US 12,075,693 B2
Organometallic compound and organic light-emitting device including the same
Jaesung Lee, Yongin-si (KR); Sungbum Kim, Yongin-si (KR); Soobyung Ko, Yongin-si (KR); Haejin Kim, Yongin-si (KR); Sujin Shin, Yongin-si (KR); Eunsoo Ahn, Yongin-si (KR); Eunyoung Lee, Yongin-si (KR); Hyunjung Lee, Yongin-si (KR); Mina Jeon, Yongin-si (KR); and Junghoon Han, Yongin-si (KR)
Assigned to Samsung Display Co., Ltd., Yongin-si (KR)
Filed by Samsung Display Co., Ltd., Yongin-si (KR)
Filed on Jul. 13, 2020, as Appl. No. 16/927,381.
Claims priority of application No. 10-2019-0092659 (KR), filed on Jul. 30, 2019.
Prior Publication US 2021/0036228 A1, Feb. 4, 2021
Int. Cl. H10K 85/30 (2023.01); C07F 15/00 (2006.01); C09K 11/06 (2006.01); H10K 50/11 (2023.01); H10K 101/10 (2023.01)
CPC H10K 85/361 (2023.02) [C07F 15/0086 (2013.01); C09K 11/06 (2013.01); H10K 85/322 (2023.02); H10K 85/346 (2023.02); C09K 2211/1022 (2013.01); C09K 2211/1048 (2013.01); C09K 2211/185 (2013.01); H10K 50/11 (2023.02); H10K 2101/10 (2023.02)] 20 Claims
 
1. An organic light-emitting device comprising:
a first electrode;
a second electrode;
an organic layer between the first electrode and the second electrode and comprising an emission layer; and
at least one organometallic compound represented by Formula 1:

OG Complex Work Unit Chemistry
wherein, in Formula 1, M1 and M2 are each independently selected from a first-row transition metal, a second-row transition metal, and a third-row transition metal of the Periodic Table of Elements,
Y1 to Y8 are each independently selected from a carbon atom (C) and a nitrogen atom (N),
T1 to T8 are each independently selected from a chemical bond, O, S, B(R′), N(R′), P(R′), C(R′)(R″), Si(R′)(R″), Ge(R′)(R″), C(═O), B(R′)(R″), N(R′)(R″), and P(R′)(R″), wherein, when T1 is a chemical bond, Y1 and M1 are directly linked to each other, when T2 is a chemical bond, Y2 and M1 are directly linked to each other, when T3 is a chemical bond, Y3 and M1 are directly linked to each other, when T4 is a chemical bond, Y4 and M1 are directly linked to each other, when T5 is a chemical bond, Y5 and M2 are directly linked to each other, when T6 is a chemical bond, Y6 and M2 are directly linked to each other, when T7 is a chemical bond, Y7 and M2 are directly linked to each other, and when T8 is a chemical bond, Y8 and M2 are directly linked to each other,
two bonds selected from a bond between Y1 or T1 and M1, a bond between Y2 or T2 and M1, a bond between Y3 or T3 and M1, and a bond between Y4 or T4 and M1 are each a coordinate bond, and the other two bonds are each a covalent bond; and two bonds selected from a bond between Y5 or T5 and M2, a bond between Y6 or T6 and M2, a bond between Y7 or T7 and M2, and a bond between Y8 or T8 and M2 are each a coordinate bond, and the other two bonds are each a covalent bond,
ring A1 is selected from a cyclopentadiene group, a furan group, a thiophene group, and a pyrrole group,
ring A2 to ring A9 are each independently selected from a C5-C60 carbocyclic group and a C1-C60 heterocyclic group,
X1 to X4 are each independently O or S,
L1 to L5 are each independently selected from a single bond, *—O—*′, *—S—*′, *—C(R10)(R11)—*′, *—C(R10)=*′, *═C(R10)—*′, *—C(R10)═C*(R11)*′, *—C(═O)—*′, *—C(═S)—*′, *—B(R10)—*′, *—N(R10)—*′, *—P(R10)(R11)—*′, and *—Ge(R10)(R11)—*′,
a1 to a3 are each independently selected from 0, 1, 2, and 3, wherein at least two of a1 to a3 are each independently selected from 1, 2, and 3,
when a1 is 0, rings A1 and A2 are not linked to each other, when a2 is 0, rings A2 and A3 are not linked to each other, and when a3 is 0, rings A1 and A4 are not linked to each other,
a4 and a5 are each independently selected from 1, 2, and 3,
R′, R″, and R1 to R11 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q1)(Q2)(Q3), —B(Q1)(Q2), —N(Q1)(Q2), —P(Q1)(Q2), —C(═O)(Q1), —S(═O)(Q1), —S(═O)2(Q1), —P(═O)(Q1)(Q2), and —P(═S)(Q1)(Q2),
b1 to b9 are each independently an integer from 1 to 20,
any two substituents selected from R1 to R11 are optionally linked to each other to form a substituted or unsubstituted C5-C60 carbocyclic group and/or a substituted or unsubstituted C1-C60 heterocyclic group,
at least one substituent of the substituted C5-C60 carbocyclic group, the substituted C1-C60 heterocyclic group, the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C1-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), and —P(═O)(Q11)(Q12);
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an am idino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), and —P(═O)(Q21)(Q22); and
—Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), and —P(═O)(Q31)(Q32),
Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an am idino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a heterocycloalkenyl group, a C6-C60 aryl group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group,
* and *′ each indicate a binding site to a neighboring atom, and
B indicates a boron atom, and O indicates an oxygen atom.