US 11,667,659 B2
Organometallic compound and organic light-emitting device including the same
Sunwoo Kang, Yongin-si (KR); Soobyung Ko, Yongin-si (KR); Taekyung Kim, Yongin-si (KR); Sangho Jeon, Yongin-si (KR); and Youngmi Cho, Yongin-si (KR)
Assigned to Samsung Display Co., Ltd., Yongin-si (KR)
Filed by SAMSUNG DISPLAY CO., LTD., Yongin-si (KR)
Filed on Apr. 19, 2019, as Appl. No. 16/389,289.
Claims priority of application No. 10-2018-0046291 (KR), filed on Apr. 20, 2018.
Prior Publication US 2019/0322689 A1, Oct. 24, 2019
Int. Cl. H01L 51/00 (2006.01); C07F 15/00 (2006.01); H01L 51/50 (2006.01)
CPC C07F 15/0033 (2013.01) [H01L 51/0085 (2013.01); H01L 51/5096 (2013.01); H01L 51/5016 (2013.01)] 18 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 including an emission layer,
wherein the organic layer includes an organometallic compound,
wherein the organometallic compound includes a hexadentate ligand bonded to a metal atom (M1), and an energy level (E3Mc) of a 3MC (triplet metal centered state) of the organometallic compound is higher than an energy level (E3MLCT) of a 3MLCT (triplet metal-to-ligand charge transfer state) of the organometallic compound, and
wherein the organometallic compound is represented by Formula 1:

OG Complex Work Unit Chemistry
wherein, in Formulae 1, 2A, and 2B,
M1 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),
A1 to A6 are each independently selected from a C5-C60 carbocyclic group and a C1-C60 heterocyclic group,
L1 to L6 are each independently selected from a single bond, *—O—*′, *—C(R1)(R2)—*′, *—C(R1)═*′, *═C(R1)—*′, *—C(R1)═C(R2)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C *′, *—N(R1)—*′, *—P(R1)—*1, *—Si(R1)(R2)—*′, *—P(R1)(R2)—*′, and *—Ge(R1)(R2)—*′,
a1, a3, and a5 are each independently selected from 1, 2, and 3,
a2, a4, and a6 are each independently selected from 0, 1, 2, and 3,
when a2 is 0, A2 and A3 are not linked,
when a4 is 0, A4 and A5 are not linked,
when a6 is 0, A6 and A1 are not linked,
Y1 to Y6 are each C,
T1 to T6 are each independently selected from a single bond, *—O—*′, and *—S—*′,
A1, A3, and A5 are linked via a clipping linker represented by Formula 2A, or 2B,
X1 is linked to X10 in Formula 2A, or 2B,
X2 is linked to X20 in Formula 2A, or 2B,
X3 is linked to X30 in Formula 2A, or 2B,
Y10, Y20, and Y30, are each independently N or C(R3), and when Y10, Y20, and Y30 are each C(R3), A1, A3, and A5 is a 5-membered heterocyclic group; or a C1-C60 condensed heteropolycyclic group including a 5-membered heterocyclic group,
Y40 is N,
L10, L20, and L30 are each independently selected from a single bond, *—O—*′, *—S—*′, *—C(R4)(R5)—*′, *—C(R4)═*′, *═C(R4)—*′, *—C(R4)═C(R5)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R4)—*′, *—N(R4)—*′, *—P(R4)—*′, *—Si(R4)(R5)—*′, *—P(R4)(R5)—*′, and *—Ge(R4)(R5)—*′,
a10, a20, and a30 are each independently selected from 0, 1, 2, 3, 4, and 5,
R1 to R5, R20, R30, R40, R50, and R60 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 hetero aryloxy group, a substituted or unsubstituted C1-C60 hetero arylthio 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),
R10 is 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, an 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 hetero aryloxy group, a substituted or unsubstituted C1-C60 hetero arylthio 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),
when A1, A3, and A5 are linked via a clipping linker represented by Formula 2B, R30 and R50 are each independently selected from —F, —Cl, —Br, —I, a cyano group, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C1-C60 heteroaryl group, and Rio is selected from —F, —Cl, —Br, —I, a cyano group, an unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C1-C60 heteroaryl group,
R1 and R20, R1 and R30, R1 and R40, R1 and R50, or R1 and R60 are optionally linked to form a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C1-C60 heterocyclic group,
R1 and R10 are optionally linked to form an unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C1-C60 heterocyclic group,
b10, b20, b30, b40, b50, and b60 are each independently selected from 1, 2, 3, 4, 5, 6, 7, and 8,
*and *′each indicate a binding site to a neighboring atom,
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), and
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-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C1-C60 hetero aryloxy group, a C1-C60 hetero arylthio 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.