KR102429872B1 - Organometallic compound and organic light-emitting device including the same - Google Patents

Abstract

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

Description

Organometallic compound and organic light-emitting device including the same

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

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

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

Embodiments of the present invention provide an organometallic compound and an organic light emitting device including the same.

One embodiment of the present invention discloses an organometallic compound represented by the following formula (1):

<Formula 1>

Ir(L ₁ ) _n (L ₂ ) _(3-n)

<Formula 2> <Formula 3>

In Formulas 1 to 3,

L ₁ is a first ligand represented by Formula 2;

L ₂ is a second ligand represented by Formula 3;

n is selected from 1, 2 and 3;

A ₁₁ is selected from a C ₆ -C ₆₀ cyclic group and a C ₁ -C ₆₀ heterocyclic group including Y ₁₁ as a ring member;

A ₂₁ is selected from a C ₆ -C ₆₀ cyclic group and a C ₁ -C ₆₀ heterocyclic group containing X ₂₃ and Y ₂₁ as ring members;

A ₂₂ is selected from a C ₆ -C ₆₀ cyclic group and a C ₁ -C ₆₀ heterocyclic group containing X ₂₄ and Y ₂₂ as ring members;

Y ₁₁ , Y ₁₂ , Y ₂₁ and Y ₂₂ are each independently selected from a carbon atom (C) and a nitrogen atom (N);

X ₁₃ is N or CR ₁₃ , X ₁₄ is N or CR ₁₄ , X ₁₅ is N or CR ₁₅ ; X ₁₆ is N or CR ₁₆ ; X ₁₇ is N or CR ₁₇ ; X ₁₈ is N or CR ₁₈ ; X ₁₉ is N or CR ₁₉ ;

X ₂₃ is N or CR ₂₃ and X ₂₄ is N or CR ₂₄ ;

R ₁₁ to R ₁₉ , R ₂₃ , R ₂₄ , R ₂₈ and R ₂₉ are each independently hydrogen, deuterium, -F (fluoro group), -Cl (chloro group), -Br (bromo group), -I (iodo group), cyano group, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, and substituted or unsubstituted selected from a C ₁ -C ₆₀ heteroaryl group;

a11, a28 and a29 are each independently selected from 1, 2, 3, 4, 5 and 6;

R ₁₂ and R ₁₃ are optionally, a single bond, *-O-*', *-S-*', *-N(Z ₁₁ )-*' and *-[C(Z ₁₁ )(Z ₁₂ )] are bonded to each other through a divalent linking group selected from _b11 -*';

Z ₁₁ and Z ₁₂ are each independently hydrogen, deuterium, -F (fluoro group), -Cl (chloro group), -Br (bromo group), -I (iodo group), substituted or unsubstituted C ₁ a -C ₆₀ alkyl group and a substituted or unsubstituted C ₆ -C ₆₀ aryl group;

b11 is selected from 1, 2, 3 and 4;

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

At least one substituent of the substituted C ₁ -C ₆₀ alkyl group, the substituted C ₁ -C ₆₀ alkoxy group, the substituted C ₆ -C ₆₀ aryl group, and the substituted C ₁ -C ₆₀ heteroaryl group is,

deuterium, -F, -Cl, -Br, -I, a C ₁ -C ₆₀ alkyl group and a C ₁ -C ₆₀ alkoxy group;

C substituted with at least one of deuterium, -F, -Cl, -Br, -I, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group and -Si(Q ₁₁ )(Q ₁₂ )(Q ₁₃ ) ₁ -C ₆₀ alkyl group and C ₁ -C ₆₀ alkoxy group;

C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group and C ₁ -C ₆₀ heteroaryl group;

Deuterium, -F, -Cl, -Br, -I, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C C _{6 -C 60 aryl group, C 6 -C 60 aryloxy} group, substituted with at least one of ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, and —Si(Q ₂₁ )(Q ₂₂ )(Q ₂₃ ) , C ₆ -C ₆₀ arylthio group and C ₁ -C ₆₀ heteroaryl group; and

-Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ); is selected from;

Q ₁₁ to Q ₁₃ , Q ₂₁ to Q ₂₃ , and Q ₃₁ to Q ₃₃ are each independently selected from a C ₁ -C ₆₀ alkyl group and a C ₆ -C ₆₀ aryl group.

Another embodiment of the present invention, the first electrode; a second electrode; and an organic layer interposed between the first electrode and the second electrode and including an emission layer, wherein the organic layer includes at least one or more of the aforementioned organometallic compounds.

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

Since the organometallic compound has excellent electrical properties and thermal stability, the organic light emitting device including the organometallic compound may have low driving voltage, high efficiency, high brightness, long lifespan, and high color purity.

1 is a cross-sectional view schematically illustrating an organic light emitting device according to an embodiment of the present invention.
2 is a ¹ H NMR spectrum of ligand 12 according to a synthesis example of the present invention.
3 is a GCMS result of ligand 12 according to a synthesis example of the present invention.
4 is an emission curve of compound 12 according to a synthesis example of the present invention.
5 is a ¹ H NMR spectrum of ligand 7 according to a synthesis example of the present invention.
6 is a GCMS result of ligand 7 according to a synthesis example of the present invention.
7 is a ¹ H NMR spectrum of ligand 8 according to a synthesis example of the present invention.
8 is a GCMS result of Ligand 8 according to a synthesis example of the present invention.

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

<Formula 1>

Ir(L ₁ ) _n (L ₂ ) _(3-n)

The organometallic compound may include at least one cyano group as a substituent, but is not limited thereto.

In Formula 1, L ₁ is a first ligand represented by Formula 2 below:

<Formula 2>

In Formula 1, L ₂ is a first ligand represented by Formula 3 below:

<Formula 3>

For example, in Formula 1, at least one of L ₁ and L ₂ may include at least one cyano group as a substituent, but is not limited thereto.

As another example, in Formula 1, L ₁ may include at least one cyano group as a substituent, but is not limited thereto.

As another example, in Formula 1, L ₂ may include at least one cyano group as a substituent, but is not limited thereto.

As another example, in Formulas 2 and 3, at least one of R ₁₁ to R ₁₉ , R ₂₃ , R ₂₄ , R ₂₈ and R ₂₉ may be a cyano group, but is not limited thereto.

As another example, in Formulas 2 and 3, at least one of R ₁₁ , R ₁₅ , and R ₂₉ may be a cyano group, but is not limited thereto.

As another example, in Formula 2, R ₁₁ may be a cyano group, but is not limited thereto.

As another example, in Formula 2, R ₁₅ may be a cyano group, but is not limited thereto.

As another example, in Formula 3, R ₂₉ may be a cyano group, but is not limited thereto.

In Formula 1, n means the number of L ₁ , and n may be selected from 1, 2, and 3. When n is 2 or more, a plurality of L ₁ may be the same as or different from each other.

For example, in Formula 1, n may be selected from 2 and 3, but is not limited thereto.

In Formulas 2 and 3, A ₁₁ is selected from a C ₆ -C ₆₀ cyclic group and a C ₁ -C ₆₀ heterocyclic group including Y ₁₁ as a ring member; A ₂₁ is selected from a C ₆ -C ₆₀ cyclic group and a C ₁ -C ₆₀ heterocyclic group containing X ₂₃ and Y ₂₁ as ring members; A ₂₂ is selected from a C ₆ -C ₆₀ cyclic group and a C ₁ -C ₆₀ heterocyclic group including X ₂₄ and Y ₂₂ as ring members.

For example, in Formulas 2 and 3, A ₁₁ , A ₂₁ , and A ₂₂ may each independently represent benzene, naphthalene, anthracene, phenanthrene, pyrrole, imidazole, pyrazole, thiazole, isothiazole, or oxazole. , isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, quinoline, isoquinoline, benzoquinoline, quinoxaline, quinazoline, benzoimidazole, benzoxazole, isobenzoxazole, triazole, tetrazole, oxadiazole , triazine, pyridoindole, pyridofuran and pyridothiophene, but is not limited thereto.

As another example, in Formula 2, A ₁₁ may be selected from benzene, naphthalene, pyrrole, imidazole, and pyrazole, but is not limited thereto.

As another example, in Formula 2, A ₁₁ may be selected from benzene and imidazole, but is not limited thereto.

As another example, in Formula 2, A ₂₁ and A ₂₂ may each independently represent benzene, naphthalene, pyrrole, imidazole, pyrazole, pyridine, pyrazine, pyrimidine, pyridazine, quinoline, isoquinoline, quinoxaline, quina It may be selected from zoline, triazole, and tetrazole, but is not limited thereto.

In Formulas 2 and 3, Y ₁₁ , Y ₁₂ , Y ₂₁ , and Y ₂₂ are each independently selected from a carbon atom (C) and a nitrogen atom (N).

For example, in Formulas 2 and 3, Y ₁₁ and Y ₁₂ may be different from each other, and Y ₂₁ and Y ₂₂ may be different from each other, but are not limited thereto.

As another example, in Formulas 2 and 3, Y ₁₁ may be N, Y ₁₂ may be C, Y ₂₁ may be N, and Y ₂₂ may be C, but is not limited thereto.

As another example, in Formulas 2 and 3, Y ₁₁ may be C, Y ₁₂ may be N, Y ₂₁ may be N, and Y ₂₂ may be C, but is not limited thereto.

In Formula 2, X ₁₃ is N or CR ₁₃ , X ₁₄ is N or CR ₁₄ , and X ₁₅ is N or CR ₁₅ ; X ₁₆ is N or CR ₁₆ ; X ₁₇ is N or CR ₁₇ ; X ₁₈ is N or CR ₁₈ ; X ₁₉ is N or CR ₁₉ .

For example, in Formula 2, at least one of X ₁₃ to X ₁₉ may be N, but is not limited thereto.

As another example, in Formula 2, at least one of X ₁₃ to X ₁₆ may be N, but is not limited thereto.

As another example, in Formula 2, at least one of X ₁₃ and X ₁₅ may be N, but is not limited thereto.

In Formula 3, X ₂₃ is N or CR ₂₃ , and X ₂₄ is N or CR ₂₄ .

For example, in Formula 3, X ₂₃ may be N, but is not limited thereto.

In Formulas 2 and 3, R ₁₁ to R ₁₉ , R ₂₃ , R ₂₄ , R ₂₈ and R ₂₉ are each independently hydrogen, deuterium, -F (fluoro group), -Cl (chloro group), -Br (bromo group), -I (iodo group), cyano group, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₆ -C ₆₀ selected from an aryl group and a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group;

At least one substituent of the substituted C ₁ -C ₆₀ alkyl group, the substituted C ₁ -C ₆₀ alkoxy group, the substituted C ₆ -C ₆₀ aryl group, and the substituted C ₁ -C ₆₀ heteroaryl group is,

deuterium, -F, -Cl, -Br, -I, a C ₁ -C ₆₀ alkyl group and a C ₁ -C ₆₀ alkoxy group;

C substituted with at least one of deuterium, -F, -Cl, -Br, -I, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group and -Si(Q ₁₁ )(Q ₁₂ )(Q ₁₃ ) ₁ -C ₆₀ alkyl group and C ₁ -C ₆₀ alkoxy group;

C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group and C ₁ -C ₆₀ heteroaryl group;

Deuterium, -F, -Cl, -Br, -I, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C C _{6 -C 60 aryl group, C 6 -C 60 aryloxy} group, substituted with at least one of ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, and —Si(Q ₂₁ )(Q ₂₂ )(Q ₂₃ ) , C ₆ -C ₆₀ arylthio group and C ₁ -C ₆₀ heteroaryl group; and

-Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ); is selected from;

Q ₁₁ to Q ₁₃ , Q ₂₁ to Q ₂₃ , and Q ₃₁ to Q ₃₃ are each independently selected from a C ₁ -C ₆₀ alkyl group and a C ₆ -C ₆₀ aryl group.

For example, in Formulas 2 and 3, R ₁₁ to R ₁₉ , R ₂₃ , R ₂₄ , R ₂₈ and R ₂₉ may each independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, cya no group, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group and C ₁ -C ₆₀ heteroaryl group;

Deuterium, -F, -Cl, -Br, -I, methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, sec-butyl group, tert-butyl group, methoxy group , an ethoxy group, a tert-butoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, and -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ) substituted with at least one of, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group and C ₁ -C ₆₀ heteroaryl group; and

Deuterium, -F, -Cl, -Br, -I, a methyl group, an ethyl group, a phenyl group, a naphthyl group, at least one of a pyridinyl group and a pyrimidinyl group substituted with at least one of a phenyl group, a naphthyl group, a pyridinyl group and a pyrimidinyl group one substituted, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group and C ₁ -C ₆₀ heteroaryl group; is selected from;

Q ₃₁ to Q ₃₃ may be each independently selected from a methyl group, an ethyl group, an iso-propyl group, a tert-butyl group, a phenyl group, and a naphthyl group, but are not limited thereto.

As another example, in Formulas 2 and 3, R ₁₁ to R ₁₉ , R ₂₃ , R ₂₄ , R ₂₈ and R ₂₉ may each independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, cya no group, methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, sec-butyl group, tert-butyl group, phenyl group, naphthyl group, pyridinyl group and pyrimidinyl group;

a phenyl group and a naphthyl group substituted with at least one of deuterium, -F, a methyl group, an ethyl group, an iso-propyl group, a tert-butyl group, and -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ); and

Deuterium, -F, -Cl, -Br, -I, methyl group, ethyl group, phenyl group, naphthyl group, substituted with at least one of a pyridinyl group and a pyrimidinyl group, substituted with at least one of a phenyl group and a naphthyl group, a phenyl group and a naphthyl group ; is selected from;

Q ₃₁ to Q ₃₃ are each independently selected from a methyl group and a phenyl group; may be selected from, but is not limited thereto.

As another example, in Formulas 2 and 3, R ₁₁ to R ₁₉ , R ₂₃ , R ₂₄ , R ₂₈ and R ₂₉ may each independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, It may be any one group selected from a cyano group and Formulas 5-1 to 5-7, but is not limited thereto:

In Formulas 5-1 to 5-7,

Z ₁ is hydrogen, deuterium, -F, a methyl group, an ethyl group, an iso-propyl group, a tert-butyl group, and -Si(CH ₃ ) ₃ ; and

deuterium, -F, -Cl, -Br, -I, a phenyl group and a naphthyl group substituted with at least one of a methyl group, an ethyl group, a phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group;

d1 is selected from 1, 2, 3, 4 and 5;

d2 is selected from 1, 2, 3, 4, 5, 6 and 7;

* is a binding site with a neighboring atom.

As another example, in Formulas 2 and 3, R ₁₁ to R ₁₉ , R ₂₃ , R ₂₄ , R ₂₈ and R ₂₉ may each independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, It may be any one group selected from a cyano group and Formulas 6-1 to 6-13, but is not limited thereto:

In Formulas 6-1 to 6-13,

* is a binding site with a neighboring atom.

In Formula 2, a11 denotes the number of R ₁₁ , and a11 is selected from 1, 2, 3, 4, 5, and 6. When a11 is 2 or more, a plurality of R ₁₁ may be the same as or different from each other.

For example, in Formula 2, a11 may be selected from 1, 2, and 3, but is not limited thereto.

In Formula 3, a28 means the number of R ₂₈ , and a28 is selected from 1, 2, 3, 4, 5, and 6. When a28 is 2 or more, a plurality of R ₂₈ may be the same as or different from each other.

For example, in Formula 2, a28 may be selected from 1, 2, and 3, but is not limited thereto.

In Formula 3, a29 means the number of R ₂₉ , and a29 is selected from 1, 2, 3, 4, 5, and 6. When a29 is 2 or more, a plurality of R ₂₉ may be the same as or different from each other.

For example, in Formula 2, a29 may be selected from 1, 2, and 3, but is not limited thereto.

In Formula 2, R ₁₂ and R ₁₃ are optionally, a single bond, *-O-*', *-S-*', *-N(Z ₁₁ )-*' and *-[C( Z ₁₁ )(Z ₁₂ )] may be bonded to each other through a divalent linking group selected from _b11 -*'. For descriptions of Z ₁₁ , Z ₁₂ and b11, refer to the bar below.

및

중 선택된 어느 하나로 표시되는 2가 연결기를 통하여 서로 결합될 수 있으나, 이에 한정되는 것은 아니다.For example, in Formula 2, R ₁₂ and R ₁₃ are optionally, a single bond;

and

It may be bonded to each other through a divalent linking group represented by any one selected from, but is not limited thereto.

로 표시되는 2가 연결기를 통하여 서로 결합될 수 있으나, 이에 한정되는 것은 아니다.As another example, in Formula 2, R ₁₂ and R ₁₃ are optionally,

It may be bonded to each other through a divalent linking group represented by, but is not limited thereto.

Z ₁₁ and Z ₁₂ are each independently hydrogen, deuterium, -F (fluoro group), -Cl (chloro group), -Br (bromo group), -I (iodo group), substituted or unsubstituted C ₁ a -C ₆₀ alkyl group and a substituted or unsubstituted C ₆ -C ₆₀ aryl group;

At least one substituent of the substituted C ₁ -C ₆₀ alkyl group and the substituted C ₆ -C ₆₀ aryl group is,

deuterium, -F, -Cl, -Br, -I, a C ₁ -C ₆₀ alkyl group and a C ₁ -C ₆₀ alkoxy group;

C substituted with at least one of deuterium, -F, -Cl, -Br, -I, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group and -Si(Q ₁₁ )(Q ₁₂ )(Q ₁₃ ) ₁ -C ₆₀ alkyl group and C ₁ -C ₆₀ alkoxy group;

C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group and C ₁ -C ₆₀ heteroaryl group;

Deuterium, -F, -Cl, -Br, -I, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C C _{6 -C 60 aryl group, C 6 -C 60 aryloxy} group, substituted with at least one of ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, and —Si(Q ₂₁ )(Q ₂₂ )(Q ₂₃ ) , C ₆ -C ₆₀ arylthio group and C ₁ -C ₆₀ heteroaryl group; and

-Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ); is selected from;

Q ₁₁ to Q ₁₃ , Q ₂₁ to Q ₂₃ , and Q ₃₁ to Q ₃₃ are each independently selected from a C ₁ -C ₆₀ alkyl group and a C ₆ -C ₆₀ aryl group.

For example, Z ₁₁ and Z ₁₂ may be each independently selected from hydrogen, deuterium, -F, a methyl group, an ethyl group, a phenyl group, and a naphthyl group, but is not limited thereto.

As another example, Z ₁₁ and Z ₁₂ may be each independently selected from hydrogen, deuterium, -F, a methyl group, and an ethyl group, but is not limited thereto.

As another example, Z ₁₁ and Z ₁₂ may be hydrogen, but is not limited thereto.

b11 means the repeating number of the moiety represented by C(Z ₁₁ )(Z ₁₂ ), and is selected from 1, 2, 3 and 4. When b11 is 2 or more, a plurality of moieties represented by C(Z ₁₁ )(Z ₁₂ ) may be the same as or different from each other.

For example, b11 may be selected from 1 and 2, but is not limited thereto.

As another example, b11 may be 2, but is not limited thereto.

In the above formulas, * and *' are independently binding sites with neighboring atoms.

In one embodiment, the first ligand may be represented by the following Chemical Formula 2A, but is not limited thereto:

<Formula 2A>

In Formula 2A,

A ₁₁ is selected from a C ₆ -C ₆₀ cyclic group and a C ₁ -C ₆₀ heterocyclic group containing Y ₁₁ as a ring member;

Y ₁₁ and Y ₁₂ are each independently selected from a carbon atom (C) and a nitrogen atom (N);

X ₁₃ is N or CR ₁₃ , X ₁₄ is N or CR ₁₄ , X ₁₅ is N or CR ₁₅ ;

R ₁₁ to R ₁₉ are each independently hydrogen, deuterium, -F (fluoro group), -Cl (chloro group), -Br (bromo group), -I (iodo group), cyano group, substituted or unsubstituted selected from a C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, and a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group ;

a11 is selected from 1, 2, 3, 4, 5 and 6;

R ₁₂ and R ₁₃ are optionally, a single bond, *-O-*', *-S-*', *-N(Z ₁₁ )-*' and *-[C(Z ₁₁ )(Z ₁₂ )] are bonded to each other through a divalent linking group selected from _b11 -*';

Z ₁₁ and Z ₁₂ are each independently hydrogen, deuterium, -F (fluoro group), -Cl (chloro group), -Br (bromo group), -I (iodo group), and substituted or unsubstituted C ₁ -C ₆₀ selected from alkyl groups;

b11 is selected from 1, 2, 3 and 4;

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

At least one substituent of the substituted C ₁ -C ₆₀ alkyl group, the substituted C ₁ -C ₆₀ alkoxy group, the substituted C ₆ -C ₆₀ aryl group, and the substituted C ₁ -C ₆₀ heteroaryl group is,

deuterium, -F, -Cl, -Br, -I, a C ₁ -C ₆₀ alkyl group and a C ₁ -C ₆₀ alkoxy group;

C substituted with at least one of deuterium, -F, -Cl, -Br, -I, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, and -Si(Q ₁₁ )(Q ₁₂ )(Q ₁₃ ) ₁ -C ₆₀ alkyl group and C ₁ -C ₆₀ alkoxy group;

C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group and C ₁ -C ₆₀ heteroaryl group;

Deuterium, -F, -Cl, -Br, -I, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C C _{6 -C 60 aryl group, C 6 -C 60 aryloxy} group, substituted with at least one of ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, and —Si(Q ₂₁ )(Q ₂₂ )(Q ₂₃ ) , C ₆ -C ₆₀ arylthio group and C ₁ -C ₆₀ heteroaryl group; and

-Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ); is selected from;

Q ₁₁ to Q ₁₃ , Q ₂₁ to Q ₂₃ , and Q ₃₁ to Q ₃₃ are each independently selected from a C ₁ -C ₆₀ alkyl group and a C ₆ -C ₆₀ aryl group.

For example, in Formula 2A, X ₁₅ is CR ₁₅ ;

Any one of R ₁₁ and R ₁₅ may be a cyano group, but is not limited thereto.

In another embodiment, the first ligand may be represented by any one of Formulas 2-1 to 2-10, but is not limited thereto:

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

<Formula 2-3> <Formula 2-4>

<Formula 2-5> <Formula 2-6>

<Formula 2-7> <Formula 2-8>

<Formula 2-9> <Formula 2-10>

In Formulas 2-1 to 2-10,

R ₁₁ to R ₁₉ are each independently hydrogen, deuterium, -F (fluoro group), -Cl (chloro group), -Br (bromo group), -I (iodo group), cyano group, substituted or unsubstituted selected from a C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, and a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group ;

a11 is selected from 1, 2, 3, 4, 5 and 6;

Z ₁₁ and Z ₁₂ are each independently hydrogen, deuterium, -F (fluoro group), -Cl (chloro group), -Br (bromo group), -I (iodo group), and substituted or unsubstituted C ₁ -C ₆₀ selected from alkyl groups;

b11 is selected from 1, 2, 3 and 4;

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

At least one substituent of the substituted C ₁ -C ₆₀ alkyl group, the substituted C ₁ -C ₆₀ alkoxy group, the substituted C ₆ -C ₆₀ aryl group, and the substituted C ₁ -C ₆₀ heteroaryl group is,

deuterium, -F, -Cl, -Br, -I, a C ₁ -C ₆₀ alkyl group and a C ₁ -C ₆₀ alkoxy group;

C substituted with at least one of deuterium, -F, -Cl, -Br, -I, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, and -Si(Q ₁₁ )(Q ₁₂ )(Q ₁₃ ) ₁ -C ₆₀ alkyl group and C ₁ -C ₆₀ alkoxy group;

C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group and C ₁ -C ₆₀ heteroaryl group;

Deuterium, -F, -Cl, -Br, -I, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C C _{6 -C 60 aryl group, C 6 -C 60 aryloxy} group, substituted with at least one of ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, and —Si(Q ₂₁ )(Q ₂₂ )(Q ₂₃ ) , C ₆ -C ₆₀ arylthio group and C ₁ -C ₆₀ heteroaryl group; and

-Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ); is selected from;

Q ₁₁ to Q ₁₃ , Q ₂₁ to Q ₂₃ , and Q ₃₁ to Q ₃₃ are each independently selected from a C ₁ -C ₆₀ alkyl group and a C ₆ -C ₆₀ aryl group.

For example, in Formulas 2-1 to 2-10, at least one of R ₁₁ to R ₁₉ may be a cyano group, but is not limited thereto.

As another example, in Formulas 2-1 to 2-10, at least one of R ₁₁ and R ₁₅ may be a cyano group, but is not limited thereto.

As another example, in Formulas 2-1, 2-2, 2-4, 2-5, 2-7, and 2-8, at least one of R ₁₁ and R ₁₅ may be a cyano group, but is not limited thereto. it is not

In another embodiment, the second ligand may be represented by the following Chemical Formula 3A, but is not limited thereto:

<Compound 3A>

In Formula 3A,

Y ₂₁ and Y ₂₂ are each independently selected from a carbon atom (C) and a nitrogen atom (N);

X ₂₁ is N or CR ₂₁ ; X ₂₃ is N or CR ₂₃ and X ₂₅ is N or CR ₂₅ ;

R ₂₁ to R ₂₇ are each independently hydrogen, deuterium, -F (fluoro group), -Cl (chloro group), -Br (bromo group), -I (iodo group), cyano group, substituted or unsubstituted selected from a C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, and a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group ;

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

At least one substituent of the substituted C ₁ -C ₆₀ alkyl group, the substituted C ₁ -C ₆₀ alkoxy group, the substituted C ₆ -C ₆₀ aryl group, and the substituted C ₁ -C ₆₀ heteroaryl group is,

deuterium, -F, -Cl, -Br, -I, a C ₁ -C ₆₀ alkyl group and a C ₁ -C ₆₀ alkoxy group;

C substituted with at least one of deuterium, -F, -Cl, -Br, -I, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group and -Si(Q ₁₁ )(Q ₁₂ )(Q ₁₃ ) ₁ -C ₆₀ alkyl group and C ₁ -C ₆₀ alkoxy group;

C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group and C ₁ -C ₆₀ heteroaryl group;

Deuterium, -F, -Cl, -Br, -I, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C C _{6 -C 60 aryl group, C 6 -C 60 aryloxy} group, substituted with at least one of ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, and —Si(Q ₂₁ )(Q ₂₂ )(Q ₂₃ ) , C ₆ -C ₆₀ arylthio group and C ₁ -C ₆₀ heteroaryl group; and

-Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ); is selected from;

Q ₁₁ to Q ₁₃ , Q ₂₁ to Q ₂₃ , and Q ₃₁ to Q ₃₃ are each independently selected from a C ₁ -C ₆₀ alkyl group and a C ₆ -C ₆₀ aryl group.

For example, in Formula 3A, X ₂₅ is N or CR ₂₅ ; R ₂₅ may be a cyano group, but is not limited thereto.

As another example, the second ligand may be represented by the following Chemical Formula 3-1, but is not limited thereto:

<Formula 3-1>

In Formula 3-1,

X ₂₁ is N or CR ₂₁ , X ₂₅ is N or CR ₂₅ ;

R ₂₁ , R ₂₂ and R ₂₄ to R ₂₇ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a cyano group, a C ₁ -C ₆₀ alkyl group, a C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group and C ₁ -C ₆₀ heteroaryl group;

Deuterium, -F, -Cl, -Br, -I, methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, sec-butyl group, tert-butyl group, methoxy group , an ethoxy group, a tert-butoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, and -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ) substituted with at least one of, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group and C ₁ -C ₆₀ heteroaryl group; and

At least one of a phenyl group, a naphthyl group, a pyridinyl group and a pyrimidinyl group substituted with at least one of deuterium, -F, -Cl, -Br, -I, a methyl group, an ethyl group, a phenyl group, a naphthyl group, a pyridinyl group and a pyrimidinyl group one substituted, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group and C ₁ -C ₆₀ heteroaryl group; is selected from;

a11 is selected from 1, 2 and 3;

* and *' are binding sites with neighboring atoms.

For example, in Formula 3-1, X ₂₅ is N or CR ₂₅ ; R ₂₅ may be a cyano group, but is not limited thereto.

In another embodiment, the organometallic compound may be represented by any one of the following Chemical Formulas 1-1 to 1-8, but is not limited thereto:

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

<Formula 1-3> <Formula 1-4>

<Formula 1-5> <Formula 1-6>

<Formula 1-7>

<Formula 1-8>

In Formulas 1-1 to 1-8,

X ₂₁ is N or CR ₂₁ ; X ₂₅ is N or CR ₂₅ ;

R ₁₁ to R ₁₉ and R ₂₁ , R ₂₂ and R ₂₄ to R ₂₇ are each independently hydrogen, deuterium, -F (fluoro group), -Cl (chloro group), -Br (bromo group), -I (iodo group), cyano group, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, and substituted or unsubstituted selected from a C ₁ -C ₆₀ heteroaryl group;

a11 is selected from 1, 2 and 3;

Z ₁₁ and Z ₁₂ are each independently selected from hydrogen, deuterium, -F, a methyl group and an ethyl group;

b11 is selected from 1 and 2;

At least one substituent of the substituted C ₁ -C ₆₀ alkyl group, the substituted C ₁ -C ₆₀ alkoxy group, the substituted C ₆ -C ₆₀ aryl group, and the substituted C ₁ -C ₆₀ heteroaryl group is,

deuterium, -F, -Cl, -Br, -I, a C ₁ -C ₆₀ alkyl group and a C ₁ -C ₆₀ alkoxy group;

C substituted with at least one of deuterium, -F, -Cl, -Br, -I, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group and -Si(Q ₁₁ )(Q ₁₂ )(Q ₁₃ ) ₁ -C ₆₀ alkyl group and C ₁ -C ₆₀ alkoxy group;

C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group and C ₁ -C ₆₀ heteroaryl group;

Deuterium, -F, -Cl, -Br, -I, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C C _{6 -C 60 aryl group, C 6 -C 60 aryloxy} group, substituted with at least one of ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, and —Si(Q ₂₁ )(Q ₂₂ )(Q ₂₃ ) , C ₆ -C ₆₀ arylthio group and C ₁ -C ₆₀ heteroaryl group; and

-Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ); is selected from;

Q ₁₁ to Q ₁₃ , Q ₂₁ to Q ₂₃ , and Q ₃₁ to Q ₃₃ are each independently selected from a C ₁ -C ₆₀ alkyl group and a C ₆ -C ₆₀ aryl group.

For example, in Formulas 1-1 to 1-8, at least one of R ₁₁ to R ₁₉ may be a cyano group, but is not limited thereto.

In another embodiment, the organometallic compound may be any one of the following compounds 1 to 14, but is not limited thereto:

The HOMO energy level, LUMO energy level, energy gap, S1 energy level, T1 energy level, T(dp*) (adiabatic condition) and T(dp*) spin density of some of the above compounds are density functional based on B3LYP Table 1 below shows the evaluation results using the Gaussian 09 program accompanied by molecular structure optimization by theory (DFT).

No. HOMO
LUMO
energy gap
S1
T1
(Vertical) T(dp*)
(Adiabatic) T(dp*)
spin density eV eV eV eV nm f ^* eV nm eV nm 7 -5.18 -1.27 1.67 3.38 367 0.0037 2.89 429 2.82 439 0.191 8 -5.72 -2.01 2.24 3.08 402 0.0258 2.86 433 2.82 440 0.241 9 -6.31 -2.66 1.96 3.04 408 0.0261 2.86 434 2.82 440 0.287 10 -4.66 -0.80 1.77 3.16 392 0.0051 2.84 436 2.89 428 0.150 11 -5.01 -1.22 2.34 3.29 377 0.1227 2.84 437 1.82 440 0.187 12 -4.51 -0.44 1.55 3.54 350 0.0147 2.96 418 2.87 432 0.174 13 -4.35 -0.33 1.98 3.49 355 0.0178 2.94 422 2.86 433 0.168 14 -4.74 -0.66 1.91 3.53 351 0.0206 2.98 416 2.89 429 0.172

*f is the oscillator strength.

The organometallic compound represented by Chemical Formula 1 includes both a partial structure having high hole transport property and a partial structure having high electron transport property, so that the charge balance in the light emitting layer may be balanced.

Since the organometallic compound represented by Formula 1 includes Ir, it forms an octahedral structure, the possibility of stacking may be low. Accordingly, the organometallic compound represented by Chemical Formula 1 may reduce a shift in the emission wavelength of an organic light emitting device including the same, and may improve stability.

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

a first electrode; a second electrode; and an organic layer including a light emitting layer interposed between the first electrode and the second electrode, wherein the organic layer may include at least one organometallic compound represented by Formula 1 above.

The organometallic compound represented by Formula 1 may be used as a dopant of an organic layer of an organic light emitting device, for example, a light emitting layer among the organic layers, but is not limited thereto.

The organic light emitting device may have a low driving voltage, high efficiency, high brightness, long lifespan, and high color purity by having an organic layer including the organometallic compound represented by Formula 1 above.

The organic light emitting device including the organometallic compound represented by Formula 1 may emit dark blue light.

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

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

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

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

For example, the first electrode is an anode, the second electrode is a cathode, and the organic layer is i) interposed between the first electrode and the light emitting layer, and is at least one of a hole injection layer, a hole transport layer, and an electron blocking layer. a hole transport region comprising one; and ii) an electron transport region interposed between the emission layer and the second electrode and including at least one of a hole blocking layer, an electron transport layer, and an electron injection layer.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

<Formula 201>

<Formula 202>

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

Phenylene, pentarenylene, indenylene, naphthylene, azulenylene, heptalenylene, acenaphthylene, fluorenylene, phenarenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylenylene , pyrenylene, chrysenylene, naphthacenylene, picenylene, perylenylene and pentacenylene; and

Deuterium, halogen atom, hydroxyl, cyano, nitro, amino amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, C ₁ -C ₆₀ alkoxy, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₃ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ Heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic phenylene, pentarenylene, indenylene, naphthylene, azulenylene, heptalenylene, acenaphthylene, fluorenylene, phenarenylene, phenanthrenylene, anthracenylene, substituted with at least one of a condensed heterocyclic group , fluoranthenylene, triphenylenylene, pyrenylene, chrysenylene, naphthacenylene, picenylene, perylenylene and pentacenylene; can be selected from

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

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

hydrogen, deuterium, halogen atom, hydroxyl, cyano, nitro, amino, amidino group, hydrazine, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₁₀ alkyl ( for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, etc.) and C ₁ -C ₁₀ alkoxy (eg, methoxy, ethoxy, propoxy, butoxy, pentoxy, etc.);

C ₁ -C substituted with one or more of deuterium, halogen atom, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof and phosphoric acid or salt thereof ₁₀ alkyl and C ₁ -C ₁₀ alkoxy;

phenyl, naphthyl, anthracenyl, fluorenyl and pyrenyl; and

deuterium, halogen atom, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₁₀ alkyl and C ₁ - phenyl, naphthyl, anthracenyl, fluorenyl and pyrenyl, substituted with one or more of C ₁₀ alkoxy; may be one, but is not limited thereto.

In Formula 201, R ₁₀₉ is phenyl, naphthyl, anthracenyl, biphenyl and pyridinyl; and deuterium, halogen atom, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₂₀ alkyl, and C phenyl, naphthyl, anthracenyl, biphenyl and pyridinyl, substituted with one or more of ₁ -C ₂₀ alkoxy; can be one of

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

<Formula 201A>

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

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

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

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

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

<Compound HT-D1> <F4-TCNQ>

The hole transport region may further include a buffer layer.

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

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

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

The host is at least one of the following TPBi, TBADN, ADN (also referred to as "DNA"), CBP, CDBP, TCP and 26DCzPpy (2,6-bis[3-(9H-carbazol-9-yl)phenyl)pyridine) may include:

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

<Formula 301>

In Formula 301, Ar ₁₁₁ and Ar ₁₁₂ are each independently selected from phenylene, naphthylene, phenanthrenylene and pyrenylene; and phenylene, naphthylene, phenanthrenylene, fluorenyl, and pyrenylene substituted with one or more of phenyl, naphthyl, and anthracenyl; can be selected from

In Formula 301, Ar ₁₁₃ to Ar ₁₁₆ may be each independently selected from C ₁ -C ₁₀ alkyl; phenyl, naphthyl, phenanthrenyl and pyrenyl; and phenyl, naphthyl, phenanthrenyl, fluorenyl, and pyrenyl substituted with one or more of phenyl, naphthyl and anthracenyl; can be selected from

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

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

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

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

deuterium, halogen atom, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C ₁ -C ₆₀ alkyl, C ₂ - phenyl, naphthyl, substituted with one or more of C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl, C ₁ -C ₆₀ alkoxy, phenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl and fluorenyl, anthracenyl, pyrenyl, phenanthrenyl and fluorenyl; and

; 중에서 선택될 수 있으나, 이에 한정되는 것은 아니다.

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

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

<Formula 302>

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

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

In Formula 302, k and l may each independently be an integer 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 the following compounds H1 to H42, but are not limited thereto.

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

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

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

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

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

For example, the electron transport region may have a structure of a hole blocking layer/electron transport layer/electron injection layer or an electron transport layer/electron injection layer, but is not limited thereto. The electron transport layer may have a single layer or a multilayer 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 BCP and Bphen, but is not limited thereto.

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

The electron transport layer further includes at least one of BCP, Bphen, and Alq ₃ , Balq, TAZ, NTAZ, and TnPyPB (1,3,5-tri[(3-pyridyl)-phen-3-yl]benzene) can do.

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

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

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

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

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

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

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

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

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

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

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

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

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

[Example]

Synthesis Example 1: Synthesis of compound 12

1) Synthesis of ligand 12

1 mmol (0.167 g) of carbazole, 2 mmol (0.322 g) of 2-bromo-N-methyl-imidazole, 40 mol% (0.046 g) of benzotriazole, 20 mol% (0.038 g) of copper iodide and 1.4 mmol ( 0.157 g) of potassium tert-butoxide were stirred in 6 mL of dimethyl sulfoxide at 135 ^o C for 48 hours. The reaction mixture was cooled, then water was added and extracted with ethyl acetate. The ethyl acetate extract was dried over magnesium sulfate, and then distilled under reduced pressure. The obtained brown solid was purified by silica column chromatography (using ethyl acetate and hexane). Finally, ligand 12 was obtained as a colorless solid. The yield of the ligand 12 was 40%. Ligand 12 was confirmed by ¹ H NMR and GCMS, and the results are shown in FIGS. 2 and 3, respectively.

2) Synthesis of compound 12

1 mmol (0.352 g) of IrCl ₃ ·3H ₂ O, 2.5 mmol (0.615 g) of Ligand 12 was refluxed in 90 mL of 2-ethoxyethanol and 3 mL of water for 24 hours. The reaction mixture was cooled, water was added thereto, and then filtered. The brown residue was washed several times with water and then dried in a vacuum at 50 ^° C to obtain a dimer. The dimer was reacted with 4 folds of ligand 12 in the presence of 2.5 folds of silver triflate in 2-ethoxyethanol at 150 ^o C for 6 hours. The solvent was distilled under reduced pressure, and the obtained residue was purified by silica column chromatography (using ethyl acetate and hexane) to obtain compound 12. The obtained compound 12 showed a 929 M/Z peak by MALDI-TOF analysis. Compound 12 showed blue light emission at 427 nm, and the results are shown in FIG. 4 .

Synthesis Example 2: Synthesis of compound 7

Ligand 7 was synthesized using the same method as that of Ligand 12, except that 3-cyano-carbazole was used instead of carbazole. Ligand 7 was confirmed by ¹ H NMR and GCMS, and the results are shown in FIGS. 5 and 6, respectively.

2) Synthesis of compound 7

Compound 7 was synthesized in the same manner as in the synthesis of compound 12, except that ligand 7 was used instead of ligand 12. The obtained compound 7 showed a 1006 M/Z peak by MALDI-TOF analysis.

Synthesis Example 3: Synthesis of compound 8

1) Synthesis of Ligand 8

Ligand 12 was synthesized using the same procedure as in the synthesis of ligand 12, except that α-carboline was used instead of carbazole and 3-bromo-benzonitrile was used instead of 2-bromo-N-methyl-imidazole. 8 was synthesized. Ligand 8 was confirmed by ¹ H NMR and GCMS, and the results are shown in FIGS. 7 and 8, respectively.

2) Synthesis of compound 8

Compound 8 was synthesized in the same manner as in the synthesis of compound 12, except that ligand 8 was used instead of ligand 12. The obtained compound 8 showed a 997 M/Z peak by MALDI-TOF analysis. Compound 8 showed an emission peak at 464 nm.

Example

A transparent electrode substrate coated with indium tin oxide (ITO) was washed, and the ITO was patterned with a photosensitive resin and an etchant to form an ITO pattern. Then, the ITO-patterned transparent electrode substrate was washed again. The ITO-patterned transparent electrode substrate was ultrasonically cleaned with isopropyl alcohol, washed with distilled water, and then subjected to UV-ozone treatment and then used for device fabrication.

The hole transport layer, the light emitting layer, and the electron transport layer were vacuum-deposited under 10 ^-7 torr conditions. Then, LiF and Al were vacuum-deposited to form an electrode. TmPyPB was used for the electron transport layer, TAPC was used for the hole transport layer, and the light emitting layer was used by doping compound 8 in 26DCzPPy at a concentration of 6%.

evaluation example

Current density-driving voltage (J-V) and luminance-driving voltage (L-V) characteristics were measured for the organic light emitting diodes manufactured in Examples above using Keithley 2635A and Minolta CS-100A luminance meters. With respect to the organic light emitting device manufactured in the above example, EL (electroluminescence) spectrum and CIE color coordinates were measured using a Minolta CS-100A luminance meter. The results are shown in Table 2 below.

EL
λmax (nm) CIE
(x, y) at 10 mA maximum efficiency
ηL (cd/A) drive voltage
(V) compound 8 467 0.17, 0.29 22.5 4.1

Referring to Table 2, it can be seen that the organic light emitting device including the compound according to an embodiment of the present invention exhibits high luminance, high efficiency, and low driving voltage.

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

Claims (20)

An organometallic compound represented by the following formula (1):
<Formula 1>
Ir(L ₁ ) ₃
<Formula 2>

In Formulas 1 and 2,
L ₁ is a first ligand represented by Formula 2;
A ₁₁ is Y ₁₁ containing as a ring member, benzene, naphthalene, anthracene, phenanthrene, pyrrole, imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, quinoline , isoquinoline, benzoquinoline, quinoxaline, quinazoline, benzoimidazole, benzoxazole, isobenzooxazole, triazole, tetrazole, oxadiazole, triazine, pyridoindole, pyridofuran and pyridothiophene is selected from;
Y ₁₁ and Y ₁₂ are each independently selected from a carbon atom (C) and a nitrogen atom (N);
X ₁₃ is N or CR ₁₃ , X ₁₄ is N or CR ₁₄ , X ₁₅ is N or CR ₁₅ ; X ₁₆ is N or CR ₁₆ ; X ₁₇ is N or CR ₁₇ ; X ₁₈ is N or CR ₁₈ ; X ₁₉ is N or CR ₁₉ ;
R ₁₁ To R ₁₉ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl a group and a C ₁ -C ₆₀ heteroaryl group;
Deuterium, -F, -Cl, -Br, -I, methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, sec-butyl group, tert-butyl group, methoxy group , an ethoxy group, a tert-butoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, and -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ) substituted with at least one of, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group and C ₁ -C ₆₀ heteroaryl group; and
At least one of a phenyl group, a naphthyl group, a pyridinyl group and a pyrimidinyl group substituted with at least one of deuterium, -F, -Cl, -Br, -I, a methyl group, an ethyl group, a phenyl group, a naphthyl group, a pyridinyl group and a pyrimidinyl group one substituted, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group and C ₁ -C ₆₀ heteroaryl group; is selected from;
Q ₃₁ to Q ₃₃ are each independently selected from a methyl group, an ethyl group, an iso-propyl group, a tert-butyl group, a phenyl group, and a naphthyl group;
a11 is selected from 1, 2, 3, 4, 5 and 6;
R ₁₂ and R ₁₃ are optionally, a single bond,

and

are bonded to each other through a divalent linking group represented by any one selected from;
Z ₁₁ and Z ₁₂ are each independently selected from hydrogen, deuterium, -F, a methyl group and an ethyl group;
* and *' are, independently of each other, binding sites with neighboring atoms. According to claim 1,
At least one of R ₁₁ to R ₁₉ is a cyano group, an organometallic compound. According to claim 1,
A ₁₁ is an organometallic compound selected from benzene, naphthalene, pyrrole, imidazole and pyrazole. According to claim 1,
Y ₁₁ and Y ₁₂ are different from each other, an organometallic compound. According to claim 1,
R ₁₁ to R ₁₉ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso- butyl group, sec-butyl group, tert-butyl group, phenyl group, naphthyl group, pyridinyl group and pyrimidinyl group;
a phenyl group and a naphthyl group substituted with at least one of deuterium, -F, a methyl group, an ethyl group, an iso-propyl group, a tert-butyl group, and -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ); and
Deuterium, -F, -Cl, -Br, -I, a methyl group, an ethyl group, a phenyl group, a naphthyl group, at least one of a pyridinyl group and a pyrimidinyl group substituted with at least one of a phenyl group and a naphthyl group substituted with at least one of a phenyl group and a naphthyl group ; is selected from;
Q ₃₁ to Q ₃₃ are each independently selected from a methyl group and a phenyl group; selected from, organometallic compounds. According to claim 1,
R ₁₁ to R ₁₉ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a cyano group, and any one group selected from the following Chemical Formulas 6-1 to 6-13, an organometallic compound:

In Formulas 6-1 to 6-13,
* is a binding site with a neighboring atom. According to claim 1,
An organometallic compound wherein the first ligand is represented by the following formula (2A):
<Formula 2A>

In Formula 2A,
A ₁₁ is Y ₁₁ containing as a ring member, benzene, naphthalene, anthracene, phenanthrene, pyrrole, imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, quinoline , isoquinoline, benzoquinoline, quinoxaline, quinazoline, benzoimidazole, benzoxazole, isobenzooxazole, triazole, tetrazole, oxadiazole, triazine, pyridoindole, pyridofuran and pyridothiophene is selected from;
Y ₁₁ and Y ₁₂ are each independently selected from a carbon atom (C) and a nitrogen atom (N);
X ₁₃ is N or CR ₁₃ , X ₁₄ is N or CR ₁₄ , X ₁₅ is N or CR ₁₅ ;
R ₁₁ To R ₁₉ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl a group and a C ₁ -C ₆₀ heteroaryl group;
Deuterium, -F, -Cl, -Br, -I, methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, sec-butyl group, tert-butyl group, methoxy group , an ethoxy group, a tert-butoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group and -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ) substituted with at least one of, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group and C ₁ -C ₆₀ heteroaryl group; and
At least one of a phenyl group, a naphthyl group, a pyridinyl group and a pyrimidinyl group substituted with at least one of deuterium, -F, -Cl, -Br, -I, a methyl group, an ethyl group, a phenyl group, a naphthyl group, a pyridinyl group and a pyrimidinyl group one substituted, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group and C ₁ -C ₆₀ heteroaryl group; is selected from;
Q ₃₁ to Q ₃₃ are each independently selected from a methyl group, an ethyl group, an iso-propyl group, a tert-butyl group, a phenyl group, and a naphthyl group;
a11 is selected from 1, 2, 3, 4, 5 and 6;
R ₁₂ and R ₁₃ are optionally, a single bond,

and

are bonded to each other through a divalent linking group represented by any one selected from;
Z ₁₁ and Z ₁₂ are each independently selected from hydrogen, deuterium, -F, a methyl group and an ethyl group;
* and *' are, independently of each other, binding sites with neighboring atoms. 8. The method of claim 7,
X ₁₅ is CR ₁₅ ;
Any one of R ₁₁ and R ₁₅ is a cyano group, an organometallic compound. According to claim 1,
An organometallic compound, wherein the first ligand is represented by any one of the following Chemical Formulas 2-1 to 2-10:
<Formula 2-1><Formula2-2>

<Formula 2-3><Formula2-4>

<Formula 2-5><Formula2-6>

<Formula 2-7><Formula2-8>

<Formula 2-9><Formula2-10>

In Formulas 2-1 to 2-10,
R ₁₁ To R ₁₉ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl a group and a C ₁ -C ₆₀ heteroaryl group;
Deuterium, -F, -Cl, -Br, -I, methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, sec-butyl group, tert-butyl group, methoxy group , an ethoxy group, a tert-butoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, and -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ) substituted with at least one of, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group and C ₁ -C ₆₀ heteroaryl group; and
At least one of a phenyl group, a naphthyl group, a pyridinyl group and a pyrimidinyl group substituted with at least one of deuterium, -F, -Cl, -Br, -I, a methyl group, an ethyl group, a phenyl group, a naphthyl group, a pyridinyl group and a pyrimidinyl group one substituted, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group and C ₁ -C ₆₀ heteroaryl group; is selected from;
a11 is selected from 1, 2, 3, 4, 5 and 6;
Z ₁₁ and Z ₁₂ are each independently selected from hydrogen, deuterium, -F, a methyl group and an ethyl group;
b11 is selected from 1 and 2;
* and *' are, independently of each other, binding sites with neighboring atoms. 10. The method of claim 9,
At least one of R ₁₁ to R ₁₉ is a cyano group, an organometallic compound. According to claim 1,
An organometallic compound represented by any one of the following Chemical Formulas 1-1 to 1-7.
<Formula 1-1><Formula1-2>

<Formula 1-3><Formula1-4>

<Formula 1-5><Formula1-6>

<Formula 1-7>

In Formulas 1-1 to 1-7,
R ₁₁ To R ₁₉ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, cyano group, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl a group and a C ₁ -C ₆₀ heteroaryl group;
Deuterium, -F, -Cl, -Br, -I, methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, sec-butyl group, tert-butyl group, methoxy group , an ethoxy group, a tert-butoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, and -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ) substituted with at least one of, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group and C ₁ -C ₆₀ heteroaryl group; and
At least one of a phenyl group, a naphthyl group, a pyridinyl group and a pyrimidinyl group substituted with at least one of deuterium, -F, -Cl, -Br, -I, a methyl group, an ethyl group, a phenyl group, a naphthyl group, a pyridinyl group and a pyrimidinyl group one substituted, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group and C ₁ -C ₆₀ heteroaryl group; is selected from;
Q ₃₁ to Q ₃₃ are each independently selected from a methyl group, an ethyl group, an iso-propyl group, a tert-butyl group, a phenyl group, and a naphthyl group;
a11 is selected from 1, 2 and 3;
Z ₁₁ and Z ₁₂ are each independently selected from hydrogen, deuterium, -F, a methyl group and an ethyl group;
b11 is selected from 1 and 2. 12. The method of claim 11,
At least one of R ₁₁ to R ₁₉ is a cyano group, an organometallic compound. According to claim 1,
Any one of the following compounds 1 to 9 and 11 to 14, an organometallic compound:

a first electrode; a second electrode; and an organic layer interposed between the first electrode and the second electrode and including a light emitting layer, wherein the organic layer comprises at least one organometallic compound according to any one of claims 1 to 13. 15. The method of claim 14,
The organometallic compound is included in the light emitting layer, an organic light emitting device. delete delete delete delete delete

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