US 12,193,320 B2
Heterocyclic compound, light-emitting device including heterocyclic compound, and electronic apparatus including light-emitting device
Heechoon Ahn, Yongin-si (KR); Soobyung Ko, Yongin-si (KR); Hyeongmin Kim, Yongin-si (KR); Hyunah Um, Yongin-si (KR); Yeseul Lee, Yongin-si (KR); and Yirang Im, Yongin-si (KR)
Assigned to Samsung Display Co., Ltd., Yongin-si (KR)
Filed by Samsung Display Co., Ltd., Yongin-si (KR)
Filed on May 18, 2021, as Appl. No. 17/323,817.
Claims priority of application No. 10-2020-0059923 (KR), filed on May 19, 2020.
Prior Publication US 2021/0376262 A1, Dec. 2, 2021
Int. Cl. H01L 51/50 (2006.01); C07F 7/08 (2006.01); C09K 11/06 (2006.01); H10K 85/40 (2023.01); H10K 50/11 (2023.01); H10K 85/60 (2023.01); H10K 101/10 (2023.01)
CPC H10K 85/40 (2023.02) [C07F 7/0812 (2013.01); C09K 11/06 (2013.01); C07B 2200/05 (2013.01); C09K 2211/1018 (2013.01); H10K 50/11 (2023.02); H10K 85/6572 (2023.02); H10K 2101/10 (2023.02)] 16 Claims
OG exemplary drawing
 
1. A heterocyclic compound represented by Formula 1:

OG Complex Work Unit Chemistry
wherein, a group represented by

OG Complex Work Unit Chemistry
in Formula 1 is a group represented by one of Formulae 7-2 to 7-13:

OG Complex Work Unit Chemistry
wherein, in Formulae 7-2 to 7-13, Ar4, R4, and a4 have, independently from one another, the same meanings as described hereinafter, a43 is an integer from 0 to 3, * indicates a binding site to an adjacent silicon atom in Formula 1, and *′ indicates a binding site to L1 in Formula 1,
Ar1 to Ar4, and Ar12 in Formula are each, independently from one another, a group represented by Formula 2 or a group represented by Formula 3, and Ar11 in Formula 1 is a group represented by Formula 2,

OG Complex Work Unit Chemistry
d1, d2, and d3 in Formula 1 are each, independently from one another, an integer from 0 to 5;
d11 in Formula 1 1;
d12 in Formula 1 is 0 or 1;
L1 in Formula 1 is a single bond or a group represented by Formula 4;
L11 in Formulae 2 and 3 is a single bond, a group represented by Formula 4, or a group represented by Formula 5

OG Complex Work Unit Chemistry
b1 and b11 in Formulae 1 to 3 are each, independently from one another, an integer from 1 to 5;
X1 in Formula 1 is a single bond, O, S, C(Z3)(Z4), or Si(Z3)(Z4);
X11 in Formulae 2 and 3 is a single bond, O, S, C(Z13)(Z14), or Si(Z13)(Z14);
X21 in Formula 4 is a single bond, O, S, C(Z23)(Z24), or Si(Z23)(Z24);
R1 to R4 in Formula 1 are each, independently from one another:
hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C20 alkyl group, or a C1-C20 alkoxy group;
a C1-C20 alkyl group or a C1-C20 alkoxy group, each, independently from one another, substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, a C1-C10 alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, or any combination thereof;
a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a C1-C10 alkylphenyl group, a fluorenyl group, a carbazolyl group, or a dibenzosilolyl group, each, independently from one another, unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a C1-C10 alkylphenyl group, a fluorenyl group, a carbazolyl group, a dibenzosilolyl group, or any combination thereof; or
—Si(Q1)(Q2)(Q3),
Z1 to Z4, Z11 to Z15, and Z21 to Z25 in Formulae 1 to 5 are each, independently from one another, 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);
a1 to a3 in Formula 1 are each, independently from one another, an integer from 0 to 5;
a4, c1, c11, c13, c21, and c25 in Formulae 1 to 5 are each, independently from one another, an integer from 0 to 4;
c2, c12, and c22 in Formulae 1, 3, and 4 are each, independently from one another, an integer from 0 to 3;
* in Formulae 2 and 4 indicates a binding site to an adjacent carbon atom, and * and *′ in Formulae 3 to 5 each indicate a binding site to an adjacent atom; and
R10a is:
-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 independently from one another, 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 independently from one another, 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 C1-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),
wherein Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 are each, independently from one another, hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; or 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 independently from one another, 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.