US 12,084,433 B2
Heterocyclic compound and organic light-emitting device including the same
Junha Park, Yongin-si (KR); Munki Sim, Yongin-si (KR); Hyoyoung Lee, Yongin-si (KR); Youngkook Kim, Yongin-si (KR); and Seokhwan Hwang, Yongin-si (KR)
Assigned to Samsung Display Co., Ltd., Yongin-si (KR)
Filed by Samsung Display Co., Ltd., Yongin-si (KR)
Filed on Jan. 17, 2019, as Appl. No. 16/250,946.
Claims priority of application No. 10-2018-0034091 (KR), filed on Mar. 23, 2018.
Prior Publication US 2019/0292169 A1, Sep. 26, 2019
This patent is subject to a terminal disclaimer.
Int. Cl. H10K 50/16 (2023.01); C07D 251/24 (2006.01); C07D 403/04 (2006.01); C07D 403/10 (2006.01); C07D 405/04 (2006.01); C07D 405/10 (2006.01); C07D 405/14 (2006.01); C07D 409/04 (2006.01); C07D 409/10 (2006.01); C07D 471/04 (2006.01); C07D 519/00 (2006.01); H10K 50/125 (2023.01); H10K 85/60 (2023.01)
CPC C07D 405/04 (2013.01) [C07D 251/24 (2013.01); C07D 403/04 (2013.01); C07D 403/10 (2013.01); C07D 405/10 (2013.01); C07D 405/14 (2013.01); C07D 409/04 (2013.01); C07D 409/10 (2013.01); C07D 471/04 (2013.01); C07D 519/00 (2013.01); H10K 50/16 (2023.02); H10K 85/626 (2023.02); H10K 85/6572 (2023.02); H10K 85/6574 (2023.02); H10K 85/6576 (2023.02); H10K 50/125 (2023.02); H10K 50/166 (2023.02); H10K 85/654 (2023.02)] 18 Claims
OG exemplary drawing
 
1. A heterocyclic compound represented by Formula 1:

OG Complex Work Unit Chemistry
wherein, in Formulae 1, and 2-2,
X1 is selected from N(R15), O, and S,
L1 to L8 and L23 are each independently a single bond, a substituted or unsubstituted C3-C60 carbocyclic group or a substituted or unsubstituted C1-C60 heterocyclic group,
a1 to a8 and a23 are each independently an integer of 1 to 5, wherein, when a1 is two or more, two more of L1(s) may be identical to or different from each other, when a2 is two or more, two more of L2(s) may be identical to or different from each other, when a3 is two or more, two more of L(s) may be identical to or different from each other, when a4 is two or more, two more of L4(s) may be identical to or different from each other, when a5 is two or more, two more of L5(s) may be identical to or different from each other, when a6 is two or more, two more of L(s) may be identical to or different from each other, when a7 is two or more, two more of L7(s) may be identical to or different from each other, when a8 is two or more, two more of L8(s) may be identical to or different from each other, and when a23 is two or more, two more of L23(s) may be identical to or different from each other,
R1 to R8 and R15 are each independently selected from a group represented by Formula 2-2, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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 C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-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 condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), and —P(═O)(Q1)(Q2),
at least one selected from R1 to R8 is a cyano group, at least one of the remaining R1 to R8 is a group represented by a group represented by Formula 2-2, wherein the L1 to L8 corresponding to the at least one selected from R1 to R8 that is a cyano group is a single bond, wherein the L1 to L8 corresponding to the at least one selected from R1 to R8 that is a group represented by Formula 2-2 is not an anthracene group or a triazine group,
R23 is selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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 C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-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 condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), and —P(═O)(Q1)(Q2), wherein R23 is not a cyano group,
b1 to b8 and b23 are each independently an integer of 1 to 5, wherein, when b1 is two or more, two more of R1(s) may be identical to or different from each other, when b2 is two or more, two more of R2(s) may be identical to or different from each other, when b3 is two or more, two more of R3(s) may be identical to or different from each other, when b4 is two or more, two more of R4(s) may be identical to or different from each other, when b5 is two or more, two more of R5(s) may be identical to or different from each other, when b6 is two or more, two more of R6(s) may be identical to or different from each other, when b7 is two or more, two more of R7(s) may be identical to or different from each other, when b8 is two or more, two more of R8(s) may be identical to or different from each other, and when b23 is two or more, two more of R23(s) may be identical to or different from each other,
R1 to R8, R15, R23, L1 to L8, and L23 do not include a carbazole group,
at least one substituent of the substituted C3-C60 carbocyclic group, the substituted C1-C60 heterocyclic group, 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, substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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 condensed polycyclic group, a monovalent non-aromatic condensed 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 condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl 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 condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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 condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), and —P(═O)(Q21)(Q22); and
—Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), and —P(═O)(Q31)(Q32), and
Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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 condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group.