US 11,744,143 B2
Organometallic compound, organic light-emitting device including the organometallic compound, and diagnostic composition including the organometallic compound
Yongsuk Cho, Hwaseong-si (KR); Sangdong Kim, Seoul (KR); Chui Baik, Suwon-si (KR); Hyun Koo, Seoul (KR); Ohyun Kwon, Seoul (KR); and Byoungki Choi, Hwaseong-si (KR)
Assigned to SAMSUNG ELECTRONICS CO., LTD., Gyeonggi-Do (KR)
Filed by SAMSUNG ELECTRONICS CO., LTD., Suwon-si (KR)
Filed on Aug. 9, 2017, as Appl. No. 15/672,621.
Claims priority of application No. 10-2016-0108379 (KR), filed on Aug. 25, 2016.
Prior Publication US 2018/0062088 A1, Mar. 1, 2018
Int. Cl. H10K 85/30 (2023.01); C07F 15/00 (2006.01); C09K 11/06 (2006.01); H05B 33/14 (2006.01); H10K 50/11 (2023.01); H10K 101/10 (2023.01); H10K 101/30 (2023.01)
CPC H10K 85/346 (2023.02) [C07F 15/0086 (2013.01); C09K 11/06 (2013.01); H05B 33/14 (2013.01); C09K 2211/1029 (2013.01); C09K 2211/185 (2013.01); H10K 50/11 (2023.02); H10K 2101/10 (2023.02); H10K 2101/30 (2023.02)] 7 Claims
 
1. An organometallic compound represented by one selected from Formulae 1-1 to 1-4:

OG Complex Work Unit Chemistry
wherein, in Formulae 1-1 to 1-4,
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),
X1 is O or X, and a bond between X1 and M is a covalent bond,
X11 is N or C(R11), X12 is N or C(R12), X13 is N or C(R13), X14 is N or C(R14),
X21 is N or C(R21), X22 is N or C(R22), and X23 is N or C(R23),
X31 is N or C(R31), X33 is N or C(R33), X34 is N or C(R34), X35 is N or C(R35), X36 is N or C(R36), and X37 is N or C(R37),
X39 is C(R39a)(R39b), N(R39), O, S, Se, or Si(R39a)(R39b),
X41 is N or C(R41), X42 is N or C(R42), X43 is N or C(R43), and X44 is N or C(R44), provided that the ring of Formulae 1-1 to 1-4 having the X41 to X44 groups is not a pyrimidine,
T1 to T3 are each independently selected from *—Si(R5)(R6)—*′, and *—Ge(R5)(R6)—*′, provided that R5 and R6 of *—Si(R5)(R6)—*′ are not simultaneously phenyl, R5 and R6 are linked to each other via a first linking group,
the first linking g coup is selected from a single bond, *—O—*′, *—S—*′, *—C(R9)(R10)—*′, *—C(R9)=*′, *═C(R9)—*′, *—C(R9)═C(R10)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—Si(R9)(R10)—*′, *—Ge(R9)(R10)—*′, *—B(R9)—*′, *—N(R9)—*′, and *—P(R9)—*′,
b1 to b3 are each independently 0, 1, 2, or 3, provided that the sum of b1 and b2 is at least 1, wherein when b1 is zero, *-(T1)b1-*′ is a single bond, when b2 is zero, *-(T2)b2-*′ is a single bond, and when b3 is zero, *-(T3)b3-*′ is a single bond,
R5, R6, R9, R10, R11 to R14, R21 to R23, R31, R33, R34 to R37, R39, R39a, R39b and R41 to R44 are each independently selected from
hydrogen, deuterium, —F, a cyano group, a nitro group, —SF5, a methyl group an ethyl croup, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a text-butyl group, an n-pentyl group, an iso-pentyl group, a sec-pentyl group, a tert-pentyl group an n-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-hexyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonyl group a sec-nonyl group, a tert-nonyl group, an n-decyl group, an iso-decyl group, a sec-decyl group, a tert-decyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;
a methyl group, an ethyl group, are n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an iso-decyl group, a sec-decyl group, a tert-decyl group, a methoxy group, an methoxy group, a propoxy group, a butoxy group, a pentoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from deuterium, —F, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a cyano group, a nitro group, a C1-C10 alkyl group, a C1-C10 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; and
N(Q1)(Q2), —Si(Q3)(Q4)(Q5), —B(Q6)(Q7), and —P(═O)(Q8)(Q9),
wherein Q1 to Q9 are each independently selected from;
—CH3, —CD3, —CD2H, —CDH2, —CH2CH3, —CH2CD3, —CH2CD2H, —CH2CDH2, —CHDCH3, —CHDCD2H, —CHDCDH2, —CHDCD3, —CD2CD3, —CD2CD2H, and —CD2CDH2;
an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group; and
an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an iso-pentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group, each substituted with at least one selected from deuterium, a C1-C10 alkyl group, and a phenyl group,
two of R11 to R14 may optionally be linked t each other to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group, provided that the condensed ring comprising the ring having the X11 to X14 groups and the C5-C30 carbocyclic group fromed by the R11 to R14 groups is not a naphthyl group,
two of R21 to R23 may optionally be linked to each other to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group,
two of R34 to R37 may optionally be linked to each other to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group, and
two of R41 to R44 may optionally be linked to each other to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group, provided that the condensed ring comprising the ring having the X41 to X44 groups and the C5-C30 carbocyclic group formed by the R41 to R44 groups is not a quinoline group,
* and *′ each indicate a binding site to a neighboring atom.