US 11,730,053 B2
Organic light-emitting device
Sooyon Kim, 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 May 4, 2016, as Appl. No. 15/146,843.
Claims priority of application No. 10-2015-0063220 (KR), filed on May 6, 2015; and application No. 10-2016-0029102 (KR), filed on Mar. 10, 2016.
Prior Publication US 2016/0329493 A1, Nov. 10, 2016
Int. Cl. H01L 51/00 (2006.01); H10K 85/60 (2023.01); C09K 11/02 (2006.01); C09K 11/06 (2006.01); H10K 85/40 (2023.01); H10K 50/81 (2023.01); H10K 50/82 (2023.01); H10K 50/12 (2023.01)
CPC H10K 85/633 (2023.02) [C09K 11/025 (2013.01); C09K 11/06 (2013.01); H10K 85/40 (2023.02); H10K 85/615 (2023.02); H10K 85/626 (2023.02); H10K 85/636 (2023.02); H10K 85/654 (2023.02); H10K 85/6572 (2023.02); C09K 2211/1014 (2013.01); C09K 2211/1029 (2013.01); C09K 2211/1088 (2013.01); H10K 50/121 (2023.02); H10K 50/81 (2023.02); H10K 50/82 (2023.02); H10K 85/623 (2023.02); H10K 85/6574 (2023.02); H10K 85/6576 (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, the organic layer comprising an emission layer,
wherein the organic layer comprises a first compound represented by Formula 1 and a second compound represented by one selected from Formulae 2-3 and 2-4:

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
wherein, in Formula 1, Formula A, and Formulae 2-3 and 2-4,
R2 and R8 are each independently the group represented by Formula A,
R1, R3 to R7, and R9 to R14 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 monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q1)(Q2)(Q3), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), and —P(═O)(Q1)(Q2),
Ar241 is selected from a benzene group, a biphenyl group, and a triphenylene group,
L101, L231 to L234, and L241 are each independently selected from a substituted or unsubstituted C3-C10 cycloalkylene group, a substituted or unsubstituted C1-C10 heterocycloalkylene group, a substituted or unsubstituted C3-C10 cycloalkenylene group, a substituted or unsubstituted C1-C10 heterocycloalkenylene group, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C1-C60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
a101 is selected from 0, 1, 2, and 3,
a231 to a234, and a241 are each independently selected from 0, 1, and 2,
R101, R102, R231 to R234, and R241 are each independently selected from 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 selected from R101 and R102 for R2 and/or at least one selected from R101 and R102 for R8 is a phenyl group substituted with —Si(CH3)3,
wherein at least one selected from R101 and R102 for R2 and/or at least one selected from R101 and R102 for R8 is selected from:
a dibenzofuranyl group, and a dibenzosilolyl group;
a dibenzofuranyl group, and a dibenzosilolyl 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-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzofuranyl group, a benzothiophenyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, and —Si(Q31)(Q32)(Q33); and
a dibenzofuranyl group, and a dibenzosilolyl group, each substituted with at least one C1-C20 alkyl group that is substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a cyano group, and a nitro group,
wherein Q31 to Q33 are each independently selected from a C1-C20 alkyl group, a C6-C60 aryl group, a biphenyl group, and a terphenyl group, b231 to b234 and b241 are each independently selected from 1, 2, and 3,
R235 to R238, and R242 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-C6o 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),
b235 to b238, and b242 are each independently selected from 1, 2, and 3,
n231 to n234 are each independently selected from 0, 1, and 2, wherein a sum of n231, n232, n233 and n234 is selected from 1, 2,3,4, 5, and 6,
n241 is selected from 3, 4,5,6, 7, and 8, and
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 monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group,
wherein a weight ratio of the first compound to the second compound is about 1:99 to about 20:80.