Heterocyclic compound and organic light-emitting device including the same

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 and including an emission layer,
• wherein the organic layer includes a heterocyclic compound represented by Formula 1:
• wherein, in Formula 1, each D1 is independently a group represented by one of Formulae 2A to 2F,
• wherein, in Formulae 1 and 2A to 2F,
• rings A1 to A3 and A11 to A13 are each independently a C5-C60 carbocyclic group or a C2-C60 heterocyclic group, with the proviso that in Formula 2F A11 and A12 are not both a benzene ring,
• K1 is B, Al, Ga, P, P═O, or P═S,
• Y1 and Y2 are each independently O, S, or N(R52),
• X1 is C(R53)(R54) or N(R55),
• L1 to L4, L21, and L22 are each independently a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C2-C60 heterocyclic group,
• a1 to a4, a21, and a22 are each independently an integer of 0 to 5,
• when a1 is 2, 3, 4, or 5, the 2, 3, 4, or 5 L1(s) are identical to or different from each other, when a2 is 2, 3, 4, or 5, the 2, 3, 4, or 5 L2(5) are identical to or different from each other, when a3 is 2, 3, 4, or 5, the 2, 3, 4, or 5 L3(5) are identical to or different from each other, when a4 is 2, 3, 4, or 5, the 2, 3, 4, or 5 L4(s) are identical to or different from each other, when a21 is 2, 3, 4, or 5, the 2, 3, 4, or 5 L21 (s) are identical to or different from each other, and when a22 is 2, 3, 4, or 5, the 2, 3, 4, or 5 L22(s) are identical to or different from each other,
• when a1 is 0, *-(L1)a1-*′ is a single bond, when a2 is 0, *-(L2)a2-*′ is a single bond, when a3 is 0, *-(L3)a3-*′ is a single bond, when a4 is 0, *-(L4)a4-*′ is a single bond, when a21 is 0, *-(L21)a21-*′ is a single bond, and when a22 is 0, *-(L22)a22-*′ is a single bond,
• R1 to R3, R11 to R13, R52 to R55, and Ar21 to Ar22 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino 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 C2-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C2-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 C1-C60 hetero aryloxy 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), —C(═O)(Q1), —N(Q1)(Q2), —P(═O)(Q1)(Q2), —P(═S)(Q1)(Q2), —S(═O)(Q1)(Q2), or —S(═O)2(Q1)(Q2), wherein at least one of R11 and R12 in Formula 2F is not hydrogen, and at least one selected from R1 and R2 is a tert-butyl group,
• b1 to b3, b11 to b13, and b21 to b22 are each independently an integer of 0 to 10,
• when b1 is 2, 3, 4, 5, 6, 7, 8, 9, or 10, the 2, 3, 4, 5, 6, 7, 8, 9, or 10 R1(s) are identical to or different from each other, when b2 is 2, 3, 4, 5, 6, 7, 8, 9, or 10, the 2, 3, 4, 5, 6, 7, 8, 9, or 10 R2(5) are identical to or different from each other, when b3 is 2, 3, 4, 5, 6, 7, 8, 9, or 10, the 2, 3, 4, 5, 6, 7, 8, 9, or 10 R3(5) are identical to or different from each other, when b11 is 2, 3, 4, 5, 6, 7, 8, 9, or 10, the 2, 3, 4, 5, 6, 7, 8, 9, or 10 R11(s) are identical to or different from each other, when b12 is 2, 3, 4, 5, 6, 7, 8, 9, or 10, the 2, 3, 4, 5, 6, 7, 8, 9, or 10 R12(s) are identical to or different from each other, when b13 is 2, 3, 4, 5, 6, 7, 8, 9, or 10, the 2, 3, 4, 5, 6, 7, 8, 9, or 10 R13(s) are identical to or different from each other, when b21 is 2, 3, 4, 5, 6, 7, 8, 9, or 10, the 2, 3, 4, 5, 6, 7, 8, 9, or 10 Ar21(s) are identical to or different from each other, and when b22 is 2, 3, 4, 5, 6, 7, 8, 9, or 10, the 2, 3, 4, 5, 6, 7, 8, 9, or 10 Ar22(s) are identical to or different from each other,
• c1 to c3 are each independently an integer of 0 to 10,
• c4 is an integer of 1 to 10,
• at least one substituent of the substituted C5-C60 carbocyclic group, the substituted C2-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-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted C1-C60 hetero aryloxy 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 amino 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 amino 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 amino 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), Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino 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 aryl group substituted with a C1-C60 alkyl group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, or a terphenyl group, and
• * and *′ each indicate a binding site to a neighboring atom, and
• wherein:
• the heterocyclic compound in the emission layer is a thermally activated delayed fluorescent emitter, and
• the emission layer emits delayed fluorescence.