US 12,144,241 B2
Organometallic compound, organic light-emitting device including the organometallic compound, and diagnostic composition including the organometallic compound
Sunyoung Lee, Seoul (KR); Hyun Koo, Seongnam-si (KR); Soyeon Kim, Seoul (KR); Jungin Lee, Seoul (KR); Hyeonho Choi, Seoul (KR); Kyuyoung Hwang, Anyang-si (KR); Yoonhyun Kwak, Seoul (KR); and Ohyun Kwon, Seoul (KR)
Assigned to SAMSUNG ELECTRONICS CO., LTD., Gyeonggi-Do (KR)
Filed by Samsung Electronics Co., Ltd., Suwon-si (KR)
Filed on Sep. 4, 2018, as Appl. No. 16/120,961.
Claims priority of application No. 10-2017-0113559 (KR), filed on Sep. 5, 2017; and application No. 10-2018-0104723 (KR), filed on Sep. 3, 2018.
Prior Publication US 2019/0074458 A1, Mar. 7, 2019
Int. Cl. H10K 85/30 (2023.01); A61K 33/24 (2019.01); A61K 33/242 (2019.01); A61K 33/243 (2019.01); C07F 15/00 (2006.01); C09K 11/06 (2006.01); H10K 50/00 (2023.01); 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) [A61K 33/24 (2013.01); A61K 33/242 (2019.01); A61K 33/243 (2019.01); C07F 15/0086 (2013.01); C09K 11/06 (2013.01); H10K 50/00 (2023.02); 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)] 20 Claims
OG exemplary drawing
 
1. An organometallic compound represented by Formula 1:

OG Complex Work Unit Chemistry
wherein, in Formula 1,
M is beryllium (Be), magnesium (Mg), aluminum (Al), calcium (Ca), titanium (Ti), manganese (Mn), cobalt (Co), copper (Cu), zinc (Zn), gallium (Ga), germanium (Ge), zirconium (Zr), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), rhenium (Re), platinum (Pt), or gold (Au),
in Formula 1, two bonds selected from a bond between A1 or X5 and M, a bond between A2 or X6 and M, a bond between A3 or X7 and M, and a bond between A4 or X8 and M are each a covalent bond, and the others thereof are each a coordinate bond,
provided that (i) M forms a covalent bond to oxygen and a covalent bond to carbon, (ii) M forms a covalent bond to oxygen and a covalent bond to nitrogen, (iii) M forms a covalent bond to nitrogen and a covalent bond to carbon, wherein A1 comprises a carbazole group, or (iv) M forms two covalent bonds to nitrogens, wherein A1 comprises a carbazole group,
in Formula 1, A1 is a ring represented by Formula A1-1, and in Formula A1-1, * indicates a binding site to X5 in Formula 1, *′ indicates a binding site to Tin Formula 1, and *″ indicates a binding site to T4 in Formula 1,
in Formula 1, A2 is a ring represented by one selected from Formulae A2-1 to A2-3, and in Formulae A2-1 to A2-3, * indicates a binding site to X6 in Formula 1, *′ indicates a binding site to T1 in Formula 1, and *″ indicates a binding site to T2 in Formula 1,
in Formula 1, A3 is a ring represented by Formula A3-1, and in Formula A3-1, * indicates a binding site to X7 in Formula 1, *″ indicates a binding site to T2 in Formula 1, and *′ indicates a binding site to T3 in Formula 1,
in Formula 1, A4 is a first atom linked to X8 or M, a non-cyclic moiety comprising the first atom linked to X8 or M, or a ring represented by Formula A4-1, and in Formula A4-1, * indicates a binding site to X8 in Formula 1, *′ indicates a binding site to T3 in Formula 1, and *″ indicates a binding site to T4 in Formula 1,
the first atom is B, P, N, C, Si, O, or S,
in Formulae A1-1, A2-1 to A2-3, A3-1, and A4-1,
X1, X3, X4, and X51 to X54 are each independently N or C, wherein at least one of X51 and X54 is N,
X2 is N,
X52a and X53a are each independently N or C(R′),
ring CY1 to ring CY4 are each independently selected from a C5-C30 carbocyclic group and a C1-C30 heterocyclic group,
ring CY5 is a C1-C3 heterocyclic group,
in Formula 1, X5 to X8 are each independently selected from a single bond, O, S, B(R5), N(R5), P(R5), C(R5)(R6), Si(R5)(R6), Ge(R5)(R6), C(═O), B(R5)(R6), N(R5)(R6), or P(R5)(R6),
T1, T3, and T4 are each independently selected from a single bond, a double bond, *—N(R7)—*′, *—B(R7)—*′, *—P(R7)—*′, *—C(R7)(R8)—*′, *—Si(R7)(R8)—*′, *—Ge(R7)(R8)—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)2—*′, *—C(R7)═*′, *═C(R7)—*′, *—C(R7)═C(R8)—*′, *—C(═S)—*′, and *—C≡C—*′, and * and *′ each indicate a binding site to a neighboring atom,
T2 is selected from a single bond, a double bond, *—N(R7)—*′, *—B(R7)—*′, *—P(R7)—*′, *—C(R7)(R8)—*′, *—Si(R7)(R8)—*′, *—Ge(R7)(R8)—*′, *—S—*′, *—Se—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)2—*′, *—C(R7)═*′, *═C(R7)—*′, *—C(R7)═C(R8)—*′, *—C(═S)—*′, and *—C≡C—*′, and * and *′ each indicate a binding site to a neighboring atom,
at least one of T1 to T4 is a direct C≡C bond,
R7 and R5 are optionally linked via a single bond, a double bond, or a first linking group to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group,
provided that T2 is a single bond when ring CY1 is a six-membered ring,
n is 0 or 1, wherein, when n is 0, T4 does not exist and CY1 and CY4 are not linked,
R1 to R8 and R′ are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, 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 monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q3)(Q4)(Q5), —B(Q6)(Q7), and —P(═O)(Q8)(Q9),
a1 to a4 are each independently 0, 1, 2, 3, 4, or 5,
at least two neighboring groups selected from R1 to R8 and R′ are optionally linked to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group,
at least one substituent of the substituted C5-C30 carbocyclic group, the substituted C1-C30 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, —CD3, —CD2H, —CDH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, 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, —CD3, —CD2H, —CDH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, 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, —N(Q11)(Q12), —Si(Q13)(Q14)(Q15), —B(Q16)(Q17), and —P(═O) (Q18)(Q19);
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, —CD3, —CD2H, —CDH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, 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, —N(Q21)(Q22), —Si(Q23)(Q24)(Q25), —B(Q26)(Q27), and —P(═O)(Q28)(Q29); and
—N(Q31)(Q32), —Si(Q33)(Q34)(Q35), —B(Q36)(Q37), and —P(═O)(Q38)(Q39), and
Q3 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, 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 is heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, C6-C60 aryl group, a C6-C60 aryl group substituted with at least one selected from a C1-C60 alkyl group and 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.