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US 2025/0040437 A1Published application
Heterocyclic compound and organic light-emitting device including the same
AssigneeSamsung Electronics Co., Ltd.
InventorsYusuke MARUYAMA, Sangmo KIM, Jiwhan KIM, Sungho NAM, Eunkyung LEE, Sooghang IHN, Daun JEONG, Yongsik JUNG, Jun CHWAE, Eunsuk KWON
Life of this patent
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Abstract
A heterocyclic compound represented by Formula 1 and an organic light-emitting device including the same:
Claims20
A heterocyclic compound represented by Formula 1:
- wherein, in Formulae 1 and 2,
- X1 is a single bond, O, S, Se, N(Ar2), N(R1), C(R1)(R2), Si(R1)(R2), Ge(R1)(R2), B(R1), P(R1), P(═O)(R1), S(═O)2, or C(═O),
- CY1 to CY3 are each independently a C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group,
- Ar1 and Ar2 are each independently a group represented by Formula 2,
- L1 is a single bond, a substituted or unsubstituted C5-C30 carbocyclic group, or a substituted or unsubstituted C1-C30 heterocyclic group,
- a1 is 1, 2, or 3,
- CY21 to CY24 are each independently a C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group,
- R1, R2, R10, R20, R30, R40, R50, R60, and R70 are each independently a group represented by Formula 2, 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 C2-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, —N(Q1)(Q2), —Si(Q1)(Q2)(Q3), —Ge(Q1)(Q2)(Q3), —C(═O)(Q1), —S(═O)(Q1), —S(═O)2(Q1), —B(Q1)(Q2), —P(Q1)(Q2), —P(═O)(Q1)(Q2), —P(═S)(Q1)(Q2), or a group represented by Formula 3,
- wherein, in Formula 3,
- X31 is a single bond, O, S, N(R301), or C(R301)(R302),
- k31 is 0 or 1,
- CY31 and CY32 are each independently a C5-C30 carbocyclic group or a C1-C30 heterocyclic group,
- L30 is a single bond, a substituted or unsubstituted C5-C30 carbocyclic group, or a substituted or unsubstituted C1-C30 heterocyclic group,
- a30 is 0, 1, 2, or 3,
- R301, R302, R310, and R320 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 C2-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, —N(Q1)(Q2), —Si(Q1)(Q2)(Q3), —Ge(Q1)(Q2)(Q3), —C(═O)(Q1), —S(═O)(Q1), —S(═O)2(Q1), —B(Q1)(Q2), —P(Q1)(Q2), —P(═O)(Q1)(Q2), or —P(═S)(Q1)(Q2),
- b310 and b320 are each independently 1, 2, 3, 4, 5, 6, 7, or 8,
- b10, b20, b30, b40, b50, b60, and b70 are each independently 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14,
- neighboring two or more of R1, R2, R10, R20, R30, R40, R50, R60, R70, R301, R302, R310, and R320 are optionally bonded to each other to form a substituted or unsubstituted C5-C30 carbocyclic group or a C1-C30 heterocyclic group,
- at least one substituent of the substituted C5-C30 carbocyclic group, the substituted C1-C30 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 C2-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C7-C60 alkylaryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted C2-C60 alkylheteroaryl group, the substituted C1-C60 heteroaryloxy group, the substituted C1-C60 heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is:
- deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group;
- a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-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, —N(Q11)(Q12), —Si(Q11)(Q12)(Q13), —Ge(Q11)(Q12)(Q13), —C(═O)(Q11), —S(═O)(Q11), —S(═O)2(Q11), —B(Q11)(Q12), —P(Q11)(Q12), —P(═O)(Q11)(Q12), —P(═S)(Q11)(Q12), or any combination thereof;
- a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-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, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, 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 C2-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, —N(Q21)(Q22), —Si(Q21)(Q22)(Q23), —Ge(Q21)(Q22)(Q23), —C(═O)(Q21), —S(═O)(Q21), —S(═O)2(Q21), —B(Q21)(Q22), —P(Q21)(Q22), —P(═O)(Q21)(Q22), —P(═S)(Q21)(Q22), or any combination thereof;
- —N(Q31)(Q32), —Si(Q31)(Q32)(Q33), —Ge(Q31)(Q32)(Q33), —C(═O)(Q31), —S(═O)(Q31), —S(═O)2(Q31), —B(Q31)(Q32), —P(Q31)(Q32), —P(═O)(Q31)(Q32), or —P(Q31)(Q32);
- or
- any combination thereof,
- 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 amidino group;
- a hydrazine group;
- a hydrazone group;
- a carboxylic acid group or a salt thereof;
- a sulfonic acid group or a salt thereof;
- a phosphoric acid group or a salt thereof;
- a C1-C60 alkyl group unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof;
- 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 C2-C10 heterocycloalkenyl group;
- a C6-C60 aryl group unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof;
- a C6-C60 aryloxy group;
- a C6-C60 arylthio group;
- a C1-C60 heteroaryl group;
- a monovalent non-aromatic condensed polycyclic group;
- or a monovalent non-aromatic condensed heteropolycyclic group, and
- * indicates a binding site to an adjacent atom.
53 more elements
Dependencies are inferred from the claim text.