US 12,193,321 B2
Compound for organic electric element, organic electric element comprising the same, and electronic device thereof
Ki Ho So, Cheonan-si (KR); Hyung Dong Lee, Cheonan-si (KR); Dae Hwan Oh, Cheonan-si (KR); Won Sam Kim, Cheonan-si (KR); and Byoung Yeop Kang, Cheonan-si (KR)
Assigned to DUK SAN NEOLUX CO., LTD., Cheonan-si (KR)
Filed by DUK SAN NEOLUX CO., LTD., Cheonan-si (KR)
Filed on Jul. 10, 2020, as Appl. No. 16/946,904.
Claims priority of application No. 10-2019-0083318 (KR), filed on Jul. 10, 2019; application No. 10-2019-0101535 (KR), filed on Aug. 20, 2019; and application No. 10-2020-0057682 (KR), filed on May 14, 2020.
Prior Publication US 2021/0013420 A1, Jan. 14, 2021
Int. Cl. H10K 85/60 (2023.01); C07D 405/12 (2006.01); C07D 409/12 (2006.01); C07D 411/12 (2006.01); C07D 411/14 (2006.01); C07D 471/06 (2006.01); C07D 513/10 (2006.01); C09K 11/06 (2006.01); H10K 50/15 (2023.01)
CPC H10K 85/636 (2023.02) [C07D 405/12 (2013.01); C07D 409/12 (2013.01); C07D 411/12 (2013.01); C07D 411/14 (2013.01); C07D 471/06 (2013.01); C07D 513/10 (2013.01); C09K 11/06 (2013.01); C09K 2211/1018 (2013.01); H10K 50/15 (2023.02); H10K 85/657 (2023.02); H10K 85/6572 (2023.02); H10K 85/6574 (2023.02); H10K 85/6576 (2023.02)] 13 Claims
OG exemplary drawing
 
1. A compound of Formula 1:

OG Complex Work Unit Chemistry
wherein:
Ar1 to Ar6 are each independently selected from the group consisting of a C6-C60 aryl group, a fluorenyl group, a C2-C60 heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, a C3-C60 aliphatic ring group, -L′-N(Ra)(Rb), Formula A-1 and Formula A-2, and at least one of Ar1 to Ar6 is Formula A-1 or Formula A-2,

OG Complex Work Unit Chemistry
X1 is O or S,
X2 is N(R′), O or S,
R1 to R6 are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano group, nitro group, a C6-C60 aryl group, a fluorenyl group, a C2-C60 heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, a C3-C60 aliphatic ring group, a C1-C30 alkyl group, a C2-C30 alkenyl group, a C2-C30 alkynyl group, a C1-C30 alkoxyl group, a C6-C30 aryloxy group and -L′-N(Ra)(Rb), and adjacent groups together may be bonded to each other to form a ring,
n, p′ and r′ are each an integer of 0 to 3, m, o, p, q and r are each an integer of 0 to 4, and where they are each an integer of 2 to 4, each of R1s, each of R2s, each of R3s, each of R4s, each of R5s, or each of R6s is the same or different from each other,
x and y are each an integer of 0 to 2, and x+y is an integer greater than or equal to 1,
L1 to L3 and L′ are each independently selected from the group consisting of a single bond, a C6-C60 arylene group, a fluorenylene group, a C3-C60 aliphatic ring group and a C2-C60 heterocyclic group containing at least one heteroatom of O, N, S, Si, and P,
R′, Ra and Rb are each independently selected from the group consisting of a C6-C60 aryl group, a fluorenyl group, a C2-C60 heterocyclic group containing at least one heteroatom of O, N, S, Si, and P and a C3-C60 aliphatic ring group,
with the proviso that, in the case where L1 and L2 are each a single bond, X2 is O or S, and y is an integer of 1, at least one of R1 to R6 forms an aromatic hydrocarbon ring with an adjacent group, and
Ar1 to Ar6, R1 to R6, L1 to L3, R′ and the ring formed by adjacent groups may be each optionally substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group unsubstituted or substituted with a C1-C20 alkyl group or a C6-C20 aryl group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a C1-C20 alkylthio group, a C1-C20 alkoxyl group, a C6-C20 aryloxy group, a C6-C20 arylthio group, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C6-C20 aryl group, a fluorenyl group, a C2-C20 heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, a C3-C20 aliphatic ring group, a C7-C20 arylalkyl group, and C8-C20 arylalkenyl group,
with the proviso that Formula 20 is excluded from Formula 1:

OG Complex Work Unit Chemistry
wherein X1, L1-L2, Ar1-Ar4, R1, and R2 are the same as defined for Formula 1, and a is an integer of 0 to 5 and m is an integer of 0 to 3.