Condensed cyclic compound, organic light-receiving device including the same, and electronic apparatus and electronic device including the light-receiving device

A condensed cyclic compound comprising:

• at least one first repeating unit;
• and
• at least one second repeating unit,
• wherein the first repeating unit comprises at least one selected from among a first-first moiety represented by Formula 1-1 and a first-second moiety represented by Formula 1-2,
• the second repeating unit comprises at least one selected from among a second-first moiety represented by Formula 2-1 and a second-second moiety represented by Formula 2-2, and
• at least one of the first repeating unit further comprises at least one π electron-rich C1-C60 group:
• wherein, in Formulae 1-1 and 1-2,
• X1 and X2 are each independently O, S, or Se,
• Y1 is C(R1), CH, or C—*,
• Y2 is C(R2) or CH,
• Y3 is C(R3) or CH,
• Y4 is C(R4), CH, or C—*,
• Y5 is C(R5) or CH,
• Y6 is C(R6) or CH,
• R1 and R2, R2 and R3, R4 and R5, R5 and R6, or R2 and R6 are optionally bonded to each other to form:
• a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a;
• a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a;
• or a π electron-rich C1-C60 group unsubstituted or substituted with at least one R10a,
• n1 and n2 are each independently an integer from 0 to 2, and a sum of n1 and n2 is 1 or more,
• when n1 is 0, the first-first moiety is not included,
• when n2 is 0, the first-second moiety is not included,
• R1 to R6 and R10a are each independently:
• deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
• a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), —P(═O)(Q11)(Q12), or any combination thereof;
• a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a π electron-rich C1-C60 group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryloxy group, or a C1-C60 heteroarylthio group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), —P(═O)(Q21)(Q22), or any combination thereof;
• or
• —Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), or —P(═O)(Q31)(Q32),
• 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;
• a C1-C60 alkyl group;
• a C2-C60 alkenyl group;
• a C2-C60 alkynyl group;
• a C1-C60 alkoxy group;
• or a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, or a π electron-rich C1-C60 group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof,
• two neighboring substituents selected from among Q11 to Q13, Q21 to Q23, and Q31 to Q33 are optionally bonded to each other to form:
• a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a;
• a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a;
• or a π electron-rich C1-C60 group unsubstituted or substituted with at least one R10a, and
• * indicates a binding site to a neighboring repeating unit, and
• wherein, in Formulae 2-1 and 2-2,
• X3 is C(R7)(R8), C(R7)(H), or N(R7),
• ring A1 and ring A2 each independently comprise:
• a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10b;
• or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10b,
• m1 and m2 are each independently an integer from 0 to 2, and a sum of m1 and m2 is 1 or more,
• when m1 is 0, the second-first moiety is not included,
• when m2 is 0, the second-second moiety is not included,
• R7, R8, and R10b are each independently:
• deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
• a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, —Si(Q41)(Q42)(Q43), —N(Q41)(Q42), —B(Q41)(Q42), —C(═O)(Q41), —S(═O)2(Q41), —P(═O)(Q41)(Q42), or any combination thereof;
• a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryloxy group, or a C1-C60 heteroarylthio group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, —Si(Q51)(Q52)(Q53), —N(Q51)(Q52), —B(Q51)(Q52), —C(═O)(Q51), —S(═O)2(Q51), —P(═O)(Q51)(Q52), or any combination thereof;
• or
• —Si(Q61)(Q62)(Q63), —N(Q61)(Q62), —B(Q61)(Q62), —C(═O)(Q61), —S(═O)2(Q61), or —P(═O)(Q61)(Q62),
• Q41 to Q43, Q51 to Q53, and Q61 to Q63 are each independently:
• hydrogen;
• deuterium;
• —F;
• —Cl;
• —Br;
• —I;
• a hydroxyl group;
• a cyano group;
• a nitro group;
• a C1-C60 alkyl group;
• a C2-C60 alkenyl group;
• a C2-C60 alkynyl group;
• a C1-C60 alkoxy group;
• or a C3-C60 carbocyclic group or a C1-C60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof, and
• two neighboring substituents selected from among Q41 to Q43, Q51 to Q53, and Q61 to Q63 are optionally bonded to each other to form:
• a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10b;
• or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10b.