US 12,256,634 B2
Arylamine compound, light-emitting device including the same, and electronic apparatus including the light-emitting device
Dongjun Kim, Yongin-si (KR); Hankyu Pak, Yongin-si (KR); Minji Kim, Yongin-si (KR); Eunjae Jeong, Yongin-si (KR); Sohee Jo, Yongin-si (KR); and Sanghyun Han, Yongin-si (KR)
Assigned to Samsung Display Co., Ltd., Yongin-si (KR)
Filed by Samsung Display Co., Ltd., Yongin-si (KR)
Filed on Aug. 19, 2021, as Appl. No. 17/445,459.
Claims priority of application No. 10-2020-0111683 (KR), filed on Sep. 2, 2020; and application No. 10-2020-0179923 (KR), filed on Dec. 21, 2020.
Prior Publication US 2022/0069227 A1, Mar. 3, 2022
Int. Cl. H10K 50/15 (2023.01); C07D 209/88 (2006.01); C09K 11/06 (2006.01); H10K 50/17 (2023.01); H10K 85/60 (2023.01)
CPC H10K 85/636 (2023.02) [C07D 209/88 (2013.01); C09K 11/06 (2013.01); H10K 85/633 (2023.02); C07B 2200/05 (2013.01); C09K 2211/1018 (2013.01); H10K 50/15 (2023.02); H10K 50/17 (2023.02); H10K 85/615 (2023.02); H10K 85/626 (2023.02); H10K 85/6572 (2023.02)] 15 Claims
OG exemplary drawing
 
1. An arylamine compound represented by Formula 1:

OG Complex Work Unit Chemistry
wherein, in Formula 1,
L1, L2, and L11 to L14 are each independently selected from a single bond, a C5-C60 carbocyclic group unsubstituted or substituted with at least one R10a, and a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
a1, a2, and a11 to a14 are each independently an integer from 1 to 3,
R11 to R14 are each independently selected from a group represented by Formula 2, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a, and a C2-C30 heterocyclic group unsubstituted or substituted with at least one R10a, wherein at least one of R11 to R14 is a group represented by Formula 2,
X is a linking group represented by Formula 3,
R21 to R23, R31, and R32 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),
d21 is an integer from 1 to 4,
d22 is an integer from 1 to 3,
d31 is an integer from 0 to 3,
d32 is an integer from 1 to 6,
* in Formula 2 indicates a binding site to a neighboring atom,
D in Formula 3 is deuterium,
b1 is an integer from 1 to 4,
the sum of d31 and b1 is 4,
* and *′ each indicate a binding site to a neighboring atom,
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, —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, —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.