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US 12,376,490 B2Granted
Organic light-emitting device
AssigneeSamsung Display Co., Ltd.
InventorsMinkyung Kim, Eunhye Song
Life of this patent
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Abstract
An organic light-emitting device is provided. The organic light-emitting device includes: 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 including an emission layer and a first compound represented by Formula 1 and a second compound represented by Formula 2.
Claims16
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, wherein the organic layer comprises an emission layer,
- the emission layer comprises a host and a dopant,
- the host comprises a first compound and a second compound,
- the dopant comprises a phosphorescent dopant or a fluorescent dopant, and
- the first compound is represented by Formula 1 and the second compound is represented by Formula 2:
- wherein, in Formulae 1 and 2,
- L10, L20, and L30 are each independently selected from groups represented by Formulae 3-1 to 3-53:
- wherein, in Formulae 3-1 to 3-53,
- Y1 is O, S, C(Z3)(Z4), N(Z5), or Si(Z6)(Z7),
- Z1 to Z7 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-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, —N(Q31)(Q32), —Si(Q31)(Q32)(Q33), —Ge(Q31)(Q32)(Q33), and —B(Q31)(Q32),
- d2 is an integer from 0 to 2;
- and when d2 is 2 or greater, at least two Z1(s) are identical to or different from each other,
- d3 is an integer from 0 to 3;
- and when d3 is 2 or greater, at least two Z1(s) are identical to or different from each other, and at least two Z2(s) are identical to or different from each other,
- d4 is an integer from 0 to 4;
- and when d4 is 2 or greater, at least two Z1(s) are identical to or different from each other, and at least two Z2(s) are identical to or different from each other,
- d5 is an integer from 0 to 5;
- and when d5 is 2 or greater, at least two Z1(s) are identical to or different from each other, and at least two Z2(s) are identical to or different from each other,
- d6 is an integer from 0 to 6;
- and when d6 is 2 or greater, at least two Z1(s) are identical to or different from each other, and at least two Z2(s) are identical to or different from each other,
- d8 is an integer from 0 to 8;
- and when d8 is 2 or greater, at least two Z1(s) are identical to or different from each other,
- wherein Q31 to Q33 are each independently selected from a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a biphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a triazinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, and
- * , *′, and *″ each indicate a binding site to an adjacent atom,
- L40, L50, L60, and L70 are each independently selected from a substituted or unsubstituted C5-C60 carbocyclic group and a substituted or unsubstituted C1-C60 heterocyclic group,
- a10, a20, a30, a40, a50, a60, and a70 are each independently an integer from 0 to 5,
- R10, R20, and R30 are each independently selected from hydrogen, deuterium, —F, —Cl , —Br, —I, 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, and a tert-butoxy 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, and a tert-butoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a cyano group, a phenyl group, and a biphenyl group;
- and
- —Si(Q1)(Q2)(Q3), —Ge(Q1)(Q2)(Q3), —B(Q1)(Q2) and —N(Q1)(Q2),
- R40, R50, R60, and R70 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), —Ge(Q1)(Q2)(Q3), —B(Q1)(Q2), —C(═O)(Q1), —N(Q1)(Q2), —P(═O)(Q1)(Q2), and —S(═O)2(Q1)(Q2),
- b10, b20, b30, b40, b50, b60, and b70 are each independently an integer from 1 to 5,
- c10 and c30 are each independently an integer from 1 to 7,
- c20 is an integer from 1 to 8,
- c40 and c50 are each independently an integer from 1 to 10,
- c60 is an integer from 1 to 6,
- A1 and A2 are each independently selected from a C5-C60 carbocyclic group and a C1-C60 heterocyclic group,
- A3 is selected from a 5-membered carbocyclic group and a 5-membered heterocyclic group,
- X1, X2, X3, X4, and X5 are each independently selected from O, S, N, C, and Si, and
- at least one substituent of the substituted C5-C60 carbocyclic group, the substituted C1-C60 heterocyclic group, the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C1-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C6-C60 aryloxy group, the substituted C6-C6o arylthio group, the substituted C1-C60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is 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, 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), —Ge(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, and a monovalent non-aromatic condensed heteropolycyclic group;
- a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C6o aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic 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, —Si(Q21)(Q22)(Q23), —Ge(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), —Ge(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 the emission layer comprises the second compound,
- wherein, when X1 is N, at least one selected from the group represented by —(L70)a70-(R70)b70 and the group represented by [(R60)b60-(L60)a60]- that is bonded to X1 is hydrogen, and
- wherein a weight ratio of the first compound to the second compound is in a range of 55:35 to 80:10.
50 more elements
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, wherein the organic layer comprises an emission layer comprising a first compound and a second compound, and
- the first compound is selected from Compounds 1-1 to 1-45, and the second compound is selected from Compounds 2-1 to 2-28, 2-32 to 2-34, 2-36, 8-1 to 8-21, 8-25, 8-26, 8-28, and 9-1 to 9-8:
2 more elements
Dependencies are inferred from the claim text.