US 12,473,257 B2
Heterocyclic compound and light-emitting device including the same
Hyunah Um, Yongin-si (KR); Hyeongmin Kim, Yongin-si (KR); Heechoon Ahn, Yongin-si (KR); Yeseul Lee, Yongin-si (KR); Hyoyoung Lee, Yongin-si (KR); Yirang Im, Yongin-si (KR); and Seowon Cho, Yongin-si (KR)
Assigned to Samsung Display Co., Ltd., Yongin-si (KR)
Filed by Samsung Display Co., Ltd., Yongin-si (KR)
Filed on Oct. 6, 2021, as Appl. No. 17/450,145.
Claims priority of application No. 10-2020-0131817 (KR), filed on Oct. 13, 2020.
Prior Publication US 2022/0112163 A1, Apr. 14, 2022
Int. Cl. C07D 209/86 (2006.01); C07D 519/00 (2006.01); C07F 7/08 (2006.01); H10K 85/40 (2023.01); H10K 85/60 (2023.01); H10K 50/11 (2023.01); H10K 101/10 (2023.01)
CPC C07D 209/86 (2013.01) [C07D 519/00 (2013.01); C07F 7/0812 (2013.01); H10K 85/40 (2023.02); H10K 85/6572 (2023.02); H10K 85/6574 (2023.02); H10K 85/6576 (2023.02); H10K 50/11 (2023.02); H10K 2101/10 (2023.02)] 14 Claims
OG exemplary drawing
 
1. A heterocyclic compound represented by Formula 1 and satisfying at least one of Condition 1 and Condition 3 to Condition 5:

OG Complex Work Unit Chemistry
wherein, Ar1 n Formula 1 is a group represented by Formula 2A,
Ar2 in Formula 1 is a group represented by Formula 2B,
a1 and a2 in Formula 1 are each independently an integer from 0 to 4, wherein a sum of a1 and a2 is 1 or more,
Ar3 in Formula 1 is a group represented by one of Formulae 3A-1 and 3B-1,

OG Complex Work Unit Chemistry
ring CY1 and ring CY2 in Formulae 3A-1 and 3B-1 are each independently a π-electron-rich C3-C60 cyclic group or a pyridine group,
R1 to R3, A1, and A2 in Formulae 1, 2A, 2B, 3A-1, and 3B-1 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, —C(Q51)(Q52)(Q53), —Si(Q51)(Q52)(Q53), —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), —P(═O)(Q1)(Q2), or —C(Q1)(Q2)(Q3), wherein Q51 to Q53 are each independently a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
R5 to R7 are each independently hydrogen, deuterium, a hydroxyl group, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a,
two neighboring groups of Q51 to Q53 are optionally linked to form 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,
R8 in Formula 3A-1 is hydrogen, deuterium, or a C1-C60 alkyl group unsubstituted or substituted with at least one deuterium,
b1 in Formula 1 is an integer from 1 to 7,
b2 and b3 in Formulae 2A and 2B are each independently an integer from 1 to 8,
c1 and c2 in Formulae 3A-1 to 3A-4 and 3B-1 to 3B-4 are each independently an integer from 1 to 10,
* indicates a binding site to a neighboring atom, and
R10a is:
deuterium (-D), —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), —P(═O)(Q11)(Q12), or any combination thereof;
a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, or a C6-C60 arylthio group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), —P(═O)(Q21)(Q22), or any combination thereof; or
—Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), —P(═O)(Q31)(Q32), or —C(Q31)(Q32)(Q33),
wherein Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 are each independently: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C1-C60 alkyl group; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; or a C3-C60 carbocyclic group or a C1-C60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof,
wherein Condition 1 to Condition 5 are as follows:
Condition 1
when Ar3 in Formula 1 is a group represented by Formula 3A-1, at least one A1 in Formula 3A-1 is a group represented by —C(Q51)(Q52)(Q53) or a group represented by —Si(Q51)(Q52)(Q53),
Condition 3
when Ar3 in Formula 1 is a group represented by Formula 3B-1, each of ring CY1 and ring CY2 in Formula 3B-1 is not a benzene group,
Condition 4
i) Ar3 in Formula 1 is a group represented by Formula 3B-1, and ii) when each of ring CY1 and ring CY2 in Formulae 3B-1 and 3B-4 is a benzene group, in Formulae 2A, 2B, and 3B-1, at least one of R2, R3, A1, and A2 is not hydrogen, and
Condition 5
i) Ar3 in Formula 1 is a group represented by Formula 3B-1, and ii) when each of ring CY1 and ring CY2 in Formula 3B-1 is a benzene group, R6 in Formula 3B-1 is a phenyl group unsubstituted or substituted with at least one R11a, wherein R11a is: deuterium, —F, —Cl, —Br, —I, a hydroxyl group, or a nitro group; or a C1-C20 alkyl group unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a nitro group, or any combination thereof,
wherein:
1) One of Condition 1, Condition 3, or Condition 4 is satisfied, and R5 to R7 in Formulae 3A-1 and 3B-1 are each independently hydrogen, deuterium, or a C1-C60 alkyl group unsubstituted or substituted with at least one deuterium,
2) Condition 3 is satisfied, and ring CY1 and ring CY2 are each independently a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a furan group, a thiophene group, an isoindole group, an indole group, an indene group, a benzofuran group, a benzothiophene group, a benzosilole group, a naphtho pyrrole group, a naphthofuran group, a naphthothiophene group, a naphtho silole group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a dibenzosilole group, or a pyridine group, or
3) Condition 5 is satisfied, and,
in Formulae 1, 2A, 2B, and 3B-1, R1, R2, R3, A1, and A2 are each independently:
hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, or a C1-C20 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, a phenyl group, a naphthyl group, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), —P(═O)(Q31)(Q32), or any combination thereof;
a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, a pyridinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a carbazolyl group, a phenanthrolinyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, or a dibenzocarbazolyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, a pyridinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a carbazolyl group, a phenanthrolinyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), —P(═O)(Q31)(Q32), or any combination thereof; or
—C(Q51)(Q52)(Q53), —Si(Q51)(Q52)(Q53), —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), —P(═O)(Q1)(Q2), or —C(Q1)(Q2)(Q3).