US 12,010,915 B2
Organic light-emitting diode having long lifespan, low voltage, and high efficiency property
Soon-Wook Cha, Goyang-si (KR); Sang-Woo Park, Seoul (KR); Jung-Ho Yoo, Seosan-si (KR); Ji-Hwan Kim, Anyang-si (KR); Sung Woo Kim, Seoul (KR); Hyeon Jun Jo, Busan (KR); and Young-Hwan Park, Cheongju-si (KR)
Assigned to SFC CO., LTD., Cheongju-si (KR)
Appl. No. 16/338,717
Filed by SFC CO., LTD., Cheongju-si (KR)
PCT Filed Sep. 14, 2017, PCT No. PCT/KR2017/010090
§ 371(c)(1), (2) Date Apr. 2, 2019,
PCT Pub. No. WO2088/066831, PCT Pub. Date Apr. 12, 2018.
Claims priority of application No. 10-2016-0128240 (KR), filed on Oct. 5, 2016.
Prior Publication US 2021/0288266 A1, Sep. 16, 2021
Int. Cl. H01L 51/00 (2006.01); C07C 211/61 (2006.01); C07D 307/91 (2006.01); C09K 11/06 (2006.01); H10K 85/60 (2023.01); H10K 50/11 (2023.01)
CPC H10K 85/6574 (2023.02) [C07C 211/61 (2013.01); C07D 307/91 (2013.01); C09K 11/06 (2013.01); H10K 85/615 (2023.02); H10K 85/626 (2023.02); H10K 85/633 (2023.02); C07B 2200/05 (2013.01); C07C 2603/40 (2017.05); C07C 2603/52 (2017.05); C09K 2211/1007 (2013.01); C09K 2211/1011 (2013.01); C09K 2211/1014 (2013.01); C09K 2211/1018 (2013.01); H10K 50/11 (2023.02); H10K 85/622 (2023.02); H10K 85/623 (2023.02)] 9 Claims
 
1. An organic light-emitting diode, comprising: a first electrode; a second electrode facing the first electrode; and a light-emitting layer intercalated between the first electrode and the second electrode,
wherein the light-emitting layer comprises at least one of the amine compounds represented by the following Chemical Formula A and at least one of the anthracene compounds represented by the following Chemical Formula B:

OG Complex Work Unit Chemistry
wherein,
Z3 is a substituted or unsubstituted aromatic hydrocarbon ring, selected from between Structural Formula 11 and Structural Formula 15:

OG Complex Work Unit Chemistry
wherein
“-*” denotes a bonding site for forming a 5-membered ring containing the carbon atom connected to both R14 and R15,
R's are as defined below for R16 to R19, and
m is an integer of 1 to 8 wherein when m is 2 or more or when R is two or more, individual R's are same or different,
the substituents R14 and R15, which are the same or different, are each independently one selected from among a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, and a substituted or unsubstituted aryl of 6 to 50 carbon atoms,
R16 to R19, which are the same or different, are each independently one selected from among a hydrogen atom, a deuterium atom, with a proviso that one of the substituents R16 to R19 represents a single bond attached to the linker L in a Q moiety,
two adjacent carbon atoms within Z3 form a five-membered ring with the carbon atom having both the substituents R14 and R15 thereon, thus establishing a fused ring,
a carbon atom of the aromatic ring of Z3 which does not participate in forming the five-membered ring is bonded to the linker L in a Q moiety,
the linker L represents a single bond,
n is an integer of 1,
the respective moieties Q's which are bonded to Z3 and to one of R16 to R19 are same or different,
the substituents Ar1 and Ar2, which are same or different, are each independently one selected from among a substituted or unsubstituted aryl of 6 to 40 carbon atoms and a substituted or unsubstituted heteroaryl of 2 to 30 carbon atoms;

OG Complex Work Unit Chemistry
wherein,
R21 to R28, which are same or different, are each independently one selected from among a hydrogen atom, and a deuterium atom,
R31 to R37, which are same or different, are each independently one selected from among a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl of 6 to 50 carbon atoms, and
the substituent Ar3 is a deuterium substituted or unsubstituted naphthyl or a substituent represented by the following Structural Formula C:

OG Complex Work Unit Chemistry
wherein R41 to R45 are same or different and are a hydrogen atom, a deuterium atom, or a deuterium substituted or unsubstituted aryl of 6 to 50 carbon atoms, or a deuterium substituted or unsubstituted alkyl of 1 to 30 carbon atoms,
wherein the term ‘substituted’ in the expression ‘substituted or unsubstituted’ means having at least one substituent selected from the group consisting of a deuterium, a halogen, an alkyl of 1 to 24 carbon atoms, a halogenated alkyl of 1 to 24 carbon atoms, an aryl of 6 to 24 carbon atoms and an alkylsilyl of 1 to 24 carbon atoms.