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US 10,541,371 B2Granted
Carbazole-based compound and organic light emitting device including the same
AssigneesSamsung Display Co., Ltd., Indsutry-Academic Cooperation Foundation Gyeongsang Nationa University
InventorsMikyung Kim, Heeyeon Kim, Yunhi Kim, Seongjong Park, Jaeyong Lee, Hyein Jeong, Jaeyoung Hwang
Life of this patent
Estimating the term…
Abstract
Provided are a carbazole-based compound and an organic light-emitting device including the same. The carbazole-based compound may have the following general structure: wherein details and examples of L1 through L6, R1 through R6, a1 through a6, and b1 through b6 are provided.
Claims20
A carbazole-based compound represented by Formula 1:
- wherein, in Formulae 1, 2A, and 2B,
- X1 is selected from P(═O)[(L11)a11-(R11)b11], P(═S)[(L12)a12-(R12)b12], and S(═O),
- ring A1 to ring A4 are each independently selected from a C5-C30 carbocyclic group and a C2-C30 heterocyclic group,
- L1 to L6, L11, and L12 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,
- a1 to a6, a11, and a12 are each independently an integer selected from 0 to 3, wherein, when a1 is two or more, two or more L1(s) are identical to or different from each other, when a2 is two or more, two or more L2(s) are identical to or different from each other, when a3 is two or more, two or more L3(s) are identical to or different from each other, when a4 is two or more, two or more L4(s) are identical to or different from each other, when a5 is two or more, two or more L5(s) are identical to or different from each other, when a6 is two or more, two or more L6(s) are identical to or different from each other, when a11 is two or more, two or more L11(s) are identical to or different from each other, and when a12 is two or more, two or more L12(s) are identical to or different from each other,
- R1 to R6, R11, R12, R20, R30, R40, and R50 are each independently selected from a group represented by Formula 2A, a group represented by Formula 2B, 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(substituted or unsubstituted monovalent non-aromatic condensed polycyclic group), a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group(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),
- b1 to b6, b11, b12, b20, b30, b40, and b50 are each independently an integer selected from 0 to 3, wherein, when b1 is two or more, two or more R1(s) are identical t or different from each other, when b1 is zero, (L1)a1 is a hydrogen atom, when b2 is two or more, two or more R2(s) are identical to or different from each other, when b2 is zero, (L2)a2 is a hydrogen atom, when b3 is two or more, two or more R3(s) are identical to or different from each other, when b3 is zero, (R3)b3 is a hydrogen atom, when b4 is two or more, two or more R4(s) are identical to or different from each other, when b4 is zero, (R4)b4 is a hydrogen atom, when b5 is two or more, two or more R5(s) are identical to or different from each other, when b5 is zero, (R5)b5 is a hydrogen atom, when b6 is two or more, two or more R6(s) are identical to or different from each other, when b6 is zero, (R6)b6 is a hydrogen atom, when b11 is two or more, two or more R11(s) are identical to or different from each other, when b12 is two or more, two or more R12(s) are identical to or different from each other, when b20 is two or more, two or more R20(s) are identical to or different from each other, when b20 is zero, (R20)b20 is a hydrogen atom, when b30 is two or more, two or more R30(s) are identical to or different from each other, when b30 is zero, (R30)b30 is a hydrogen atom, when b40 is two or more, two or more R40(s) are identical to or different from each other, when b40 is zero, (R40)b40 is a hydrogen atom, when b50 is two or more, two or more R50(s) are identical to or different from each other, and when b50 is zero, (R50)b50 is a hydrogen atom, wherein at least one of b1 and b2 is zero;
- at least one selected from R1 to R6 is a group represented by Formula 2A, and at least one selected from R1 to R6 is a group represented by Formula 2B,
- when all of a1 to a6 are 0, both b20 and b30 are 0 and at least one of b1 to b6 is 0,
- at least one substituent selected from the substituted C3-C10 cycloalkylene group, the substituted C1-C10 heterocycloalkylene group, the substituted C3-C10 cycloalkenylene group, the substituted C1-C10 heterocycloalkenylene group, the substituted C6-C60 arylene group, the substituted C1-C60 heteroarylene group, the substituted divalent non-aromatic condensed polycyclic group, the substituted divalent non-aromatic condensed heteropolycyclic 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-C60 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), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q1), —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-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, 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), —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), and
- 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.
14 more elements
A carbazole-based compound, wherein the carbazole-based compound is one selected from Compounds 1 to 23:
Dependencies are inferred from the claim text.