US 11,925,104 B2
Organometallic compound and organic light-emitting device including the same
Soobyung Ko, Yongin-si (KR); Sungbum Kim, Yongin-si (KR); Mina Jeon, 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. 15/868,949.
Claims priority of application No. 10-2017-0092947 (KR), filed on Jul. 21, 2017.
Prior Publication US 2019/0027699 A1, Jan. 24, 2019
Int. Cl. H10K 85/30 (2023.01); C07F 15/00 (2006.01); C09K 11/06 (2006.01); H10K 50/11 (2023.01); H10K 50/81 (2023.01); H10K 50/82 (2023.01); H10K 101/10 (2023.01)
CPC H10K 85/346 (2023.02) [C07F 15/0086 (2013.01); C09K 11/06 (2013.01); H10K 85/341 (2023.02); H10K 85/371 (2023.02); C09K 2211/1029 (2013.01); C09K 2211/1044 (2013.01); C09K 2211/1059 (2013.01); C09K 2211/185 (2013.01); C09K 2211/188 (2013.01); H10K 50/11 (2023.02); H10K 50/81 (2023.02); H10K 50/82 (2023.02); H10K 85/322 (2023.02); H10K 2101/10 (2023.02)] 19 Claims
OG exemplary drawing
 
1. An organic light-emitting device comprising:
a first electrode;
a second electrode; and
an organic layer disposed between the first electrode and the second electrode,
wherein the organic layer comprises an emission layer,
the emission layer comprises a phosphorescent dopant, and
the phosphorescent dopant comprises 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 selected from N, C, O, S, a single bond, a substituted or unsubstituted C5-C60 carbocyclic group, and a substituted or unsubstituted C1-C60 heterocyclic group,
Z12 is a substituted or unsubstituted C2 or C3 heterocyclic group,
a bond between the B atom and the O atom is a covalent bond,
a bond between the B atom and Z12 is a coordinate bond,
the B atom is coordinated with a C atom of Z12,
T11 to T14 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(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,
at least two of a12, a13, and a14 are each independently selected from 1, 2, and 3,
when a11 is zero, (L11)a11 is a single bond, when a12 is zero, A11 and A12 are not linked to each other, when a13 is zero, A12 and A13 are not linked to each other, and when a14 is zero, A13 and A14 are not linked to each other,
R11 to R14, R17, and R18 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,
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 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.