US 12,035,615 B2
Organic light-emitting device, apparatus including the same, and organometallic compound
Myeongsuk Kim, Yongin-si (KR); Byeongwook Yoo, Yongin-si (KR); Jimyoung Ye, Yongin-si (KR); Illhun Cho, Yongin-si (KR); Sunjae Kim, Goyang-si (KR); and Jaeho Jeong, Incheon (KR)
Assigned to Samsung Display Co., Ltd., Yongin-si (KR)
Filed by SAMSUNG DISPLAY CO., LTD., Yongin-si (KR)
Filed on Jun. 19, 2019, as Appl. No. 16/446,405.
Claims priority of application No. 10-2018-0161188 (KR), filed on Dec. 13, 2018.
Prior Publication US 2020/0194693 A1, Jun. 18, 2020
Int. Cl. H10K 85/30 (2023.01); C07F 15/00 (2006.01); C09K 11/06 (2006.01); H10K 50/11 (2023.01); H10K 50/15 (2023.01); H10K 50/16 (2023.01); H10K 50/17 (2023.01); H10K 50/18 (2023.01); H10K 101/10 (2023.01)
CPC H10K 85/346 (2023.02) [C07F 15/0086 (2013.01); C09K 11/06 (2013.01); C09K 2211/1029 (2013.01); C09K 2211/1044 (2013.01); C09K 2211/185 (2013.01); H10K 50/11 (2023.02); H10K 50/15 (2023.02); H10K 50/16 (2023.02); H10K 50/17 (2023.02); H10K 50/171 (2023.02); H10K 50/18 (2023.02); H10K 2101/10 (2023.02)] 18 Claims
OG exemplary drawing
 
1. 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 organic layer comprises an organometallic compound represented by Formula 1:
M1(L1)n1(L2)n2  Formula 1
Formula 1-1

OG Complex Work Unit Chemistry
Formula 2

OG Complex Work Unit Chemistry
Formula 3

OG Complex Work Unit Chemistry
wherein, in Formulae 1, 1-1, 2, and 3,
M1 is selected from a first-row transition metal, a second-row transition metal, and a third-row transition metal of the Periodic Table of Elements,
*1 to *4 each indicate a binding site to M1,
L1 is a ligand represented by Formula 1-1,
L2 is selected from a monodentate ligand and a bidentate ligand,
n1 is 1,
n2 is selected from 0, 1, and 2,
A12 is selected from a group represented by Formula 2, a group represented by Formula 3, a C5-C60 carbocyclic group, and a C1-C60 heterocyclic group,
A13 is a group represented by Formula 3,
A14 is selected from a quinoxaline group, and a phenazine group,
Y11 is N,
Y12 to Y14 are each independently selected from N and C,
T11 to T14 are each independently selected from a single bond, *—O—*′, *—S—*′, *—C(R15)(R16)—*′, *—N(R15)—*′, and *—P(R15)—*′,
L11 to L14 are each independently selected from a single bond, *—O—*′, *—S—*′, *—C(R17)(R18)—*′, *—C(R17)═*′, *═C(R17)—*′, *—C(R17)═C(R18)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R17)—*′, *—N(R17)—*′, *—P(R17)—*′, *—Si(R17)(R18)—*′, *—P(R17)(R18)—*′, and *—Ge(R17)(R18)—*′,
a11 to a14 are each independently selected from 0, 1, 2, and 3, wherein at least three selected from a11 to a14 are selected from 1, 2, and 3,
when a11 is 0, A11 and A12 are not linked, when a12 is 0, A12 and A13 are not linked, when a13 is 0, A13 and A14 are not linked, and when a14 is 0, A14 and A11 are not linked,
X21 is N, N—*, C—*, or C(R21), X22 is N, N—*, C—*, or C(R22), X23 is N, N—*, C—*, or C(R23), X24 is N, N—*, C—*, or C(R24), and X25 is N or N—*,
X31 is N, N—*, C—*, or C(R31), X32 is N, N—*, C—*, or C(R32), X33 is N, N—*, C—*, or C(R33), X34 is N, N—*, C—*, or C(R34), X35 is N, N—*, C—*, or C(R35), and X36 is N, N—*, C—*, or C(R36),
R11 to R18, R21 to R24, and R31 to R36 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),
R17 and R11, R17 and R12, R17 and R13, and/or R17 and R14 are optionally linked to form a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C1-C60 heterocyclic group,
R17 and R18 are optionally linked to form a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C1-C60 heterocyclic group,
R21 to R24 are optionally linked to form a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C1-C60 heterocyclic group,
R31 to R36 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 *′ each indicate a binding site to a neighboring atom,
wherein A11 is represented by one selected from Formulae 2-1 to 2-7:

OG Complex Work Unit Chemistry
wherein, in Formulae 2-1 to 2-7,
X22 to X24 are each independently the same as described with respect to Formula 2,
R25 to R27 are each independently the same as described in connection with R21 in Formula 2,
R25 to R27 are optionally linked to form a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C1-C60 heterocyclic group,
b25 to b27 are each independently selected from 1, 2, 3, 4, 5, 6, 7, and 8,
A21 to A23 are each independently selected from a benzene group, a naphthalene group, a phenalene group, an anthracene group, a pyrene group, a chrysene group, and a triphenylene group,
* indicates a binding site to a neighboring atom, and
wherein the organometallic compound emits red light or near-infrared light having a maximum emission wavelength of about 720 nm or more and about 2,500 nm or less.