US 12,457,894 B2
Organometallic compound and organic light-emitting device including the same
Sungbum Kim, Yongin-si (KR); Soobyung Ko, Yongin-si (KR); Junha Park, Yongin-si (KR); Munki Sim, Yongin-si (KR); Heechoon Ahn, Yongin-si (KR); Hyoyoung Lee, Yongin-si (KR); Mina Jeon, Yongin-si (KR); Mieun Jun, Yongin-si (KR); Junghoon Han, Yongin-si (KR); Youngkook Kim, Yongin-si (KR); and Seokhwan Hwang, Yongin-si (KR)
Assigned to Samsung Display Co., Ltd., Yongin-si (KR)
Filed by Samsung Display Co., Ltd., Yongin-si (KR)
Filed on Nov. 28, 2018, as Appl. No. 16/203,554.
Claims priority of application No. 10-2018-0028303 (KR), filed on Mar. 9, 2018.
Prior Publication US 2019/0280222 A1, Sep. 12, 2019
Int. Cl. C07F 1/08 (2006.01); C07F 1/10 (2006.01); C07F 1/12 (2006.01); C07F 15/00 (2006.01); C09K 11/06 (2006.01); H10K 50/11 (2023.01); H10K 50/12 (2023.01); H10K 50/15 (2023.01); H10K 85/30 (2023.01); H10K 85/40 (2023.01); H10K 101/00 (2023.01); H10K 101/10 (2023.01)
CPC H10K 85/346 (2023.02) [C07F 1/08 (2013.01); C07F 1/10 (2013.01); C07F 1/12 (2013.01); C07F 15/006 (2013.01); C07F 15/0086 (2013.01); H10K 85/371 (2023.02); H10K 50/11 (2023.02); H10K 2101/10 (2023.02); H10K 2101/90 (2023.02)] 20 Claims
OG exemplary drawing
 
1. An organic light-emitting device comprising:
a first electrode;
a second electrode facing the first electrode; and
an organic layer between the first electrode and the second electrode and comprising an emission layer,
wherein the organic layer further comprises at least one of an organometallic compound represented by Formula 2:

OG Complex Work Unit Chemistry
wherein, in Formula Formulae 2,
M11 is selected from platinum (Pt), palladium (Pd), copper (Cu), zinc (Zn), silver (Ag), gold (Au), rhenium (Re), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), and europium (Eu),
A11 to A13 are each independently selected from a C5-C60 carbocyclic group and a C1-C60 heterocyclic group,
Y11 to Y13 are each independently selected from a carbon atom (C) and a nitrogen atom (N),
B11 to B14 are each independently selected from a single bond, O, and S,
L11 to L14 are each independently selected from a single bond, *—O—*′, *—S—*′, *—C(R15)(R16)—*′, *—C(R15)═*′, *═C(R15)—*′, *—C(R15)═C(R16)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R15)—*′, *—N(R15)—*′, *—P(R15)—*′, *—Si(R15)(R16)—*, *—P(R15)(R16)—*, and *—Ge(R15)(R16)—*′,
a13 is an integer from 1 to 3,
in Formula 2, a11, a12, and a14 are each independently an integer from 0 to 3, wherein at least two selected from among a11, a12, and a14 are each independently an integer from 1 to 3,
when a11 is 0, A11 and A12 are not linked to each other, when a12 is 0, A12 and A13 are not linked to each other, when a14 is 0, A11 and X19 in Formula 2 are not linked to each other,
X11 is N or C(R14),
X16 is C(R21)(R22), X17 is C(R23)(R24), and X18 is C(R25)(R26),
X19 is C(R27)(R28) when a14 is 0, and X19 is C(R27) when a14 is not 0,
R11 to R16 and R21 to R28 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 C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio 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),
R15 and R11, R15 and R12, and/or R15 and R13 are optionally linked to form a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C1-C60 heterocyclic group,
b11 to b13 are each independently an integer from 1 to 8,
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 C1-C60 heteroaryloxy group, the substituted C1-C60 heteroarylthio 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-Coo 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 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-Coo aryl group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C1-C60 alkyl group substituted with at least one selected from deuterium, —F, and a cyano group, a C6-C60 aryl group substituted with at least one selected from deuterium, —F, and a cyano group, a biphenyl group, and a terphenyl group, and
*, *′, and *″ each indicate a binding site to a neighboring atom.