US 12,391,871 B2
Light-emitting device including condensed cyclic compound and electronic apparatus including the light-emitting device
Jangyeol Baek, Yongin-si (KR); Seran Kim, Yongin-si (KR); Sunyoung Pak, Yongin-si (KR); Hankyu Pak, Yongin-si (KR); Munki Sim, Yongin-si (KR); Chanseok Oh, Yongin-si (KR); and Hyoyoung Lee, Yongin-si (KR)
Assigned to Samsung Display Co., Ltd., Yongin-si (KR)
Filed by Samsung Display Co., Ltd., Yongin-si (KR)
Filed on Apr. 29, 2021, as Appl. No. 17/244,782.
Claims priority of application No. 10-2020-0101393 (KR), filed on Aug. 12, 2020.
Prior Publication US 2022/0052264 A1, Feb. 17, 2022
Int. Cl. C09K 11/06 (2006.01); C07F 5/02 (2006.01); H10K 50/11 (2023.01); H10K 50/15 (2023.01); H10K 50/16 (2023.01); H10K 50/17 (2023.01); H10K 50/18 (2023.01); H10K 50/844 (2023.01); H10K 59/12 (2023.01); H10K 59/80 (2023.01); H10K 85/30 (2023.01); H10K 85/60 (2023.01); H10K 101/10 (2023.01)
CPC C09K 11/06 (2013.01) [C07F 5/027 (2013.01); H10K 85/322 (2023.02); H10K 85/658 (2023.02); C07B 2200/05 (2013.01); C09K 2211/1022 (2013.01); H10K 50/11 (2023.02); H10K 50/15 (2023.02); H10K 50/16 (2023.02); H10K 50/17 (2023.02); H10K 50/171 (2023.02); H10K 50/18 (2023.02); H10K 50/844 (2023.02); H10K 59/12 (2023.02); H10K 59/873 (2023.02); H10K 2101/10 (2023.02)] 20 Claims
OG exemplary drawing
 
1. 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, the interlayer comprising an emission layer,
wherein the interlayer further comprises a hole transport region between the first electrode and the emission layer,
the hole transport region comprises a compound represented by Formula 201, a compound represented by Formula 202, or a combination thereof, and
the emission layer comprises at least one condensed cyclic compound represented by Formula 1:

OG Complex Work Unit Chemistry
wherein, in Formula 1,
a1 to a4 are each independently an integer from 0 to 20,
a5 is an integer from 0 to 2,
the sum of a1, a2, a3, a4, and a5 is an integer of 1 or more,
R1, R2, and R11 to R15 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, d2, and d11 to d14 are each independently an integer from 1 to 20,
d15 is an integer from 0 to 2,
the sum of a5 and d15 is 2,
two or more groups of R1, R2, and R11 to R15 are optionally linked to each other 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,
Z1 to Z3 are each independently a single bond or a non-bond,
L1 and L2 are each independently a single bond, or a benzene group, a naphthalene group, an anthracene group, an pyrrole group, a carbazole group, a dibenzofuran group, or a dibenzothiophene group, each unsubstituted or substituted with at least one R10a, and
E1 and E2 are each independently selected from:
a C1-C60 alkyl group unsubstituted or substituted with at least one R10a;
a C5-C30 carbocyclic group and a C2-C30 heterocyclic group, each unsubstituted or substituted with at least one R10a;
N(Q4)(Q5); and
a group represented by Formula A-1 and a group represented by Formula A-2:

OG Complex Work Unit Chemistry
wherein, in Formulae A-1 and A-2,
X1 is a non-bond, a single bond, 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),
R1a, R1b, Ra2, and R2b are each independently the same as described in connection with R11,
d10 is an integer from 0 to 8,
* indicates a binding site to a neighboring atom,
n1 and n2 are each independently an integer from 1 to 5, and
o1 and o2 are each independently an integer from 0 to 3,
wherein, in Formulae 201 and 202,
L201 to L204 are each independently a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
L205 is *—O—*′, *—S—*′, *—N(Q201)-*′, a C1-C20 alkylene group unsubstituted or substituted with at least one R10a, a C2-C20 alkenylene group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
xa1 to xa4 are each independently an integer from 0 to 5,
xa5 is an integer from 1 to 10,
R201 to R204 and Q201 are each independently a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a or a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a,
R201 and R202 are optionally linked to each other via a single bond, a C1-C5 alkylene group unsubstituted or substituted with at least one R10a, or a C2-C5 alkenylene group unsubstituted or substituted with at least one R10a, to form a C8-C60 polycyclic group unsubstituted or substituted with at least one R10a,
R203 and R204 are optionally linked to each other via a single bond, a C1-C5 alkylene group unsubstituted or substituted with at least one R10a, or a C2-C5 alkenylene group unsubstituted or substituted with at least one R10a, to form a C8-C60 poly cyclic group unsubstituted or substituted with at least one R10a,
na1 is an integer from 1 to 4, and
R10a is:
deuterium (—D), —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
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; 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.