Organic light-emitting device and display apparatus including the same
AssigneeSamsung Display Co., Ltd.
InventorsKyungsik Kim, Seulong Kim, Sungsoo Bae, Dongchan Lee, Jaeweon Hur
Life of this patent
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Abstract
An organic light-emitting device includes a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode. The organic layer includes an emission layer. The emission layer includes a first compound, a second compound, and a third compound. The first compound is represented by Formula 1, the second compound is represented by Formula 2, the third compound is represented by Formula 3, and the first compound and the second compound are different from each other.
Claims21
An organic light-emitting device comprising:
- a first electrode;
- a second electrode;
- and
- an organic layer between the first electrode and the second electrode,
- wherein the organic layer comprises an emission layer,
- the emission layer comprises a first compound, a second compound, and a third compound,
- the first compound is represented by Formula 1,
- the second compound is represented by Formula 2,
- the third compound is represented by Formula 3, and
- the first compound and the second compound are different from each other:
- wherein, in Formulae 1 to 3, 1A, and 2A to 2C,
- L11 is selected from the group consisting of:
- a π electron-depleted nitrogen-free cyclic group;
- and
- a π electron-depleted nitrogen-free cyclic group substituted with at least one selected from the group consisting of deuterium, a C1-C60 alkyl group, a π electron-depleted nitrogen-free cyclic group, and —Si(Q31)(Q32)(Q33),
- a11 is selected from the group consisting of 0, 1, 2, and 3,
- Y11 is a group represented by Formula 1A,
- Y12 is selected from the group consisting of:
- —F, a cyano group, and a π electron-depleted nitrogen-containing cyclic group;
- a C1-C60 alkyl group, a π electron-depleted nitrogen-containing cyclic group, and a π electron-depleted nitrogen-free cyclic group, each substituted with at least one selected from the group consisting of —F and a cyano group;
- and
- a π electron-depleted nitrogen-containing cyclic group substituted with at least one selected from the group consisting of deuterium, a C1-C60 alkyl group, a π electron-depleted nitrogen-containing cyclic group, and a π electron-depleted nitrogen-free cyclic group,
- c11 and c12 are each independently selected from the group consisting of 1, 2, and 3,
- X11 is selected from the group consisting of a single bond, N(R13), O, and S,
- X12 is selected from the group consisting of a single bond, N(R14), O, and S,
- X11 and X12 are not a single bond at the same time,
- A11 and A12 are each independently a π electron-depleted nitrogen-free cyclic group or a substituted or unsubstituted carbazole group,
- R11 to R14 are each independently selected from the group consisting of:
- a binding site, hydrogen, deuterium, a C1-C60 alkyl group, a π electron-depleted nitrogen-free cyclic group, and —Si(Q1)(Q2)(Q3);
- a π electron-depleted nitrogen-free cyclic group substituted with at least one selected from the group consisting of deuterium, a C1-C60 alkyl group, a π electron-depleted nitrogen-free cyclic group, and —Si(Q31)(Q32)(Q33);
- and
- a π electron-depleted nitrogen-free cyclic group substituted with a π electron-depleted nitrogen-free cyclic group that is substituted with at least one selected from the group consisting of deuterium, a C1-C60 alkyl group, a π electron-depleted nitrogen-free cyclic group, and —Si(Q21)(Q22)(Q23), wherein one selected from the group consisting of R11 to R14 is a binding site,
- b11 and b12 are each independently selected from the group consisting of 1, 2, 3, 4, 5, and 6,
- L21 is selected from the group consisting of a substituted or unsubstituted C5-C60 carbocyclic group and a substituted or unsubstituted C1-C60 heterocyclic group,
- a21 is selected from the group consisting of 0, 1, 2, and 3,
- Y21 is a group represented by one selected from the group consisting of Formulae 2A to 2C,
- Y22 is selected from the group consisting of:
- —F, a cyano group, and a π electron-depleted nitrogen-containing cyclic group;
- a C1-C60 alkyl group, a π electron-depleted nitrogen-containing cyclic group, and a π electron-depleted nitrogen-free cyclic group, each substituted with at least one selected from the group consisting of —F and a cyano group;
- and
- a π electron-depleted nitrogen-containing cyclic group substituted with at least one selected from the group consisting of deuterium, a C1-C60 alkyl group, a π electron-depleted nitrogen-containing cyclic group, and a π electron-depleted nitrogen-free cyclic group,
- c21 and c22 are each independently selected from the group consisting of 1, 2, 3, 4, 5, and 6,
- X21 is selected from the group consisting of a single bond, N(R24), O, and S,
- X22 is selected from the group consisting of a single bond, N(R25), O, and S,
- X23 is selected from the group consisting of a single bond, N(R26), O, and S,
- A21 to A23 are each independently a π electron-depleted nitrogen-free cyclic group,
- R21 to R26 are each independently selected from the group consisting of:
- a binding site, hydrogen, deuterium, a C1-C60 alkyl group, a π electron-depleted nitrogen-free cyclic group, —N(Q1)(Q2), and —Si(Q1)(Q2)(Q3);
- a π electron-depleted nitrogen-free cyclic group substituted with at least one selected from the group consisting of deuterium, a C1-C60 alkyl group, a π electron-depleted nitrogen-free cyclic group, —N(Q31)(Q32), and —Si(Q31)(Q32)(Q33);
- and
- a π electron-depleted nitrogen-free cyclic group substituted with a π electron-depleted nitrogen-free cyclic group that is substituted with at least one selected from the group consisting of deuterium, a C1-C60 alkyl group, a π electron-depleted nitrogen-free cyclic group, —N(Q21)(Q22), and —Si(Q21)(Q22)(Q23), wherein one selected from the group consisting of R21 to R24 in Formula 2A is a binding site, one selected from the group consisting of R21 to R25 in Formula 2B is a binding site, and one selected from the group consisting of R21 to R26 in Formula 2C is a binding site,
- b21 to b23 are each independently selected from the group consisting of 1, 2, 3, 4, 5, and 6,
- L31 is selected from the group consisting of a substituted or unsubstituted C5-C60 carbocyclic group and a substituted or unsubstituted C1-C60 heterocyclic group,
- a31 is selected from the group consisting of 0, 1, 2, and 3,
- R31 to R37 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 amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, 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), —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), wherein R31 to R37 are optionally linked to form a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C1-C60 heterocyclic group,
- b31 is selected from the group consisting of 1, 2, 3, 4, 5, and 6,
- Y31 and Y32 are each independently selected from the group consisting of —F, —Cl, —Br, —I, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C6-C60 aryloxy group, wherein Y31 and Y32 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, Q21 to Q23, and Q31 to Q33 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-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 C1-C60 hetero aryloxy group, a C1-C60 hetero arylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group, and
- indicates a binding site to a neighboring atom, and
- a weight ratio among the first compound, the second compound and the third compound is 70:29:1 to 80:19.5:0.5.
An organic light-emitting device comprising:
- a first electrode;
- a second electrode;
- and
- an organic layer between the first electrode and the second electrode,
- wherein the organic layer comprises an emission layer,
- the emission layer comprises a first compound, a second compound, and a third compound,
- the first compound is represented by Formula 1,
- the second compound is represented by Formula 2,
- the third compound is represented by Formula 3, and
- the first compound and the second compound are different from each other:
- wherein, in Formulae 1 to 3, 1A, and 2A to 2C,
- L11 is selected from the group consisting of:
- a π electron-depleted nitrogen-free cyclic group;
- and
- a π electron-depleted nitrogen-free cyclic group substituted with at least one selected from the group consisting of deuterium, a C1-C60 alkyl group, a π electron-depleted nitrogen-free cyclic group, and —Si(Q31)(Q32)(Q33),
- a11 is selected from the group consisting of 0, 1, 2, and 3,
- Y11 is a group represented by Formula 1A,
- Y12 is selected from the group consisting of:
- —F, a cyano group, and a π electron-depleted nitrogen-containing cyclic group;
- a C1-C60 alkyl group, a π electron-depleted nitrogen-containing cyclic group, and a π electron-depleted nitrogen-free cyclic group, each substituted with at least one selected from the group consisting of —F and a cyano group;
- and
- a π electron-depleted nitrogen-containing cyclic group substituted with at least one selected from the group consisting of deuterium, a C1-C60 alkyl group, a π electron-depleted nitrogen-containing cyclic group, and a π electron-depleted nitrogen-free cyclic group,
- c11 and c12 are each independently selected from the group consisting of 1, 2, and 3,
- X11 is selected from the group consisting of a single bond, N(R13), O, and S,
- X12 is selected from the group consisting of a single bond, N(R14), O, and S,
- X11 and X12 are not a single bond at the same time,
- A11 and A12 are each independently a π electron-depleted nitrogen-free cyclic group or a substituted or unsubstituted carbazole group,
- R11 to R14 are each independently selected from the group consisting of:
- a binding site, hydrogen, deuterium, a C1-C60 alkyl group, a π electron-depleted nitrogen-free cyclic group, and —Si(Q1)(Q2)(Q3);
- a π electron-depleted nitrogen-free cyclic group substituted with at least one selected from the group consisting of deuterium, a C1-C60 alkyl group, a π electron-depleted nitrogen-free cyclic group, and —Si(Q31)(Q32)(Q33);
- and
- a π electron-depleted nitrogen-free cyclic group substituted with a π electron-depleted nitrogen-free cyclic group that is substituted with at least one selected from the group consisting of deuterium, a C1-C60 alkyl group, a π electron-depleted nitrogen-free cyclic group, and —Si(Q21)(Q22)(Q23), wherein one selected from the group consisting of R11 to R14 is a binding site,
- b11 and b12 are each independently selected from the group consisting of 1, 2, 3, 4, 5, and 6,
- L21 is selected from the group consisting of a substituted or unsubstituted C5-C60 carbocyclic group and a substituted or unsubstituted C1-C60 heterocyclic group,
- a21 is selected from the group consisting of 0, 1, 2, and 3,
- Y21 is a group represented by one selected from the group consisting of Formulae 2A to 2C,
- Y22 is selected from the group consisting of:
- —F, a cyano group, and a π electron-depleted nitrogen-containing cyclic group;
- a C1-C60 alkyl group, a π electron-depleted nitrogen-containing cyclic group, and a π electron-depleted nitrogen-free cyclic group, each substituted with at least one selected from the group consisting of —F and a cyano group;
- and
- a π electron-depleted nitrogen-containing cyclic group substituted with at least one selected from the group consisting of deuterium, a C1-C60 alkyl group, a π electron-depleted nitrogen-containing cyclic group, and a π electron-depleted nitrogen-free cyclic group,
- c21 and c22 are each independently selected from the group consisting of 1, 2, 3, 4, 5, and 6,
- X21 is selected from the group consisting of a single bond, N(R24), O, and S,
- X22 is selected from the group consisting of a single bond, N(R25), O, and S,
- X23 is selected from the group consisting of a single bond, N(R26), O, and S,
- A21 to A23 are each independently a π electron-depleted nitrogen-free cyclic group,
- R21 to R26 are each independently selected from the group consisting of:
- a binding site, hydrogen, deuterium, a C1-C60 alkyl group, a π electron-depleted nitrogen-free cyclic group, —N(Q1)(Q2), and —Si(Q1)(Q2)(Q3);
- a π electron-depleted nitrogen-free cyclic group substituted with at least one selected from the group consisting of deuterium, a C1-C60 alkyl group, a π electron-depleted nitrogen-free cyclic group, —N(Q31)(Q32), and —Si(Q31)(Q32)(Q33);
- and
- a π electron-depleted nitrogen-free cyclic group substituted with a π electron-depleted nitrogen-free cyclic group that is substituted with at least one selected from the group consisting of deuterium, a C1-C60 alkyl group, a π electron-depleted nitrogen-free cyclic group, —N(Q21)(Q22), and —Si(Q21)(Q22)(Q23), wherein one selected from the group consisting of R21 to R24 in Formula 2A is a binding site, one selected from the group consisting of R21 to R25 in Formula 2B is a binding site, and one selected from the group consisting of R21 to R26 in Formula 2C is a binding site,
- b21 to b23 are each independently selected from the group consisting of 1, 2, 3, 4, 5, and 6,
- L31 is selected from the group consisting of a substituted or unsubstituted C5-C60 carbocyclic group and a substituted or unsubstituted C1-C60 heterocyclic group,
- a31 is selected from the group consisting of 0, 1, 2, and 3,
- R31 to R37 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 amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, 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), —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), wherein R31 to R37 are optionally linked to form a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C1-C60 heterocyclic group,
- b31 is selected from the group consisting of 1, 2, 3, 4, 5, and 6,
- Y31 and Y32 are each independently selected from the group consisting of —F, —Cl, —Br, —I, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C6-C60 aryl group, and a substituted or unsubstituted C6-C60 aryloxy group, wherein Y31 and Y32 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, Q21 to Q23, and Q31 to Q33 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-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 C1-C60 hetero aryloxy group, a C1-C60 hetero arylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group, and
- * indicates a binding site to a neighboring atom, and
- wherein the first compound is about 60 wt % to about 90 wt % in amount, the second compound is about 10 wt % to about 40 wt % in amount, and the third compound is about 0.5 wt % to about 5 wt % in amount, each based on a total weight of the emission layer, and
- a weight ratio among the first compound, the second compound and the third compound is 70:29:1 to 80:19.5:0.5.
Dependencies are inferred from the claim text.