US 11,997,919 B2
Organic electric element, display panel comprising the same and display device comprising the same
Jicheol Shin, Paju-si (KR); Seonkeun Yoo, Paju-si (KR); Jeongdae Seo, Paju-si (KR); Shinhan Kim, Paju-si (KR); JooYong Yoon, Paju-si (KR); Jun Yun, Paju-si (KR); DongHeon Kim, Paju-si (KR); YongHan Lee, Paju-si (KR); and SungJae Lee, Paju-si (KR)
Assigned to LG DISPLAY CO., LTD., Seoul (KR); and LG CHEM, LTD., Seoul (KR)
Filed by LG DISPLAY CO., LTD., Seoul (KR); and LG CHEM, LTD., Seoul (KR)
Filed on Dec. 24, 2020, as Appl. No. 17/133,856.
Claims priority of application No. 10-2019-0180077 (KR), filed on Dec. 31, 2019.
Prior Publication US 2021/0202857 A1, Jul. 1, 2021
Int. Cl. H10K 50/17 (2023.01); H10K 85/60 (2023.01)
CPC H10K 85/615 (2023.02) [H10K 85/633 (2023.02); H10K 50/17 (2023.02)] 17 Claims
 
1. An organic electric element comprising:
a first electrode;
a second electrode; and
an organic layer positioned between the first electrode and the second electrode,
wherein the organic layer comprises a first layer and a light emitting layer, and
the first layer comprises at least one first compound selected from the group consisting of chemical formula 1, chemical formula 2, and combinations thereof; and further comprises at least one second compound represented by the following chemical formula 3:

OG Complex Work Unit Chemistry
wherein in the chemical formula 1 and the chemical formula 2:
R1 to R6, which are same or different, and are each independently selected from the group consisting of a hydrogen; a deuterium; a tritium; a halogen; a cyano group; a nitro group; a C6-C60 aryl group; a fluorenyl group; a C2-C60 hetero ring group containing at least one hetero atom from O, N, S, Si and P; a fused ring group of a C3-C60 aliphatic ring or a C6-C60 aromatic ring; a C1-C50 alkyl group; a C2-C20 alkenyl group; a C2-C20 alkynyl group; a C1-C30 alkoxy group; a C6-C30 aryloxy group; a C3-C60 alkylsilyl group; a C18-C60 arylsilyl group; and a C8-C60 alkylarylsilyl group,
wherein one or more of R1 to R6 is a cyano group,
wherein A1 to A4, which may be the same or different, and are each independently one selected from the group consisting of a hydrogen; a deuterium; a tritium; a halogen; a cyano group; a nitro group; a C6-C60 aryl group; a fluorenyl group; a C2-C60 hetero ring group containing at least one hetero atom from O, N, S, Si and 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; a C1-C30 alkoxy group; a C6-C30 aryloxy group; a C3-C60 alkylsilyl group; a C18-C60 arylsilyl group; and a C8-C60 alkylarylsilyl group;
wherein in R1 to R6 and A1 to A4 of the chemical formula 1 and the chemical formula 2, the aryl group, the fluorenyl group, the hetero ring group, the fused ring group, the alkyl group, the alkenyl group, the alkynyl group, the alkoxy group, the aryloxy group, the alkylsilyl group, the arylsilyl group and the alkylarylsilyl group can each be further substituted with at least one substituent selected from the group consisting of a deuterium; a nitro group; a cyano group; a halogen; an amino group; a C1-C20 alkoxyl 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 the deuterium; a fluorenyl group; a C2-C20 hetero ring group; a C3-C60 alkylsilyl group; a C18-C60 arylsilyl group; and a C8-C60 alkylarylsilyl group,
wherein in the chemical formula 3,
X1 to X3, may be the same or different, and are each independently one selected from the group consisting of a C6-C60 aryl group; a C2-C60 hetero ring group containing at least one hetero atom from O, S, Si and P; a fused ring group of a C3-C60 aliphatic ring and a C6-C60 aromatic ring, or are represented by chemical formula 3-4 or 3-5,
wherein in X1 to X3 of the chemical formula 3, the aryl group, the hetero ring group, and the fused ring group may each be further substituted with at least one substituent selected from the group consisting of a deuterium; a nitro group; a cyano group; a halogen; a C1-C20 alkoxyl 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 the deuterium; a C2-C20 hetero ring group containing at least one hetero atom from O, S, Si and P; a C3-C60 alkylsilyl group; a C18-C60 arylsilyl group; and a C8-C60 alkylarylsilyl group,

OG Complex Work Unit Chemistry
wherein in the chemical formula 3-4 or 3-5:
either one of the broken lines can be bonded to N of the chemical formula 3, and the other one of the broken lines can be bonded to hydrogen,
m and n are each independently an integer of 0 to 3,
R1 is each independently selected from the group consisting of a hydrogen; a deuterium; a tritium; a halogen; a cyano group; a nitro group; a C6-C60 aryl group; a fluorenyl group; a C2-C60 hetero ring group containing at least one hetero atom from O, N, S, Si and 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; a C1-C30 alkoxy group; a C6-C30 aryloxy group; a C3-C60 alkylsilyl group; a C18-C60 arylsilyl group; and a C8-C60 alkylarylsilyl group,
L is one selected from the group consisting of a C6-C60 arylene group; a fluorylene group; a C2-C60 divalent hetero ring group containing at least one heteroatom from 0 N, S, Si and P; a divalent fused ring group of a C3-C60 aliphatic ring and a C6-C60 aromatic ring,
in R1 and L of the chemical formula 3-4 or 3-5, the aryl group, the fluorenyl group, the hetero ring group, the fused ring group, the alkyl group, the alkenyl group, the alkynyl group, the alkoxy group, the aryloxy group, the alkylsilyl group, the arylsilyl group, the alkylarylsilyl group, the arylene group, the fluorylene group, the divalent fused ring group, the divalent fused ring group may each be further substituted with at least one substituent selected from the group consisting of a deuterium; a nitro group; a cyano group; a halogen; an amino group; a C1-C20 alkoxyl 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 the deuterium; a fluorenyl group; a C2-C20 hetero ring group; a C3-C60 alkylsilyl group; a C18-C60 arylsilyl group; and a C8-C60 alkylarylsilyl group,
with the proviso that in the chemical formula 3, X1 to X3 is not a fluorenyl group.