| CPC H10K 85/6572 (2023.02) [C09K 11/025 (2013.01); C09K 11/06 (2013.01); H10K 50/11 (2023.02); H10K 85/342 (2023.02); H10K 85/622 (2023.02); H10K 85/654 (2023.02); H10K 85/657 (2023.02); C09K 2211/1007 (2013.01); C09K 2211/1029 (2013.01); C09K 2211/185 (2013.01); H10K 50/12 (2023.02); H10K 50/15 (2023.02); H10K 85/633 (2023.02); H10K 85/636 (2023.02); H10K 85/6574 (2023.02); H10K 85/6576 (2023.02); H10K 2101/10 (2023.02); H10K 2101/30 (2023.02); H10K 2101/40 (2023.02); H10K 2101/90 (2023.02)] | 24 Claims |
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1. An organic light-emitting device comprising:
a first electrode;
a second electrode facing the first 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 one of Formulae 1-1, 2-1, 2-2, and 3-1, a second compound represented by one of Formulae 1-2, 2-3, 2-4, and 3-2, a third compound represented by Formula 4, and a fourth compound,
wherein when the first compound is represented by Formula 1-1, the second compound is represented by one of Formulae 2-3, 2-4, and 3-2, when the first compound is represented by Formulae 2-1 or 2-2, the second compound is represented by one of Formulae 1-2 and 3-2, and when the first compound is represented by Formula 3-1, the second compound is represented by one of Formulae 1-2, 2-3, and 2-4, and
wherein the first compound to the fourth compound satisfy Equations 1 to 8:
E1,LUMO≥E2,LUMO+0.15 electron volts (eV) Equation 1
E1,HOMO≥E2,HOMO+0.15 eV Equation 2
E1,T1≥E4,T1 Equation 3
E2,T1≥E4,T1 Equation 4
E3,T1≥E4,T1 Equation 5
E3,LUMO≥E2,LUMO+0.1 eV Equation 6
−5.6 eV≥E3,HOMO Equation 7
Egap1≥Egap3, Equation 8
wherein, in Equations 1 to 8,
E1,LUMO indicates a lowest unoccupied molecular orbital (LUMO) energy level of the first compound,
E2,LUMO indicates a LUMO energy level of the second compound, E3,LUMO indicates a LUMO energy level of the third compound,
E1,HOMO indicates a highest occupied molecular orbital (HOMO) energy level of the first compound,
E2,HOMO indicates a HOMO energy level of the second compound,
E3,HOMO indicates a HOMO energy level of the third compound,
E1,T1 indicates a lowest excited triplet energy level of the first compound,
E2,T1 indicates a lowest excited triplet energy level of the second compound,
E3,T1 indicates a lowest excited triplet energy level of the third compound,
E4,T1 indicates a lowest excited triplet energy level of the fourth compound,
Egap1 indicates a gap between the LUMO energy level of the first compound and the HOMO energy level of the first compound, and
Egap3 indicates a gap between the LUMO energy level of the third compound and the HOMO energy level of the third compound,
  wherein, in Formulae 1-1, 1-2, 2-1 to 2-4, 3-1, 3-2, 4, and 5,
A11 to A14, A21 to A23, and A51 are each independently selected from a C5-C20 carbocyclic group and a C1-C20 heterocyclic group,
X11 is selected from O, S, N[(L12)a12-R12], C[(L12)a12-R12](R17), Si[(L12)a12-R12](R17), P[(L12)a12-R12], B[(L12)a12-R12], and P(═O)[(L12)a12-R12],
X12 is selected from O, S, N[(L15)a15-R19], C[(L15)a15-R19](R20), Si[(L15)a15-R19](R20), P[(L15)a15-R19], B[(L15)a15-R19], and P(═O)[(L15)a15-R19],
X21 is selected from N[(L21)a21-R21], C[(L21)a21-R21](R23), O, and S,
X22 is selected from N[(L22)a22-R22], C[(L22)a22-R22](R24), O, and S,
X51 is selected from N and CR51,
X71 is selected from N[(L71)a71-R71], C[(L71)a71-R71](R73), O, and S,
X72 is selected from N[(L72)a72-R72], C[(L72)a72-R72](R74), O, and S,
R12 and R17 are optionally bound to form a saturated or unsaturated ring,
R19 and R20 are optionally bound to form a saturated or unsaturated ring,
L11 to L15, L21, L22, L41 to L43, L61 to L63, L71, and L72 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, provided that L61 to L63 are not each independently a carbazolylene group,
L31 to L33 are each independently selected from the group consisting of:
a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a triphenylenylene group, a thiophenylene group, a furanylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a dibenzosilolylene group, a benzocarbazolylene group, and a dibenzocarbazolylene group; and
a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a triphenylenylene group, a thiophenylene group, a furanylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a dibenzosilolylene group, a benzocarbazolylene group, and a dibenzocarbazolylene group, each substituted with at least one selected from deuterium, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, a methoxy group, an ethoxy group, an n-propoxy group, an iso-propoxy group, an n-butoxy group, a sec-butoxy group, an iso-butoxy group, a 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 triphenylenyl group, a thiophenyl group, a furanyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, —N(Q31)(Q32), —Si(Q31)(Q32)(Q33), and —B(Q31)(Q32),
wherein Q31 to Q33 are each independently selected from a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group,
a11 to a15, a21, a22, a31 to a33, a41 to a43, a61 to a63, a71, and a72 are each independently selected from 0, 1, 2, 3, 4, and 5,
at least one selected from L41 to L43 is a group represented by Formula 5,
wherein when L41 is a group represented by Formula 5, a41 is selected from 1, 2, 3, 4, and 5; when L42 is a group represented by Formula 5, a42 is selected from 1, 2, 3, 4, and 5; and when L43 is a group represented by Formula 5, a43 is selected from 1, 2, 3, 4, and 5,
R11 to R27, R41 to R43, R51, R52, R61 to R66, and R71 to R77 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), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), and —P(═O)(Q1)(Q2),
at least one selected from R41 to R43 is selected from a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,
R31 to R36 are each independently selected from a C1-C20 alkyl group, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), and a group represented by any of Formulae 5-1 to 5-16, 5-18, and 5-19:
   wherein, in Formulae 5-1 to 5-16, 5-18, and 5-19,
Y11 is selected from O, S, C(Z13)(Z14), and Si(Z13)(Z14),
Z11 to Z14 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 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 pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl 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 benzofuranyl group, a benzothiophenyl group, a benzosilolyl group, an isobenzothiazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), and —P(═O)(Q31)(Q32); and
a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a carbazolyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group, each substituted with at least one selected from a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a carbazolyl group, a fluorenyl group, —Si(Q21)(Q22)(Q23), and —N(Q21)(Q22),
wherein Q1 to Q3, Q21 to Q23, and Q31 to Q33 are each independently selected from a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group,
e2 is an integer selected from 1 and 2, e3 is an integer selected from 1 to 3, e4 is an integer selected from 1 to 4, e5 is an integer selected from 1 to 5, e6 is an integer selected from 1 to 6, e7 is an integer selected from 1 to 7, e9 is an integer selected from 1 to 9, and
* indicates a binding site to an adjacent atom,
b13 to b16, b25 to b27, b43 to b48, b52, and b75 to b77 are each independently selected from 1, 2, 3, and 4,
n31 to n33 and n61 to n63 are each independently selected from 0, 1, 2, 3, and 4,
* indicates a binding site to an adjacent atom, and
at least one selected from substituents of the substituted C3-C10 cycloalkylene group, substituted C1-C10 heterocycloalkylene group, substituted C3-C10 cycloalkenylene group, substituted C1-C10 heterocycloalkenylene group, substituted C6-C60 arylene group, substituted C1-C60 heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C1-C60 alkyl group, substituted C2-C60 alkenyl group, substituted C2-C60 alkynyl group, substituted C1-C60 alkoxy group, substituted C3-C10 cycloalkyl group, substituted C1-C10 heterocycloalkyl group, substituted C3-C10 cycloalkenyl group, substituted C1-C10 heterocycloalkenyl group, substituted C6-C60 aryl group, substituted C6-C60 aryloxy group, substituted C6-C60 arylthio group, substituted C1-C60 heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group, and substituted monovalent non-aromatic condensed heteropolycyclic group is selected from the group consisting of:
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, and a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy 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 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 monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), and —P(═O)(Q11)(Q12);
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 monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl 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 monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl 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-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 monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, a terphenyl group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), and —P(═O)(Q21)(Q22); and
—Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), and —P(═O)(Q31) (Q32),
wherein Q1 to Q3, Q11 to Q13, 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,
wherein when, the first compound is represented by Formula 1-1, the second compound is represented by Formula 3-2, and X11 is N[(L12)a12-R12], L11 and L12 are each independently selected from the group consisting of:
a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a triphenylenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a dibenzosilolylene group, a benzocarbazolylene group, and a dibenzocarbazolylene group; and
a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a triphenylenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a dibenzosilolylene group, a benzocarbazolylene group, and a dibenzocarbazolylene group, each substituted with at least one selected from deuterium, —F, a cyano group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, a methoxy group, an ethoxy group, an n-propoxy group, an iso-propoxy group, an n-butoxy group, a sec-butoxy group, an iso-butoxy group, a 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 triphenylenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, —N(Q31)(Q32), —Si(Q31)(Q32)(Q33), and —B(Q31)(Q32),
R11 and R12 are each independently selected from a C1-C20 alkyl group, —Si(Q1)(Q2)(Q3), —N(Q1)(Q2), and a group represented by any of Formulae 5-1 to 5-19:
   wherein, in Formulae 5-1 to 5-19,
Y11 is selected from O, S, C(Z13)(Z14), N(Z13), and Si(Z13)(Z14),
Z11 to Z14 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 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 pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl 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 benzofuranyl group, a benzothiophenyl group, a benzosilolyl group, an isobenzothiazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), and —P(═O)(Q31)(Q32); and
a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a carbazolyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group, each substituted with at least one selected from a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a carbazolyl group, a fluorenyl group, —Si(Q21)(Q22)(Q23), and —N(Q21)(Q22),
wherein Q1 to Q3, Q21 to Q23, and Q31 to Q33 are each independently selected from a C1-C10 alkyl group, a C1-C10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group,
e2 is an integer selected from 1 and 2, e3 is an integer selected from 1 to 3, e4 is an integer selected from 1 to 4, e5 is an integer selected from 1 to 5, e6 is an integer selected from 1 to 6, e7 is an integer selected from 1 to 7, e9 is an integer selected from 1 to 9, and
* indicates a binding site to an adjacent atom, and
wherein when, the first compound is represented by Formula 3-1 and the second compound is represented by Formula 1-2, X12 is selected from O, S, C[(L15)a15-R19](R20), Si[(L15)a15-R19](R20), P[(L15)a15-R19], B[(L15)a15-R19], and P(═O)[(L15)a15-R19].
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