US 11,957,042 B2
Heterocyclic compound and organic light-emitting device including the same
Munki Sim, Yongin-si (KR); Sunyoung Pak, Yongin-si (KR); Junha Park, Yongin-si (KR); Hankyu Pak, Yongin-si (KR); Jangyeol Baek, Yongin-si (KR); Chanseok Oh, Yongin-si (KR); Hyoyoung Lee, Yongin-si (KR); Minjung Jung, 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 Aug. 26, 2020, as Appl. No. 17/003,260.
Claims priority of application No. 10-2019-0150485 (KR), filed on Nov. 21, 2019.
Prior Publication US 2021/0159412 A1, May 27, 2021
Int. Cl. H01L 51/00 (2006.01); C07F 5/02 (2006.01); C09K 11/06 (2006.01); H10K 85/30 (2023.01); H10K 50/11 (2023.01)
CPC H10K 85/322 (2023.02) [C07F 5/027 (2013.01); C09K 11/06 (2013.01); C09K 2211/1018 (2013.01); H10K 50/11 (2023.02)] 20 Claims
OG exemplary drawing
 
1. An organic light-emitting device comprising:
a first electrode;
a second electrode;
an organic layer comprising an emission layer and located between the first electrode and the second electrode, and
at least one heterocyclic compound represented by Formula 1,
wherein the first electrode comprises indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), or any combination thereof, and
the second electrode comprises lithium (Li), Ag, Mg, Al, Al—Li, Ca, Mg—In, Mg—Ag, ITO, IZO, or any combination thereof:

OG Complex Work Unit Chemistry
wherein, in Formula 1,
X11 is NR15, O, S, or Se,
A11 is a group represented by one of Formulae 10A to 10D,
Y11 to Y13 are each a carbon atom in a group represented by one of Formulae 10A to 10D,
A12 to A14 are each independently selected from C5-C60 carbocyclic groups,
R12 to R15 are each independently selected from the group consisting of hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an am idino 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 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 C7-C60 arylalkyl 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 C2-C60 heteroarylalkyl group, a substituted or unsubstituted C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio 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), —B(Q1)(Q2), —N(Q1)(Q2), —P(Q1)(Q2), —C(═O)(Q1), —S(═O)(Q1), —S(═O)2(Q1), —P(═O)(Q1)(Q2), and —P(═S)(Q1)(Q2), and
b12 to b14 are each independently selected from the group consisting of 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10,

OG Complex Work Unit Chemistry
wherein, in Formulae 10A to 10D,
X111 is NR114, O, S, or Se,
X112 is NR115, O, S, or Se,
A111 and A112 are each independently selected from C5-C60 carbocyclic groups,
Y11 to Y13 are each a carbon atom in Formula 1,
R111 to R115 are each independently selected from the group consisting of hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an am idino 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 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 C7-C60 arylalkyl 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 C2-C60 heteroarylalkyl group, a substituted or unsubstituted C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio 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), —B(Q1)(Q2), —N(Q1)(Q2), —P(Q1)(Q2), —C(═O)(Q1), —S(═O)(Q1), —S(═O)2(Q1), —P(═O)(Q1)(Q2), and —P(═S)(Q1)(Q2),
b111 and b112 are each independently selected from the group consisting of 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10,
adjacent two groups selected from R12 to R15 and R111 to R115 are optionally linked to form a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C1-C60 heterocyclic group,
Q1 to Q3 are each independently selected from the group consisting 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 C7-C60 arylalkyl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 heteroarylalkyl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C1-C60 alkyl group substituted with at least one selected from deuterium, —F, and a cyano group, a C6-C60 aryl group substituted with at least one selected from the group consisting of deuterium, —F, and a cyano group, a biphenyl group, and a terphenyl group, and
adjacent two groups selected from Q1 to Q3 are optionally linked to form a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C1-C60 heterocyclic group, and
wherein at least one of R13 or R111 is selected from Formula 3-2 or

OG Complex Work Unit Chemistry
 and
A31 is selected from the group consisting of a benzene group, a naphthalene group, a phenanthrene group, a triphenylene group, and an anthracene group,
R31 to R37 are each independently selected from the group consisting of hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group, an isobutoxy group, tert-butoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a thiophenyl group, a furanyl group, a silolyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a benzosilolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)(Q31), —S(═O)2(Q31), —P(═O)(Q31)(Q32), and —P(═S)(Q31)(Q32),
Q31 to Q33 are each independently selected from the group consisting of a C1-C60 alkyl group, a phenyl group, a biphenyl group, and a terphenyl group,
b31 is selected from the group consisting of 1, 2, 3, 4, 5, 6, 7, 8, and 9, and
* indicates a binding site to a neighboring atom.