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US 12,655,163 B2Granted
Condensed cyclic compound, light-emitting device including condensed cyclic compound, and electronic apparatus including light-emitting device
AssigneeSamsung Display Co., Ltd.
InventorsChanseok Oh, Sunyoung Pak, Junha Park, Taeil Kim, Jangyeol Baek, Kyoung Sunwoo, Munki Sim, Minjung Jung
Life of this patent
Estimating the term…
Abstract
A condensed cyclic compound is represented by Formula 1. A light-emitting device includes a first electrode, a second electrode facing the first electrode, and an interlayer disposed between the first electrode and the second electrode, wherein the interlayer includes an emission layer and at least one condensed cyclic compound represented by Formula 1. An electronic apparatus includes the light-emitting device.
Claims19
A light-emitting device comprising:
- a first electrode;
- a second electrode facing the first electrode;
- and
- an interlayer disposed between the first electrode and the second electrode, wherein
- the interlayer comprises:
- an emission layer;
- and
- at least one condensed cyclic compound represented by Formula 1-1 or Formula 1-2:
- wherein in Formula 1-1 and 1-2,
- T1 is B, P(═O), or P(═S),
- Y1 is O, S, Se, or N(R1a),
- Y2 is O, S, Se, or N(R2a),
- Ar3 is are each independently a C5-C30 carbocyclic group or a C2-C30 heterocyclic group,
- X1 is O, S, Se, C(R13)(R14), Si(R13)(R14), or N(R13),
- X2 is O, S, Se, C(R23)(R24), Si(R23)(R24), or N(R23),
- R21 to R24, R3, R1a, R2a, and R11 to R14 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, 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, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, —Si(Q1)(Q2)(Q3), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2),
- d21 is an integer from 1 to 4,
- d22 is 1 or 2, and
- d3, and d11 are each independently an integer from 1 to 10,
- d12 is 1 or 2,
- at least one of R11 in the number of d11, R12 in the number of d12, R21 in the number of d21, R22 in the number of d22, and R3 in the number of d3 is each independently:
- deuterium, a C3-C60 carbocyclic group unsubstituted or substituted with R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with R10a, and
- R10a is:
- 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 C7-C60 aryl alkyl group, a C2-C60 heteroaryl alkyl group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), —P(═O)(Q11)(Q12), or a combination thereof;
- a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 aryl alkyl group, or a C2-C60 heteroaryl alkyl 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 C7-C60 aryl alkyl group, a C2-C60 heteroaryl alkyl group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), —P(═O)(Q21)(Q22), or a combination thereof;
- or
- —Si(Q31)(Q32)(Q3), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), or —P(═O)(Q31)(Q32),
- wherein 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;
- 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 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 a combination thereof;
- a C7-C60 aryl alkyl group;
- or a C2-C60 heteroaryl alkyl group.
42 more elements
A condensed cyclic compound represented by Formula 1-1 or Formula 1-2:
- in Formula 1-1 and 1-2,
- T1 is B, P(═O), or P(═S),
- Y1 is O, S, Se, or N(R1a),
- Y2 is O, S, Se, or N(R2a),
- Ar3 is are each independently a C5-C30 carbocyclic group or a C2-C30 heterocyclic group,
- X1 is O, S, Se, C(R13)(R14), Si(R13)(R14), or N(R13),
- X2 is O, S, Se, C(R23)(R24), Si(R23)(R24), or N(R23),
- R21 to R24, R3, R1a, R2a, and R11 to R14 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, 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, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, —Si(Q1)(Q2)(Q3), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2),
- d21 is an integer from 1 to 4,
- d22 is 1 or 2, and
- d3, and d11 are each independently an integer from 1 to 10,
- d12 is 1 or 2,
- at least one of R11 in the number of d11, R12 in the number of d12, R21 in the number of d21, R22 in the number of d22, and R3 in the number of d3 is each independently:
- deuterium, a C3-C60 carbocyclic group unsubstituted or substituted with R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with R10a, and R10a is:
- 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 C7-C60 aryl alkyl group, a C2-C60 heteroaryl alkyl group, Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), —P(═O)(Q11)(Q12), or a combination thereof;
- a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 aryl alkyl group, or a C2-C60 heteroaryl alkyl 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 C7-C60 aryl alkyl group, a C2-C60 heteroaryl alkyl group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), —P(═O)(Q21)(Q22), or a 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),
- wherein 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;
- 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 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 a combination thereof;
- a C7-C60 aryl alkyl group;
- or a C2-C60 heteroaryl alkyl group.
33 more elements
Dependencies are inferred from the claim text.