US 11,807,630 B2
Compound for organic electronic element, organic electronic element comprising the same, and electronic device thereof
Jae Duk Yoo, Cheonan-si (KR); Jin Ho Yun, Yongin-si (KR); Jae Taek Kwon, Cheonan-si (KR); Moo Jin Park, Cheonan-si (KR); Sun Hee Lee, Hwaseong-si (KR); and Byoung Yeop Kang, Cheonan-si (KR)
Assigned to DUK SAN NEOLUX CO., LTD., Cheonan-si (KR)
Appl. No. 16/770,922
Filed by DUK SAN NEOLUX CO., LTD., Cheonan-si (KR)
PCT Filed Nov. 22, 2018, PCT No. PCT/KR2018/014459
§ 371(c)(1), (2) Date Jun. 8, 2020,
PCT Pub. No. WO2019/112214, PCT Pub. Date Jun. 13, 2019.
Claims priority of application No. 10-2017-0168507 (KR), filed on Dec. 8, 2017.
Prior Publication US 2021/0163452 A1, Jun. 3, 2021
Int. Cl. C07D 405/04 (2006.01); H01L 51/00 (2006.01); H10K 85/60 (2023.01); H10K 50/15 (2023.01); H10K 50/16 (2023.01); H10K 50/17 (2023.01)
CPC C07D 405/04 (2013.01) [H10K 85/624 (2023.02); H10K 85/654 (2023.02); H10K 85/6572 (2023.02); H10K 85/6574 (2023.02); H10K 85/6576 (2023.02); H10K 50/15 (2023.02); H10K 50/16 (2023.02); H10K 50/171 (2023.02)] 11 Claims
 
1. A compound of Formula 1:

OG Complex Work Unit Chemistry
wherein:
X1 is S, 0 or N(Ar′),
R1 to R4 are each independently selected from the group consisting of hydrogen, deuterium, halogen, a cyano 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, 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 together may be bonded to each other to form a ring, wherein the ring is selected from the group consisting of a C2-C60 heterocyclic ring, a C3-C60 aliphatic ring and a combination thereof,
R5 and R6 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 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 together may be bonded to each other to form a ring, wherein the ring is selected from the group consisting of a C6-C60 aromatic hydrocarbon, a C2-C60 heterocyclic ring, a C3-C60 aliphatic ring and a combination thereof,
a, b, c and e are each represent an integer of 0-4, d and f are each represent an integer of 0-3, and when each of these is an integer of 2 or more, each of R1s, each of R2s, each of R3s, each of R4s, each of R5s or each of R6s may be the same or different from each other,
L1 is selected from the group consisting of a C6-C60 arylene group, a fluorenylene group, a C3-C60 aliphatic ring, a C2-C60 heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, and a combination thereof,
L2 is selected from the group consisting of a single bond, a C6-C60 arylene group, a fluorenylene group, a C3-C60 aliphatic ring, a C2-C60 heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, and a combination thereof,
Ar′ is 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 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),
Ar1 is 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, S, Si, and P, 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),
L′ is selected from the group consisting of a single bond, a C6-C60 arylene group, a fluorenylene group, a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring, and a C2-C60 heterocyclic group containing at least one heteroatom of O, N, S, Si, and P,
Ra and Rb are each independently selected from the group consisting of a C6-C60 aryl group, a fluorenyl group, a fused ring group formed by a C3-C60 aliphatic ring with a C6-C60 aromatic ring, and a C2-C60 heterocyclic group containing at least one heteroatom of O, N, S, Si, and P,
R1 to R6, Ar1 , L1, L2, L′, Ra, Rb, a ring formed by adjacent R1 groups, adjacent R2 groups, adjacent R3 groups, adjacent R4 groups, adjacent R5 groups and adjacent R6 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 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 of O, N, S, Si, and P, a C3-C20 cycloalkyl group, a C7-C20 arylalkyl group and a C8-C20 arylalkenyl group, and
the Ar1 may be 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 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 of O, S, Si, and P, a C3-C20 cycloalkyl group, a C7-C20 arylalkyl group and a C8-C20 arylalkenyl group.