US 12,225,819 B2
Organic electronic device
Soung Yun Mun, Cheonan-si (KR); Min Ji Jo, Cheonan-si (KR); Chi Hyun Park, Cheonan-si (KR); Yong Wook Park, Cheonan-si (KR); Sun Hee Lee, Cheonan-si (KR); and Jung Geun Lee, Cheonan-si (KR)
Assigned to Duk San Neolux Co., Ltd., (KR)
Appl. No. 17/631,592
Filed by DUK SAN NEOLUX CO., LTD., Cheonan-si (KR)
PCT Filed Jul. 30, 2020, PCT No. PCT/KR2020/010045
§ 371(c)(1), (2) Date Jan. 31, 2022,
PCT Pub. No. WO2021/025372, PCT Pub. Date Feb. 11, 2021.
Claims priority of application No. 10-2019-0094551 (KR), filed on Aug. 2, 2019; application No. 10-2020-0047638 (KR), filed on Apr. 20, 2020; and application No. 10-2020-0082278 (KR), filed on Jul. 3, 2020.
Prior Publication US 2022/0376189 A1, Nov. 24, 2022
Int. Cl. H01L 51/50 (2006.01); H10K 85/60 (2023.01); H10K 50/125 (2023.01); H10K 50/15 (2023.01)
CPC H10K 85/6574 (2023.02) [H10K 85/631 (2023.02); H10K 85/6576 (2023.02); H10K 50/125 (2023.02); H10K 50/15 (2023.02)] 22 Claims
OG exemplary drawing
 
1. An organic electronic device comprising:
a first electrode;
a second electrode; and
an organic material layer positioned between the first electrode and the second electrode and comprising a first stack, a second stack, and a third stack,
wherein the first stack comprises a first hole transport region, a first emission layer, and a first electron transport region,
the first hole transport region comprises a first hole transport layer and a first auxiliary emission layer,
the first hole transport layer or the first auxiliary emission layer comprises a first compound represented by the following Formula 1,
the thickness of the first hole transport layer ranges from 250 Å to 700 Å, and
10% to 50% of the thickness of the first hole transport layer is doped with a first doping material,

OG Complex Work Unit Chemistry
wherein each of m and n is independently 0 or 1, where m+n is 1,
each of Ar1 and Ar2 is selected from the group consisting of a C6-C60 aryl group; a fluorenyl group; a C2-C60 heterocyclic group including at least one hetero atom of O, N, S, Si, or P; or a fused ring group of a C3-C60 aliphatic ring and a C6-C60 aromatic ring,
each of Ar3 and Ar4 is independently selected from the group consisting of a C6-C60 aryl group; a fluorenyl group; a C2-C60 heterocyclic group including at least one hetero atom of O, N, S, Si, or P; or a fused ring group of a C3-C60 aliphatic ring and a C6-C60 aromatic ring,
each of L1 to L6 is independently selected from the group consisting of a single bond; a C6-C60 arylene group; a fluorenylene group; a C2-C60 heterocyclic group including at least one hetero atom of O, N, S, Si, or P; or a fused ring group of a C3-C60 aliphatic ring and a C6-C60 aromatic ring,
X is selected from the group consisting of hydrogen; deuterium; a C6-C30 aryl group; a fluorenyl group; a C2-C30 heterocyclic group including at least one hetero atom of O, N, S, Si, or P; a fused ring group of a C3-C30 aliphatic ring and a C6-C30 aromatic ring; a C1-C30 alkyl group; a C2-C20 alkenyl group; or a C2-C20 alkynyl group,
i) when n is 0, Y is selected from the group consisting of hydrogen; deuterium; a C6-C30 aryl group; a fluorenyl group; a C2-C30 heterocyclic group including at least one hetero atom of O, N, S, Si, or P; a fused ring group of a C3-C30 aliphatic ring and a C6-C30 aromatic ring; a C1-C30 alkyl group; a C2-C20 alkenyl group; or a C2-C20 alkynyl group, and ii) when n is 1, Y is selected from the group consisting of a C6-C60 arylene group; a fluorenylene group; a C2-C60 heterocyclic group including at least one hetero atom of O, N, S, Si, or P; or a fused ring group of a C3-C60 aliphatic ring and a C6-C60 aromatic ring,
X and Y are bonded to form a spiro compound,
each of ring A and ring B is independently a C6-C10 aryl group,
each of R1 and R2 is independently selected from the group consisting of deuterium; a halogen; a C6-C30 aryl group; a fluorenyl group; a C2-C30 heterocyclic group including at least one hetero atom of O, N, S, Si, or P; a fused ring group of a C3-C30 aliphatic ring and a C6-C30 aromatic ring; a C1-C30 alkyl group; a C2-C20 alkenyl group; a C2-C20 alkynyl group; a C1-C30 alkoxyl group; or a C6-C30 aryloxy group,
a is an integer from 0 to 7, and b is an integer from 0 to 8,
each of the aryl group, the fluorenyl group, the heterocyclic group, the fused ring group, the alkyl group, the alkenyl group, the alkynyl group, the alkoxyl group, the aryloxy group, the arylene group, and the fluorenylene group is further substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a C1-C20 alkoxyl group; a C1-C20 alkyl group; a C2-C20 alkenyl group; a C2-C20 alkynyl group; a C6-C25 aryl group; a C6-C25 aryl group substituted with deuterium; a fluorenyl group; a C2-C20 heterocyclic group; or a C3-C20 cycloalkyl group, and
each of the further substituted substituents is capable of being further substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a C1-C20 alkoxyl group; a C1-C20 alkyl group; a C2-C20 alkenyl group; a C2-C20 alkynyl group; a C6-C25 aryl group; a C6-C25 aryl group substituted with deuterium; a fluorenyl group; a C2-C20 heterocyclic group; or a C3-C20 cycloalkyl group, and the substituents are bonded to each other to form a ring.