US 11,844,266 B2
Organometallic compound and organic light-emitting device including the same
Minsik Min, Suwon-si (KR); Sangmo Kim, Hwaseong-si (KR); Hosuk Kang, Suwon-si (KR); Wook Kim, Suwon-si (KR); Sungho Nam, Daegu (KR); Hyejin Bae, Suwon-si (KR); Jhunmo Son, Yongin-si (KR); Yongsik Jung, Seoul (KR); and Jun Chwae, Suwon-si (KR)
Assigned to SAMSUNG ELECTRONICS CO., LTD., Gyeonggi-Do (KR); and SAMSUNG SDI CO., LTD, Gyeonggi-Do (KR)
Filed by Samsung Electronics Co., Ltd., Suwon-si (KR); and SAMSUNG SDI CO., LTD., Yongin-si (KR)
Filed on Jan. 23, 2020, as Appl. No. 16/750,214.
Claims priority of application No. 10-2019-0012817 (KR), filed on Jan. 31, 2019; and application No. 10-2020-0008761 (KR), filed on Jan. 22, 2020.
Prior Publication US 2020/0280003 A1, Sep. 3, 2020
Int. Cl. H01L 51/54 (2006.01); H10K 85/30 (2023.01); C07F 15/00 (2006.01); C09K 11/06 (2006.01); H10K 50/11 (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 2101/10 (2023.02)] 20 Claims
 
1. An organometallic compound represented by Formula 1:

OG Complex Work Unit Chemistry
wherein, in Formula 1,
M is a transition metal,
X1 is C, and X2 to X4 are each independently C or N,
a bond between X1 and M is a coordinate bond,
one of a bond between X2 and M, a bond between X3 and M, and a bond between X4 and M is a coordinate bond, and the other two bonds are covalent bonds,
X11 is O, S, or N(R1a),
a group represented by

OG Complex Work Unit Chemistry
is a group represented by one of Formulae CY1-5 to CY1-15,

OG Complex Work Unit Chemistry
wherein, in Formulae CY1-5 to CY1-15,
R11 to R14 are each independently an unsubstituted or substituted C1-C60 alkyl group or an unsubstituted or substituted C3-C10 cycloalkyl group,
* indicates a binding site to M in Formula 1, and *′ indicates a binding site to ring CY2 in Formula 1,
ring CY2 to ring CY4 are each independently a C5-C30 carbocyclic group or a C1-C30 heterocyclic group,
T1 is a single bond, a double bond, *—N(R5)—*′, *—B(R5)—*′, *—P(R5)—*′, *—C(R5) (R6)—*′, *—Si(R5)(R6)—*′, *—Ge(R5)(R6)—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)2—*′, *—C(R5)═*′, *═C(R5)—*′, *—C(R5)═C(R6)—*′, *—C(═S)—*′, or *—C≡C—*′,
T2 is 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)—*′, or *C≡C—*′,
R1a, R1 to R8 are each independently 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 C1-C60 alkylthio 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 C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C7-C60 alkylaryl 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 C2-C60 alkyl heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q1)(Q2), —Si(Q3)(Q4)(Q5), —Ge(Q3)(Q4)(Q5), —B(Q6)(Q7), —P(═O)(Q8)(Q9), or —P(Q8)(Q9),
a1 is an integer from 1 to 4,
a2 to a4 are each independently an integer from 0 to 20,
at least one of R1 in the number of a1 is each independently an unsubstituted or substituted C1-C60 alkyl group or an unsubstituted or substituted C3-C10 cycloalkyl group,
two or more of a plurality of R1(s) are optionally linked to each other to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a,
two or more of a plurality of R2(s) are optionally linked to each other to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a,
two or more of a plurality of R3(s) are optionally linked to each other to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a,
two or more of a plurality of R4(s) are optionally linked to each other to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a,
two or more of R1a and R1 to R8 are optionally linked to each other to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a,
R10a is the same as described in connection with R2,
* and *′ each indicate a binding site to a neighboring atom,
a substituent of the substituted C1-C60 alkyl group, the substituted C2-Coo alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C1-C60 alkylthio group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted with C3-C10 cycloalkyl group, the substituted C2-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted, a C7-C60 alkylaryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted C2-C60 alkylheteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is:
deuterium, —F, —Cl, —Br, —I, -CD3, -CD2H, -CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino 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, or a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each substituted with deuterium, —F, —Cl, —Br, —I, -CD3, -CD2H, -CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino 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 C2-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), —Ge(Q13)(Q14)(Q15), —B(Q16)(Q17), —P(═O)(Q18)(Q19), —P(Q18)(Q19), or any combination thereof;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-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, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, -CD3, -CD2H, -CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino 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 C2-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), —Ge(Q23)(Q24)(Q25), —B(Q26)(Q27), —P(═O)(Q28)(Q29), —P(Q28)(Q29), or any combination thereof;
—N(Q31)(Q32), —Si(Q33)(Q34)(Q35), —Ge(Q33)(Q34)(Q35), —B(Q36)(Q37), —P(═O)(Q38)(Q39), or —P(Q38)(Q39); or
any combination thereof,
wherein Q1 to Q9, Q11 to Q19, Q21 to Q29 and Q31 to Q39 are each independently 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 that is unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof; 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 C2-C10 heterocycloalkenyl group; a C6-C60 aryl group that is unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof; a C6-C60 aryloxy group; a C6-C60 arylthio group; a C1-C60 heteroaryl group; a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic condensed heteropolycyclic group.