| CPC H10K 85/654 (2023.02) [C09K 11/025 (2013.01); C09K 11/06 (2013.01); H10K 85/342 (2023.02); H10K 85/622 (2023.02); H10K 85/6572 (2023.02); H10K 85/6574 (2023.02); H10K 85/6576 (2023.02); C09K 2211/1007 (2013.01); C09K 2211/1011 (2013.01); C09K 2211/1022 (2013.01); C09K 2211/1029 (2013.01); C09K 2211/1037 (2013.01); C09K 2211/1044 (2013.01); C09K 2211/1092 (2013.01); C09K 2211/185 (2013.01); H10K 50/11 (2023.02); H10K 2101/10 (2023.02); H10K 2101/90 (2023.02)] | 16 Claims |
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1. An organic light-emitting device comprising:
a first electrode;
a second electrode; and
an organic layer disposed between the first electrode and the second electrode and comprising an emission layer,
wherein the organic layer comprises host compounds that include a first compound represented by Formula 1 and a second compound represented by Formula 2:
 wherein, in Formulae 1, 2, and 9,
L11 to L13 are each independently selected from:
a C3-C10 cycloalkylene group, a C1-C10 heterocycloalkylene group, a C3-C10 cycloalkenylene group, a C1-C10 heterocycloalkenylene group, a C6-C60 arylene group, a C1-C60 heteroarylene group, a divalent non-aromatic condensed polycyclic group, and a divalent non-aromatic condensed heteropolycyclic group;
a C3-C10 cycloalkylene group, a C1-C10 heterocycloalkylene group, a C3-C10 cycloalkenylene group, a C1-C10 heterocycloalkenylene group, a C6-Coo arylene group, a C1-C60 heteroarylene group, a divalent non-aromatic condensed polycyclic group, and a divalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a carbazolyl group, a carbolinyl group, a group represented by Formula 9, —N(Q31)(Q32), —Si(Q31)(Q32)(Q33), and —B(Q31)(Q32); and
a C3-C10 cycloalkylene group, a C1-C10 heterocycloalkylene group, a C3-C10 cycloalkenylene group, a C1-C10 heterocycloalkenylene group, a C6-C60 arylene group, a C1-C60 heteroarylene group, a divalent non-aromatic condensed polycyclic group, and a divalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from a C6-C60 aryl group, a C1-C60 heteroaryl group, a carbazolyl group, and a carbolinyl group, each substituted with at least one selected from deuterium, —F, —Cl , —Br, —I, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a carbazolyl group, a carbolinyl group, a group represented by Formula 9, —N(Q21)(Q22), —Si(Q21)(Q22)(Q23), and —B(Q21)(Q22),
L21 to L23 are each independently selected from:
a C3-C10 cycloalkylene group, a C1-C10 heterocycloalkylene group, a C3-C10 cycloalkenylene group, a C1-C10 heterocycloalkenylene group, a C6-C60 arylene group, and a C1-C60 heteroarylene group;
a C3-C10 cycloalkylene group, a C1-C10 heterocycloalkylene group, a C3-C10 cycloalkenylene group, a C1-C10 heterocycloalkenylene group, a C6-C60 arylene group, and a C1-C60 heteroarylene group, each substituted with at least one selected from deuterium, —F, —Cl , —Br, —I, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a group represented by Formula 9, —N(Q31)(Q32), —Si(Q31)(Q32)(Q33), and —B(Q31)(Q32); and
a C3-C10 cycloalkylene group, a C1-C10 heterocycloalkylene group, a C3-C10 cycloalkenylene group, a C1-C10 heterocycloalkenylene group, a C6-C60 arylene group, and a C1-C60 heteroarylene group, each substituted with at least one selected from a C6-C60 aryl group and a C1-C60 heteroaryl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a group represented by Formula 9, —N(Q21)(Q22), —Si(Q21)(Q22)(Q23), and —B(Q21)(Q22),
a11 to a13 and a21 to a23 are each independently selected from 1, 2, 3, 4 and 5,
R11 to R13 are each independently selected from RHT and RET, provided that at least one selected from R11 to R13 is RET,
R21 to R23 are RHT,
R14 to R16 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 C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a carbazolyl group, a carbolinyl group, a group represented by Formula 9, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2 (Q1), and —P(═O)(Q1)(Q2); and
a C6-C60 aryl group, a C1-C60 heteroaryl group, a carbazolyl group, and a carbolinyl group, each substituted with at least one selected from a C1-C60 alkyl group, a C1-C60 alkoxy group, a C6-C60 aryl group, a C1-C60 heteroaryl group, a carbazolyl group, a carbolinyl group, and a group represented by Formula 9,
R24 to R26 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 C3-C10 cycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a group represented by Formula 9, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), and —P(═O)(Q1)(Q2); and
a C6-C60 aryl group, substituted with at least one selected from a C1-C60 alkyl group, a C1-C60 alkoxy group, a C6-C60 aryl group, and a group represented by Formula 9,
n11 to n13 and n21 to n23 are each independently selected from 0, 1 and 2,
the sum of n11, n12, and n13 is selected from 1, 2, 3, 4, 5 and 6,
the sum of n21, n22, and n23 is selected from 1, 2, 3, 4, 5 and 6,
RHT is selected from:
a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a benzofuranyl group, a benzothiophenyl group, a group represented by Formula 9, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), and —B(Q1)(Q2);
a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a benzofuranyl group, and a benzothiophenyl group, each substituted with at least one selected from deuterium, —F, —Cl , —Br, —I, a hydroxyl 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 group represented by Formula 9, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), and —B(Q31)(Q32); and
a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a benzofuranyl group, and a benzothiophenyl group, each substituted with at least one selected from a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, each substituted with at least one selected from deuterium, —F, —Cl , —Br, —I, a hydroxyl group, a nitro 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 group represented by Formula 9, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), and —B(Q21)(Q22),
RET is selected from groups represented by Formulae 7-24 to 7-26, 7-28 to 7-37, and 7-39 to 7-51:
     wherein, in Formulae 7-24 to 7-26, 7-28 to 7-37, and 7-39 to 7-51,
R71 and R72 are each independently selected from:
hydrogen, deuterium, —F, a methyl group, an ethyl group, a tert-butyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, groups represented by Formulae 10-1 to 10-24, —Si(Q31)(Q32)(Q33), and —N(Q31)(Q32); and
a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, each substituted with at least one selected from deuterium, —F, a methyl group, an ethyl group, a tert-butyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a group represented by one of Formulae 10-1 to 10-24, —Si(Q21)(Q22)(Q23), and —N(Q21)(Q22),
provided that,
(i) in Formulae 7-24 to 7-26, 7-28 to 7-37, 7-39, and 7-48, at least one of R71 is selected from:
groups represented by Formulae 10-1 to 10-24; and
a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, each substituted with at least one group represented by one of Formulae 10-1 to 10-24, and
(ii) in Formulae 7-40 to 7-47 and 7-49 to 7-51, at least one of R71 and/or at least one of R72 is selected from:
groups represented by Formulae 10-1 to 10-24; and
a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, each substituted with at least one group represented by one of Formulae 10-1 to 10-24,
b71 is selected from 1, 2, 3 and 4,
b72 is selected from 1, 2 and 3,
b73 is selected from 1, 2, 3, 4, 5 and 6,
b74 is selected from 1, 2, 3, 4 and 5,
b75 is selected from 1 and 2, and
* indicates a binding site to a neighboring atom:
   wherein, in Formulae 10-1 to 10-24,
* indicates a binding site to a neighboring atom,
X91 is selected from a single bond, O, S, C(R93)(R94), B(R93), P(R93), and P(R93)(R94),
X92 is selected from O, S, C(R95)(R96), B(R95), P(R95), and P(R95)(R96), provided that, when RHT is a group represented by Formula 9 and one of X91 and X92 is S, the other one of X91 and X92 is not O or S, nor is X91 a single bond when X92 is S,
A91 and A92 are each independently selected from a benzene group, a naphthalene group, an anthracene group, and a phenanthrene group,
R91 to R96 are each independently selected from:
hydrogen, deuterium, —F, —Cl , —Br, —I, a hydroxyl 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, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), and —B(Q31)(Q32); and
a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, each substituted with at least one selected from deuterium, —F, —Cl , —Br, —I, a hydroxyl 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, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), and —B(Q21)(Q22),
b91 is selected from 1, 2, 3, 4 and 5,
b92 is selected from 1, 2, 3, 4, 5 and 6, and
Q1 to Q3, 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,
except that in Formulae 7-24 to 7-26, 7-28 to 7-37, and 7-39 to 7-51,
Q21 to Q23 and Q31 to Q33 are each independently selected from a methyl group, an ethyl group, a tert-butyl group, an unsubstituted phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.
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