US 11,944,006 B2
Diamine compound and organic light-emitting device including the same
Jongwoo Kim, Yongin-si (KR); Dongjun Kim, Yongin-si (KR); Jangyeol Baek, Yongin-si (KR); Eunjae Jeong, Yongin-si (KR); Sanghyun Han, 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 Feb. 15, 2019, as Appl. No. 16/277,289.
Claims priority of application No. 10-2018-0049403 (KR), filed on Apr. 27, 2018.
Prior Publication US 2019/0334096 A1, Oct. 31, 2019
Int. Cl. H10K 85/60 (2023.01); C07D 209/88 (2006.01); C07D 405/12 (2006.01); H10K 50/17 (2023.01); H10K 50/155 (2023.01)
CPC H10K 85/6572 (2023.02) [C07D 209/88 (2013.01); C07D 405/12 (2013.01); H10K 50/17 (2023.02); H10K 85/633 (2023.02); H10K 85/636 (2023.02); H10K 85/6574 (2023.02); H10K 50/155 (2023.02)] 19 Claims
OG exemplary drawing
 
1. An organic light-emitting device comprising:
a first electrode;
a second electrode; and
an organic layer between the first electrode and the second electrode and comprising an emission layer,
wherein the organic layer comprises a diamine compound comprising a naphthyl-phenyl linker and a 2-carbazolyl group,
wherein the diamine compound is a diamine compound represented by Formula 1:

OG Complex Work Unit Chemistry
wherein, in Formula 1,
L11 to L14 are each independently selected from a single bond, a substituted or unsubstituted C5-C60 carbocyclic group, and a substituted or unsubstituted C1-C60 heterocyclic group,
a11 to a14 are each independently selected from 0, 1, 2, and 3,
R11 to R14 are each independently selected from a group represented by Formula 2, 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 C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,
wherein at least one of R11 to R14 is a group represented by Formula 2, and one of R11 to R14 which is represented by Formula 2 is different from the remaining R11 to R14,
R15, R16, and R21 to R23 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 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 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),
b15 is selected from 1, 2, 3, 4, 5, and 6,
b16 and b23 are each independently selected from 1, 2, 3, and 4,
b22 is selected from 1, 2, and 3,
Q1 to Q3 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 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 deuterium, —F, and a cyano group, a biphenyl group, and a terphenyl group, and
* indicates a binding site to a neighboring atom.