KR20230087388A - Organometallic compound, organic light emitting device including the same and electronic apparatus comprising organic light emitting device - Google Patents

Abstract

다른 치환기에 대한 설명은 발명의 설명을 참조한다.Disclosed are an organometallic compound represented by Formula 1 below, an organic light emitting device including the organometallic compound, and an electronic device including the organic light emitting device:
<Formula 1>
M ₁ (Ln ₁ ) _n1 (Ln ₂ ) _n2
Ln ₁ is a ligand represented by Formula 1A below;
Ln ₂ is a ligand represented by Formula 1B below;
<Formula 1A><Formula1B>

For a description of other substituents, see the description of the invention.

Description

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

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

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

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

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

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

<Formula 1>

M ₁ (Ln ₁ ) _n1 (Ln ₂ ) _n2

<Formula 1A> <Formula 1B>

<Formula 41>

In Formula 1,

M ₁ is a transition metal;

Ln ₁ is a ligand represented by Formula 1A below;

Ln ₂ is a ligand represented by Formula 1B below;

n1 is 1 or 2;

n2 is 1 or 2;

Among Formulas 1A, 1B and 41,

CY ₁ and CY ₂ are each independently a C ₅ -C ₃₀ carbocyclic group or a C ₁ -C ₃₀ heterocyclic group;

CY ₄₁ is a group represented by Formula 41;

X ₁ is C or N, X ₂ is C or N,

X ₃₁ is C(R ₃₁ ) or N, X ₃₂ is C(R ₃₂ ) or N;

X ₄₁ is C(R ₄₁ ) or N, X ₄₂ is C(R ₄₂ ) or N;

Y ₄ is O, S, Se or C(R ₁ )(R ₂ );

Y ₄₁ is O, S, Se, C(R ₃ )(R ₄ ), N(R ₃ ) or B(R ₃ );

Y ₄₂ is O, S, Se, C(R ₅ )(R ₆ ), N(R ₅ ) or B(R ₅ );

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

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

R ₁ to R ₇ , R ₁₀ , R ₂₀ , R ₃₁ , R ₃₂ and R ₄₀ to R ₄₂ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , hydroxy A real group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or its salt thereof, a sulfonic acid group or its salt thereof, a phosphoric acid group or its 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, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cyclo group Alkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted A C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, A substituted or unsubstituted C ₁ -C ₆₀ heteroaryloxy group, a substituted or unsubstituted C ₁ -C ₆₀ heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted 1 is a non-aromatic heterocondensed polycyclic group, -Si(Q ₁ )(Q ₂ )(Q ₃ ), -Ge(Q ₁ )(Q ₂ )(Q ₃ ), -N(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ) or -P(=0)(Q ₈ )(Q ₉ );

Two or more adjacent R ₁₀ may be optionally bonded to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group; ,

Two or more adjacent R ₂₀ may be optionally bonded to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group; ,

Two or more adjacent R ₄₀ may be optionally bonded to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group; ,

Two or more adjacent R ₁ to R ₇ , R ₁₀ , R ₂₀ , R ₃₁ , R ₃₂ and R ₄₀ to R ₄₂ are optionally bonded to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group, or may form a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group;

b7 is 1, 2, 3, 4, 5, 6, 7 or 8;

b10, b20 and b30 are each independently 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;

b40 is 1, 2, 3, 4, 5 or 6;

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

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

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , a hydroxyl group, a cyano group, a nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt thereof, sulfonic acid group or its salt thereof, phosphoric acid group or its salt thereof, C ₁ -C ₆₀ Alkyl group, C ₂ -C ₆₀ Alkenyl group, C ₂ -C ₆₀ an alkynyl group or a C ₁ -C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , a hydroxyl group, a cyano group, a nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt thereof, sulfonic acid group or its salt thereof, phosphoric acid group or its salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ - C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group , C ₁ -C ₆₀ heteroaryloxy group, C ₁ -C ₆₀ heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q ₁₁ )(Q ₁₂ ) (Q ₁₃ ), -Ge(Q ₁₁ )(Q ₁₂ )(Q ₁₃ ), -N(Q ₁₄ )(Q ₁₅ ), -B(Q ₁₆ )(Q ₁₇ ), -P(=O)(Q _a C ₁ -C ₆₀ alkyl group, a _{C 2 -C 60 alkenyl group, a C 2} -C ₆₀ alkynyl group, or a C ₁ -C ₆₀ alkoxy group, substituted with ₁₈ )(Q ₁₉ ) or any combination 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 aryl an oxy group, a C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a C ₁ -C ₆₀ heteroaryloxy group, a C ₁ -C ₆₀ heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, or monovalent non-aromatic condensed heteropolycyclic groups;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , a hydroxyl group, a cyano group, a nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt thereof, sulfonic acid group or its salt thereof, phosphoric acid group or its salt thereof, C ₁ -C ₆₀ Alkyl group, C ₂ -C ₆₀ Alkenyl group, C ₂ -C ₆₀ Alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ - C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, C ₁ -C ₆₀ heteroaryloxy group, C ₁ -C ₆₀ heteroaryl group Ogi, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, -Si(Q ₂₁ )(Q ₂₂ )(Q ₂₃ ), -Ge(Q ₂₁ )(Q ₂₂ )(Q ₂₃ ) , -N(Q ₂₄ )(Q ₂₅ ), -B(Q ₂₆ )(Q ₂₇ ), -P(=0)(Q ₂₈ )(Q ₂₉ ), or any combination 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, a C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed polycyclic group; or

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

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

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

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

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

The organometallic compound has excellent electrical properties and thermal stability. In particular, the organometallic compound has a high glass transition temperature, so crystallization can be prevented and electrical mobility can be improved. Accordingly, an electronic device employing the organometallic compound, for example, an organic light emitting device, has a low driving voltage, high efficiency, long lifespan, reduced roll-off ratio, and a relatively narrow half-width at half maximum (FWHM) of the emission peak of the EL spectrum. can have

Therefore, by using the organometallic compound, a high-quality organic light emitting device can be implemented. In addition, an electronic device including the organic light emitting device may be provided.

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

The organometallic compound may be represented by Formula 1 below:

<Formula 1>

M ₁ (Ln ₁ ) _n1 (Ln ₂ ) _n2

M ₁ in Formula 1 may be a transition metal.

For example, M ₁ may be a period 1 transition metal, a period 2 transition metal, or a period 3 transition metal.

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

According to one embodiment, M ₁ may be Ir, Pt, Os or Rh.

According to one embodiment, M ₁ can be Ir.

In Formula 1, n1 may be 1 or 2, and n2 may be 1, 2 or 3.

According to one embodiment, n1 + n2 may be 2 or 3.

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

According to one embodiment, M ₁ may be Pt, and n1 + n2 may be 2.

In Formula 1, Ln ₁ is a ligand represented by Formula 1A below.

<Formula 1A>

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

In Formula 1A, CY ₁ and CY ₂ are each independently a C ₅ -C ₃₀ carbocyclic group or a C ₁ -C ₃₀ heterocyclic group.

According to one embodiment, CY ₁ and CY ₂ are independently of each other, i) a first ring, ii) a second ring, iii) a condensed ring in which two or more first rings are condensed with each other, iv) two or more second rings A condensed ring condensed with each other or v) a condensed ring in which one or more first rings and one or more second rings are condensed with each other,

The first ring is a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a silol group, an indene group, a benzofuran group, a benzothiophene group, an indole group, a benzosilol group, an oxazole group, Isoxazole group, oxadiazole group, isoxadiazole group, oxatriazole group, isoxatriazole group, thiazole group, isothiazole group, thiadiazole group, isothiadiazole group, thiatriazole group, an isothiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azasilol group, a diazacylol group, or a triazacylol group;

The second ring is an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, and a pyridazine group. or a triazine group.

According to one embodiment, CY ₁ and CY ₂ are each independently selected from a cyclopentane group, a cyclohexane group, a cyclohexane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, a benzene group, a naphthalene group, an anthracene group, and a phenan. Trene group, triphenylene group, pyrene group, chrysene group, cyclopentadiene group, 1,2,3,4-tetrahydronaphthalene group, thiophene group, furan group, indole group, benzoborol group, benzophosphole group, indene group, benzosilol group, benzozermol group, benzothiophene group, benzoselenophene group, benzofuran group, carbazole group, dibenzoborol group, dibenzo Phosphole group, fluorene group, dibenzosilol group, dibenzozermol group, dibenzothiophene group, dibenzoselenophene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluorene-9 -On group, dibenzothiophene 5,5-dioxide group, azaindole group, azabenzoborol group, azabenzophosphole group, azaindene group, azabenzosilol group, azabenzozermol group, azabenzothiophene group , azabenzoselenophen group, azabenzofuran group, azacarbazole group, azadibenzobolol group, azadibenzophosphole group, azafluorene group, azadibenzosilol group, azadibenzolowmol group, azadibenzo Thiophene group, azadibenzoselenophene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluorene-9-one group, azadibenzothiophene 5,5-dioxide group , Pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, phenanthroline group, pyrrole group, pyrazole group, imidazole group, Triazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzoimidazole group, benzooxazole group, benzothiazole group, benzoxadiazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline (5,6,7,8-tetrahydroisoquinoline) group or 5,6,7,8-tetrahydroquinoline (5,6,7,8-tetrahydroquinoline) group.

According to one embodiment, CY ₁ and CY ₂ are each independently a benzene group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a tree Azine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, phenanthroline group, benzofuran group, benzothiophene group, fluorene group, carbazole group, dibenzofuran group, dibenzothiophene group , a dibenzosilol group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, or an azadibenzosilol group.

According to one embodiment, CY ₁ may be a pyridine group, a pyrimidine group, a pyrazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, or a quinazoline group.

According to one embodiment, CY ₂ is benzene group, naphthalene group, pyridine group, pyrimidine group, pyrazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, fluorene group, carbazole group, a dibenzofuran group, a dibenzothiophene group or a dibenzosilol group.

According to one embodiment, Ln ₁ may be represented by Formula 1A-1:

<Formula 1A-1>

In Formula 1A-1,

X ₁₁ is C(R ₁₁ ) or N, X ₁₂ is C(R ₁₂ ) or N, X ₁₃ is C(R ₁₃ ) or N, X ₁₄ is C(R ₁₄ ) or N,

X ₂₁ is C(R ₂₁ ) or N, X ₂₂ is C(R ₂₂ ) or N, X ₂₃ is C(R ₂₃ ) or N, X ₂₄ is C(R ₂₄ ) or N,

R ₁₁ to R ₁₄ are independently of each other, see the description for R ₁₀ ,

R ₂₁ to R ₂₄ are independently of each other, see the description for R ₂₀ ,

* and *' are binding sites with neighboring atoms.

According to one embodiment, Ln ₁ may be represented by any one of Formulas 1A-9 to 1A-26:

In Formulas 1A-9 to 1A-26,

R ₁₀ and R ₂₀ each refer to the description set forth herein;

b51 and b54 are each independently 1 or 2;

b53 and b55 are each independently 1, 2 or 3;

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

* and *' are binding sites with neighboring atoms.

모이어티가 하기 화학식 1-1 내지 1-16 중 어느 하나로 표시될 수 있다:According to one embodiment, in Formula 1A

The moiety can be represented by any one of Formulas 1-1 to 1-16:

In Formulas 1-1 to 1-16,

R ₁₁ to R ₁₄ may be independently of each other, and the description of R ₁₀ may be referred to.

According to one embodiment, each of R ₁₁ to R ₁₄ may not be hydrogen.

For example, R ₁₁ to R ₁₄ are each independently deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, 2-methylbutyl group , sec-pentyl group, tert-pentyl group, neo-pentyl group, 3-pentyl group, 3-methyl-2-butyl group, phenyl group, biphenyl group, naphthyl group, -Si(Q ₁ )(Q ₂ )(Q ₃ ) or -Ge(Q ₁ )(Q ₂ )(Q ₃ ),

Q ₁ to Q ₃ are independently of each other,

-CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CH 2 CH ₃ , -CH ₂ CD ₃ , -CH ₂ CD ₂ H, -CH _{2 CDH 2} , -CHDCH ₃ , -CHDCD ₂ H , -CHDCDH ₂ , -CHDCD ₃ , -CD ₂ CD ₃ , -CD ₂ CD ₂ H or -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 or naph til group; or

Substituted with heavy hydrogen, a C ₁ -C ₁₀ alkyl group, a phenyl group, or any combination thereof, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n- It may be a pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group or naphthyl group.

In Chemical Formulas 1-1 to 1-16, * and *' are binding sites with neighboring atoms, respectively.

모이어티가 하기 화학식 2-1 내지 2-16 중 어느 하나로 표시될 수 있다:According to one embodiment, in Formula 1A

The moiety can be represented by any one of Formulas 2-1 to 2-16:

In Chemical Formulas 2-1 to 2-16,

R ₂₁ to R ₂₄ may be independently of each other, and the description of R ₂₀ may be referred to.

According to one embodiment, each of R ₂₁ to R ₂₄ may not be hydrogen.

For example, R ₂₁ to R ₂₄ are independently of each other, deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, 2-methylbutyl group , sec-pentyl group, tert-pentyl group, neo-pentyl group, 3-pentyl group, 3-methyl-2-butyl group, phenyl group, biphenyl group, naphthyl group, -Si(Q ₁ )(Q ₂ )(Q ₃ ) or -Ge(Q ₁ )(Q ₂ )(Q ₃ ),

Q ₁ to Q ₃ are independently of each other,

-CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CH 2 CH ₃ , -CH ₂ CD ₃ , -CH ₂ CD ₂ H, -CH _{2 CDH 2} , -CHDCH ₃ , -CHDCD ₂ H , -CHDCDH ₂ , -CHDCD ₃ , -CD ₂ CD ₃ , -CD ₂ CD ₂ H or -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 or naph til group; or

Substituted with heavy hydrogen, a C ₁ -C ₁₀ alkyl group, a phenyl group, or any combination thereof, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n- It may be a pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group or naphthyl group.

In Formulas 2-1 to 2-16, *' and *" respectively represent binding sites with neighboring atoms.

In Formula 1, Ln ₂ is a ligand represented by Formula 1B below.

<Formula 1B>

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

In Formula 1B, X ₃₁ is C(R ₃₁ ) or N, and X ₃₂ is C(R ₃₂ ) or N.

According to one embodiment, X ₃₁ is C(R ₃₁ ), X ₃₂ is C(R ₃₂ ), R ₃₁ and R ₃₂ are optionally bonded to each other, and R ₃₀ is substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a C ₁ -C ₃₀ heterocyclic group unsubstituted or substituted with R ₃₀ , and for description of R ₃₀ , refer to R ₃₁ in claim 1 .

In Formula 1B, X ₄₁ is C(R ₄₁ ) or N, and X ₄₂ is C(R ₄₂ ) or N.

In Formula 1B, CY ₄₁ is a group represented by Formula 41.

<Formula 41>

In Formula 41, Y ₄₁ is O, S, Se, C(R ₃ )(R ₄ ), N(R ₃ ), or B(R ₃ ).

According to one embodiment, Y ₄₁ may be O, S or C(R ₃ )(R ₄ ).

In Formula 41, Y ₄₂ is O, S, Se, C(R ₅ )(R ₆ ), N(R ₅ ), or B(R ₅ ).

According to one embodiment, Y ₄₂ may be O, S or C(R ₅ )(R ₆ ).

According to one embodiment, Ln ₂ may be represented by any one of Formulas 1B-1 to 1B-3:

<Formula 1B-1>

<Formula 1B-2>

<Formula 1B-3>

In Formulas 1B-1 to 1B-3

For descriptions of X ₃₁ , X ₃₂ , L ₁ , a1, R ₇ , b7, Y ₄ , Y ₄₁ , Y ₄₂ , R ₃₁ to R ₃₄ and R ₄₁ to R ₄₈ , refer to those described herein,

R ₄₁ to R ₄₈ are independently of each other, see the description for R ₄₀ ;

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

According to an embodiment, in Formula 1B may be represented by Formula 3-1 or 3-2:

In Chemical Formulas 3-1 and 3-2,

X ₃₃ is C(R ₃₃ ) or N, X ₃₄ is C(R ₃₄ ) or N, X ₃₅ is C(R ₃₅ ) or N, X ₃₆ is C(R ₃₆ ) or N,

R ₃₃ to R ₃₆ are independently of each other, see the description for R ₃₁ ,

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

In Formula 1B, L ₁ is a single bond; A substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group; or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group;

According to one embodiment, L ₁ is a single bond, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ Cycloalkenylene group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted or unsubstituted C ₆ -C ₆₀ arylene group, substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group, substituted Alternatively, it may be an unsubstituted divalent non-aromatic condensed polycyclic group or a substituted or unsubstituted divalent non-aromatic condensed polycyclic group.

According to one embodiment, L ₁ is a single bond, a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an acenaphthylene group, a fluorenylene group, a phenarenylene group, a phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrycenylene group, naphthacenylene group, picenylene group, perylenylene group and pentacenylene group; and

Heavy hydrogen, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt thereof, sulfonic acid group or its salt thereof, phosphoric acid group or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a C ₃ -C ₁₀ cycloalke Nyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ - A phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, a C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocondensed polycyclic group, or any combination thereof Zulenylene group, heptalenylene group, acenaphthylene group, fluorenylene group, phenarenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, It may be a naphthacenylene group, a picenylene group, a perylene group or a pentacenylene group.

In Formula 1B, a1 may be 1, 2, 3, 4, or 5.

According to one embodiment, a1 may be 1, 2 or 3.

According to one embodiment, a1 may be 1 or 2.

According to one embodiment, a1 may be 1.

In Formulas 1A and 1B, R ₁ to R ₇ , R ₁₀ , R ₂₀ , R ₃₁ , R ₃₂ and R ₄₀ to R ₄₂ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I , SF ₅ , a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkenyl group , a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ - A C ₆₀ heteroaryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryloxy group, a substituted or unsubstituted C ₁ -C ₆₀ heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, A substituted or unsubstituted monovalent non-aromatic polycyclic group, -Si(Q ₁ )(Q ₂ )(Q ₃ ), -Ge(Q ₁ )(Q ₂ )(Q ₃ ), -N(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ) or -P(=0)(Q ₈ )(Q ₉ ).

In Formula 1B, b7 is 1, 2, 3, 4, 5, 6, 7 or 8.

According to one embodiment, b7 may be 1, 2, 3, 4 or 5.

According to one embodiment, b7 may be 1, 2 or 3.

In Formula 1A, b10 and b20 may be each independently 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

According to one embodiment, b10 and b20 may be 1, 2, 3, 4, 5, 6, 7, or 8 independently of each other.

According to one embodiment, b10 and b20 may be 1, 2, 3, or 4 independently of each other.

According to one embodiment, b10 and b20 may be 1 or 2 independently of each other.

According to one embodiment, b10 and b20 may be 1 independently of each other.

In Formula 1B, b40 is 1, 2, 3, 4, 5 or 6.

According to one embodiment, b40 may be 1, 2, 3 or 4.

According to one embodiment, b40 may be 1 or 2.

According to one embodiment, R ₁ to R ₇ , R ₁₀ , R ₂₀ , R ₃₁ , R ₃₂ and R ₄₀ to R ₄₂ are each independently hydrogen, 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, carboxyl group an acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, -SF ₅ , a C ₁ -C ₂₀ alkyl group, or a C ₁ -C ₂₀ alkoxy group;

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

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

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , a hydroxyl group, a cyano group, a nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt thereof, sulfonic acid group or its salt thereof, phosphoric acid group or its salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, cyclopentyl group, cyclo Hexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, naphthyl group, Fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group , Isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, iso Quinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzooxa Zolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazophy A cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, norbornene, substituted with a ridinyl group, an imidazopyrimidinyl group, or any combination thereof Nyl 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, cryo Senyl 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, pyr Dajinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthroly Nyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzooxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, di A benzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group or an imidazopyrimidinyl group; or

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

According to one embodiment, R ₁ to R ₇ , R ₁₀ , R ₂₀ , R ₃₁ , R ₃₂ and R ₄₀ to R ₄₂ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , C ₁ -C ₆₀ Alkyl group, C ₂ -C ₆₀ Alkenyl group, C ₂ -C ₆₀ Alkynyl group or C ₁ -C ₆₀ alkoxy group; or

It may be a group represented by any one of Formulas 9-1 to 9-67, 9-201 to 9-244, 10-1 to 10-154, and 10-201 to 10-350:

In Formulas 9-1 to 9-67, 9-201 to 9-244, 10-1 to 10-154, and 10-201 to 10-350, * is a binding site with a neighboring atom, Ph is a phenyl group, TMS is a trimethylsilyl group, and TMG is a trimethylgermyl group.

two or more of a plurality of R ₁₀ in Formulas 1A and 1B; at least two of a plurality of R ₂₀ ; or R ₁ to R ₇ , R ₁₀ , R ₂₀ , R ₃₁ , R ₃₂ , and R ₄₀ to R ₄₂ , two or more adjacent; 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.

According to one embodiment, two or more of a plurality of R ₁₀ ; at least two of a plurality of R ₂₀ ; Or two or more neighboring R ₁ to R ₇ , R ₁₀ , R ₂₀ , R ₃₁ , R ₃₂ and R ₄₀ to R ₄₂ ; are optionally bonded to each other through a single bond, double bond or a first linking group, at least A C ₅ -C ₃₀ carbocyclic group optionally substituted with one R _10a or a C 1 -C 30 heterocyclic group optionally substituted with at least one R _10a (eg, a C ₁ -C ₃₀ heterocyclic group optionally substituted with at least one R _10a substituted or unsubstituted, fluorene group, xanthene group, acridine group, etc.) may be formed. The description of R _10a refers to the description of R ₁₀ in this specification.

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

According to one embodiment, Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ are independently of each other,

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

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 or naph til group; or

Substituted with heavy hydrogen, a C ₁ -C ₁₀ alkyl group, a phenyl group, or any combination thereof, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n- It may be a pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, or a naphthyl group.

According to one embodiment, the organometallic compound may be a compound represented by any one of Formulas 30-1 to 30-6:

<Formula 30-1>

<Formula 30-2>

<Formula 30-3>

<Formula 30-4>

<Formula 30-5>

<Formula 30-6>

In Formulas 30-1 to 30-6,

For descriptions of M ₁ , n1, n2, X ₃₁ , X ₃₂ , L ₁ , a ₁ , R ₇ , b7, Y ₁ , Y ₄₁ , Y ₄₂ and R ₄₁ to R ₄₈ , refer to those described herein,

X ₃₃ is C(R ₃₃ ) or N, X ₃₄ is C(R ₃₄ ) or N, X ₃₅ is C(R ₃₅ ) or N, X ₃₆ is C(R ₃₆ ) or N,

R ₁₁ to R ₁₄ are independently of each other, see the description for R ₁₀ ,

R ₂₁ to R ₂₄ are independently of each other, see the description for R ₂₀ ,

R ₃₃ to R ₃₆ are independently of each other, see the description for R ₃₁ ,

R ₄₁ to R ₄₈ are independently of each other, see the description for R ₄₀ .

According to one embodiment, the "C ₅ -C ₃₀ carbocyclic group optionally substituted with at least one R _10a or C ₁ -C ₃₀ heterocyclic group optionally substituted with at least one R _10a " For example, a benzene group, a naphthalene group, a cyclopentane group, a cyclopentadiene group, a cyclohexane group, a cycloheptane group, a bicyclo[2.2.1]heptane, a furan group, unsubstituted or substituted with at least one R _10a . , a thiophene group, a pyrrole group, a silol group, an indene group, a benzofuran group, a benzothiophene group, an indole group, or a benzosilol group. The description of R _10a refers to the description of R ₁₀ in this specification. Descriptions of the C ₅ -C ₃₀ carbocyclic group and the C ₁ -C ₃₀ heterocyclic group are referred to as described herein, respectively.

According to one embodiment, at least one of R ₁ to R ₇ , b10 R ₁₀ , b20 R ₂₀ and b40 R ₄₀ , R ₄₁ and R ₄₂ is unsubstituted or substituted with deuterium, a methyl group, an ethyl group, an n- Propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, 2-methylbutyl group, sec-pentyl group, tert-pentyl group , neo-pentyl group, 3-pentyl group, 3-methyl-2-butyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, phenyl group, biphenyl group, C It may be _{a 1} -C ₂₀ alkylphenyl group, a naphthyl group, -Si(Q ₁ )(Q ₂ )(Q ₃ ) or -Ge(Q ₁ )(Q ₂ )(Q ₃ ).

According to one embodiment, the organometallic compound may be any one of the following compounds 1 to 40:

.

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

The organometallic compound represented by Chemical Formula 1 satisfies the structure of Chemical Formula 1 described above and includes a structure in which CY ₄₁ is condensed with a ligand represented by Chemical Formula 1B. Due to this structure, the organometallic compound represented by Chemical Formula 1 has excellent light emitting properties, and in particular, it may have properties suitable for use as a light emitting material of high color purity by controlling the light emitting wavelength range.

In addition, since the organometallic compound represented by Chemical Formula 1 has excellent electrical mobility, an electronic device including the organometallic compound, for example, an organic light emitting device, can exhibit a low driving voltage, high efficiency and long lifespan, and a roll-off phenomenon. this may be reduced.

In addition, the photochemical stability of the organometallic compound represented by Chemical Formula 1 is improved, so that an electronic device employing the organometallic compound, for example, an organic light emitting device, can exhibit excellent luminous efficiency, lifespan, and color purity. there is.

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

compound HOMO
(eV) LUMO
(eV) _S1
(eV) _T1
(eV) compound 1 -4.787 -1.241 2.903 2.510 compound 21 -4.727 -1.253 2.872 2.479

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

According to one embodiment, the full width at half maximum (FWHM) of the emission peak of the emission spectrum or the electroluminescence spectrum of the organometallic compound may be 70 nm or less. For example, the full width at half maximum (FWHM) of the emission peak of the emission spectrum or the electroluminescence spectrum of the organometallic compound may be in the range of 30 nm to 65 nm, 40 nm to 63 nm, or 45 nm to 62 nm.

According to one embodiment, the maximum emission wavelength (emission peak wavelength, λ _max ) of the emission peak of the emission spectrum or electroluminescence spectrum of the organometallic compound may be in the range of 490 nm to 550 nm.

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

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

The organic light-emitting device may exhibit excellent driving voltage, current efficiency, power efficiency, external quantum efficiency, lifespan, and/or color purity characteristics by including an organic layer including an organometallic compound represented by Formula 1 as described above, and roll- The off-effect is reduced and a relatively narrow full width at half maximum (FWHM) of the emission peak of the EL spectrum can be exhibited.

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

According to one embodiment, the light emitting layer may emit green light. For example, the emission layer may emit green light having a maximum emission wavelength of 490 nm to 550 nm.

In the present specification, “(the organic layer) contains one or more kinds of organometallic compounds” means “(the organic layer) includes one kind of organometallic compound belonging to the category of Chemical Formula 1 or two different kinds belonging to the category of Chemical Formula 1 above.” It may contain more than one organometallic compound".

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

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

For example, 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 disposed between the first electrode and the light emitting layer and the light emitting layer and the second electrode. further comprising an electron transport region disposed therebetween, wherein the hole transport region comprises a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof, wherein the electron transport region comprises a hole blocking layer, an electron transport layer, electron injection layer, or any combination thereof.

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

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

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

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

The first electrode 11 may have a single layer 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 above the first electrode 11 .

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

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

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

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

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

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

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

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

<Formula 201>

<Formula 202>

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

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

Heavy hydrogen, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt thereof, sulfonic acid or its salt thereof, phosphoric acid or A salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a C ₃ -C ₁₀ 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 A phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, and azule, substituted with a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, or any combination thereof Nylene group, heptalenylene group, acenaphthylene group, fluorenylene group, phenarenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, naphtha It may be a cenylene group, a picenylene group, a perylene group or a pentacenylene group.

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

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

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

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

A phenyl group, naphthyl group, anthracenyl group, fluorenyl group or pyrenyl group; or

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

In Formula 201, R ₁₀₉ is

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

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

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

<Formula 201A>

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

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

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

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

The charge-generating material may be, for example, a p-dopant. The p-dopant may be one 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 tetracyanoquinondimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinondimethane quinone derivatives such as phosphorus (F4-TCNQ); metal oxides such as tungsten oxide and molybdenum oxide; and cyano group-containing compounds such as the following compounds HT-D1 and F12, 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 an optical resonance distance according to a wavelength of light emitted from the light emitting layer.

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

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

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

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

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

<Formula 301>

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

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

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

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

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

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

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

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

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

A phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group or fluorenyl group;

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

;

;

can be

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

<Formula 302>

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

In the present specification, a 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 a methyl group, an ethyl group, a propyl group, an isobutyl group, and a sec-butyl group. group, tert-butyl group, pentyl group, iso-amyl group, hexyl group and the like. In the present specification, a C ₁ -C ₆₀ alkylene group means a divalent group having the same structure as the C ₁ -C ₆₀ alkyl group.

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

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

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

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

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

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

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

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

In the present specification, the C ₁ -C ₆₀ heteroaryl group is a monovalent group having at least one hetero atom selected from N, O, P, Si and S as a ring-forming atom and having a cyclic aromatic system having 1 to 60 carbon atoms. Means, C ₁ -C ₆₀ heteroarylene group includes at least one heteroatom selected from N, O, P and S as a ring-forming atom and refers to a divalent group having a cyclic 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. The C ₂ -C ₆₀ alkylheteroaryl group refers to a C ₁ -C ₆₀ heteroaryl group substituted with at least one C ₁ -C ₆₀ alkyl group.

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

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

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

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

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

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

In this specification, TMS represents *-Si(CH ₃ ) ₃ , and TMG represents *-Ge(CH ₃ ) ₃ .

The substituted C ₅ -C ₃₀ carbocyclic group, C ₁ -C ₃₀ heterocyclic group, 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 hetero Cycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C ₆ -C ₆₀ arylthio group, substituted C ₁ -C ₆₀ heteroaryl group, substituted C At least one of the substituents of _{a 1} -C ₆₀ heteroaryloxy group, a substituted C ₁ -C ₆₀ heteroarylthio group, a substituted monovalent non-aromatic condensed polycyclic group, and a substituted monovalent non-aromatic condensed polycyclic group,

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , a hydroxyl group, a cyano group, a nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt thereof, sulfonic acid group or its salt thereof, phosphoric acid group or its salt thereof, C ₁ -C ₆₀ Alkyl group, C ₂ -C ₆₀ Alkenyl group, C ₂ -C ₆₀ an alkynyl group or a C ₁ -C ₆₀ alkoxy group;

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

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , a hydroxyl group, a cyano group, a nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt thereof, sulfonic acid group or its salt thereof, phosphoric acid group or its salt thereof, C ₁ -C ₆₀ Alkyl group, C ₂ -C ₆₀ Alkenyl group, C ₂ -C ₆₀ Alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ - C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, C ₁ -C ₆₀ heteroaryloxy group, C ₁ -C ₆₀ heteroaryl group Ogi, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, -Si(Q ₂₁ )(Q ₂₂ )(Q ₂₃ ), -Ge(Q ₂₁ )(Q ₂₂ )(Q ₂₃ ) , -N(Q ₂₄ )(Q ₂₅ ), -B(Q ₂₆ )(Q ₂₇ ), -P(=0)(Q ₂₈ )(Q ₂₉ ), or any combination 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, a C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed polycyclic group; or

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

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

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

[Example]

Synthesis Example 1: Synthesis of Compound 1

(1) Synthesis of Compound 1A (1)

2-phenylpyridine (5.2 g, 33.1 mmol) and iridium chloride (5.2 g, 14.7 mmol) were mixed with 120 mL of ethoxyethanol and 40 mL of distilled water (DI water), followed by 24 After stirring under reflux for an hour, the temperature was lowered to room temperature. The solid produced therefrom was separated by filtration, thoroughly washed in the order of water/methanol/hexane, and the obtained solid was dried in a vacuum oven to obtain 8.2 g of Compound 1A (92% yield). The obtained compound 1A (1) was used in the next reaction without further purification.

(2) Synthesis of Compound 1A

After mixing compound 1A (1.6 g, 1.5 mmol) with 45 mL of methylene chloride, AgOTf (0.8 g, 3.1 mmol) was added after mixing with 15 mL of methanol. Thereafter, after stirring at room temperature for 18 hours in a state of blocking light with aluminum foil, the solid produced by celite filtration was removed, and the filtrate was reduced under reduced pressure without further purification of the obtained solid (Compound 1A). It was used for the next reaction.

(3) Synthesis of Compound 1B

2-Bromo-1-(3,5-diisopropyl-[1,1′-biphenyl]-4-yl)-1H-benzo[d]imidazole (1.0g, 2.3mmol) under nitrogen environment and 2-(benzo[b]benzo[5,6][1,4]dioxino[2,3-g]benzofuran-11-yl)-4,4,5,5-tetramethyl-1,3 After dissolving 2-dioxoborolane (1.0g, 2.5mmol) in 60ml of 1,4-dioxane. After dissolving potassium carbonate (K ₂ CO ₃ ) (0.7g, 6.9 mmol) in 20 mL of distilled water (DI water), it was added to the reaction mixture, and a palladium catalyst (Pd(PPh ₃ ) ₄ ) (0.13g, 0.12 mmol) was added to the reaction mixture. added. Then, the reaction mixture was stirred while refluxing at 110 °C. After extraction, the obtained solid was subjected to column chromatography (eluent: EA (ethyl acetate) and hexane) to obtain compound 1B (2-(benzo [b] benzo [5,6] [1,4] dioxyno [ 2,3-g] benzofuran-11-yl) -1- (3,5-diisopropyl- [1,1'-biphenyl] -4-yl) -1H- benzo [d] imidazole) 1.3 g (yield of 92%) was obtained. The material was confirmed through mass and HPLC analysis.

HRMS(MALDI) calcd for C ₄₃ H ₃₄ N ₂ O ₃ : m/z: 626.76 Found: 627.55

(4) Synthesis of Compound 1

Compound 1A (1.3 g, 1.8 mmol) and Compound 1B (2-(benzo[b]benzo[5,6][1,4]dioxino[2,3-g]benzofuran-11-yl)-1 To -(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-1H-benzo[d]imidazole) (1.3 g, 2.0 mmol) was added 20 mL of 2-ethoxyethanol. After mixing and stirring at reflux for 24 hours, the temperature was lowered. The resulting mixture was subjected to column chromatography (eluent: MC (methylene chloride) and hexane) on the obtained solid under reduced pressure to obtain 1.1 g of Compound 1 (49% yield). The material was confirmed through mass and HPLC analysis.

HRMS(MALDI) calcd for C ₆₅ H ₄₉ IrN ₄ O ₃ : m/z: 1126.35 Found: 1127.22

Synthesis Example 2: Synthesis of Compound 21

In the synthesis example of compound 1, 2- (benzo [b] benzo [5,6] [1,4] dioxino [2,3-g] benzofuran-11-yl) -4,4,5,5- 2-(benzo[b]benzo[5,6][1,4]dioxino[2,3-f]benzofuran-4-yl)-4 instead of tetramethyl-1,3,2-dioxobororane; 1.0 g (yield of 44%) of compound 21 was obtained in the same manner as in the synthesis of compound 1 using 4,5,5-tetramethyl-1,3,2-dioxobororane. The material was confirmed through mass and HPLC analysis.

HRMS(MALDI) calcd for C ₆₅ H ₄₉ IrN ₄ O ₃ : m/z: 1126.35 Found: 1127.15

Synthesis Example 3: Synthesis of Compound 22

In the synthesis method of Compound 1, 0.9 g (41% yield) of Compound 22 was obtained in the same manner as in the synthesis of Compound 1, using 5-(methyl-d3)-2-phenylpyridine instead of 2-phenylpyridine. The material was confirmed through mass and HPLC analysis.

HRMS(MALDI) calcd for C ₆₇ H ₄₇ D ₆ IrN ₄ O ₃ : m/z: 1160.44 Found: 1161.38

Example 1

An ITO-patterned glass substrate as an anode was cut into 50 mm x 50 mm x 0.5 mm size, ultrasonically cleaned using isopropyl alcohol and pure water for 5 minutes each, irradiated with ultraviolet rays for 30 minutes, exposed to ozone, and vacuum deposited. installed on the device.

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

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

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

Example 2, Comparative Examples 1 and 2

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

For each of the organic light emitting devices prepared in Examples 1 and 2 and Comparative Examples 1 and 2, driving voltage, maximum emission wavelength (λ _max ) of emission spectrum, external quantum efficiency (Max EQE), roll-off (roll- off) ratio was evaluated and the results are shown in Table 2. As evaluation devices, a current-voltmeter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used. The roll-off ratio was calculated according to Equation 20 below, and is shown as a relative value in Table 2 below.

<Formula 20>

Roll-off ratio = {1- (efficiency / maximum luminous efficiency)} X 100%

No. Dopant in the light emitting layer Driving voltage (V) Max EQE(%) Roll-off (%) λmax(EL) Example 1 compound 1 4.0 25 12 525 Example 2 compound 21 4.0 25 12 527 Comparative Example 1 compound A 4.2 22 15 524 Comparative Example 2 compound B 4.4 22 15 532

From Table 2, it can be seen that the organic light emitting diodes of Examples 1 and 2 had low driving voltage and low roll-off ratio and excellent external quantum efficiency. In addition, it was found that the organic light emitting devices of Examples 1 and 2 had a lower driving voltage and a lower roll-off ratio and higher external quantum efficiency than the organic light emitting devices of Comparative Examples 1 and 2.

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

Claims (20)

An organometallic compound represented by Formula 1 below:
<Formula 1>
M ₁ (Ln ₁ ) _n1 (Ln ₂ ) _n2
In Formula 1,
M ₁ is a transition metal;
Ln ₁ is a ligand represented by Formula 1A below;
Ln ₂ is a ligand represented by Formula 1B below;
n1 is 1 or 2;
n2 is 1 or 2;
<Formula 1A><Formula1B>

<Formula 41>

Among Formulas 1A, 1B and 41,
CY ₁ and CY ₂ are each independently a C ₅ -C ₃₀ carbocyclic group or a C ₁ -C ₃₀ heterocyclic group;
CY ₄₁ is a group represented by Formula 41;
X ₁ is C or N, X ₂ is C or N,
X ₃₁ is C(R ₃₁ ) or N, X ₃₂ is C(R ₃₂ ) or N;
X ₄₁ is C(R ₄₁ ) or N, X ₄₂ is C(R ₄₂ ) or N;
Y ₄ is O, S, Se or C(R ₁ )(R ₂ );
Y ₄₁ is O, S, Se, C(R ₃ )(R ₄ ), N(R ₃ ) or B(R ₃ );
Y ₄₂ is O, S, Se, C(R ₅ )(R ₆ ), N(R ₅ ) or B(R ₅ );
L ₁ is a single bond; A substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group; or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group;
a1 is 1, 2, 3, 4 or 5;
R ₁ to R ₇ , R ₁₀ , R ₂₀ , R ₃₁ , R ₃₂ and R ₄₀ to R ₄₂ are each independently hydrogen, heavy hydrogen, -F, -Cl, -Br, -I, a hydroxyl group, or a cyano group , Nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt thereof, sulfonic acid group or its salt thereof, phosphoric acid group or its salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or Unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryloxy group, substituted or unsubstituted C ₁ -C ₆₀ heteroarylthio group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic group Heterocondensed polycyclic group, -Si(Q ₁ )(Q ₂ )(Q ₃ ), -Ge(Q ₁ )(Q ₂ )(Q ₃ ), -N(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ) or -P(=0)(Q ₈ )(Q ₉ );
Two or more adjacent R ₁₀ may be optionally bonded to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group; ,
Two or more adjacent R ₂₀ may be optionally bonded to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group; ,
Two or more adjacent R ₄₀ may be optionally bonded to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group; ,
Two or more adjacent R ₁ to R ₇ , R ₁₀ , R ₂₀ , R ₃₁ , R ₃₂ and R ₄₀ to R ₄₂ are optionally bonded to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group, or may form a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group;
b7 is 1, 2, 3, 4, 5, 6, 7 or 8;
b10 and b20 are each independently 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;
b40 is 1, 2, 3, 4, 5 or 6;
* and *' are binding sites with neighboring atoms, respectively;
The above substituted C ₅ -C ₃₀ carbocyclic group, substituted C ₁ -C ₃₀ heterocyclic group, substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, substituted C ₁ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C ₆ -C ₆₀ arylthio group, substituted C ₁ -C ₆₀ heteroaryl group Among substituents of a substituted C ₁ -C ₆₀ heteroaryloxy group, a substituted C ₁ -C ₆₀ heteroarylthio group, a substituted monovalent non-aromatic condensed polycyclic group, and a substituted monovalent non-aromatic hetero condensed polycyclic group, at least one
Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , a hydroxyl group, a cyano group, a nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt thereof, sulfonic acid group or its salt thereof, phosphoric acid group or its salt thereof, C ₁ -C ₆₀ Alkyl group, C ₂ -C ₆₀ Alkenyl group, C ₂ -C ₆₀ an alkynyl group or a C ₁ -C ₆₀ alkoxy group;
Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , a hydroxyl group, a cyano group, a nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt thereof, sulfonic acid group or its salt thereof, phosphoric acid group or its salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ - C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group , C ₁ -C ₆₀ heteroaryloxy group, C ₁ -C ₆₀ heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q ₁₁ )(Q ₁₂ ) (Q ₁₃ ), -Ge(Q ₁₁ )(Q ₁₂ )(Q ₁₃ ), -N(Q ₁₄ )(Q ₁₅ ), -B(Q ₁₆ )(Q ₁₇ ), -P(=O)(Q a C ₁ -C ₆₀ alkyl group, a _{C 2 -C 60 alkenyl group, a C 2 -C 60} alkynyl group, or a C ₁ -C ₆₀ alkoxy group, substituted with ₁₈ )(Q ₁₉ ) or any combination 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 aryl an oxy group, a C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a C ₁ -C ₆₀ heteroaryloxy group, a C ₁ -C ₆₀ heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, or monovalent non-aromatic condensed heteropolycyclic groups;
Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , a hydroxyl group, a cyano group, a nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt thereof, sulfonic acid group or its salt thereof, phosphoric acid group or its salt thereof, C ₁ -C ₆₀ Alkyl group, C ₂ -C ₆₀ Alkenyl group, C ₂ -C ₆₀ Alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ - C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, C ₁ -C ₆₀ heteroaryloxy group, C ₁ -C ₆₀ heteroaryl group Ogi, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, -Si(Q ₂₁ )(Q ₂₂ )(Q ₂₃ ), -Ge(Q ₂₁ )(Q ₂₂ )(Q ₂₃ ) , -N(Q ₂₄ )(Q ₂₅ ), -B(Q ₂₆ )(Q ₂₇ ), -P(=0)(Q ₂₈ )(Q ₂₉ ), or any combination 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, a C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed polycyclic group; or
-Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -Ge(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₄ )(Q ₃₅ ), -B(Q ₃₆ )(Q ₃₇ ) or -P(=0)(Q ₃₈ )(Q ₃₉ );
Wherein Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano No group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt thereof, sulfonic acid group or its salt thereof, phosphoric acid group or its salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted substituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted Or an unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ - C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted a cyclic C ₁ -C ₆₀ heteroaryloxy group, a substituted or unsubstituted C ₁ -C ₆₀ heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group; or a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group; According to claim 1,
M ₁ is iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm) or rhodium ( Rh), an organometallic compound. According to claim 1,
M ₁ is Ir;
An organometallic compound in which the sum of n1 + n2 is 3. According to claim 1,
CY ₁ and CY ₂ are each independently a benzene group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a triazine group, a quinoline group, Isoquinoline group, quinoxaline group, quinazoline group, phenanthroline group, benzofuran group, benzothiophene group, fluorene group, carbazole group, dibenzofuran group, dibenzothiophene group, dibenzosilol group, An organometallic compound which is an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group or an azadibenzosilol group. According to claim 1,
Ln ₁ is an organometallic compound represented by Formula 1A-1:
<Formula 1A-1>

In Formula 1A-1,
X ₁₁ is C(R ₁₁ ) or N, X ₁₂ is C(R ₁₂ ) or N, X ₁₃ is C(R ₁₃ ) or N, X ₁₄ is C(R ₁₄ ) or N,
X ₂₁ is C(R ₂₁ ) or N, X ₂₂ is C(R ₂₂ ) or N, X ₂₃ is C(R ₂₃ ) or N, X ₂₄ is C(R ₂₄ ) or N,
R ₁₁ to R ₁₄ are independently of each other, refer to the description of R ₁₀ in claim 1,
R ₂₁ to R ₂₄ are independently of each other, refer to the description of R ₂₀ in claim 1,
* and *' are binding sites with neighboring atoms. According to claim 1,
Ln ₁ is an organometallic compound represented by any one of Formulas 1A-9 to 1A-26:

In Formulas 1A-9 to 1A-26,
R ₁₀ and R ₂₀ refer to the description of claim 1, respectively;
b51 and b54 are each independently 1 or 2;
b53 and b55 are each independently 1, 2 or 3;
b52 and b56 are each independently 1, 2, 3 or 4;
* and *' are binding sites with neighboring atoms. According to claim 1,
X ₃₁ is C(R ₃₁ ), X ₃₂ is C(R ₃₂ ),
R ₃₁ and R ₃₂ are optionally bonded to each other to form a C ₅ -C ₃₀ carbocyclic group optionally substituted with R ₃₀ or a C ₁ -C ₃₀ heterocyclic group optionally substituted with R ₃₀ ; ,
The description of R ₃₀ refers to R ₃₁ in claim 1, an organometallic compound. According to claim 1,
Ln ₂ is an organometallic compound represented by any one of Formulas 1B-1 to 1B-3:
<Formula 1B-1>

<Formula 1B-2>

<Formula 1B-3>

In Formulas 1B-1 to 1B-3
For descriptions of X ₃₁ , X ₃₂ , L ₁ , a1, R ₇ , b7, Y ₄ , Y ₄₁ , Y ₄₂ , R ₃₁ to R ₃₄ and R ₄₁ to R ₄₈ , refer to claim 1,
R ₄₁ to R ₄₈ are independently from each other, refer to the description of R ₄₀ in claim 1,
* and *' are binding sites with neighboring atoms, respectively. According to claim 1,
An organometallic compound in which Y ₄ is O or S. According to claim 1,
Y ₄₁ is O, S or C(R ₃ )(R ₄ );
and Y ₄₂ is O, S or C(R ₅ )(R ₆ ). According to claim 1,
R ₁ to R ₇ , R ₁₀ , R ₂₀ , R ₃₁ , R ₃₂ and R ₄₀ to R ₄₂ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , C ₁ -C ₆₀ Alkyl group, C ₂ -C ₆₀ Alkenyl group, C ₂ -C ₆₀ Alkynyl group, C ₁ -C ₆₀ Alkoxy group , -Si(Q ₁ )(Q ₂ )(Q ₃ ) or -Ge(Q ₁ )(Q ₂ )(Q ₃ ); or
An organometallic compound, which is a group represented by any one of Formulas 9-1 to 9-67, 9-201 to 9-244, 10-1 to 10-154, and 10-201 to 10-350:

In Formulas 9-1 to 9-67, 9-201 to 9-244, 10-1 to 10-154, and 10-201 to 10-350, * is a binding site with a neighboring atom, Ph is a phenyl group, TMS is a trimethylsilyl group, and TMG is a trimethylgermyl group. According to claim 1,
At least one of R ₁ to R ₇ , R ₁₀ , R ₂₀ , R ₃₁ , R ₃₂ and R ₄₀ to R ₄₂ is a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, sec -Butyl group, tert-butyl group, n-pentyl group, isopentyl group, 2-methylbutyl group, sec-pentyl group, tert-pentyl group, neo-pentyl group, 3-pentyl group or 3-methyl-2- A butyl group, an organometallic compound. According to claim 1,
The organometallic compound is a compound represented by any one of the following Chemical Formulas 30-1 to 30-6:
<Formula 30-1>

<Formula 30-2>

<Formula 30-3>

<Formula 30-4>

<Formula 30-5>

<Formula 30-6>

In Formulas 30-1 to 30-6,
For a description of M ₁ , n1, n2, X ₃₁ , X ₃₂ , L ₁ , a ₁ , R ₇ , b7, Y ₁ , Y ₄₁ , Y ₄₂ and R ₄₁ to R ₄₈ , see claim 1,
X ₃₃ is C(R ₃₃ ) or N, X ₃₄ is C(R ₃₄ ) or N, X ₃₅ is C(R ₃₅ ) or N, X ₃₆ is C(R ₃₆ ) or N,
R ₁₁ to R ₁₄ are independently of each other, refer to the description of R ₁₀ in claim 1,
R ₂₁ to R ₂₄ are independently of each other, refer to the description of R ₂₀ in claim 1,
R ₃₃ to R ₃₆ are independently of each other, refer to the description of R ₃₁ in claim 1,
R ₄₁ to R ₄₈ are independently from each other, see the description of R ₄₀ in claim 1. According to claim 1,
The organometallic compound is an electrically neutral, organometallic compound. According to claim 1,
An organometallic compound, which is any one of Compounds 1 to 40:

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

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