US 11,672,172 B2
Heterocyclic compound comprising aromatic amine group and organic light-emitting diode including the same
Soon-Wook Cha, Goyang (KR); Seok-Bae Park, Geumsan-gun (KR); Hee-Dae Kim, Miryang (KR); Yu-rim Lee, Chuncheon (KR); Sang-Woo Park, Seoul (KR); and Ju-man Song, Mokpo (KR)
Assigned to SFC CO., LTD., Cheongju (KR)
Appl. No. 15/306,867
Filed by SFC CO., LTD., Cheongju (KR)
PCT Filed May 7, 2015, PCT No. PCT/KR2015/004552
§ 371(c)(1), (2) Date Oct. 26, 2016,
PCT Pub. No. WO2015/174682, PCT Pub. Date Nov. 19, 2015.
Claims priority of application No. 10-2014-0056951 (KR), filed on May 13, 2014; and application No. 10-2014-0072710 (KR), filed on Jun. 16, 2014.
Prior Publication US 2017/0062729 A1, Mar. 2, 2017
This patent is subject to a terminal disclaimer.
Int. Cl. H01L 51/00 (2006.01); C09K 11/06 (2006.01); C07D 405/14 (2006.01); C07D 493/04 (2006.01); C07C 211/61 (2006.01); C07D 209/94 (2006.01); C07D 307/77 (2006.01); C07D 493/10 (2006.01); C07D 495/10 (2006.01); C07F 7/08 (2006.01); H01L 51/50 (2006.01)
CPC H01L 51/0061 (2013.01) [C07C 211/61 (2013.01); C07D 209/94 (2013.01); C07D 307/77 (2013.01); C07D 405/14 (2013.01); C07D 493/04 (2013.01); C07D 493/10 (2013.01); C07D 495/10 (2013.01); C07F 7/0812 (2013.01); C09K 11/06 (2013.01); H01L 51/006 (2013.01); H01L 51/0052 (2013.01); H01L 51/0067 (2013.01); H01L 51/0071 (2013.01); H01L 51/0072 (2013.01); H01L 51/0073 (2013.01); H01L 51/0074 (2013.01); H01L 51/0094 (2013.01); C07C 2603/94 (2017.05); C09K 2211/1007 (2013.01); C09K 2211/1011 (2013.01); C09K 2211/1014 (2013.01); C09K 2211/1029 (2013.01); C09K 2211/1088 (2013.01); C09K 2211/1092 (2013.01); H01L 51/0056 (2013.01); H01L 51/0058 (2013.01); H01L 51/5012 (2013.01)] 17 Claims
OG exemplary drawing
 
1. An amine compound represented by the following:

OG Complex Work Unit Chemistry
wherein,
A1, A2, E, and F are same or different, and are each independently a substituted or unsubstituted aromatic hydrocarbon ring of 6 to 50 carbon atoms, or a substituted or unsubstituted heteroaromatic ring of 2 to 40 carbon atoms,
wherein,
two adjacent carbon atoms of the aromatic ring A1 and two adjacent carbon atoms of the aromatic ring A2 form a 5-membered fused ring together with a carbon atom to which substituents R1 and R2 are bonded;
linkers L1 to L12 are same or different, and are each independently selected from among a direct bond and a substituted or unsubstituted arylene of 6 to 60 carbon atoms;
M is any one selected from among N—R3, CR4R5, O, and S;
R1 to R5 and Ar1 to Ar8 are same or different, and are each independently any one selected from among hydrogen, deuterium, a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted aryl of 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl of 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl of 2 to 50 carbon atoms, a substituted or unsubstituted alkylsilyl of 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl of 6 to 30 carbon atoms,
in the alternative for R1 and R2, R1 and R2 together form a mono- or polycyclic aliphatic or aromatic ring, and
in the alternative for Ar1 to Ar8, Ar1 forms a ring with Ar2, Ar3 forms a ring with Ar4, Ar5 forms a ring with Ar6, and/or Ar7 forms a ring with Ar8,
p1 to p4, r1 to r4, and s1 to s4 are each independently an integer of 1 to 3, with the proviso that when any of them is 2 or greater, the corresponding linkers are same or different, and
x is 1 with an amine radical having substituents Ar1 and Ar2 being bonded to the A2 ring moiety,
y is 0 or 1 and z is 0 or 1, with a proviso that:
an amine radical having substituents Ar3 and Ar4 is bonded to the A1 ring moiety, or an amine radical having substituents Ar5 and Ar6 is bonded to the E ring moiety, or an amine radical having substituents A7 and Ar8 is bonded to the F ring moiety; and
two adjacent carbon atoms of the A2 ring moiety occupy respective positions * of Structural Formula Q1 to form a fused ring, and
two adjacent carbon atoms of the A1 ring moiety occupy respective positions * of structural Formula Q2 to form a fused ring,
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 cyano, a halogen, a nitro, 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, an arylalkyl of 7 to 24 carbon atoms, a heteroaryl of 2 to 24 carbon atoms, a heteroarylalkyl of 2 to 24 carbon atoms, an alkylsilyl of 1 to 24 carbon atoms, and an arylsilyl of 6 to 24 carbon atoms.