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

1. An organometallic compound represented by Formula 1:

Formula 1

M(L 1 ) n1 (L 2 ) n2

wherein, in Formula 1,

M is a transition metal,

L 1 is a ligand represented by Formula 2A,

L 2 is a ligand represented by Formula 2B,

n1 and n2 are each independently 1 or 2, wherein, when n1 is 2, two L 1 (s) are identical to or different from each other, and when n2 is 2, two L 2 (s) are identical to or different from each other,

the sum of n1 and n2 is 2 or 3, and

L 1 and L 2 are different from each other:

wherein, in Formulae 2A and 2B,

Y 4 is C or N,

X 21 is O, S, Se, S(═O), or N(R 29 ),

T 1 to T 4 are each independently C, N, carbon bonded to ring CY 1 , or carbon bonded to M in Formula 1, wherein one of T 1 to T 4 is the carbon bonded to M in Formula 1, and one of the remaining groups T 1 to T 4 that is not bonded to M in Formula 1 is the carbon bonded to ring CY 1 ,

T 5 to T 8 are each independently C or N,

ring CY 1 and ring CY 3 are each independently a C 1 -C 30 heterocyclic group,

ring CY 4 is a C 3 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group,

Z 1 , Z 3 , Z 2 , and Z 4 are each a fluoro group or a fluorinated C 1 -C 20 alkyl group,

a1, a3, and a4 are each independently an integer from 0 to 20, wherein a2 is an integer from 0 to 6, and the sum of a1, a2, a3, and a4 is 1 or more,

R 1 to R 4 and R 29 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, 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 1 -C 60 alkylthio group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or 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, 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 7 -C 60 arylalkyl 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 C 2 -C 60 heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q 1 )(Q 2 ), —Si(Q 3 )(Q 4 )(Q 5 ), —Ge(Q 3 )(Q 4 )(Q 5 ), —B(Q 6 )(Q 7 ), —P(═O)(Q 8 )(Q 9 ), or —P(Q 8 )(Q 9 ),

b1 and b4 are each independently an integer from 0 to 20, b2 is an integer from 0 to 6, and b3 is an integer from 1 to 20,

when i) none of T 1 to T 8 in Formula 2A is N, ii) a2 in Formula 2A is not 0, and iii) Z 2 in Formula 2A is a fluoro group, then at least one of R 3 (s) in the number of b3 in Formula 2B is —Si(Q 3 )(Q 4 )(Q 5 ) or —Ge(Q 3 )(Q 4 )(Q 5 ),

in Formula 2B, and at least one of R 3 (s) in the number of b 3 is —Si(Q 3 )(Q 4 )(Q 5 ), —Ge(Q 3 )(Q 4 )(Q 5 ), or a C 1 -C 20 alkyl group unsubstituted or substituted with at least one deuterium,

two or more of a plurality of R 1 (s) are optionally linked together to form a C 3 -C 30 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,

two or more of a plurality of R 2 (s) are optionally linked together to form a C 3 -C 30 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,

two or more of a plurality of R 3 (s) are optionally linked together to form a C 3 -C 30 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,

two or more of a plurality of R 4 (s) are optionally linked together to form a C 3 -C 30 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,

R 10a is the same as described in connection with R 1 ,

* and *′ in Formulae 2A and 2B each indicate a binding site to M in Formula 1, and

a substituent of the substituted C 1 -C 60 alkyl group, the substituted C 2 -C 60 alkenyl group, the substituted C 2 -C 60 alkynyl group, the substituted C 1 -C 60 alkoxy group, the substituted C 1 -C 60 alkylthio group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 1 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 1 -C 10 heterocycloalkenyl group, the substituted C 6 -C 60 aryl group, the substituted C 6 -C 60 aryloxy group, the substituted C 6 -C 60 arylthio group, the substituted C 7 -C 60 arylalkyl group, the substituted C 1 -C 60 heteroaryl group, the substituted C 1 -C 60 heteroaryloxy group, the substituted C 1 -C 60 heteroarylthio group, the substituted C 2 -C 60 heteroarylalkyl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is:

deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a 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, or a C 1 -C 60 alkylthio group;

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, or a C 1 -C 60 alkylthio group, each independently substituted with deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 7 -C 60 arylalkyl group, a C 1 -C 60 heteroaryl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a C 2 -C 60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q 11 )(Q 12 ), —Si(Q 13 )(Q 14 )(Q 15 ), —Ge(Q 13 )(Q 14 )(Q 15 ), —B(Q 16 )(Q 17 ), —P(═O)(Q 18 )(Q 19 ), —P(Q 18 )(Q 19 ), or a combination thereof;

a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 7 -C 60 arylalkyl group, a C 1 -C 60 heteroaryl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a C 2 -C 60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each independently unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a 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 1 -C 60 alkylthio group, C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -Coo aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 7 -C 60 arylalkyl group, a C 1 -C 60 heteroaryl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a C 2 -C 60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q 21 )(Q 22 ), —Si(Q 23 )(Q 24 )(Q 25 ), —Ge(Q 23 )(Q 24 )(Q 25 ), —B(Q 26 )(Q 27 ), —P(═O)(Q 28 )(Q 29 ), —P(Q 28 )(Q 29 ), or a combination thereof;

—N(Q 31 )(Q 32 ), —Si(Q 33 )(Q 34 )(Q 35 ), —Ge(Q 33 )(Q 34 )(Q 35 ), —B(Q 36 )(Q 37 ), —P(═O)(Q 38 )(Q 39 ), or —P(Q 38 )(Q 39 ); or

a combination thereof,

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: hydrogen;

deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; an amino group; an amidino group; a hydrazine group; a hydrazone group; a carboxylic acid group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphoric acid group or a salt thereof; a C 1 -C 60 alkyl group which is unsubstituted or substituted with deuterium, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, or a combination thereof; a C 2 -C 60 alkenyl group; a C 2 -C 60 alkynyl group; a C 1 -C 60 alkoxy group; a C 1 -C 60 alkylthio group; a C 3 -C 10 cycloalkyl group; a C 1 -C 10 heterocycloalkyl group; a C 3 -C 10 cycloalkenyl group; a C 1 -C 10 heterocycloalkenyl group; a C 6 -C 60 aryl group which is unsubstituted or substituted with deuterium, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, or a combination thereof; a C 6 -C 60 aryloxy group; a C 6 -C 60 arylthio group; a C 7 -C 60 arylalkyl group; a C 1 -C 60 heteroaryl group; a C 1 -C 60 heteroaryloxy group; a C 1 -C 60 heteroarylthio group; a C 2 -C 60 heteroarylalkyl group; a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic condensed heteropolycyclic group.

2. The organometallic compound of claim 1 , wherein

in Formula 1, M is Ir, and the sum of n1 and n2 is 3; or

in Formula 1, M is Pt, and the sum of n1 and n2 is 2.

3. The organometallic compound of claim 1 , wherein

ring CY 1 and ring CY 3 are each independently a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a 5,6,7,8-tetrahydroisoquinoline group, a 5,6,7,8-tetrahydroquinoline group, or a pyridine group condensed with a norbornane group,

Y 4 is C, and

ring CY 4 is a benzene group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, or a benzene group condensed with a norbornane group.

4. The organometallic compound of claim 1 , wherein

a1 is 1, and a2, a3, and a4 are each independently 0,

a2 is 1 or 2, and a1, a3, and a4 are each independently 0,

a3 is 1, and a1, a2, and a4 are each independently 0,

a4 is 1, and a1, a2, and a3 are each independently 0,

a2 and a4 are each independently 1, and a1 and a3 are each independently 0, or

a1 and a2 are each independently 1, and a3 and a4 are each independently 0.

5. The organometallic compound of claim 1 , wherein

R 1 to R 4 and R 29 are each independently:

hydrogen, deuterium, or a cyano group;

a C 1 -C 20 alkyl group unsubstituted or substituted with deuterium, a cyano group, a C 3 -C 10 cycloalkyl group, a deuterated C 3 -C 10 cycloalkyl group, a (C 1 -C 20 alkyl)C 3 -C 10 cycloalkyl group, a deuterated (C 1 -C 20 alkyl)C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a deuterated C 1 -C 10 heterocycloalkyl group, a (C 1 -C 20 alkyl)C 1 -C 10 heterocycloalkyl group, a deuterated (C 1 -C 20 alkyl)C 1 -C 10 heterocycloalkyl group, a phenyl group, a deuterated phenyl group, a (C 1 -C 20 alkyl)phenyl group, a deuterated (C 1 -C 20 alkyl)phenyl group, a biphenyl group, a deuterated biphenyl group, a (C 1 -C 20 alkyl)biphenyl group, a deuterated (C 1 -C 20 alkyl)biphenyl group, or a combination thereof;

a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a phenyl group, or a biphenyl group, each independently unsubstituted or substituted with deuterium, a cyano group, a C 1 -C 20 alkyl group, a deuterated C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a deuterated C 1 -C 20 alkoxy group, a C 3 -C 10 cycloalkyl group, a deuterated a C 3 -C 10 cycloalkyl group, a (C 1 -C 20 alkyl)C 3 -C 10 cycloalkyl group, a deuterated (C 1 -C 20 alkyl)C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a deuterated C 1 -C 10 heterocycloalkyl group, a (C 1 -C 20 alkyl)C 1 -C 10 heterocycloalkyl group, a deuterated (C 1 -C 20 alkyl)C 1 -C 10 heterocycloalkyl group, a phenyl group, a deuterated phenyl group, a (C 1 -C 20 alkyl)phenyl group, a deuterated (C 1 -C 20 alkyl)phenyl group, a biphenyl group, a deuterated biphenyl group, a (C 1 -C 20 alkyl)biphenyl group, a deuterated (C 1 -C 20 alkyl)biphenyl group, or a combination thereof, or

—Si(Q 3 )(Q 4 )(Q 5 ) or —Ge(Q 3 )(Q 4 )(Q 5 ).

6. The organometallic compound of claim 1 , wherein

in Formula 2B, at least one of R 3 (s) in the number of b3 is —Si(Q 3 )(Q 4 )(Q 5 ) or —Ge(Q 3 )(Q 4 )(Q 5 ).

7. The organometallic compound of claim 1 , wherein

the organometallic compound comprises at least one deuterium.

8. The organometallic compound of claim 1 , wherein a group represented by

in Formula 2A is a group represented by one of Formulae CY1(1) to CY1(22):

wherein, in Formulae CY1(1) to CY1(22), * indicates a binding site to M in Formula 1, and *” indicates a binding site to a neighboring carbon atom in Formula 2A.

9. The organometallic compound of claim 1 , wherein a group represented by

in Formula 2A is a group represented by one of Formulae CY1-1 to CY1-16 and CY1-1F to CY1-32F:

wherein, in Formulae CY1-1 to CY1-16 and CY1-1F to CY1-32F,

Z 11 to Z 14 are each the same as described in connection with Z 1 in claim 1 ,

R 11 to R 14 are each the same as described in connection with R 1 in claim 1 , wherein each of R 11 to R 14 is not hydrogen,

* indicates a binding site to M in Formula 1, and

*” indicates a binding site to a neighboring carbon atom in Formula 2A.

10. The organometallic compound of claim 1 , wherein a group represented by

in Formula 2A is a group represented by one of Formulae CY2-1 to CY2-6:

wherein, in Formulae CY2-1 to CY2-6, *′ indicates a binding site to M in Formula 1, and *” indicates a binding site to ring CY1 in Formula 2A.

11. The organometallic compound of claim 1 , wherein a group represented by

in Formula 2A is a group represented by one of Formulae CY2-1-1 to CY2-1-22, CY2-1-1N to CY2-1-16N, CY2-4-1 to CY2-4-22, CY2-4-1N to CY2-4-16N, CY2-1-1F to CY2-1-21F, CY2-1-1NF to CY2-1-15NF, CY2-4-1F to CY2-4-21F, and CY2-4-1NF to CY2-4-15NF:

wherein, in Formulae CY2-1-1 to CY2-1-22, CY2-1-1N to CY2-1-16N, CY2-4-1 to CY2-4-22, CY2-4-1N to CY2-4-16N, CY2-1-1F to CY2-1-21F, CY2-1-1NF to CY2-1-15NF, CY2-4-1F to CY2-4-21F, and CY2-4-1NF to CY2-4-15NF,

Z 21 to Z 28 are each the same as described in connection with Z 2 in claim 1 ,

R 21 to R 28 are each the same as described in connection with R 2 in claim 1 , wherein each of R 21 to R 28 is not hydrogen,

*′ indicates a binding site to M in Formula 1, and

*” indicates a binding site to ring CY1 in Formula 2A.

12. The organometallic compound of claim 1 , wherein a group represented by

in Formula 2B is a group represented by Formula CY3(1):

wherein, in Formula CY3(1),

X 31 is Si or Ge,

Z 3 , R 3 , and Q 3 to Q 5 are each the same as described in claim 1 ,

a33 and b33 are each independently an integer from 0 to 3,

two or more of R 3 (s) in the number of a33 are optionally linked together to form a C 3 -C 30 carbocyclic group that is unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group that is unsubstituted or substituted with at least one R 10a ,

R 10a is the same as described in connection with R 1 in claim 1 ,

* indicates a binding site to M in Formula 1, and

*” indicates a binding site to ring CY4 in Formula 2B.

13. The organometallic compound of claim 1 , wherein a group represented by

in Formula 2B is a group represented by one of Formulae CY3-2 to CY3-16, CY3-2F to CY3-8F, or CY3-10F to CY3-16F, CY3-18F to CY3-24F, or CY3-26F to CY3-32F:

wherein, in Formulae CY3-2 to CY3-16, CY3-2F to CY3-8F, or CY3-10F to CY3-16F, CY3-18F to CY3-24F, or CY3-26F to CY3-32F,

Z 31 to Z 34 are each the same as described in connection with Z 3 in claim 1 ,

R 31 to R 34 are each the same as described in connection with R 3 in claim 1 , wherein each of R 31 to R 34 is not hydrogen,

* indicates a binding site to M in Formula 1, and

*” indicates a binding site to ring CY 4 in Formula 2B.

14. The organometallic compound of claim 1 , wherein a group represented by

in Formula 2B is a group represented by one of Formulae CY4-1 to CY4-16 and CY4-1F to CY4-32F:

wherein, in Formulae CY4-1 to CY4-16 and CY4-1F to CY4-32F,

Z 41 to Z 44 are each the same as described in connection with Z 4 in claim 1 ,

R 41 to R 44 are each the same as described in connection with R 4 in claim 1 , wherein each of R 41 to R 44 is not hydrogen,

* indicates a binding site to M in Formula 1, and

*” indicates a binding site to ring CY 3 in Formula 2B.

15. An organic light-emitting device comprising:

a first electrode;

a second electrode; and

an organic layer arranged between the first electrode and the second electrode, wherein the organic layer comprises an emission layer,

wherein the organic layer further comprises at least one organometallic compound of claim 1 .

16. The organic light-emitting device of claim 15 , wherein

the first electrode is an anode,

the second electrode is a cathode,

the organic layer further comprises a hole transport region between the first electrode and the emission layer and an electron transport region between the emission 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 a combination thereof, and

the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

17. The organic light-emitting device of claim 15 , wherein the emission layer comprises the at least one organometallic compound.

18. The organic light-emitting device of claim 17 , wherein

the emission layer further comprises a host, and an amount of the host in the emission layer is greater than an amount of the at least one organometallic compound in the emission, each based on total weight of the emission layer.

19. An electronic apparatus comprising the organic light-emitting device of claim 15 .

20. The organometallic compound of claim 1 , wherein the sum of a1, a2, and a4 is 1 or more.