US 12,004,422 B2
Heterocyclic compound and organic light-emitting device including the same
Yeseul Lee, Yongin-si (KR); Hyeongmin Kim, Yongin-si (KR); Heechoon Ahn, Yongin-si (KR); Hyunah Um, Yongin-si (KR); Yirang Im, Yongin-si (KR); Soobyung Ko, Yongin-si (KR); and Jongwoo Kim, Yongin-si (KR)
Assigned to SAMSUNG DISPLAY CO., LTD., Yongin-si (KR)
Filed by Samsung Display Co., Ltd., Yongin-Si (KR)
Filed on Nov. 1, 2019, as Appl. No. 16/672,159.
Claims priority of application No. 10-2019-0027637 (KR), filed on Mar. 11, 2019.
Prior Publication US 2020/0295269 A1, Sep. 17, 2020
Int. Cl. H10K 50/12 (2023.01); H10K 85/40 (2023.01); H10K 85/60 (2023.01); H10K 50/15 (2023.01); H10K 50/16 (2023.01); H10K 50/81 (2023.01); H10K 50/82 (2023.01)
CPC H10K 85/6572 (2023.02) [H10K 85/40 (2023.02); H10K 85/615 (2023.02); H10K 85/6574 (2023.02); H10K 85/6576 (2023.02); H10K 50/12 (2023.02); H10K 50/15 (2023.02); H10K 50/16 (2023.02); H10K 50/81 (2023.02); H10K 50/82 (2023.02)] 13 Claims
OG exemplary drawing
 
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
at least one heterocyclic compound represented by one of Formulae 1-1A, 1-1B, 1-2A, 1-3A, 1-3B, 1-4A, and 1-4B:

OG Complex Work Unit Chemistry
wherein, in Formulae 1-1A, 1-1B, 1-2A, 1-3A, 1-3B, 1-4A, and 1-4B,
in Formula 1-1A, 1-1B, 1-3A, 1-3B, 1-4A, and 1-4B, Ar1 is selected from groups represented by Formulae 6-1 to 6-35, and
in Formula 1-2A, Ar1 is selected from groups represented by Formulae 6-1 to 6-33 and 6-35:

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
wherein, in Formulae 6-1 to 6-35,
Ph indicates a phenyl group, t-Bu indicates a tert-butyl group, and Cz indicates a carbazolyl group, and
* indicates a binding site to a neighboring atom,
D1a and D1b are each independently a group represented by Formula 2, and
D1a and D1b are identical to or different from each other:

OG Complex Work Unit Chemistry
wherein, in Formula 2,
X1 is selected from a single bond, C(R5)(R6), Si(R5)(R6), N(R5), O, and S,
A1 and A2 are each independently a C5-C60 carbocyclic group or a C1-C60 heterocyclic group,
a1 is 0,
* indicates a binding site to a neighboring atom,
in Formulae 1-1A, 1-1B, 1-2A, 1-3A, 1-3B, 1-4A, 1-4B, and 2,
R1 to R6 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 carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, 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), —S(═O)2(Q1), and —P(═O)(Q1)(Q2),
except that
in Formulae 1-1A, 1-1B, 1-2A, 1-3A, 1-3B, 1-4A, and 1-4B, R1 is not a C1-C60 alkyl group substituted with three —F, and R2 is not a C1-C60 alkyl group substituted with three —F, and
in Formulae 1-3A, 1-3B, 1-4A, and 1-4B, R1 and
R2 are each hydrogen,
c1 is an integer from 1 to 3,
c2 is an integer from 1 to 4,
c3 and c4 are each independently an integer from 1 to 5,
at least one substituent of the substituted C3-C10 cycloalkylene group, the substituted C1-C10 heterocycloalkylene group, the substituted C3-C10 cycloalkenylene group, the substituted C1-C10 heterocycloalkenylene group, the substituted C6-C60 arylene group, the substituted C1-C60 heteroarylene group, the substituted divalent non-aromatic condensed polycyclic group, the substituted divalent non-aromatic condensed heteropolycyclic 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, the 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, and a monovalent non-aromatic condensed heteropolycyclic 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.