US 12,096,680 B2
Organometallic compound and organic light-emitting device including the same
Mina Jeon, Yongin-si (KR); Soobyung Ko, Yongin-si (KR); Sungbum Kim, Yongin-si (KR); Heechoon Ahn, Yongin-si (KR); Mieun Jun, 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 Jan. 11, 2018, as Appl. No. 15/868,386.
Claims priority of application No. 10-2017-0089664 (KR), filed on Jul. 14, 2017.
Prior Publication US 2019/0019964 A1, Jan. 17, 2019
Int. Cl. C07F 15/00 (2006.01); C09K 11/06 (2006.01); H10K 50/11 (2023.01); H10K 50/12 (2023.01); H10K 50/81 (2023.01); H10K 50/82 (2023.01); H10K 85/00 (2023.01); H10K 85/30 (2023.01); H10K 85/40 (2023.01); H10K 85/60 (2023.01); H10K 101/00 (2023.01); H10K 101/10 (2023.01)
CPC H10K 85/346 (2023.02) [C07F 15/0086 (2013.01); C09K 11/06 (2013.01); H10K 85/322 (2023.02); H10K 85/361 (2023.02); C09K 2211/1029 (2013.01); C09K 2211/1044 (2013.01); C09K 2211/1059 (2013.01); C09K 2211/1088 (2013.01); C09K 2211/1092 (2013.01); C09K 2211/1096 (2013.01); C09K 2211/185 (2013.01); H10K 50/11 (2023.02); H10K 50/81 (2023.02); H10K 50/82 (2023.02); H10K 85/40 (2023.02); H10K 2101/10 (2023.02); H10K 2101/27 (2023.02); H10K 2101/90 (2023.02)] 17 Claims
OG exemplary drawing
 
1. An organometallic compound represented by Formula 1:

OG Complex Work Unit Chemistry
wherein, in Formula 1,
M11 is selected from platinum (Pt), palladium (Pd), copper (Cu), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm),
A11 to A14 are each independently a C5-C60 carbocyclic group or a C1-C60 heterocyclic group,
Y11 to Y14 are each independently N or C,
Z11 is N or B,
Ar1 is a group represented by one selected from Formulae 40A, 40B, 41A, and 41B, wherein Ar1 is bonded to Z11 at least at X41 or X48 position:

OG Complex Work Unit Chemistry
and
wherein the Formulae 40A, 40B, 41A and 41B,
L41 is selected from *—O—*′, *—S—*′, *—C(R43)(R44)−*′, *—B(R43)—*′, and *N(R43)—′,
provided that when L41 is *—C(R43)(R44)—*′, or *—N(R43)—*′, R43 and R44 are not a phenyl group,
a41 is selected rom 1,2, and 3,
X41 to X48 are each independently C or N, and at least one of X41 and X48 is C, wherein when X41 or X48 correspond to a position at which Ar1 is bonded to Z11, then the corresponding X41 or X48 is C,
R41 to R44 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 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 group, a substituted or unsubstituted C1-C10 heterocyloalkyl 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, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,
wherein when a plurality of adjacent R41 are linked, and/or when a plurality of adjacent R42 are linked, the plurality of adjacent R41 and the plurality of adjacent R42 each independently form a group selected from:
a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, and a triazine group; and
a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, and a triazine 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 C6-C60 aryl group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group,
provided that in Formulae 40B and 41B, at least two R41 or at least two R42 are linked,
b41 and b42 are each independently selected from 1, 2, 3, and 4, and
one selected from R41 and R42 is a binding site to Formula 1,
T11 to T14 are each independently selected from a single bond, O, and S,
L11 to L13 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)—*′, and
a11 to a13 are each independently selected from 0, 1, 2, and 3, and
wherein 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; and when a13 is 0, A13 and A14 are not linked to each other,
R11 to R16 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),
provided that, when Y12 is N, R12 is not —Si(Q1)(Q2)(Q3), and
when Y13 is N, R13 is not —Si(Q1)(Q2)(Q3),
R15 and R11, R15 and R12, R15 and R13, and R15 and R14 are each independently optionally linked to form a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C1-C60 heterocyclic group, R15 and R16 are optionally linked to form a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C1-C60 heterocyclic group,
b11 to b14 are each independently selected from 1, 2, 3, 4, 5, 6, 7, and 8,
Q1 to Q3 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-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group, and
and *′ each indicate a binding site to a neighboring atom.