US 12,069,890 B2
Light-emitting device and an electronic device including the same
Hyewon Choi, Yongin-si (KR); Soungwook Kim, Yongin-si (KR); Seulong Kim, Yongin-si (KR); Sungsoo Bae, Yongin-si (KR); Hyein Jeong, Yongin-si (KR); and Jaeweon Hur, Yongin-si (KR)
Assigned to Samsung Display Co., Ltd., Yongin-si (KR)
Filed by Samsung Display Co., Ltd., Yongin-si (KR)
Filed on Dec. 14, 2021, as Appl. No. 17/551,016.
Claims priority of application No. 10-2020-0176599 (KR), filed on Dec. 16, 2020.
Prior Publication US 2022/0190296 A1, Jun. 16, 2022
Int. Cl. H10K 85/60 (2023.01); H10K 50/858 (2023.01); H10K 50/82 (2023.01); H10K 59/122 (2023.01)
CPC H10K 50/858 (2023.02) [H10K 85/633 (2023.02); H10K 85/636 (2023.02); H10K 85/6572 (2023.02); H10K 50/82 (2023.02); H10K 59/122 (2023.02); H10K 85/626 (2023.02)] 20 Claims
OG exemplary drawing
 
1. A light-emitting device comprising:
a first electrode;
a second electrode facing the first electrode;
an interlayer between the first electrode and the second electrode and comprising an emission layer; and
a first capping layer and a second capping layer outside the second electrode,
wherein the first capping layer comprises at least one compound selected from compounds represented by Formulae 1-1 to 1-3, and
the second capping layer comprises at least one compound selected from compounds represented by Formulae 2-1 to 2-6:

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
wherein, in Formulae 1-1, 2-2, and 2-6,
n8 is 0 or 1,
when n8 is 0, (A8)n8 is represented by *—R8,
when n8 is 1, (A8)n8 is represented by Formula 1A,

OG Complex Work Unit Chemistry
n45 is 1 or 2,
when n45 is 1, A45 is: *—O—*′; *—S—*′; *—Se—*′; *—N(R45a)—*; *—C(R45a)(R45b)—*′; *—Si(R45a)(R45b)—*; *—S(═O)2—*; *—P(═O)(R45a)—*′; 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,
when n45 is 2, A45 is 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,
n89 is 0 or 1,
when n89 is 0, A89 is *—N(R89a)(R89b), 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,
when n89 is 1, A89 is: *—O—*′; *—S—*′; *—Se—*′; *—N(R89a)—*′; *—C(R89a)(R89b)—*′; *—Si(R89a)(R89b)—*′; *—S(═O)2—*′; *—P(═O)(R89a)—*′; 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,
wherein, in Formulae 1-1, 1-A, 1-2, 1-3, 1-1-1, 2-1, 2-2, 2-3, 2-4, 2-5, and 2-6,
X1 is C-(L1)a1-R1 or N,
X2 is C-(L2)a2-R2 or N,
X3 is C-(L3)a3-R3 or N,
X4 is C-(L4)a4-R4 or N,
X1a is C-(L1a)a1a-R1a or N,
X2a is C-(L2a)a2a-R2a or N,
X3a is C-(L3a)a3a-R2a or N,
X4a is C-(L4a)a4a-R4a or N,
X81 is C(R81a)(R81b), Si(R81a)(R81b), N(R81a), O, S, or Se,
X82 is C(R82a) or N,
X83 is C(R83a)(R83b), Si(R83a)(R83b), N(R83a), O, S, or Se,
X84 is C(R84a) or N,
ring A1 is a substituted or unsubstituted benzene ring,
ring A2 is a 5-membered ring represented by Formula 2A,

OG Complex Work Unit Chemistry
wherein, in Formula 2A,
X74 is C(R74a)(R74b), Si(R74a)(R74b), N(R74a), O, S, or Se,
L1 to L8, L1a to L7a, L11 to L13, L21 to L25, L31 to L33, L41 to L44, L51 to L52, L61, L66, L67, L71, L85, and L86 are each, independently from one another: *—O—*′; *—S—*′; *—Se—*′; *—N(R10)—*′; *—C(R10)(R20)—*′; *—Si(R10)(R20)—*′; *—S(═O)2—*′; *—P(═O)(R10)—*′; 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,
a1 to 8, a1a to a7a, a11 to a13, a21 to a25, a31 to a33, a41 to a45, a51 to a52, a61, a66, a67, a71, a85, and a86 are each, independently from one another, an integer from 1 to 5,
R1 to R8, R1a to R7a, R10, R20, R11 to R13, R21 to R24, R31 to R33, R41 to R44, R45a, R45b, R51 to R54, R61 to R66, R71 to R73, R74a, R74b, R81a, R81b, R82a, R83a, R83b, R84a, R87, R88, R89a, and R89b are each independently selected from 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), and —P(═O)(Q1)(Q2),
b53, b54, b62, b65, b72, b73, b87, and b88 are each, independently from one another, an integer from 0 to 4,
b63 and b64 are each, independently from one another, an integer from 0 to 3,
two neighboring groups among R1 to R8, R1a to R7a, R10, R20, R11 to R13, R21 to R24, R31 to R33, R41 to R44, R45a, R45b, R51 to R54, R61 to R66, R71 to R73, R74a, R74b, R81a, R81b, R82a, R83a, R83b, R84a, R87, R88, R89a, and R89b are optionally linked to each other, via a single bond, a C1-C5 alkylene group unsubstituted or substituted with at least one R10a, or a C2-C5 alkenylene group unsubstituted or substituted with at least one R10a, to form a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group substituted or unsubstituted at least one R10a,
R10a is:
deuterium (-D), —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each, independently from one another, 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 any combination thereof,
a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, or a C6-C60 arylthio group, each, independently from one another, 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 any 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 from one another: 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, independently from one another 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 any combination thereof, and
* and *′ each indicate a binding site to a neighboring atom.