US 11,691,966 B2
Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
Mi Young Chae, Cheonan-si (KR); Moo Jin Park, Cheonan-si (KR); Jae Taek Kwon, Cheonan-si (KR); Jin Bae Jeon, Cheonan-si (KR); and Sun Hee Lee, Cheonan-si (KR)
Assigned to DUK SAN NEOLUX CO., LTD., Cheonan-si (KR)
Appl. No. 16/652,369
Filed by DUK SAN NEOLUX CO., LTD., Cheonan-si (KR)
PCT Filed Aug. 8, 2018, PCT No. PCT/KR2018/009014
§ 371(c)(1), (2) Date Mar. 30, 2020,
PCT Pub. No. WO2019/066242, PCT Pub. Date Apr. 4, 2019.
Claims priority of application No. 10-2017-0127656 (KR), filed on Sep. 29, 2017; and application No. 10-2018-0017403 (KR), filed on Feb. 13, 2018.
Prior Publication US 2020/0231581 A1, Jul. 23, 2020
Int. Cl. C07D 409/14 (2006.01); C07D 405/14 (2006.01); H01L 51/00 (2006.01); H01L 51/50 (2006.01); H10K 85/60 (2023.01); H10K 50/11 (2023.01); H10K 50/15 (2023.01); H10K 50/16 (2023.01); H10K 50/17 (2023.01); H10K 101/10 (2023.01); H10K 101/00 (2023.01)
CPC C07D 409/14 (2013.01) [C07D 405/14 (2013.01); H10K 85/615 (2023.02); H10K 85/622 (2023.02); H10K 85/654 (2023.02); H10K 85/6572 (2023.02); H10K 85/6574 (2023.02); H10K 85/6576 (2023.02); H10K 50/11 (2023.02); H10K 50/15 (2023.02); H10K 50/16 (2023.02); H10K 50/171 (2023.02); H10K 2101/10 (2023.02); H10K 2101/90 (2023.02)] 21 Claims
OG exemplary drawing
 
1. A compound of Formula 1:

OG Complex Work Unit Chemistry
wherein:
X1 and X2 are each independently O or S,
Ar1 to Ar3 are each independently a C6-C60 aryl group,
R1 R2, R4 and R5 are each independently selected from the group consisting of hydrogen, deuterium, halogen, a C6-C60 aryl group, a fluorenyl group, a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C60 aliphatic ring, a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring, a C1-C50 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C1-C30 alkoxyl group, a C6-C30 aryloxy group and -L′-N(Ra)(Rb), and adjacent groups may be optionally linked to each other to form a ring, wherein the ring is selected from the group consisting of a C6-C60 aromatic ring, a C2-C60 heterocyclic group, a C3-C60 aliphatic ring, and a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring, and wherein the ring formed by adjacent groups of R2 or adjacent groups of R5 is a benzene ring in the case where X1 is O,
R3 is selected from the group consisting of deuterium, halogen, a C6-C60 aryl group, a fluorenyl group, a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C60 aliphatic ring, a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring, a C1-C50 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C1-C30 alkoxyl group, a C6-C30 aryloxy group and -L′-N(Ra)(Rb), and adjacent groups may be optionally linked to each other to form a ring, wherein the ring is selected from the group consisting of a C6-C60 aromatic ring, a C2-C60 heterocyclic group, a C3-C60 aliphatic ring, and a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring,
a and b are each an integer of 0 to 3, c, d, e, and I are each an integer of 0 to 4 with the proviso that c+l is an integer of 1 or more, m is an integer of 1 to 4, and n is an integer of 1 to 5,
L′ is selected from the group consisting of a single bond, a C6-C60 arylene group, a fluorenylene group, a C2-C60 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C60 aliphatic ring and a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring, and
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 selected from the group consisting of O, N, S, Si, and P, a C3-C60 aliphatic ring and a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring,
wherein Ar1 to Ar3, R1 to R5, L′, Ra, Rb, and a ring formed by the adjacent groups of R1 to R5 may be each further 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 phosphine oxide group unsubstituted or substituted with a C1-C20 alkyl group or a C6-C20 aryl group, a C1-C20 alkylthio group, a C1-C20 alkoxyl group, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C6-C20 aryl group, a C6-C20 aryl group substituted with deuterium, a fluorenyl group, a C2-C20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C3-C20 cycloalkyl group, a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring, a C7-C20 arylalkyl group, and a C8-C20 arylalkenyl group.