US 12,356,853 B2
Light-emitting device including condensed cyclic compound, and electronic apparatus including the light-emitting device
Junha Park, Yongin-si (KR); Seokhwan Hwang, Yongin-si (KR); Sunyoung Pak, Yongin-si (KR); Jangyeol Baek, Yongin-si (KR); Munki Sim, Yongin-si (KR); Hyoyoung Lee, Yongin-si (KR); and Minjung Jung, Yongin-si (KR)
Assigned to Samsung Display Co., Ltd., Yongin-si (KR)
Filed by Samsung Display Co., LTD., Yongin-si (KR)
Filed on Mar. 19, 2024, as Appl. No. 18/610,157.
Application 18/610,157 is a continuation of application No. 17/302,279, filed on Apr. 29, 2021, granted, now 11,968,896.
Claims priority of application No. 10-2020-0087708 (KR), filed on Jul. 15, 2020.
Prior Publication US 2024/0224801 A1, Jul. 4, 2024
Int. Cl. H01L 51/50 (2006.01); G02B 5/20 (2006.01); H10H 20/851 (2025.01); H10K 85/00 (2023.01); H10K 85/60 (2023.01); H10K 50/15 (2023.01); H10K 50/16 (2023.01); H10K 50/17 (2023.01); H10K 50/18 (2023.01)
CPC H10K 85/636 (2023.02) [G02B 5/20 (2013.01); H10H 20/851 (2025.01); H10K 85/00 (2023.02); H10K 85/6572 (2023.02); H10K 85/658 (2023.02); H10K 50/15 (2023.02); H10K 50/16 (2023.02); H10K 50/171 (2023.02); H10K 50/18 (2023.02)] 19 Claims
OG exemplary drawing
 
1. A condensed cyclic compound represented by Formula 1:

OG Complex Work Unit Chemistry
wherein, in Formula 1,
ring A1 to ring A4 are each independently a C5-C30 carbocyclic group or a C2-C30 heterocyclic group,
X1 is O, S, Se, C(R1a)(R1b), Si(R1a)(R1b), or N(R1a),
X2 is O, S, Se, C(R2a)(R2b), Si(R2a)(R2b), or N(R2a),
X3 is O, S, Se, C(R3a)(R3b), Si(R3a)(R3b), or N(R3a),
X4 is O, S, Se, C(R4a)(R4b), Si(R4a)(R4b), or N(R4a),
Y1 and Y2 are each independently B, P(═O), or P(═S),
R1 to R4, R1a to R4a, and R1b to R4b 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), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2),
d1 to d4 are each independently an integer in a range from 1 to 20, and
two or more groups selected from R1 to R4, R1a to R4a, and R1b to R4b are optionally linked together to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a or a C2-C30 heterocyclic group unsubstituted or substituted with at least one 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, —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 C6-C60 aryloxy group, or a C6-C60 arylthio group, each unsubstituted or substituted with deuterium, —F, —C1, —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, —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), and
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; 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.
 
16. A light-emitting device comprising:
a first electrode;
a second electrode facing the first electrode; and
an interlayer between the first electrode and the second electrode and comprising an emission layer,
the emission layer comprises at least one condensed cyclic compound represented by Formula 1:

OG Complex Work Unit Chemistry
wherein, in Formula 1,
ring A1 to ring A4 are each independently a C5-C30 carbocyclic group or a C2-C30 heterocyclic group,
X1 is O, S, Se, C(R1a)(R1b), Si(R1a)(R1b), or N(R1a),
X2 is O, S, Se, C(R2a)(R2b), Si(R2a)(R2b), or N(R2a),
X3 is O, S, Se, C(R3a)(R3b), Si(R3a)(R3b), or N(R3a),
X4 is O, S, Se, C(R4a)(R4b), Si(R4a)(R4b), or N(R4a),
Y1 and Y2 are each independently B, P(═O), or P(═S),
R1 to R4, R1a to R4a, and R1b to R4b 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), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2),
d1 to d4 are each independently an integer in a range from 1 to 20, and
two or more groups selected from R1 to R4, R1a to R4a, and R1b to R4b are optionally linked together to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a or a C2-C30 heterocyclic group unsubstituted or substituted with at least one 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, —C1, —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, —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 C6-C60 aryloxy group, or a C6-C60 arylthio group, each unsubstituted or substituted with deuterium, —F, —C1, —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, —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), and
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; 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.