US 11,697,645 B2
Heterocyclic compound, composition including heterocyclic compound, and organic light-emitting device including heterocyclic compound
Masaki Numata, Kanagawa (JP); Mitsunori Ito, Kanagawa (JP); Norihito Ishii, Kanagawa (JP); and Rie Sakurai, Kanagawa (JP)
Assigned to SAMSUNG ELECTRONICS CO., LTD., Gyeonggi-Do (KR)
Filed by Samsung Electronics Co., Ltd., Suwon-si (KR)
Filed on Dec. 20, 2019, as Appl. No. 16/722,261.
Claims priority of application No. 2018-248443 (JP), filed on Dec. 28, 2018; and application No. 10-2019-0079003 (KR), filed on Jul. 1, 2019.
Prior Publication US 2020/0207732 A1, Jul. 2, 2020
Int. Cl. H01L 51/50 (2006.01); C07D 333/76 (2006.01); C07D 307/91 (2006.01); C07D 403/04 (2006.01); C07D 403/14 (2006.01); C07D 487/04 (2006.01); H01L 51/00 (2006.01)
CPC C07D 333/76 (2013.01) [C07D 307/91 (2013.01); C07D 403/04 (2013.01); C07D 403/14 (2013.01); C07D 487/04 (2013.01); H01L 51/0058 (2013.01); H01L 51/0059 (2013.01); H01L 51/0072 (2013.01); H01L 51/0073 (2013.01); H01L 51/0074 (2013.01); H01L 51/5016 (2013.01)] 19 Claims
OG exemplary drawing
 
1. A heterocyclic compound represented by Formula 1:

OG Complex Work Unit Chemistry
wherein the heterocyclic compound satisfies Equation 1:
|EHOMO−ELUMO|≥3.0 eV  Equation 1
wherein, in Equation 1, EHOMO indicates a HOMO energy level value of the heterocyclic compound, and ELUMO indicates a LUMO energy level value of the heterocyclic compound,
wherein, in Formulae 1 and 2,
X1 is O, S, or Se,
L1 and L11 are each independently a single bond, a substituted or unsubstituted benzene group, or a substituted or unsubstituted naphthalene group,
a1 and a11 are each independently an integer from 1 to 10,
Ar1 and Ar11 are each independently a substituted or unsubstituted benzene group, or a substituted or unsubstituted naphthalene group,
R1 to R6 are each independently a group represented by Formula 2, hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, or a substituted or unsubstituted C1-C60 alkoxy group,
b3 is an integer from 0 to 3,
b4 is an integer from 0 to 4,
b5 is an integer from 0 to 5,
at least one substituent of the substituted benzene group, the substituted naphthalene group, the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, and the substituted C1-C60 alkoxy group is:
deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, —NCS, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, or any combination thereof,
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each substituted with at least one deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, —NCS, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —C(═O)(Q11), or any combination thereof;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, or any combination thereof,
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, or any combination thereof, each substituted with at least one deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —C(═O)(Q21), or any combination thereof; or
—Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —C(═O)(Q31), or any combination thereof,
wherein Q11 to Q13, Q21 to Q23, and Q31 to Q33 are each independently hydrogen, deuterium, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, or a biphenyl group, and
* indicates a binding site to an adjacent atom.