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, the organic layer comprising an emission layer and at least one heterocyclic compound represented by Formula 1,
• wherein the first electrode is an anode,
• the second electrode is a cathode,
• the organic layer further comprises a hole transport region, between the first electrode and the emission layer, and an electron transport region, between the emission layer and the second electrode,
• the hole transport region comprises at least one layer selected from a hole injection layer, a hole transport layer, a buffer layer, an emission auxiliary layer, and an electron blocking layer,
• the electron transport region comprises at least one layer selected from a hole blocking layer, an electron transport layer, and an electron injection layer,
• the heterocyclic compound is in the emission layer and is a delayed fluorescent dopant,
• the emission layer further comprises a host, and
• the delayed fluorescent dopant and the host satisfy Equation 2 or Equation 3:
• |EH,HOMO-ED,HOMO|≤0.5eV Equation 2
• EH,LUMO-ED,LUMO|≤0.5 eV, Equation 3
• wherein, in Equations 2 and 3,
• EH, HOMO is a highest occupied molecular orbital level of the host,
• ED, HOMO is a highest occupied molecular orbital level of the dopant,
• EH, LUMO is a lowest unoccupied molecular orbital level of the host, and
• ED, LUMO is a lowest unoccupied molecular orbital level of the dopant:
• wherein, in Formulae 1, 2-1, 2-2, 3-1, and 3-2,
• X1 is O or S,
• Ar1 and Ar2 are each independently a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C2-C60 heterocyclic group,
• a1 and a2 are each independently an integer from 0 to 3,
• b1 and b2 are each independently 0 or 1,
• a1, a2, b1, and b2 satisfy a1+b1≥1 and a2+b2≥1,
• R1 and R2 are each independently a group represented by Formula 2-1,
• R3 is a group represented by Formula 2-2,
• A1 to A4 are each independently selected from a benzene group, a naphthalene group, a phenanthrene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, and a tetrazine group,
• A5 to A8 are each independently selected from a benzene group, a naphthalene group, a phenanthrene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, and a tetrazine group,
• Y1 is a single bond, O, S, SO2, N(R19), C(R19)(R20), Si(R19)(R20), S(═O)(R19), S(═O)2(R19), or P(═O)(R19),
• Y2 is a single bond, O, S, SO2, N(R19), C(R19)(R20), Si(R19)(R20), S(═O)(R19), S(═O)2(R19), or P(═O)(R19),
• Y3 is a single bond, O, S, SO2, N(R19), C(R19)(R20), Si(R19)(R20), S(═O)(R19), S(═O)2(R19), or P(═O)(R19),
• Y4 is a single bond, O, S, SO2, N(R19), C(R19)(R20), Si(R19)(R20), S(═O)(R19), S(═O)2(R19), or P(═O)(R19),
• Y5 is a single bond, O, S, SO2, N(R19), C(R19)(R20), Si(R19)(R20), S(═O)(R19), S(═O)2(R19), or P(═O)(R19),
• wherein (i) when Y2 is a single bond, S, or O, a group represented by Formula 2-1 and a group represented by Formula 2-2 are different from each other, and
• (ii) when -(Ar1)a1-(R1)b1 and -(Ar2)a2-(R2)b2 each represent a phenyl group, either Y2 is S(═O)(R19) or S(═O)2(R19), or at least one of R13 and R14 is selected from a group represented by Formula 3-1 and a group represented by Formula 3-2,
• R11 to R14 are each independently selected from a group represented by Formula 3-1, a group represented by Formula 3-2, 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-C10cycloalkyl 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, —S(═O)(Q1), and —P(═O)(Q1)(Q2),
• wherein two or more R11(s) are optionally linked to form a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C2-C60 heterocyclic group, two or more R12(s) are optionally linked to form a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C2-C60 heterocyclic group, two or more R13(s) are optionally linked to form a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C2-C60 heterocyclic group, and two or more R14(s) are optionally linked to form a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C2-C60 heterocyclic group,
• b11 to b14 are each independently an integer from 1 to 8,
• when X1 is O, at least one of R13 and R14 is a group represented by Formula 3-1 or a group represented by Formula 3-2, provided that Y2 and Y3 are not both a single bond at the same time, and Y2 and Y4 or Y2 and Y5 are not both a single bond at the same time,
• R15 to R20 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-C60heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic, —S(═O)(Q1), and —P(═O)(Q1)(Q2),
• b15 to b18 are each independently an integer from 1 to 8,
• 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 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)(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-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-C60alkoxy 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-C60aryloxy 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),
• Q1, Q2, Q11 to Q13, Q21 to Q23, and Q31 to Q33 are each independently selected from 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 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, and
• *indicates a binding site to a neighboring atom.