US 12,490,651 B2
Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
Moon Sung Kang, Cheonan-si (KR); Jung Geun Lee, Cheonan-si (KR); and Sang Yong Park, 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 May 27, 2025, as Appl. No. 19/219,335.
Application 19/219,335 is a continuation of application No. 19/057,277, filed on Feb. 19, 2025.
Claims priority of application No. 10-2024-0023290 (KR), filed on Feb. 19, 2024; and application No. 10-2024-0048775 (KR), filed on Apr. 11, 2024.
Prior Publication US 2025/0287833 A1, Sep. 11, 2025
Int. Cl. H10K 85/60 (2023.01); C07C 211/61 (2006.01); C07D 209/88 (2006.01); C07D 263/60 (2006.01); C07D 307/91 (2006.01); C07D 319/24 (2006.01); C07D 333/76 (2006.01); C07D 409/04 (2006.01); H10K 50/11 (2023.01); H10K 50/19 (2023.01)
CPC H10K 85/633 (2023.02) [C07C 211/61 (2013.01); C07D 209/88 (2013.01); C07D 263/60 (2013.01); C07D 307/91 (2013.01); C07D 319/24 (2013.01); C07D 333/76 (2013.01); C07D 409/04 (2013.01); H10K 85/636 (2023.02); C07B 2200/05 (2013.01); C07C 2601/14 (2017.05); C07C 2602/10 (2017.05); C07C 2602/42 (2017.05); C07C 2603/18 (2017.05); C07C 2603/40 (2017.05); C07C 2603/48 (2017.05); C07C 2603/74 (2017.05); C07C 2603/97 (2017.05); H10K 50/11 (2023.02); H10K 50/19 (2023.02); H10K 85/615 (2023.02); H10K 85/622 (2023.02); H10K 85/626 (2023.02); H10K 85/6574 (2023.02); H10K 85/6576 (2023.02)] 11 Claims
OG exemplary drawing
 
1. A compound represented by Formula 1-2:

OG Complex Work Unit Chemistry
wherein:
R1, R2, R3 and R4 are independently the same or different from each other and are independently selected from the group consisting of hydrogen; deuterium; a C6-C60 aryl group; a fluorenyl group; a C2-C60 heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C3-C60 aliphatic ring and a C6-C60 aromatic ring; a C1-C50 alkyl group; a C2-C20 alkenyl group; a C2-C20 alkynyl group; and a C3-C30 aliphatic ring, and a plurality of adjacent groups thereof may be bonded to each other to form a ring, wherein the ring formed by adjacent R3 groups is a C6 ring,
L1 and L2 are independently a single bond, or selected from the group consisting of Formulae L-1 to L-27:

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
wherein Z is O or S,
R18, R19, R20, R21, R22, R23, R24, R25, R26 and R27 are independently the same or different from each other and are independently selected from the group consisting of hydrogen; deuterium; a C1-C20 alkyl group; a C6-C20 aryl group; a C6-C20 aryl group substituted with deuterium; a fluorenyl group; a C2-C20 heterocyclic group; a C3-C20 aliphatic group; a C7-C20 arylalkyl group; and a C7-C20 alkylaryl group, and a plurality of adjacent groups thereof may be bonded to each other to form a ring,
r, t, v, w, x, y and z are independently an integer of 0 to 4, s is an integer of 0 to 6, u is an integer of 0 to 2, aa is an integer of 0 to 5,
Ar1 is represented by any one of Formulas Ar-1 to Ar-13:

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
wherein
R7, R8, R9, R10, R11, R12, R13, R14, R15, R16 and R17 are independently the same or different from each other and are independently selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; a nitro group; a C1-C20 alkyl group; a C2-C20 alkenyl group; a C6-C20 aryl group; a C6-C20 aryl group substituted with deuterium; a fluorenyl group; a C2-C20 heterocyclic group; a C3-C20 aliphatic group; C7-C20 arylalkyl group; and a C7-C20 alkylaryl group, and a plurality of adjacent groups thereof may be bonded to each other to form a ring,
Rc is selected from the group consisting of a C1-C20 alkyl group; a C6-C20 aryl group; and a C2-C20 heterocyclic group including at least one heteroatom of O, N, S, Si or P;
Rd is selected from the group consisting of hydrogen; deuterium; a C1-C20 alkyl group; a C6-C20 aryl group; and a C2-C20 heterocyclic group including at least one heteroatom of O, N, S, Si or P;
Rc and Rd may be bonded to each other to form a spiro,
g is an integer of 0 to 5, h, k, l, o, p and q are independently an integer of 0 to 4, i is an integer of 0 to 7, j is an integer of 0 to 9, m and n are independently an integer of 0 to 3,
W is O, S or NR30, wherein R30 are selected from a group consisting of a C1-C20 alkyl group; a C2-C20 alkenyl group; C6-C20 aryl group; C6-C20 aryl group substituted with deuterium; a fluorenyl group; a C2-C20 heterocyclic group including at least one heteroatom of O, N, S, Si or P; C3-C20 aliphatic group; C7-C20 arylalkyl group; C8-C20 arylalkenyl group; and a C7-C20 alkylaryl group; or, R27 and R28 may be bonded to each other to form a ring,
Ra and Rb are independently selected from the group consisting of a C1-C20 alkyl group; a C1-C20 alkyl group substituted with deuterium; a C2-C20 alkenyl group; a C6-C20 aryl group; a C6-C20 aryl group substituted with deuterium; a fluorenyl group; a C2-C20 heterocyclic group including at least one heteroatom of O, N, S, Si or P; a C3-C20 aliphatic group; a C7-C20 arylalkyl group; and a C7-C20 alkylaryl group, and Ra and Rb may be bonded to each other to form a spiro,
R101 and R102 are the same as the definition of R7, or adjacent groups thereof may be bonded to each other to form a ring,
Ar2 is selected from the group consisting of a C1-C20 alkyl group substituted or unsubstituted with deuterium; a C6-C20 aryl group substituted or unsubstituted with deuterium; and a C2-C20 heterocyclic group including at least one heteroatom of O, N, S, Si and P;
ab′ is an integer of 0 to 2, ac is an integer of 0 to 4, and ab and ac′ are independently an integer of 0 to 3,
Ak is a C1-C50 alkyl group; or a C3-C30 aliphatic ring group;
a, c and d are independently an integer of 0 to 4, b is an integer of 0 to 3,
* indicates a position to be bonded,
wherein the aryl group, heterocyclic group, fluorenyl group, aliphatic ring group, fused ring group, alkyl group, alkenyl group and the ring formed by the adjacent groups may be substituted with one or more substituents selected from the group consisting of deuterium; halogen; a cyano group; a nitro 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; a C3-C20 aliphatic ring; a C7-C20 arylalkyl group; a C8-C20 arylalkenyl group; and a C7-C20 alkylaryl group, and the hydrogen of these substituents may be further substituted with one or more deuterium.