US 11,812,657 B2
Organic electric element
Dae Sic Kim, Cheonan-si (KR); Jung Geun Lee, Cheonan-si (KR); Dong Hee Shin, Cheonan-si (KR); Bu Yong Yun, Cheonan-si (KR); and Jeong Seok Kim, Cheongju-si (KR)
Assigned to Duk San Neolux Co., Ltd.
Filed by Duk San Neolux Co., Ltd., Cheonan-si (KR)
Filed on May 5, 2023, as Appl. No. 18/312,639.
Application 18/312,639 is a division of application No. 17/604,912, previously published as PCT/KR2020/008149, filed on Jun. 23, 2020.
Claims priority of application No. 10-2019-0075219 (KR), filed on Jun. 24, 2019.
Prior Publication US 2023/0276699 A1, Aug. 31, 2023
Int. Cl. H01L 51/00 (2006.01); H01L 51/50 (2006.01); C09K 11/06 (2006.01); H10K 85/60 (2023.01); C07D 409/14 (2006.01); C07D 417/12 (2006.01); H10K 50/84 (2023.01)
CPC H10K 85/636 (2023.02) [C07D 409/14 (2013.01); C07D 417/12 (2013.01); C09K 11/06 (2013.01); C09K 2211/1018 (2013.01); H10K 50/84 (2023.02); H10K 85/657 (2023.02); H10K 85/6572 (2023.02); H10K 85/6574 (2023.02); H10K 85/6576 (2023.02)] 9 Claims
OG exemplary drawing
 
1. An organic electric element comprising:
a first electrode;
a second electrode;
an organic material layer located between the first electrode and the second electrode, and
a capping layer disposed on at least one of one surface of the first electrode opposite to the organic material layer and one surface of the second electrode opposite to the organic material layer,
wherein the capping layer comprises a compound represented by following Formula 1-T:

OG Complex Work Unit Chemistry
in the Formula 1-T,
1) Ar1 to Ar4 are each independently selected from a group consisting of a C6-C60 aryl group; a fluorenyl group; a C2-C60 hetero ring group comprising at least one heteroatom selected from among O, N, S, Si, or P; and a fused ring group of a C3-C60 aliphatic ring and a C6-C60 aromatic ring,
2) At least one of Ar1 to Ar4 is represented by formula 1-1,
3) L1 and L2 are each independently selected from a group consisting of a single bond; a C6-C60 arylene group; a fluorenylene group; a C2-C60 hetero ring group comprising at least one heteroatom selected from among 0, N, S, Si, or P; and a fused ring group of a C3-C60 aliphatic ring and a C6-C60 aromatic ring,
4) L3 to L6 are each independently selected from a group consisting of a single bond; a C6-C60 arylene group; a fluorenylene group; a C2-C60 hetero ring group comprising at least one heteroatom selected from among 0, N, S, Si, or P; and a fused ring group of a C3-C60 aliphatic ring and a C6-C60 aromatic,
5) R1 and R2 are each independently selected from the group consisting of deuterium; a C6-C60 aryl group; a fluorenyl group; a C2-C60 hetero ring group comprising at least one heteroatom selected from among 0, N, S, Si, or P; a fused ring group of a C3-C60 aliphatic ring and a C6-C60 aromatic ring; and -L′-N(Ra) (Rb), and one or more adjacent R1s are the same or different and the adjacent R1s may be bonded to each other to form a ring, and one or more adjacent R2s are the same or different and the adjacent R2s may be bonded to each other to form a ring,
6) R3 is each independently selected from the group consisting of deuterium; a C6-C60 aryl group; a fluorenyl group; a C2-C60 hetero ring group comprising at least one heteroatom selected from among 0, N, S, Si, or P; and a fused ring group of a C3-C60 aliphatic ring and a C6-C60 aromatic ring; and -L′-N(Ra) (Rb), and one or more adjacent R3s are the same or different and the adjacent R3s may be bonded to each other to form a ring,
7) A and b are each independently an integer of 0 to 3, c is an integer of 0 to 4, and when two or more of Ar1 to Ar4 are represented by the formula 1-1, a plurality of c's are the same or may be different,
8) L′ is each independently selected from a group consisting of a single bond; C6-C60 arylene group; fluorenylene group; a C2-C60 hetero ring group comprising at least one heteroatom selected from among O, N, S, Si, or P; and a fused ring group of a C3-C60 aliphatic ring and a C6-C60 aromatic ring,
9) Ra and Rb are each independently selected from a group consisting of a C6-C60 aryl group; a fluorenyl group; a C2-C60 hetero ring group comprising at least one heteroatom selected from among O, N, S, Si, or P; and a fused ring group of a C3-C60 aliphatic ring and a C6-C60 aromatic ring,
10) X is O or S,
11) Ring A is each independently selected from the group consisting of benzene, naphthalene, phenanthrene and anthracene,
12) Y is each independently CRaRb or NRc, and when Y is bonded to the formula 1-T, it may be N or C;
13) Y′ is each independently N, O or S,
14) Ra, Rb and Rc are each independently hydrogen; deuterium; a C6-C60 aryl group; a fluorenyl group; a C2-C60 hetero ring group comprising at least one heteroatom selected from among O, N, S, Si, or P; and a fused ring group of a C3-C60 aliphatic ring and a C6-C60 aromatic ring,
15) Adjacent L1 and R1, L1 and Ar1, L1 and Ar2, L1 and L3, and L4, adjacent L2 and R2, L2 and Ara, L2 and Ar4, L2 and L5, L2 and L6 may be bonded to form a ring,
16) In Ar1 to Ar4, L1 to L6, R1 to R3, Ra and Rb, each of the aryl group, the fluorenyl group, the hetero ring group, the fused ring group, the arylene group and the fluorenylene group is further substituted with one or more substituents selected from a group consisting of deuterium; a nitro group; a nitrile group; a halogen group; an amino group; a C1-C20 alkylthio group; a C1-C20 alkoxy 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 hetero ring group; a C3-C20 cycloalkyl group; a C7-C20 aryl alkyl group; and a C8-C20 aryl alkenyl group, the substituents are allowed to be bonded to form a ring, and each of the substituents is further substituted with one or more substituents selected from a group consisting of deuterium; a nitro group; a nitrile group; a halogen group; an amino group; a C1-C20 alkylthio group; a C1-C20 alkoxy 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 hetero ring group; a C3-C20 cycloalkyl group; a C7-C20 aryl alkyl group;
and a C8-C20 aryl alkenyl group, and the substituents are allowed to be bonded to form a ring.