US 12,466,837 B2
Compound for organic electric device, organic electric device using the same, and electronic device thereof
Je Woo Lee, Cheonan-si (KR); Dae Sic Kim, Cheonan-si (KR); Hyun Ji Oh, Cheonan-si (KR); Won Sam Kim, Cheonan-si (KR); and Jung Geun Lee, Cheonan-si (KR)
Assigned to DUK SAN NEOLUX CO., LTD., Cheonan-si (KR)
Appl. No. 17/597,873
Filed by Duksan Neolux Co., LTD, Cheonan-si (KR)
PCT Filed Jul. 29, 2020, PCT No. PCT/KR2020/009974
§ 371(c)(1), (2) Date Jan. 27, 2022,
PCT Pub. No. WO2021/020873, PCT Pub. Date Feb. 4, 2021.
Claims priority of application No. 10-2019-0092820 (KR), filed on Jul. 31, 2019; and application No. 10-2020-0074494 (KR), filed on Jun. 18, 2020.
Prior Publication US 2022/0251063 A1, Aug. 11, 2022
Int. Cl. C07D 495/04 (2006.01); C07D 401/04 (2006.01); C07D 401/14 (2006.01); C07D 405/14 (2006.01); C07D 407/14 (2006.01); C07D 409/14 (2006.01); C07D 487/04 (2006.01); C07D 487/14 (2006.01); C07D 491/048 (2006.01); C07D 491/147 (2006.01); C07D 519/00 (2006.01); H10K 50/13 (2023.01); H10K 50/15 (2023.01); H10K 50/16 (2023.01); H10K 50/844 (2023.01); H10K 59/80 (2023.01); H10K 85/60 (2023.01)
CPC C07D 495/04 (2013.01) [C07D 401/04 (2013.01); C07D 401/14 (2013.01); C07D 405/14 (2013.01); C07D 407/14 (2013.01); C07D 409/14 (2013.01); C07D 487/04 (2013.01); C07D 487/14 (2013.01); C07D 491/048 (2013.01); C07D 491/147 (2013.01); C07D 519/00 (2013.01); H10K 85/622 (2023.02); H10K 85/626 (2023.02); H10K 85/654 (2023.02); H10K 85/6572 (2023.02); H10K 85/6574 (2023.02); H10K 85/6576 (2023.02); C07B 2200/13 (2013.01); H10K 50/13 (2023.02); H10K 50/15 (2023.02); H10K 50/16 (2023.02); H10K 50/844 (2023.02); H10K 59/873 (2023.02)] 17 Claims
OG exemplary drawing
 
1. A compound represented by Formula 1:

OG Complex Work Unit Chemistry
wherein:
1) R1 to R3 are each independently selected from the group consisting of hydrogen; deuterium; a halogen; an amino group; a cyano group; a nitro group; a C6-60 aryl group; a fluorenyl group; a C2-60 heterocyclic group comprising at least one heteroatom among O, N, S, Si, and P; a fused ring group between a C3-60 aliphatic ring and a C6-60 aromatic ring; a C1-50 alkyl group; a C2-20 alkenyl group; a C2-20 alkynyl group; a C1-30 alkoxyl group; a C6-30 aryloxy group; Formula 1-1; Formula 1-2; and Formula 1-3, or adjacent groups thereof can bind to one another to form a ring, wherein at least one of R1 to R3 is any one of Formula 1-1 to Formula 1-3:

OG Complex Work Unit Chemistry
2) L′ is selected from the group consisting of a single bond; a C6-60 arylene group; a fluorenylene group; a fused ring group between a C3-60 aliphatic ring and a C6-60 aromatic ring; a C2-60 heterocyclic group comprising at least one heteroatom among O, N, S, Si, and P; and a combination thereof; and
3) Ra and Rb are each independently selected from the group consisting of a C6-60 aryl group; a fluorenyl group; a C3-60 aliphatic ring group; a C2-60 heterocyclic group comprising at least one heteroatom among O, N, S, Si, and P; and a combination thereof;
4) A is an integer of 0 to 4; b is an integer of 0 to 6; c is an integer of 0 to 3; and a+b+c is greater than or equal to 1;
5) When a, b, and care 2 or greater, a plurality of R1 to R3 are the same as or different from one another, and a plurality of R1, or a plurality of R2, or a plurality of R3 may bind to one another to form a ring;
6) X1 to X9 are each independently N or C(Rc);
7) at least one of X1 to X5 and at least one of X6 to X9 are N;
8) L1 is selected from the group consisting of a single bond; a C6-60 arylene group; a fluorenylene group; a fused ring group between a C3-60 aliphatic ring and a C6-60 aromatic ring; a C2-60 heterocyclic group comprising at least one heteroatom among O, N, S, Si, and P; and a combination thereof;
9) Rc is selected from the group consisting of hydrogen; deuterium; a halogen; an amino group; a cyano group; a nitro group; a C6-60 aryl group; a fluorenyl group; a C2-60 heterocyclic group comprising at least one heteroatom among O, N, S, Si, and P; a fused ring group between a C3-60 aliphatic ring and a C6-60 aromatic ring; a C1-50 alkyl group; a C2-20 alkenyl group; a C2-20 alkynyl group; a C1-30 alkoxyl group; a C6-30 aryloxy group; and —L′—N(Rc)(Rd);
10) the definitions of Rc and Rd are the same as those of Ra and Rb above;
11) the ring A of Formula 1-2 is selected from the group consisting of Formula A-1 to Formula A-16:

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
wherein:
11-1) * is a site to be bound to a ring comprising X6 to X9;
11-2) V is N or C(Re);
11-3) W1 and W2 are each independently a single bond, —N—L3-Ar3, S, O, or CR′R″, with the proviso that W1 and W2 are not a single bond at the same time;
11-4) L3 is the same as the definition of L1 in Formula 1;
11-5) Ar3 is selected from the group consisting of a C6-60 aryl group; a fluorenyl group; a fused ring group between a C3-60 aliphatic ring and a C6-60 aromatic ring; a C2-60 heterocyclic group comprising at least one heteroatom among O, N, S, Si, and P; and a combination thereof; and
11-6) Re, R′, and R″ are each selected from the group consisting of hydrogen; deuterium; a halogen; an amino group; a cyano group; a nitro group; a C6-60 aryl group; a fluorenyl group; a C2-60 heterocyclic group comprising at least one heteroatom among O, N, S, Si, and P; a fused ring group between a C3-60 aliphatic ring and a C6-60 aromatic ring; a C1-50 alkyl group; a C2-20 alkenyl group; a C2-20 alkynyl group; a C1-30 alkoxyl group; a C6-30 aryloxy group; or —L′—N(Rc)(Rd); or these groups can bind to one another to form a ring; or R′ and R″ can bind to one another to form a spiro ring; and
12) The rings formed by R1 to R3, L1, L′, L3, Ar3, Ra to Rd, Rc, Re, R′, R″, and adjacent groups thereof can be each further substituted with one or more substituents selected from the group consisting of deuterium; a halogen; a silane group substituted or unsubstituted with a C1-20 alkyl group or a C6-20 aryl group; a siloxane group; a boron group; a germanium group; a cyano group; an amino group; a nitro group; a C1-20 alkylthio group; a C1-20 alkoxy group; a C6-20 arylalkoxy group; a C1-20 alkyl group; a C2-20 alkenyl group; a C2-20 alkynyl group; a C6-20 aryl group; a C6-20 aryl group substituted with a deuterium; a fluorenyl group; a C2-20 heterocyclic group comprising at least one heteroatom among O, N, S, Si, and P; a C3-20 aliphatic ring group; a C7-20 arylalkyl group; a C8-20 arylalkenyl group; and a combination thereof; or adjacent groups thereof can form a ring with one another.