US 12,319,706 B2
Organometallic compound, light-emitting device including the same, and electronic apparatus including the light-emitting device
Junghoon Han, Yongin-si (KR); Soobyung Ko, Yongin-si (KR); Sungbum Kim, Yongin-si (KR); Eunsoo Ahn, Yongin-si (KR); Jaesung Lee, Yongin-si (KR); and Hyunjung Lee, Yongin-si (KR)
Assigned to SAMSUNG DISPLAY CO., LTD., Yongin-si (KR)
Filed by Samsung Display Co., Ltd., Yongin-si (KR)
Filed on May 25, 2021, as Appl. No. 17/329,880.
Claims priority of application No. 10-2020-0131816 (KR), filed on Oct. 13, 2020.
Prior Publication US 2022/0112231 A1, Apr. 14, 2022
Int. Cl. H01L 51/54 (2006.01); C07F 15/00 (2006.01); H10K 85/30 (2023.01)
CPC C07F 15/0086 (2013.01) [H10K 85/346 (2023.02)] 20 Claims
 
1. A light-emitting device comprising:
a first electrode;
a second electrode facing the first electrode; and
an interlayer disposed between the first electrode and the second electrode and including an emission layer, wherein
the emission layer comprises an organometallic compound represented by Formula 1:

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
wherein in Formulae 1 and 2-1 to 2-3,
M is 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), or thulium (Tm),
X1 is C,
X2 to X7 are each independently C or N,
C1 to C4 each indicate a carbon atom,
a moiety represented by

OG Complex Work Unit Chemistry
 in Formula 1 is a group represented by one of Formulae 2-1 to 2-3,
CY3 to CY6 are each independently a C3-C60 carbocyclic group or a C1-C60 heterocyclic group,
Y1 is O, S, N(R21), C(R21)(R22), or Si(R21)(R22),
Z11, Z12, and Z21 to Z24 are each independently C or N,
L1 is a single bond, *—O—*′, *—S—*′, *—Se—*′, *—S(═O)2—*′, *—C(R7)(R8)—*′, *—C(R7)═*′, *═C(R7)—*′, *—C(R7)═C(R8)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R7)—*′, *—N(R7)—*′, *—P(R7)—*′, *—Si(R7)(R8)—*′, *—P(═O)(R7)—*′, or *—Ge(R7)(R8)—*′,
L2 is a single bond, *—O—*′, *—S—*′, *—Se—*′, *—S(═O)2—*′, *—C(R9)(R10)—*′, *—C(R9)—*′, *═C(R9)—*′, *—C(R9)═C(R10)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R9)—*′, *—N(R9)—*′, *—P(R9)—*′, *—Si(R9)(R10)—*′, *—P(═O)(R9)—*′, or *—Ge(R9)(R10)—*′,
L3 is a single bond, *—O—*′, *—S—*′, *—Se—*′, *—S(═O)2—*′, *—C(R11)(R12)—*′, *—C(R11)═*′, *═C(R11)*′, *—C(R11)═C(R12)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R11)—*′, *—N(R11)—*′, *—P(R11)—*′, *—Si(R11)(R12)—*′, *—P(═O)(R11)—*′, or *—Ge(R11)(R12)—*′,
a1 to a3 are each independently an integer from 1 to 3,
B1 and B2 are each independently a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
R1 to R12, R21, and R22 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2),
b1 is 1 or 2,
b2 is an integer from 1 to 4,
b3 to b6 are each independently an integer from 1 to 10,
two or more groups of R1 to R12 are optionally bonded to each other to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
* and *′ each indicate a binding site to a neighboring atom,
R10a is:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
a C1-C00 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), —P(═O)(Q11)(Q12), or a combination thereof;
a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, or a C6-C60 arylthio group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), —P(═O)(Q21)(Q22), or a combination thereof; or
—Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), or —P(═O)(Q31)(Q32),
wherein Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 are each independently: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C1-C60 alkyl group; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; or a C3-C60 carbocyclic group or a C1-C60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or a combination thereof, and
in Formulae 2-1 to 2-3, * indicates a binding site to M, and *′ indicates a binding site to a neighboring atom.