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US 12,740,306 B2Granted
Heterocyclic compound, organic light-emitting device including the heterocyclic compound, and electronic apparatus including the organic light-emitting device
AssigneeSamsung Display Co., Ltd.
InventorsSangmo Kim, Yongsik Jung, Eunsuk Kwon, Juhyun Kim, Yusuke Maruyama, Eunkyung Lee, Inkoo Kim, Sungho Nam, Youngmok Son, Sooghang Ihn
Life of this patent
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Abstract
Provided are a heterocyclic compound represented by Formula 1-1 or 1-2, an organic light-emitting device including the heterocyclic compound, and an electronic apparatus including the organic light-emitting device: wherein Formulae 1-1 and 1-2 are respectively the same as described in the present specification.
Claims21
A heterocyclic compound represented by Formula 1-1:
- wherein, in Formulae 1-1,
- A11 to A16 are each independently a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group,
- X11 to X16 are each independently a group represented by Formula 2-1 or 2-2,
- n11 to n16 are each independently 0, 1, or 2,
- the sum of n11 to n16 in Formula 1-1 is 2 or more,
- Y11 to Y16 are each independently a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C7-C60 alkylaryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, or a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group,
- m11 to m16 are each independently 0, 1, or 2,
- the sum of n11 to n16 and m11 to m16 in Formula 1-1 is 3 or more, the
- Z11 to Z16 are each independently a carbon atom, and a bond between Z11 and Z12, a bond between Z13 and Z14, and a bond between Z15 and Z16 are each independently a single bond or a double bond,
- wherein, in Formulae 2-1 and 2-2,
- X21 is a single bond, O, S, N(R25), or C(R25)(R26),
- L21 and L22 are each independently a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group,
- a21 and a22 are each independently 0, 1, or 2,
- R21 and R22 are each independently a substituted or unsubstituted C6-C60 aryl group,
- R11 to R16 and R23 to R26 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, 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 C7-C60 alkylaryl 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 C2-C60 alkylheteroaryl group, a substituted or unsubstituted C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio 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), —C(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), or —P(═S)(Q1)(Q2),
- b11 to b16 are each independently 0, 1, 2, or 3,
- b23 and b24 are each independently 0, 1, 2, 3, or 4,
- Q1 to Q3 are each independently 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 C7-C60 alkylaryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 alkylheteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C1-C60 alkyl group that is substituted with at least one deuterium, —F, a cyano group, a C1-C60 alkyl group, a C6-C60 aryl group, or a combination thereof, or a C6-C60 aryl group that is substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C6-C60 aryl group, or a combination thereof, and
- * indicates a binding site to a neighboring atom.
16 more elements
A heterocyclic compound represented by Formula 1-1 or 1-2, and
- wherein the heterocyclic compound satisfies Condition 5:
- wherein, in Formulae 1-1 and 1-2,
- A11 to A16 are each independently a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group,
- X11 to X16 are each independently a group represented by Formula 2-1 or 2-2,
- n11 to n16 are each independently 0, 1, or 2,
- the sum of n11 to n16 in Formula 1-1 is 1 or more, and the sum of n11 to n15 in Formula 1-2 is 1 or more,
- Y11 to Y16 are each independently a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C7-C60 alkylaryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, or a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group,
- m11 to m16 are each independently 0, 1, or 2,
- the combined sum of n11 to n16 and m11 to m16 in Formula 1-1 is 2 or more, and the combined sum of n11 to n15 and m11 to m15 in Formula 1-2 is 2 or more,
- Z11 to Z16 are each independently a carbon atom, and a bond between Z11 and Z12, a bond between Z13 and Z14, and a bond between Z15 and Z16 are each independently a single bond or a double bond,
- wherein, in Formulae 2-1 and 2-2,
- X21 is a single bond, O, S, N(R25), or C(R25)(R26),
- L21 and L22 are each independently a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group,
- a21 and a22 are each independently 0, 1, or 2,
- R21 and R22 are each independently a substituted or unsubstituted C6-C60 aryl group,
- R11 to R16 and R23 to R26 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, 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 C7-C60 alkylaryl 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 C2-C60 alkylheteroaryl group, a substituted or unsubstituted C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio 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), —C(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), or —P(═S)(Q1)(Q2),
- b11 to b16 are each independently 0, 1, 2, or 3,
- b23 and b24 are each independently 0, 1, 2, 3, or 4,
- Q1 to Q3 are each independently hydrogen, deuterium, —F, —C1, —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 C7-C60 alkylaryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 alkylheteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C1-C60 alkyl group that is substituted with at least one deuterium, —F, a cyano group, a C1-C60 alkyl group, a C6-C60 aryl group, or a combination thereof, or a C6-C60 aryl group that is substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C6-C60 aryl group, or a combination thereof, and
- * indicates a binding site to a neighboring atom,
- 0 μs<Tdecay(HC)<5 μs Condition 5
- wherein, in Condition 5,
- Tdecay(HC) indicates a decay time of the heterocyclic compound.
20 more elements
Dependencies are inferred from the claim text.