Bipyridine derivatives and their uses for organic light emitting diodes

A condensed cyclic compound represented by Formula 1:

• Ar1-(L1)a1-B-(L2)a2-Ar2 Formula 1
• wherein, in Formula 1,
• B is a group represented by Formula 2:
• wherein, in Formula 2,
• X1 is N or CH, X2 is N or CH, and X3 is N or CH;
• L1 and L2 are each independently selected from 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 C7-C60 arylalkyl group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C2-C60 heteroaryloxy group, a substituted or unsubstituted C2-C60 heteroarylthio group, a substituted or unsubstituted C3-C60 heteroarylalkyl group,
• wherein at least one of substituents of the substituted C6-C60 aryl group, substituted C6-C60 aryloxy group, substituted C6-C60 arylthio group, substituted C7-C60 arylalkyl group, substituted C1-C60 heteroaryl group, substituted C2-C60 heteroaryloxy group, substituted C2-C60 heteroarylthio group, and substituted C3-C60 heteroarylalkyl group is selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino 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, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C60 cycloalkyl group, a C1-C60 heterocycloalkyl group, a C3-C60 cycloalkenyl group, a C1-C60 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C2-C60 heteroaryloxy group, a C2-C60 heteroarylthio group, a C3-C60 heteroarylalkyl group, and —Si(Q1)(Q2)(Q3), wherein Q1 to Q3 are each independently selected from a hydrogen, a C1-C60 alkyl group, a C1-C60 alkoxy group, a C3-C60 cycloalkyl group, a C1-C60 heterocycloalkyl group, a C3-C60 cycloalkenyl group, a C1-C60 heterocycloalkenyl group, a C6-C60 aryl group, and a C1-C60 heteroaryl group;
• * represents a point of connection to Ar1;
• *′ represents a point of connection to Ar2;
• a1 and a2 are each independently an integer selected from 0 to 5, provided that
• when a1 is 2 or greater, two or more groups L1 are identical to or different from each other, and
• when a2 is 2 or greater, two or more groups L2 are identical to or different from each other;
• Ar1 and Ar2 are each independently a group represented by one of Formulae 3A to 3F
• wherein, in Formulae 3A to 3F,
• CY is a substituted or unsubstituted C6-C60 aryl ring or a substituted or unsubstituted C1-C60 heteroaryl ring,
• X4 is O, S, Se, N(R3), P(═O)(R4), C(R5)(R6), or Si(R7)(R8),
• n1 is 0, 1, 2, or 4,
• n2 is 0 or 1,
• R1, R2, and R5 to R8 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino 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 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-C60 cycloalkyl group, a substituted or unsubstituted C1-C60 heterocycloalkyl group, a substituted or unsubstituted C3-C60 cycloalkenyl group, a substituted or unsubstituted C1-C60 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 C7-C60 arylalkyl group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C2-C60 heteroaryloxy group, a substituted or unsubstituted C2-C60 heteroarylthio group, a substituted or unsubstituted C3-C60 heteroarylalkyl group, and —Si(Q4)(Q5)(Q6), wherein Q4 to Q6 are each independently selected from a hydrogen, a C1-C60 alkyl group, a C1-C60 alkoxy group, a C3-C60 cycloalkyl group, a C1-C60 heterocycloalkyl group, a C3-C60 cycloalkenyl group, a C1-C60 heterocycloalkenyl group, a C6-C60 aryl group, and a C1-C60 heteroaryl group,
• R3 and R4 is a substituted or unsubstituted C6-C60 aryl group or a substituted or unsubstituted C1-C60 heteroaryl group,
• wherein at least one of substituents of the substituted C1-C60 alkyl group, substituted C2-C60 alkenyl group, substituted C2-C60 alkynyl group, substituted C1-C60 alkoxy group, substituted C3-C10 cycloalkyl group, substituted C1-C60 heterocycloalkyl group, substituted C3-C60 cycloalkenyl group, substituted C1-C60 heterocycloalkenyl group, substituted C6-C60 aryl group, substituted C6-C60 aryloxy group, substituted C6-C60 arylthio group, substituted C7-C60 arylalkyl group, substituted C1-C60 heteroaryl group, substituted C2-C60 heteroaryloxy group, substituted C2-C60 heteroarylthio group, and substituted C3-C60 heteroarylalkyl group is selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino 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, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C60 cycloalkyl group, a C1-C60 heterocycloalkyl group, a C3-C60 cycloalkenyl group, a C1-C60 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C2-C60 heteroaryloxy group, a C2-C60 heteroarylthio group, a C3-C60 heteroarylalkyl group, and —Si(Q7)(Q8)(Q9), wherein Q7 to Q9 are each independently selected from a hydrogen, a C1-C60 alkyl group, a C1-C60 alkoxy group, a C3-C60 cycloalkyl group, a C1-C60 heterocycloalkyl group, a C3-C60 cycloalkenyl group, a C1-C60 heterocycloalkenyl group, a C6-C60 aryl group, and a C1-C60 heteroaryl group, and
• *″ represents a point of connection to B.