US 11,793,067 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 May 12, 2020, as Appl. No. 15/930,248.
Claims priority of application No. 10-2019-0094936 (KR), filed on Aug. 5, 2019.
Prior Publication US 2021/0043855 A1, Feb. 11, 2021
Int. Cl. C07F 15/00 (2006.01); H01L 51/00 (2006.01); H10K 85/30 (2023.01); C07F 1/08 (2006.01); C07F 1/10 (2006.01); C07F 1/12 (2006.01); H10K 50/12 (2023.01); H10K 30/30 (2023.01); H10K 50/15 (2023.01); H10K 50/16 (2023.01); H10K 50/17 (2023.01)
CPC H10K 85/346 (2023.02) [C07F 1/08 (2013.01); C07F 1/10 (2013.01); C07F 1/12 (2013.01); C07F 15/002 (2013.01); C07F 15/006 (2013.01); C07F 15/0033 (2013.01); C07F 15/0046 (2013.01); C07F 15/0073 (2013.01); C07F 15/0086 (2013.01); H10K 50/12 (2023.02); H10K 30/353 (2023.02); H10K 50/15 (2023.02); H10K 50/16 (2023.02); H10K 50/171 (2023.02)] 17 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 Pt, Pd, Cu, Ag, Au, Rh, Ir, Ru, and Os,
Y1 to Y8 are each independently selected from a carbon atom (C) and a nitrogen atom (N),
T1 to T8 are each independently a chemical bond, wherein, when T1 is the chemical bond, Y1 and M1 are directly linked to each other, when T2 is the chemical bond, Y2 and M1 are directly linked to each other, when T3 is the chemical bond, Y3 and M1 are directly linked to each other, when T4 is the chemical bond, Y4 and M1 are directly linked to each other, when T5 is the chemical bond, Y5 and M2 are directly linked to each other, when T6 is the chemical bond, Y6 and M2 are directly linked to each other, when T7 is the chemical bond, Y7 and M2 are directly linked to each other, and when T8 is the 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, ring A2, ring A5, and ring A6 are each independently a 5-membered ring containing two nitrogen (N) atoms,
ring A9 is a phenyl group,
ring A3, ring A4, ring A7, and ring A8 are each independently a 6-membered ring optionally containing one nitrogen (N) atom,
X1 to X4 are each independently O or S,
L1 to L6 are each independently a single bond,
a1 to a6 are each independently selected from 0 and 1, wherein at least two of a1 to a3 are each independently 1, and at least two of a4 to a6 are each independently 1,
when a1 is 0, A1 and A2 are not linked to each other, when a2 is 0, A2 and A3 are not linked to each other, and when a3 is 0, A1 and A4 are not linked to each other,
when a4 is 0, A5 and A6 are not linked to each other, when a5 is 0, A6 and A7 are not linked to each other, and when a6 is 0, A5 and A8 are not linked to each other,
R1 to R9 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 C1-C20 alkyl group, and a C1-C20 alkoxy group;
a C1-C20 alkyl group and a C1-C20 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 C1-C20 alkyl group, and a C1-C20 alkoxy group;
a cyclopentyl group, a cyclohexyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a pyrrolyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, and a triazinyl group; and
a cyclopentyl group, a cyclohexyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, and a triazinyl 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 C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, and a triazinyl group, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), and —P(═O)(Q31)(Q32); and
—Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), and —P(═O)(Q1)(Q2),
b1 to b9 are each independently an integer from 0 to 20,
two substituents selected from R1 to R9 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 amidino 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 amidino 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.