was mixed with 130 mL of benzonitrile, and then 1.51 g (3.20 mmol) of PtCl ₂ (NCPh) ₂ was added and heated to reflux at 150°C for 18 hours. . After confirming that the reaction was complete by LCMS, the reaction mixture was concentrated under reduced pressure and purified by liquid chromatography to obtain 0.6 g (28% yield) of Compound 1, the target compound. The produced compound was confirmed by Mass and HPLC.

HRMS (MALDI) calcd for C ₄₈ H ₃₅ N ₃ Pt: m/z 848.2479, Found: 848.2477.

Synthesis Example 2: Synthesis of Compound 2

Synthesis of Intermediate 2-2

Mix 5.50 g (17.0 mmol) of Intermediate 1-2 with 80 mL of toluene, 2.87 g (17.0 mmol) of [1,1'-biphenyl]-2-amine, 0.976 g (1.7 mmol) of Pd(dba) ₂ , and P Add 2.06 g (0.30 mmol) of (tBu) _{3 and} 4.89 g (50.9 mmol) of sodium butoxide and heat and reflux at 130°C for 18 hours. The result obtained from this was concentrated under reduced pressure, mixed with 200 mL of dichloromethane, filtered through diatomaceous earth, and the obtained organic layer was dried over magnesium sulfate, distilled under reduced pressure, and purified by liquid chromatography to obtain 4.3 g of Intermediate 2-2 (yield 61%) was obtained. LC-MS m/z = 413 (M+H) ⁺ .

Synthesis of Intermediate 2-1

Instead of intermediate 1-2 and [1,1'-biphenyl]-2-amine, 2.88 g (7.00 mmol) of intermediate 2-2 and 2.83 g (7.00 mmol) of 2-(3-bromophenyl)-4-phenylpyridine (intermediate 2-3) were used ( Intermediate 2-1 (3.5 g, 78%) was obtained using the same method as the synthesis method of Intermediate 1-1 in Synthesis Example 1, except that 9.1 mmol) was used, respectively.

LC-MS m/z = 642 (M+H) ⁺ .

Synthesis of Compound 2

Using the same method as the synthesis method for Compound 1 in Synthesis Example 1, Compound 2 (0.40 g, 24 %) was obtained. Compound 2 was confirmed by mass and HPLC.

HRMS (MALDI) calcd for C ₄₇ H ₃₃ N ₃ Pt: m/z 834.2322, Found: 834.2322.

Synthesis Example 3: Synthesis of Compound 4

Synthesis of intermediate 4-2

Instead of 3-bromophenylboronic acid {(3-bromophenyl)boronic acid}, use 3-bromo-5-terbutylphenylboronic acid {(3-bromo-5-(tert-butyl)phenyl)boronic acid } Intermediate 4-2 (3.9 g, 85%) was obtained using the same method as the synthesis method of Intermediate 1-2 in Synthesis Example 1, except that 3.42 g (13.3 mmol) was used. .

LC-MS m/z = 380 (M+H) ⁺ .

Synthesis of intermediate 4-1

Using the same method as the synthesis method for Intermediate 1-1 in Synthesis Example 1, Intermediate 4-1 (2.94 g, 79%) was obtained.

LC-MS m/z = 768 (M+H) ⁺ .

Synthesis of Compound 4

Using the same method as the synthesis method for Compound 1 in Synthesis Example 1, Compound 4 (0.43 g, 12 %) was obtained. Compound 4 was confirmed by mass and HPLC.

HRMS (MALDI) calcd for C ₅₆ H ₅₁ N ₃ Pt: m/z 960.3731, Found: 960.3730.

Synthesis Example 4: Synthesis of Compound 7

Synthesis of intermediate 7-1

Using the same method as the synthesis method for Intermediate 1-1 in Synthesis Example 1, Intermediate 7-1 (2.80 g, 58%) was obtained.

LC-MS m/z = 756 (M+H) ⁺ .

Synthesis of compound 7

Using the same method as the synthesis method for Compound 1 in Synthesis Example 1, Compound 7 (0.90 g, 26 %) was obtained. Compound 7 was confirmed by mass and HPLC.

HRMS (MALDI) calcd for C ₅₆ H ₃₉ N ₃ Pt: m/z 948.2792, Found: 948.2790.

Synthesis Example 5: Synthesis of Compound 9

Synthesis of intermediate 9-3

Intermediate 9-4 (17.1 g, 54.9 mmol) and THF (550 mL) were mixed and stirred for 10 minutes at -78°C. Next, n -Butyllithium (23.0 mL of a 2.5 M solution in hexanes, 57.6 mmol) was slowly added dropwise over 30 minutes, and then stirred under -78°C for 4 hours. Afterwards, 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (12.3 mL, 60.4 mmol) was added, the temperature was raised to room temperature after 15 minutes, and then stirred for 5 hours. , 200 mL of distilled water was added and stirred. Then, the organic layer obtained by adding methylene chloride (200 _mL %) was obtained. MALDI-TOF m/z = 359 (M+H) ⁺

Synthesis of intermediate 9-2

Intermediate 1-2 of Synthesis Example 1, except that Intermediate 9-3 (5.83 g, 16.2 mmol) was used instead of 3-bromophenylboronic acid {(3-bromophenyl)boronic acid} Using the same method as the synthesis method, Intermediate 9-2 (4.55 g, 85%) was obtained.

LC-MS m/z = 400 (M+H) ⁺ .

Synthesis of intermediate 9-1

Using the same method as the synthesis method for Intermediate 1-1 in Synthesis Example 1, except that 4.52 g (11.3 mmol) of 9-2 was used instead of Intermediate 1-2, Intermediate 9-1 (2.30 g) , 61%) was obtained.

LC-MS m/z = 808 (M+H) ⁺ .

Synthesis of compound 9

Compound 9 (0.30 g, 11 %) was obtained. Compound 9 was confirmed by mass and HPLC.

HRMS (MALDI) calcd for C ₆₀ H ₄₃ N ₃ Pt: m/z 1000.3105, Found: 1000.3105.

Synthesis Example 6: Synthesis of Compound 17

Synthesis of intermediate 17-2

Using the same method as the synthesis method for Intermediate 2-2 in Synthesis Example 2, Intermediate 17-2 (4.11 g, 59%) was obtained.

LC-MS m/z = 399 (M+H) ⁺ .

Synthesis of intermediate 17-1

The intermediate of Synthesis Example 2, except that Intermediate 17-2 (2.07 g, 5.20 mmol) and Intermediate 17-4 (3.12 g, 7.80 mmol) were used instead of Intermediate 2-2 and Intermediate 2-3, respectively. Intermediate 17-1 (2.4 g, 64%) was obtained using the same method as the synthesis method of 2-1.

LC-MS m/z = 718 (M+H) ⁺ .

Synthesis of compound 17

Compound 17 (1.2 g, 41% %) was obtained. Compound 17 was confirmed by mass and HPLC.

HRMS (MALDI) calcd for C ₅₃ H ₃₇ N ₃ Pt: m/z 910.2635, Found: 910.2633.

Synthesis Example 7: Synthesis of Compound 18

Synthesis of intermediate 18-4

Intermediate 18-4 ( 2.70 g, 59%) was obtained.

LC-MS m/z = 323 (M+H) ⁺ .

Synthesis of intermediate 18-2

Except that Intermediate 18-3 and Intermediate 9-3 (4.33 g, 12.1 mmol) were used instead of Intermediate 1-3 and 3-bromophenylboronic acid {(3-bromophenyl)boronic acid}, Intermediate 18-2 (2.50 g, 50%) was obtained using the same method as the synthesis method of Intermediate 1-2 in Synthesis Example 1.

LC-MS m/z = 476 (M+H) ⁺ .

Synthesis of intermediate 18-1

The intermediate of Synthesis Example 2, except that Intermediate 18-4 (1.78 g, 5.57 mmol) and Intermediate 18-2 (2.65 g, 5.57 mmol) were used instead of Intermediate 2-2 and Intermediate 2-3, respectively. Intermediate 18-1 (2.47 g, 62%) was obtained using the same method as the synthesis method of 2-1.

LC-MS m/z = 718 (M+H) ⁺ .

Synthesis of compound 18

Compound 18 (1.1 g, 50% %) was obtained. Compound 18 was confirmed by mass and HPLC.

HRMS (MALDI) calcd for C ₅₃ H ₃₇ N ₃ Pt: m/z 910.2635, Found: 910.2634.

Synthesis Example 8: Synthesis of Compound 21

Synthesis of Intermediate 21-2

Instead of 2-bromo-5-methyl-4-phenylpyridine and intermediate 1-2, 2-bromo-4-phenyl-5-trimethylsilylpyridine (2- The same method as the synthesis method of Intermediate 1-2 in Synthesis Example 1, except that bromo-4-phenyl-5-(trimethylsilyl)pyridine) and Intermediate 21-3 (5.21 g, 17 mmol) were used. Using , intermediate 21-2 (4.55g, 70%) was obtained.

LC-MS m/z = 382(M+H) ⁺

Synthesis of Intermediate 21-1

The intermediate of Synthesis Example 2, except that Intermediate 2-2 (2.31 g, 5.60 mmol) and Intermediate 21-2 (2.14 g, 5.60 mmol) were used instead of Intermediate 2-2 and Intermediate 2-3, respectively. Intermediate 21-1 (2.45 g, 61%) was obtained using the same method as the synthesis method of 2-1.

LC-MS m/z = 714 (M+H) ⁺

Synthesis of compound 21

Compound 21 (1.10 g, 37% %) was obtained. Compound 21 was confirmed by mass and HPLC.

HRMS (MALDI) calcd for C ₄₈ H ₃₅ N ₃ Pt: m/z 848.2479, Found: 848.2478.

Synthesis Example 9: Synthesis of Compound 26

Synthesis of Intermediate 26-1

Using the same method as the synthesis method of Intermediate 1-1 in Synthesis Example 1, Intermediate 26-1 ( 2.04 g, 61%) was obtained.

LC-MS m/z = 960 (M+H) ⁺ .

Synthesis of compound 26

Compound 26 (0.70 g, 43% %) was obtained. Compound 26 was confirmed by mass and HPLC.

HRMS (MALDI) calcd for C ₇₂ H ₅₁ N ₃ Pt: m/z 1152.3731, Found: 1152.3732.

Synthesis Example 10: Synthesis of Compound 55

Synthesis of intermediate 55-2

Except that intermediate 55-3 (4.62 g, 12 mmol) and naphthalen-1-amine (2.69 g, 15.0 mmol) were used instead of intermediate 1-2 and [1,1'-biphenyl]-2-amine, respectively. Then, using the same method as the synthesis method of Intermediate 2-2 in Synthesis Example 2, Intermediate 55-2 (4.54 g, 63%) was obtained.

LC-MS m/z = 478 (M+H) ⁺ .

Synthesis of intermediate 55-1

The intermediate of Synthesis Example 2, except that Intermediate 55-2 (1.53 g, 3.40 mmol) and Intermediate 1-2 (1.43 g, 4.42 mmol) were used instead of Intermediate 2-2 and Intermediate 2-3, respectively. Intermediate 55-1 (1.41 g, 60%) was obtained using the same method as the synthesis method of 2-1.

LC-MS m/z = 692 (M+H) ⁺ .

Synthesis of compound 55

Compound 55 (0.7 g, 26% %) was obtained. Compound 55 was confirmed by mass and HPLC.

HRMS (MALDI) calcd for C ₅₁ H ₃₅ N ₃ Pt: m/z 884.2479, Found: 884.2478.

Synthesis Example 11: Synthesis of Compound 59

Synthesis of intermediate 59-1

Synthesis Example 1 above, except that intermediate 7-2 and naphthalen-1-amine (0.72 g, 4.00 mmol) were used instead of intermediate 1-2 and [1,1'-biphenyl]-2-amine, respectively. Using the same method as the synthesis method of Intermediate 1-1, Intermediate 59-1 (1.80 g, 57%) was obtained.

LC-MS m/z = 782 (M+H) ⁺ .

Synthesis of compound 59

Compound 59 (0.60 g, 49 %) was obtained. Compound 59 was confirmed by mass and HPLC.

HRMS (MALDI) calcd for C ₅₄ H ₃₇ N ₃ Pt: m/z 922.2635, Found: 922.2634.

Synthesis Example 12: Synthesis of Compound 78

Synthesis of intermediate 78-1

Except that intermediate 17-2 (2.35 g, 4.96 mmol) and naphthalen-1-amine (0.40 g, 2.44 mmol) were used instead of intermediate 1-2 and [1,1'-biphenyl]-2-amine, respectively. Then, using the same method as the synthesis method of Intermediate 1-1 in Synthesis Example 1, Intermediate 78-1 (1.80 g, 86%) was obtained.

LC-MS m/z = 935 (M+H) ⁺ .

Synthesis of compound 78

Compound 78 (1.3 g, 62% %) was obtained. Compound 78 was confirmed by mass and HPLC.

HRMS (MALDI) calcd for C ₇₀ H ₄₉ N ₃ Pt: m/z 1126.3574, Found: 1126.3572.

Synthesis Example 13: Synthesis of Compound 127

Synthesis of intermediate 127-1

The above synthesis example, except that 4-(9H-carbazol-9-yl)-2,6-dimethylaniline (1.47 g, 5.18 mmol) was used instead of [1,1'-biphenyl]-2-amine. Using the same method as the synthesis method for Intermediate 1-1 in 1, Intermediate 127-1 (1.80 g, 45%) was obtained.

LC-MS m/z = 773 (M+H) ⁺ .

Synthesis of compound 127

Compound 127 (0.80 g, 38% %) was obtained. Compound 127 was confirmed by mass and HPLC.

HRMS(MALDI) calcd for C ₅₅ H ₄₂ N ₃ Pt: m/z 965.3057, Found: 965.3053

Synthesis Example 14: Synthesis of Compound 155

Synthesis of intermediate 155-1

Instead of intermediate 1-2 and [1,1'-biphenyl]-2-amine, intermediate 7-2 and 3,5-dimethyl-[1,1'-biphenyl]-2-amine (0.947 g, 4.80 mmol) were used. Intermediate 155-1 (2.00 g, 53%) was obtained using the same method as the synthesis method of Intermediate 1-1 in Synthesis Example 1, except that it was obtained.

LC-MS m/z = 785 (M+H) ⁺ .

Synthesis of compound 155

Compound 155 (0.60 g, 27% %) was obtained. Compound 155 was confirmed by mass and HPLC.

HRMS (MALDI) calcd for C ₅₈ H ₄₃ N ₃ Pt: m/z 976.3105, Found: 976.3101.

Example 1

As an anode, a glass substrate on which ITO/Ag/ITO was deposited to a thickness of 70Å/1000Å/70Å was cut into 50mm It was cleaned by irradiating ultraviolet rays and exposing it to ozone, and then installed in a vacuum evaporation device.

After depositing 2-TNATA on the anode to form a hole injection layer with a thickness of 600 Å, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter referred to as NPB) was added to the anode. By vapor deposition, a hole transport layer with a thickness of 1350 Å was formed.

CBP (host) and Compound 1 (dopant) were co-deposited on top of the hole transport layer at a weight ratio of 98:2 to form a 400Å-thick light-emitting layer, and then BCP was deposited on top of the light-emitting layer to form a 50Å-thick hole blocking layer. formed. Next, Alq ₃ was deposited on the hole blocking layer to form an electron transport layer with a thickness of 350 Å, then LiF was deposited on the electron transport layer to form an electron injection layer with a thickness of 10 Å, and MgAg was added on the electron injection layer. An organic light emitting device was manufactured by depositing at a weight ratio of 90:10 to form a cathode with a thickness of 120 Å.

Examples 2 to 14 and Comparative Examples 1 to 3

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

Evaluation Example 1: Evaluation of characteristics of organic light-emitting device

For the organic light emitting devices manufactured in Examples 1 to 14 and Comparative Examples 1 to 3, the driving voltage, quantum luminescence efficiency, lifetime characteristics, and maximum were measured using a current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A). Luminescence was evaluated, and the results are shown in Table 2. Lifespan (T ₉₇ ) measures the time it takes to achieve 97% luminance (based on initial luminance 100%) after operation. The driving voltage, quantum luminous efficiency, and lifespan of Examples 1 to 14 and Comparative Examples 1 and 2 were expressed as relative values when the driving voltage, quantum luminous efficiency, and lifespan of Comparative Example 3 were each set to 100%.

No. dopant
compound
No. driving voltage
(%, relative value) Quantum luminous efficiency (EQE)
(%, relative value) life span
(T ₉₇ )
(%, relative value) Maximum emission wavelength (nm) Example 1 One 83 126 556 615 Example 2 2 87 125 483 629 Example 3 4 69 125 250 620 Example 4 7 78 133 500 621 Example 5 9 78 136 556 623 Example 6 17 88 126 400 617 Example 7 18 70 123 294 618 Example 8 21 75 123 211 623 Example 9 26 72 144 444 625 Example 10 55 71 132 389 627 Example 11 59 70 140 633 619 Example 12 78 70 137 361 630 Example 13 127 74 126 339 612 Example 14 155 77 133 222 623 Comparative Example 1 A 84 122 170 607 Comparative Example 2 B 97 121 167 645 Comparative Example 3 C 100 100 100 604

From Table 2, it can be seen that the organic light-emitting devices of Examples 1 to 14 have improved driving voltage, quantum luminescence efficiency, and lifespan characteristics compared to the organic light-emitting devices of Comparative Examples 1 to 3.

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

Claims (21)

Organometallic compounds represented by the following formula (1):
<Formula 1>

<Formula 71>
*-(L ₇₁ ) _b71 -(T ₇₁ ) _c71
<Formula 72>
*-(L ₇₂ ) _b72 -(T ₇₂ ) _c72
Of formulas 1, 71 and 72
M is Pt or Pd,
X ₁ is N,
X ₂ to X ₄ are each independently C or N,
Among the bonds between X ₁ and M, _the bond between X ₂ and M, the bond between X ₃ and M, and the bond between
Y ₁ to Y ₆ are each independently C or N,
Y ₇ and Y ₈ are independently of each other C, N, O, Si, or S,
X ₁ and Y ₇ , X ₁ and Y _{1 ,} X ₂ and Y ₂ , X ₂ and Y ₃ , X ₃ and Y ₄ , X ₃ and Y ₅ , X ₄ and Y _{6 and} are connected through bonding,
CY ₁ is pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, phenanthroline group, pyrrole group, pyrazole group, imidazole group, triazole group, tetrazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzoimidazole group, benzoxa Sol group, benzothiazole group, benzoxadiazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group and 5,6,7 , selected from the group of 8-tetrahydroquinoline (5,6,7,8-tetrahydroquinoline),
CY ₂ to CY ₄ are independently of each other, benzene group, naphthalene group, anthracene group, phenanthrene group, triphenylene group, pyrene group, chrysene group, cyclopentadiene group, 1,2,3,4-tetra Hydronaphthalene (1,2,3,4-tetrahydronaphthalene) group, pyrrole group, thiophene group, furan group, indole group, benzoborole group, benzophosphopol group, indene group, benzosilol group, benzogermol group, benzoti ophene group, benzoselenophene group, benzofuran group, carbazole group, dibenzoborole group, dibenzophosphole group, fluorene group, dibenzosilol group, dibenzogermol group, dibenzothiophene group, dibenzosele Norphene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, azacarbazole group, azadibenzoborole group, aza Dibenzophosphole group, azafluorene group, azadibenzosilol group, azadibenzogermol group, azadibenzothiophene group, azadibenzoselenophene group, azadibenzofuran group, azadibenzothiophene 5- Oxide group, aza-9H-fluoren-9-one group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, phenanthroline group, pyrazole group, imidazole group, triazole group, tetrazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, oxa Diazole group, thiadiazole group, benzopyrazole group, benzoimidazole group, benzoxazole group, benzothiazole group, benzoxadiazole group, benzothiadiazole group, 5,6,7,8-tetra Selected from the hydroisoquinoline (5,6,7,8-tetrahydroisoquinoline) group and the 5,6,7,8-tetrahydroquinoline (5,6,7,8-tetrahydroquinoline) group,
T ₁ is *-N[(L ₅ ) _b5 -(R ₅ )]-*', *-C(R ₅ )(R ₆ )-*', *-Si(R ₅ )(R ₆ )-* ', *-Ge(R ₅ )(R ₆ )-*', *-S-*', *-O-*',
T ₂ and T ₃ are independently of each other, *-N[(L ₅ ) _b5 -(R ₅ )]-*', *-B(R ₅ )-*', *-P(R ₅ )-*' , *-C(R ₅ )(R ₆ )-*', *-Si(R ₅ )(R ₆ )-*', *-Ge(R ₅ )(R ₆ )-*', *-S- *', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) ₂ -*' , *-C(R ₅ )=*', *=C(R ₅ )-*', *-C(R ₅ )=C(R ₆ )-*', *-C(=S)-*' and *-C≡C-*',
L ₅ is selected from a single bond, a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group and a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,
b5 is selected from 1 to 3, and when b5 is 2 or more, 2 or more L _5s are the same or different from each other,
R ₅ and R ₆ are optionally bonded to each other through a first linking group, forming a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group. can form,
The first linking group is a single bond, *-N[(L ₉ ) _b9 -(R ₉ )]-*', *-B(R ₉ )-*', *-P(R ₉ )-*', *-C(R ₉ )(R ₁₀ )-*', *-Si(R ₉ )(R ₁₀ )-*', *-Ge(R ₉ )(R ₁₀ )-*', *-S-* ', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) ₂ -*', selected from *-C(R ₉ )=C(R ₁₀ )-*', *-C(=S)-*' and *-C≡C-*',
The description of L ₉ and b9 is the same as the description of L ₅ and b5,
The description of R ₉ and R ₁₀ above is the same as that of R ₅ ,
* and *' are, independently of each other, binding sites with neighboring atoms,
n1 is 1, and n2 and n3 are independently of each other, 0, 1, 2 or 3. If n2 is 0, *-(T ₂ ) _n2 -*' becomes a single bond, and if n3 is 0, *- (T ₃ ) _n3 -*' becomes a single bond,
R ₇₁ is a group represented by formula 71 above,
L ₇₁ is,
C ₂ -C ₆₀ alkylene group; and
A C ₂ -C ₆₀ alkylene group substituted _with at least one selected from deuterium, deuterated C 1 _-C 60 alkyl group, C ₃ -C ₁₀ cycloalkyl group, and C ₃ -C ₁₀ cycloalkenyl group;
is selected from,
b71 is 0, 1, or 2,
T ₇₁ is,
C ₁ -C ₆₀ alkyl group; and
C ₁ -C ₆₀ alkyl group substituted with at least one selected from deuterated, deuterated C 1 -C 60 alkyl group, C ₃ -C ₁₀ cycloalkyl group, and _{C 3} -C _{10 cycloalkenyl} group;
is selected from,
c71 is an integer selected from 1 to 10,
R ₇₂ is a group represented by Formula 72 above,
L ₇₂ is,
C ₆ -C ₆₀ arylene group, C ₁ -C ₆₀ heteroarylene group, divalent non-aromatic condensed polycyclic group and divalent non-aromatic condensed heteropolycyclic group; and
Deuterium, C ₁ -C ₆₀ alkyl group, deuterated C ₁ -C ₆₀ alkyl group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ hetero C ₆ -C substituted with _at least one selected from cycloalkenyl group, C 6 -C ₆₀ aryl group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group. ₆₀ arylene group, C ₁ -C ₆₀ heteroarylene group, divalent non-aromatic condensed polycyclic group and divalent non-aromatic condensed heteropolycyclic group;
is selected from,
b72 is 0, 1, or 2,
T ₇₂ is,
C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group; and
Deuterium, C ₁ -C ₆₀ alkyl group, deuterated C ₁ -C ₆₀ alkyl group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ hetero C ₆ -C substituted with at least one selected from cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group. ₆₀ aryl group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group;
is selected from,
c72 is an integer selected from 1 to 10,
a71 and a72 are independently selected from integers from 1 to 5,
R ₁ to R ₆ are each independently hydrogen, deuterium, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or a salt thereof, Sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted 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 cyclo Alkenyl 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, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group groups, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ) and -P(=O)(Q ₈ )( Q ₉ ) is selected,
a1 to a4 are independently of each other 0, 1, 2, 3, 4 or 5,
Formula 1 does not include fluorine (-F),
Two of a1 R ₁ may optionally be combined with each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,
Two of a2 R ₂ may optionally be combined with each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,
Two of a3 R ₃ may optionally be combined with each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,
Two of a4 R ₄ may optionally be combined with each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,
Two or more adjacent R ₁ to R ₄ may optionally be combined with each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group. can,
One of R ₅ and R ₆ and one of R ₁ to R ₄ are optionally combined with each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group. can form a cyclic group,
The substituted C ₅ -C ₃₀ carbocyclic group, substituted C ₁ -C ₃₀ heterocyclic group, substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, substituted C ₁ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C ₆ -C ₆₀ arylthio group, substituted C ₁ -C ₆₀ heteroaryl group , the substituents of the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic heterocondensed polycyclic group are,
Deuterium, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH 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 and C ₁ -C ₆₀ alkoxy group;
Deuterium, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH 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 ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group groups, -N(Q ₁₁ )(Q ₁₂ ), -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ), -B(Q ₁₆ )(Q ₁₇ ), and -P(=O)(Q ₁₈ )( Q ₁₉ ) substituted with at least one selected from C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group and C ₁ -C ₆₀ alkoxy group;
C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl Oxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group;
Deuterium, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH 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 group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ ) (Q ₂₄ ) (Q ₂₅ ), -B (Q ₂₆ ) (Q ₂₇ ), and -P (=O) (Q ₂₈ ) (Q ₂₉ ), substituted with at least one selected from C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ aryl Thio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group; and
-N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), -B(Q ₃₆ )(Q ₃₇ ) and -P(=O)(Q ₃₈ )(Q ₃₉ );
is selected from,
Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ are independently selected from hydrogen, deuterium, -Cl, -Br, -I, 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 ₁ -C ₆₀ alkyl group and C ₆ -C ₆₀ aryl group substituted with at least one of C 6 -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C _{6 -C 60} arylthio group, C ₁ -C ₆₀ is selected from heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed polycyclic group.
delete delete According to paragraph 1,
In Formula 1 above,

The moiety represented by

The moieties indicated by are identical to each other,

The moiety represented by

An organometallic compound in which the moieties indicated by are identical to each other. According to paragraph 1,
T ₁ to T ₃ are independently of each other, *-N[(L ₅ ) _b5 -(R ₅ )]-*', *-C(R ₅ )(R ₆ )-*', *-Si(R ₅ )(R ₆ )-*', *-S-*' and *-O-*',
n1 + n2 + n3 is 1, an organometallic compound. According to paragraph 1,
L ₇₁ is,
C ₂ -C ₁₀ alkylene group; and
Deuterated, deuterated C ₁ -C ₂₀ alkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbonanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group and cyclohepte. A C ₂ -C ₁₀ alkylene group substituted with at least one selected from among nyl groups;
is selected from,
b71 is 0 or 1,
T ₇₁ is,
C ₁ -C ₁₀ alkyl group; and
Deuterated, deuterated C ₁ -C ₂₀ alkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbonanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group and cyclohepte. A C ₁ -C ₁₀ alkyl group substituted with at least one selected from among nyl groups;
is selected from,
c71 is 1 or 2, an organometallic compound. According to paragraph 1,
L ₇₂ is,
Phenylene group, naphthylene group, pyridinylene group, pyrimidinylene group, triazinylene group, quinolinylene group, isoquinolinylene group, quinoxalinylene group, quinazolinylene group, fluorenylene group, carbazonylene group, Dibenzofuranylene group and dibenzothiophenylene group; and
Deuterium, C ₁ -C ₂₀ alkyl group, deuterated C ₁ -C ₂₀ alkyl group, phenyl group, naphthyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazoly A phenylene group, a naphthylene group, a pyridinylene group, a pyrimidinylene group, a triazinylene group, and a quinolinylene group substituted with at least one selected from a nyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group. , isoquinolinenylene group, quinoxalinylene group, quinazolinylene group, fluorenylene group, carbazonylene group, dibenzofuranylene group and dibenzothiophenylene group;
is selected from,
b72 is 0 or 1,
T ₇₂ is,
Phenyl group, naphthyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, fluorenyl group, carbazolyl group, dibenzofuranyl group and dibenzothio phenyl group; and
Deuterium, C ₁ -C ₂₀ alkyl group, deuterated C ₁ -C ₂₀ alkyl group, phenyl group, naphthyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazoly Phenyl group, naphthyl group, pyridinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolyl group, substituted with at least one selected from the group consisting of nyl group, fluorenyl group, carbazolyl group, dibenzofuranyl group and dibenzothiophenyl group. Nyl group, quinoxalinyl group, quinazolinyl group, fluorenyl group, carbazolyl group, dibenzofuranyl group and dibenzothiophenyl group;
is selected from,
c72 is 1 or 2, an organometallic compound. According to paragraph 1,
R ₁ to R ₆ are independently of each other,
Hydrogen, deuterium, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salts thereof, C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group;
Deuterium, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or Its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C ₁ -C ₁₀ alkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group. , a C ₁ -C ₂₀ alkyl group substituted with at least one of norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridinyl and pyrimidinyl groups, and C ₁ -C ₂₀ alkoxy group;
Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, Phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazole Diary group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, Quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothia Zolyl group, benzooxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazole diary group, imidazopyridinyl group and imidazopyrimidinyl group;
Deuterium, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or Its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group ), norbornanyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl. , triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridi Nyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group , cinolinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group. , oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, -N(Q ₃₁ )( Q ₃₂ ) and -Si (Q ₃₃ ) (Q ₃₄ ) (Q ₃₅ ) substituted with at least one selected from cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbona Nyl group (norbornanyl), norbornenyl group (norbornenyl), cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl group Nyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cynolinyl group , carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazole diyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group and imidazopyrimidinyl group; and
-N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ) and -P(=O)(Q ₈ )(Q ₉ );
is selected from,
Q ₁ to Q ₉ and Q ₃₁ to Q ₃₅ are independently of each other,
-CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CH 2 CH ₃ , -CH ₂ CD ₃ , -CH ₂ CD ₂ H, -CH _{2 CDH 2} , -CHDCH ₃ , -CHDCD ₂ H , -CHDCDH ₂ , -CHDCD ₃ , -CD ₂ CD ₃ , -CD ₂ CD ₂ H and -CD ₂ CDH ₂ ;
n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group and naph. til group; and
Substituted with at least one selected from deuterium, C ₁ -C ₁₀ alkyl group and phenyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group and naphthyl group;
selected from among organometallic compounds. According to paragraph 1,
Wherein R ₁ to R ₆ are each independently selected from hydrogen, deuterium, cyano group, nitro group, -CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -OCH ₃ , of the following formulas 9-1 to 9- selected from the group represented by 19, the group represented by the following formulas 10-1 to 10-168, -N(Q ₁ )(Q ₂ ) and -Si(Q ₃ )(Q ₄ )(Q ₅ ),
R ₇₁ is -CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , a group represented by the following formulas 9-1 to 9-19 and formulas 10-5 to 10-8, 10-11 and 10-12 is selected from the group indicated by,
R ₇₂ is an organometallic compound selected from the group represented by formulas 10-13 to 10-152 and 10-159 to 10-168.

In Formulas 9-1 to 9-19 and 10-1 to 10-168, * is a bonding site with an adjacent atom, Ph is a phenyl group, Cz is a carbazolyl group, and TMS is a trimethylsilyl group. According to paragraph 1,
In Formula 1 above,

An organometallic compound wherein the moiety represented by is selected from the group represented by the formulas CY1-1 to CY1-6:

Among the formulas CY1-1 to CY1-6
The descriptions of X ₁ , R ₇₁ , R ₇₂ and R ₁ are the same as those described in paragraph 1,
c2 is selected from an integer of 0 to 2,
* and *' are each binding sites with neighboring atoms. According to paragraph 1,
In Formula 1 above,

An organometallic compound in which the moiety represented by is selected from the group represented by the formulas CY2-1 to CY2-25:

Of the formulas CY2-1 to CY2-25
The descriptions of X ₂ and R ₂ are the same as those described in paragraph 1, respectively,
X ₂₁ is O, S, N(R ₂₁ ) or C(R ₂₁ )(R ₂₂ ),
The description of R ₂₁ to R ₂₈ is the same as the description of R ₂ in paragraph 1,
c5 is selected from an integer from 0 to 5,
c4 is selected from an integer from 0 to 4,
c3 is selected from an integer of 0 to 3,
c2 is selected from an integer of 0 to 2,
*, *' and *" are each binding sites with neighboring atoms. According to paragraph 1,
In Formula 1 above,

An organometallic compound wherein the moiety represented by is selected from the group represented by the formulas CY3-1 to CY3-25:

Of the formulas CY3-1 to CY3-25
The descriptions of X ₃ and R ₃ are the same as those described in paragraph 1,
X ₃₁ is O, S, N(R ₃₁ ) or C(R ₃₁ )(R ₃₂ ),
The description of R ₃₁ to R ₃₈ is the same as the description of R ₃ in paragraph 1,
c5 is selected from an integer from 0 to 5,
c4 is selected from an integer from 0 to 4,
c3 is selected from an integer of 0 to 3,
c2 is selected from an integer of 0 to 2,
*, *' and *" are each binding sites with neighboring atoms. According to paragraph 1,
In Formula 1 above,

An organometallic compound wherein the moiety represented by is selected from the group represented by the formulas CY4-1 to CY4-35:

Among the formulas CY4-1 to CY4-35
The descriptions of X ₄ and R ₄ are the same as those described in paragraph 1, respectively,
X ₄₁ is O, S, N(R ₄₁ ) or C(R ₄₁ )(R ₄₂ ),
R _71a is the same as the description for R ₇₁ in paragraph 1,
R _72a is the same as the description for R ₇₂ in paragraph 1,
The description of R ₄₁ to R ₄₈ is the same as the description of R ₄ in paragraph 1,
c6 is selected from integers from 0 to 6,
c5 is selected from an integer from 0 to 5,
c4 is selected from an integer from 0 to 4,
c3 is selected from an integer of 0 to 3,
c2 is selected from an integer of 0 to 2,
* and *' are each binding sites with neighboring atoms. According to paragraph 1,
In Formula 1 above,

The moiety represented by is selected from the group represented by the formulas CY1(1) and CY1(2),
In Formula 1 above,

The moiety represented by is selected from the group represented by the formulas CY2(1) to CY2(4),
In Formula 1 above,

The moiety represented by is selected from the group represented by the formulas CY3(1) to CY3(4),
In Formula 1 above,

An organometallic compound wherein the moiety represented by is selected from the group represented by the formulas CY4(1) to CY4(19):

Among the formulas CY1(1), CY1(2), CY2(1) to CY2(4), CY3(1) to CY3(4), and CY4(1) to CY4(19),
The descriptions of X ₁ , R ₁ , R _{71 ,} R ₇₂ , X ₂ , _{R 2} , X ₃ , R ₃ ,
X ₄₁ is O, S, N(R ₄₁ ) or C(R ₄₁ )(R ₄₂ ),
The descriptions of R _4a , R _4b , R ₄₁ and R ₄₂ are each the same as the description of R ₄ in clause 1,
R _71a is the same as the description for R ₇₁ in paragraph 1,
R _72a is the same as the description for R ₇₂ in paragraph 1,
*, *' and *" are each binding sites with neighboring atoms. According to paragraph 1,
An organometallic compound, represented by the formula 1(1):
<Formula 1(1)>

In the above formula 1(1)
_{M , _ _ _ _ _ _ _ _ _ _} The descriptions are the same as those described in paragraph 1, respectively,
CY ₅ and CY ₆ are, independently of each other, a C ₅ -C ₂₉ carbocyclic group or a C ₁ -C ₂₉ heterocyclic group,
The descriptions of R ₅₁ and R ₆₁ are independent of each other and are the same as the description of R ₁ in clause 1,
a51 and a61 are independently of each other 0, 1, 2 or 3,
T ₄ is C, Si or Ge,
T ₅ is a single bond, *-N[(L ₇ ) _b7 -(R ₇ )]-*', *-C(R ₇ )(R ₈ )-*', *-Si(R ₇ )(R ₈ )-*', *-Ge(R ₇ )(R ₈ )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-* ', *-S(=O)-*', *-S(=O) ₂ -*', *-C(R ₇ )=C(R ₈ )-*', *-C(=S)- is selected from *' and *-C≡C-*',
The descriptions of L ₇ and b7 are the same as the descriptions of L ₅ and b5 in clause 1, respectively,
The descriptions of R ₇ and R ₈ are the same as those of R ₅ in clause 1,
* and *' are, independently of each other, binding sites with neighboring atoms. According to paragraph 1,
Organometallic compounds selected from the following compounds 1 to 201:

first electrode;
second electrode; and
an organic layer interposed between the first electrode and the second electrode and including a light-emitting layer;
Including,
The organic layer is an organic light-emitting device comprising at least one organometallic compound according to any one of claims 1 and 4 to 16. According to clause 17,
The first electrode is an anode,
The second electrode is a cathode,
The organic layer further includes a hole transport region between the first electrode and the light-emitting layer and an electron transport region between the light-emitting layer and the second electrode,
The hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof,
The electron transport region is an organic light emitting device comprising a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof. According to clause 17,
An organic light-emitting device wherein the organometallic compound is included in the light-emitting layer. According to clause 19,
An organic light-emitting device wherein the light-emitting layer further includes a host, and the weight of the host in the light-emitting layer is greater than the weight of the organometallic compound in the light-emitting layer. A composition for monitoring, sensing, or detecting a biological material, comprising at least one organometallic compound according to any one of claims 1 and 4 to 16.

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