IP Library Granted Patent US 12,371,612
Granted Patent B2
US 12,371,612 · App. 17/229,659 · Granted Jul 29, 2025

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

Inventors: Jeoungin Yi (Seoul, KR); Byungjoon Kang (Seoul, KR); Sangdong Kim (Seongnam-si, KR); Hyungjun Kim (Suwon-si, KR); Yong Joo Lee (Suwon-si, KR); Byoungki Choi (Hwaseong-si, KR); Youngki Hong (Anyang-si, KR); Kyuyoung Hwang (Anyang-si, KR)
Assignee: SAMSUNG ELECTRONICS CO., LTD.
H10K85/346C07F15/0086C09K11/06C07B2200/05C09K2211/1044C09K2211/185H10K50/11H10K50/15H10K50/16H10K50/17H10K50/171H10K50/18
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Quick Facts
Patent No.
US 12,371,612
App. No.
17/229,659
Granted
Jul 29, 2025
Kind
B2
Abstract

Provided are an organometallic compound, an organic light-emitting device including the organometallic compound, and an electronic apparatus including the organic light-emitting device, in which the organometallic compound may be represented by Formula 1-1: wherein Formula 1-1 may be understood by referring to the description of Formula 1-1 provided herein.

Claims (143)

1. An organometallic compound represented by Formula 1-1:

wherein, in Formula 1-1,

M is a transition metal,

X 1 is O, S, or N(R′″),

a bond between X 1 and M is a covalent bond,

X 2 to X 4 and Y 1 are each independently C or N,

one bond of a bond between X 2 and M, a bond between X 3 and M, and a bond between X 4 and M is a covalent bond, while the remaining bonds are each a coordinate bond,

X 51 is O, S, N-[(L 7 ) b7 -(R 7 ) c7 ], C(R 7 )(R 8 ), Si(R 7 )(R 8 ), Ge(R 7 )(R 8 ), or C(═O),

Z 11 is N or C-[(L 11 ) b11 -(T 11 ) c11 ], Z 12 is N or C-[(L 12 ) b12 -(T 12 ) c12 ], Z 13 is N or C-[(L 13 ) b13 -(T 13 ) c13 ], and Z 14 is N or C-[(L 14 ) b14 -(T 14 ) c14 ],

Z 21 is N or C-[(L 21 ) b21 -(T 21 ) c21 ], Z 22 is N or C-[(L 22 ) b22 -(T 22 ) c22 ], and Z 23 is N or C-[(L 23 ) b23 -(T 23 ) c23 ],

Z 31 is N or C-[(L 31 ) b31 -(T 31 ) c31 ], Z 32 is N or C-[(L 32 ) b32 -(T 32 ) c32 ], and Z 33 is N or C-[(L 33 ) b33 -(T 33 ) c33 ],

Z 41 is N or C-[(L 41 ) b41 -(T 41 ) c41 ], Z 42 is N or C-[(L 42 ) b42 -(T 42 ) c42 ], Z 43 is N or C-[(L 43 ) b43 -(T 43 ) c43 ], and Z 44 is N or C-[(L 44 ) b44 -(T 44 ) c44 ],

L 7 , L 11 to L 14 , L 21 to L 23 , L 31 to L 33 and L 41 to L 44 are each independently a single bond, a C 1 -C 10 alkylene group unsubstituted or substituted with at least one R 10a , a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,

b7, b11 to b14, b21 to b23, b31 to b33 and b41 to b44 are each independently 1, 2, 3, 4, or 5,

R′″, R 7 , R 8 , T 11 to T 14 , T 21 to T 23 , T 31 to T 33 and T 41 to T 44 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF 5 , a hydroxyl group, a cyano group, a nitro 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 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 1 -C 60 heteroaryl 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 ),

c7, c11 to c14, c21 to c23, c31 to c33 and c41 to c44 are each independently 1, 2, 3, 4, or 5,

wherein, the organometallic compound represented by Formula 1-1 satisfies:

1) Condition 11,

2) Condition 12,

3) Condition 13,

4) Condition 11 and Condition 13, or

5) Condition 12 and Condition 13,

provided then when the organometallic compound represented by Formula 1-1 satisfies 1), 3) or 4), then i) ΔST of the organometallic compound is in a range of about 0.1 electron volts (eV) to about 0.2 eV, and ΔST indicates an energy gap between a singlet (S 1 ) energy level and a triplet (T 1 ) energy level of the organometallic compound, ii) a horizontal orientation ratio of the organometallic compound is in a range of about 85 percent (%) to about 95%, iii) a sublimation temperature of the organometallic compound is in a range of about 200° C. to about 350° C., or a combination thereof,

Z 42 in Formula 1-1 is C-[(L 42 ) b42 -(T 42 ) c42 ],  Condition 11

T 42 is 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, or a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, and

c42 is 1,

Z 42 in Formula 1-1 is C-[(L 42 ) b42 -(T 42 ) c42 ],  Condition 12

T 42 is a group represented by Formula 41, and

c 42 is 1:

*—C(Q 41 )(Q 42 )(Q 43 )  Formula 41

wherein in Formula 41,

Q 41 to Q 43 are each independently deuterium, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 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 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,

at least one of Q 41 to Q 43 are each independently a substituted or unsubstituted C 2 -C 60 alkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, or a substituted or unsubstituted C 6 -C 60 aryl group, and

* indicates a binding site to an adjacent atom,

X 51 in Formula 1-1 is N-[(L 7 ) b7 -(R 7 ) c7 ],  Condition 13

L 7 is a benzene group, or a naphthalene group, each unsubstituted or substituted with at least one R 10a ,

R 7 is 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, or a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, and

c7 is 1,

each of i) at least two of T 11 to T 14 , ii) at least two of T 21 to T 23 , iii) at least two of T 31 to T 33 , iv) at least two of T 41 to T 44 and v) at least two of T 11 to T 14 , T 21 to T 23 , T 31 to T 33 , and T 41 to T 44 are optionally bound to each other to form a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,

R 10a is understood by referring to the description of T 11 provided herein,

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 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 1 -C 60 heteroaryl 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 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, or a C 1 -C 60 alkoxy group;

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, each 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 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 1 -C 60 heteroaryl 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 any 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 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each 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 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 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 1 -C 60 heteroaryl 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 any 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

any 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 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 unsubstituted or substituted with deuterium, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, or any 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 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 unsubstituted or substituted with deuterium, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, or any combination thereof; a 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 heteropolycyclic group.

2. The organometallic compound of claim 1 , wherein the organometallic compound represented by Formula 1-1 satisfies 2) or 5) and ΔST of the organometallic compound is in a range of about 0.1 electron volts (eV) to about 0.2 eV, and

ΔST indicates an energy gap between a singlet (S 1 ) energy level and a triplet (T 1 ) energy level of the organometallic compound.

3. The organometallic compound of claim 1 , wherein ΔST of the organometallic compound is in a range of about 0.13 electron volts (eV) to about 0.2 eV, and

ΔST indicates an energy gap between a singlet (S 1 ) energy level and a triplet (T 1 ) energy level of the organometallic compound.

4. The organometallic compound of claim 1 , wherein the organometallic compound represented by Formula 1-1 satisfies 2) or 5) and a horizontal orientation ratio of the organometallic compound is in a range of about 85 percent (%) or greater.

5. The organometallic compound of claim 1 , wherein the organometallic compound represented by Formula 1-1 satisfies 2) or 5) and a horizontal orientation ratio of the organometallic compound is in a range of about 85 percent (%) to about 95%.

6. The organometallic compound of claim 1 , wherein the organometallic compound represented by Formula 1-1 satisfies 2) or 5) and a sublimation temperature of the organometallic compound is in a range of about 200° C. to about 350° C.

7. The organometallic compound of claim 1 , wherein the organometallic compound satisfies Condition 11, and

L 42 is a benzene group, or a naphthalene group, each unsubstituted or substituted with at least one R 10a .

8. The organometallic compound of claim 1 , wherein the organometallic compound satisfies Condition 12, and

L 42 is a benzene group, or a naphthalene group, each unsubstituted or substituted with at least one R 10a .

9. The organometallic compound of claim 1 , wherein the organometallic compound satisfies Condition 11 or Condition 13, and

T 42 and R 7 are each independently a C 3 -C 10 cycloalkyl group unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 20 alkyl group, a deuterated C 1 -C 20 alkyl group, a fluorinated C 1 -C 20 alkyl group, a phenyl group, a (C 1 -C 20 alkyl)phenyl group, a deuterated phenyl group, a fluorinated phenyl group, or any combination thereof.

10. The organometallic compound of claim 1 , wherein the organometallic compound satisfies Condition 12, and

Q 41 to Q 43 in Formula 41 are each independently:

deuterium; or

a C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, a phenyl group, a biphenyl group or a naphthyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 20 alkyl group, a deuterated C 1 -C 20 alkyl group, a fluorinated C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, a (C 1 -C 20 alkyl) C 3 -C 10 cycloalkyl group, a deuterated C 3 -C 10 cycloalkyl group, a fluorinated C 3 -C 10 cycloalkyl group, or any combination thereof.

11. The organometallic compound of claim 1 , wherein the organometallic compound satisfies Condition 12, and

at least one of Q 41 to Q 43 in Formula 41 is a C 2 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, a phenyl group, a biphenyl group or a naphtyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 20 alkyl group, a deuterated C 1 -C 20 alkyl group, a fluorinated C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, a (C 1 -C 20 alkyl) C 3 -C 10 cycloalkyl group, a deuterated C 3 -C 10 cycloalkyl group, or a fluorinated C 3 -C 10 cycloalkyl group.

12. The organometallic compound of claim 1 , wherein X 51 in Formula 1-1 is N-[(L 7 ) b7 -(R 7 ) c7 ], and a group represented by *-[(L 7 ) b7 -(R 7 ) c7 ] is Formula N51:

wherein, in Formula N51,

ring CY 51 is a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group,

L 51 , b51, R 51 , and c51 are respectively understood by referring to the descriptions of L 7 , b7, R 7 , and c7 in claim 1 ,

R 52 and c52 are respectively understood by referring to the descriptions of R 7 and c7 in claim 1 ,

A 51 is a C 1 -C 60 alkyl group unsubstituted or substituted with a C 3 -C 10 cycloalkyl group,

A 52 is a deuterated C 1 -C 60 alkyl group unsubstituted or substituted with a C 3 -C 10 cycloalkyl group,

a51 and a52 are each independently an integer from 0 to 10, and a sum of a51 and a52 is 1 or greater,

a53 is an integer from 1 to 10, and

* indicates a binding site to an adjacent nitrogen atom.

13. The organometallic compound of claim 1 , wherein Z 32 in Formula 1-1 is C-[(L 32 ) b32 -(T 32 ) c32 ],

L 32 is a single bond, and

T 32 is a substituted or unsubstituted C 1 -C 60 alkyl group, or a substituted or unsubstituted C 6 -C 60 aryl group.

14. An organic light-emitting device comprising:

a first electrode;

a second electrode; and

an organic layer between the first electrode and the second electrode and comprising an emission layer and

at least one of the organometallic compound of claim 1 .

15. The organic light-emitting device of claim 14 , wherein the first electrode is an anode,

the second electrode is a cathode, and

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,

wherein the hole transport region comprises a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, and

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

16. The organic light-emitting device of claim 14 , wherein the emission layer comprises the organometallic compound.

17. The organic light-emitting device of claim 16 , wherein the emission layer further comprises a host in an amount greater than an amount of the organometallic compound.

18. An organic light-emitting device comprising,

a first electrode;

a second electrode; and

an organic layer between the first electrode and the second electrode and comprising an emission layer,

wherein the emission layer comprises an organometallic compound represented by Formula 1-1:

wherein, in Formula 1-1,

M is a transition metal,

X 1 is O, S, or N(R′″),

a bond between X 1 and M is a covalent bond,

X 2 to X 4 are Y 1 are each independently C or N,

one bond of a bond between X 2 and M, a bond between X 3 and M, and a bond between X 4 and M is a covalent bond, while the remaining bonds are each a coordinate bond,

X 51 is O, S, N-[(L 7 ) b7 -(R 7 ) c7 ], C(R 7 )(R 8 ), Si(R 7 )(R 8 ), Ge(R 7 )(R 8 ), or C(═O),

Z 11 is N or C-[(L 11 ) b11 -(T 11 ) c11 ], Z 12 is N or C-[(L 12 ) b12 -(T 12 ) c12 ], Z 13 is N or C-[(L 13 ) b13 -(T 13 ) c13 ], and Z 14 is N or C-[(L 14 ) b14 -(T 14 ) c14 ],

Z 21 is N or C-[(L 21 ) b21 -(T 21 ) c21 ], Z 22 is N or C-[(L 22 ) b22 -(T 22 ) c22 ], and Z 23 is N or C-[(L 23 ) b23 -(T 23 ) c23 ],

Z 31 is N or C-[(L 31 ) b31 -(T 31 ) c31 ], Z 32 is N or C-[(L 32 ) b32 -(T 32 ) c32 ], and Z 33 is N or C-[(L 33 ) b33 -(T 33 ) c33 ],

Z 41 is N or C-[(L 41 ) b41 -(T 41 ) c41 ], Z 42 is N or C-[(L 42 ) b42 -(T 42 ) c42 ], Z 43 is N or C-[(L 43 ) b43 -(T 43 ) c43 ], and Z 44 is N or C-[(L 44 ) b44 -(T 44 ) c44 ],

L 7 , L 11 to L 14 , L 21 to L 23 , L 31 to L 33 and L 41 to L 44 are each independently a single bond, a C 1 -C 10 alkylene group unsubstituted or substituted with at least one R 10a , a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,

b7, b11 to b14, b21 to b23, b31 to b33 and b41 to b44 are each independently 1, 2, 3, 4, or 5,

R′″, R 7 , R 8 , T 11 to T 14 , T 21 to T 23 , T 31 to T 33 and T 41 to T 44 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF 5 , a hydroxyl group, a cyano group, a nitro 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 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 1 -C 60 heteroaryl 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 ),

c7, c11 to c14, c21 to c23, c31 to c33 and c41 to c44 are each independently 1, 2, 3, 4, or 5,

wherein, the organometallic compound represented by Formula 1-1 satisfies,

1) one of Condition 11, Condition 12 and Condition 13,

2) Condition 11 and Condition 13, or

3) Condition 12 and Condition 13,

Z 42 in Formula 1-1 is C-[(L 42 ) b42 -(T 42 ) c42 ],  Condition 11

T 42 is 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, or a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, and

c42 is 1,

Z 42 in Formula 1-1 is C-[(L 42 ) b42 -(T 42 ) c42 ],  Condition 12

T 42 is a group represented by Formula 41, and

c42 is 1,

*—C(Q 41 )(Q 42 )(Q 43 )  Formula 41

wherein in Formula 41,

Q 41 to Q 43 are each independently deuterium, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 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 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,

at least one of Q 41 to Q 43 are each independently a substituted or unsubstituted C 2 -C 60 alkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, or a substituted or unsubstituted C 6 -C 60 aryl group, and

* indicates a binding site to an adjacent atom,

X 51 in Formula 1-1 is N-[(L 7 ) b7 -(R 7 ) c7 ],  Condition 13

L 7 is a benzene group, or a naphthalene group, each unsubstituted or substituted with at least one R 10a ,

R 7 is 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, or a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, and

c7 is 1,

each of i) at least two of T 11 to T 14 , ii) at least two of T 21 to T 23 , iii) at least two of T 31 to T 33 , iv) at least two of T 41 to T 44 and v) at least two of T 11 to T 14 , T 21 to T 23 , T 31 to T 33 , and T 41 to T 44 are optionally bound to each other to form a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,

R 10a may be understood by referring to the description of T 11 provided herein,

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 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 1 -C 60 heteroaryl 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 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, or a C 1 -C 60 alkoxy group,

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, each 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 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 1 -C 60 heteroaryl 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 any 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 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each 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 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 6 alkoxy 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, a 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, 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 any 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

any 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 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 unsubstituted or substituted with deuterium, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, or any 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 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 unsubstituted or substituted with deuterium, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, or any combination thereof; a 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 heteropolycyclic group,

wherein the emission layer comprises a host in an amount greater than an amount of the organometallic compound, and

wherein the host comprises an electron transporting host and a hole transporting host, and the electron transporting host is different from the hole transporting host.

19. The organic light-emitting device of claim 18 , wherein the electron transporting host comprises a triphenylene group and a triazine group, and the hole transporting host comprises a carbazole group.

20. An electronic apparatus comprising the organic light-emitting device of claim 14 .

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 24, 2025
From: SAMSUNG ELECTRONICS CO., LTD.
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 072945/0453 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 14, 2021
From: YI, JEOUNGIN; KANG, BYUNGJOON; KIM, SANGDONG; KIM, HYUNGJUN; LEE, YONG JOO; CHOI, BYOUNGKI; HONG, YOUNGKI; HWANG, KYUYOUNG
To: SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 055912/0607 →
Priority Claims (2)
KR 10-2020-0045374 · Apr 14, 2020 · national
KR 10-2021-0046891 · Apr 12, 2021 · national
Continuity (1)
Related Publication 20220102654A1 · Mar 31, 2022
References Cited (22)
US 20070032000A1 · Yeh · 2007 [cited by examiner]
US 20160240800A1 · Ma et al. · 2016 [cited by applicant]
US 20180114928A1 · Lee · 2018 [cited by examiner]
US 20190140192A1 · Cho et al. · 2019 [cited by applicant]
US 20200111977A1 · Choi et al. · 2020 [cited by applicant]
US 20200115406A1 · Yi et al. · 2020 [cited by applicant]
US 20210159431A1 · Lee et al. · 2021 [cited by applicant]
US 20230287024A1 · Lee et al. · 2023 [cited by applicant]
CN 107068888A · 2017 [cited by applicant]
EP 3508491A1 · 2019 [cited by applicant]
JP 2012079901A · 2012 [cited by applicant]
KR 1020180005128A · 2018 [cited by applicant]
KR 1020190052545A · 2019 [cited by applicant]
KR 20190083984A · 2019 [cited by applicant]
KR 1020200026093A · 2020 [cited by applicant]
KR 1020200040198A · 2020 [cited by applicant]
English Abstract of CN 107068888. [cited by applicant]
English Abstract of JP 2012-079901. [cited by applicant]
Extended European Search Report dated Sep. 10, 2021 issued in EP Patent Application No. 21167798.4. [cited by applicant]
Yafei Luo, Exploring the Photodeactivation Pathways of Pt[O [cited by applicant]
English Translation of Office Action dated Oct. 10, 2024, issued in corresponding KR Patent Application No. 10-2021-0046891, 11 pp. [cited by applicant]
Office Action dated Oct. 10, 2024, issued in corresponding KR Patent Application No. 10-2021-0046891, 8 pp. [cited by applicant]