US 12,075,694 B2
Composition, organic optoelectronic device and display device
Jongwoo Won, Suwon-si (KR); Dong Min Kang, Suwon-si (KR); Jun Seok Kim, Suwon-si (KR); Jinhyun Lui, Suwon-si (KR); Byoungkwan Lee, Suwon-si (KR); Sangshin Lee, Suwon-si (KR); Hyungyu Lee, Suwon-si (KR); Sung-Hyun Jung, Suwon-si (KR); Ho Kuk Jung, Suwon-si (KR); and Kyunghee Hyung, Suwon-si (KR)
Assigned to SAMSUNG SDI CO., LTD., Yongin-si (KR); and SAMSUNG ELECTRONICS CO., LTD., Suwon-si (KR)
Appl. No. 17/047,445
Filed by SAMSUNG SDI CO., LTD., Yongin-si (KR); and Samsung Electronics Co., Ltd., Suwon-si (KR)
PCT Filed Mar. 25, 2019, PCT No. PCT/KR2019/003444
§ 371(c)(1), (2) Date Oct. 14, 2020,
PCT Pub. No. WO2019/208937, PCT Pub. Date Oct. 31, 2019.
Claims priority of application No. 10-2018-0046910 (KR), filed on Apr. 23, 2018.
Prior Publication US 2021/0119136 A1, Apr. 22, 2021
Int. Cl. H01L 51/50 (2006.01); C07D 209/80 (2006.01); C07D 403/10 (2006.01); C07D 405/12 (2006.01); C07D 405/14 (2006.01); H10K 85/60 (2023.01); H10K 50/11 (2023.01); H10K 101/10 (2023.01)
CPC H10K 85/636 (2023.02) [C07D 209/80 (2013.01); C07D 403/10 (2013.01); C07D 405/12 (2013.01); C07D 405/14 (2013.01); H10K 85/654 (2023.02); H10K 85/6572 (2023.02); H10K 85/6574 (2023.02); H10K 50/11 (2023.02); H10K 2101/10 (2023.02)] 17 Claims
OG exemplary drawing
 
1. A composition, comprising
a first compound represented by a combination of Chemical Formula 1 and Chemical Formula 2, and
a second compound represented by Chemical Formula 3:

OG Complex Work Unit Chemistry
wherein, in Chemical Formula 1 and Chemical Formula 2,
Ar1 is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
adjacent two of a1* to a4* are linked with b1* and b2*, respectively,
remaining two of a1* to a4* not being linked with b1* and b2* are independently C-La-Ra,
La and L1 to L4 are independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,
Ra and R1 to R4 are independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, and
at least one of Ra and R1 to R4 is a group represented by Chemical Formula A,

OG Complex Work Unit Chemistry
wherein, in Chemical Formula A,
Rb and Rc are independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, and
* is a linking point with La and L1 to L4;

OG Complex Work Unit Chemistry
wherein, in Chemical Formula 3,
L5 to L9 are independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,
Ar2 is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
R5 to R8 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a halogen, a cyano group, or a combination thereof,
R5 to R8 are independently present or adjacent groups thereof are linked with each other to form a substituted or unsubstituted aromatic monocyclic or polycyclic ring, and
at least one of Ar2 and R5 to R8 is a group represented by Chemical Formula B,

OG Complex Work Unit Chemistry
wherein, in Chemical Formula B,
Z1 to Z5 are independently N or C-Lb-Rd,
at least one of Z1 to Z5 is N,
wherein Lb is independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,
Rd is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a halogen, a cyano group, or a combination thereof,
Rd is independently present or adjacent groups thereof are linked with each other to form a substituted or unsubstituted aromatic monocyclic or polycyclic ring, or a substituted or unsubstituted aromatic monocyclic or polycyclic heteroring, and
* is a linking point with L5 to L9.
 
13. An organic optoelectronic device, comprising
an anode and a cathode facing each other,
at least one organic layer disposed between the anode and the cathode,
wherein the organic layer comprises the composition of claim 1.