US 11,818,953 B2
Heterocyclic compound, organic light-emitting device including heterocyclic compound, and electronic apparatus including organic light-emitting device
Sunyoung Pak, Yongin-si (KR); Seokhwan Hwang, Yongin-si (KR); Junha Park, Yongin-si (KR); Hankyu Pak, Yongin-si (KR); Jangyeol Baek, Yongin-si (KR); Chanseok Oh, Yongin-si (KR); and Hyoyoung Lee, Yongin-si (KR)
Assigned to Samsung Display Co., Ltd., Yongin-si (KR)
Filed by Samsung Display Co., Ltd., Yongin-si (KR)
Filed on Sep. 24, 2020, as Appl. No. 17/031,774.
Claims priority of application No. 10-2020-0022371 (KR), filed on Feb. 24, 2020.
Prior Publication US 2021/0280798 A1, Sep. 9, 2021
Int. Cl. H10K 85/60 (2023.01); C07D 487/14 (2006.01); H10K 50/11 (2023.01)
CPC H10K 85/6572 (2023.02) [C07D 487/14 (2013.01); H10K 85/654 (2023.02); H10K 50/11 (2023.02)] 19 Claims
 
1. An organic light-emitting device comprising:
a first electrode;
a second electrode facing the first electrode;
an organic layer between the first electrode and the second electrode and comprising an emission layer; and
a heterocyclic compound represented by Formula 1:

OG Complex Work Unit Chemistry
wherein, in Formula 1,
E1 to E3 are each, independently from one another, a cyano group, a fluoro group, a cyano group-containing C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a fluoro group-containing C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a cyano group-containing C1-C30 cyclic group unsubstituted or substituted with at least one R10a, a fluoro group-containing C1-C30 cyclic group, a π electron-depleted nitrogen-containing C1-C30 cyclic group unsubstituted or substituted with at least one R10a, a boron-containing C1-C30 cyclic group unsubstituted or substituted with at least one R10a, a C1-C30 cyclic group unsubstituted or substituted with at least one R10a and comprising *—S(═O)2-*′ as a ring-forming moiety, a group represented by *—B(Q51)(Q52), a group represented by *—C(═O)(Q51), a group represented by *—S(═O)2(Q51), or a group represented by *—P(═O)(Q51)(Q52);
L1 to L3 are each, independently from one another, a single bond, a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a, or a C2-C30 heterocyclic group unsubstituted or substituted with at least one R10a;
a1 to a3 and b1 to b3 are each, independently from one another, an integer from 1 to 10;
n1 to n3 are each, independently from one another, an integer from 0 to 4, and at least one of n1 to n3 is 1 or greater;
R1 to R3, R10a, Q51, Q52, and R21 to R23 are each, independently from one another, of hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone 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, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2);
d21 to d23 are each, independently from one another, an integer from 0 to 4; and
a substituent of the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C1-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group is:
deuterium (-D), —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each, independently from one another, substituted with at least one of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), and —P(═O)(Q11)(Q12);
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group, each, independently from one another, unsubstituted or substituted with at least one of deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, 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, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), and —P(═O)(Q21)(Q22); or
—Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), or —P(═O)(Q31)(Q32),
wherein Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 are each, independently from one another, of: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; an amidino group; a hydrazine group; a hydrazone group; 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; a C6-C60 aryl group; a C1-C60 heteroaryl group; a monovalent non-aromatic fused polycyclic group; a monovalent non-aromatic fused heteropolycyclic group; a C1-C60 alkyl group substituted with at least one of deuterium, —F, and a cyano group; a C6-C60 aryl group substituted with at least one of deuterium, —F, and a cyano group; a biphenyl group; or a terphenyl group.