US 12,069,948 B2
Heterocyclic compound and organic light-emitting device including the same
Heechoon Ahn, Yongin-si (KR); Soobyung Ko, Yongin-si (KR); Mieun Jun, Yongin-si (KR); Sungbum Kim, Yongin-si (KR); Mina Jeon, Yongin-si (KR); Youngkook Kim, Yongin-si (KR); and Seokhwan Hwang, Yongin-si (KR)
Assigned to Samsung Display Co., Ltd., Yongin-si (KR)
Filed by SAMSUNG DISPLAY CO., LTD., Yongin-si Gyeonggi-do (KR)
Filed on Sep. 29, 2021, as Appl. No. 17/489,613.
Application 17/489,613 is a continuation of application No. 15/788,605, filed on Oct. 19, 2017, granted, now 11,145,823, issued on Oct. 12, 2021.
Claims priority of application No. 10-2017-0048532 (KR), filed on Apr. 14, 2017.
Prior Publication US 2022/0020937 A1, Jan. 20, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. H10K 85/60 (2023.01); C07F 9/572 (2006.01); C07F 9/64 (2006.01); C07F 9/6561 (2006.01); C07F 9/6596 (2006.01); C09K 11/02 (2006.01); C09K 11/06 (2006.01); H10K 50/00 (2023.01); H10K 50/11 (2023.01); H10K 85/40 (2023.01); H10K 101/00 (2023.01); H10K 101/10 (2023.01); H10K 101/30 (2023.01); H10K 101/40 (2023.01)
CPC H10K 85/6572 (2023.02) [C07F 9/5728 (2013.01); C07F 9/64 (2013.01); C07F 9/65616 (2013.01); C07F 9/6596 (2013.01); C09K 11/025 (2013.01); C09K 11/06 (2013.01); H10K 50/00 (2023.02); H10K 50/11 (2023.02); H10K 85/40 (2023.02); H10K 85/654 (2023.02); H10K 85/656 (2023.02); H10K 85/6574 (2023.02); H10K 85/6576 (2023.02); C09K 2211/1018 (2013.01); H10K 2101/10 (2023.02); H10K 2101/27 (2023.02); H10K 2101/30 (2023.02); H10K 2101/40 (2023.02)] 18 Claims
 
1. An organic light-emitting device comprising:
a first electrode;
a second electrode facing the first electrode; and
an organic layer between the first electrode and the second electrode, the organic layer comprising an emission layer,
wherein the emission layer comprises a first compound represented by Formula 1, and a second compound,
the first compound is a delayed fluorescent dopant,
the second compound is a host, and
the first compound and the second compound satisfy Equation 2 or Equation 3:
|EH, HOMO−ED, HOMO|≤0.5 eV  Equation 2
|EH, LOMO−ED, LOMO|≤0.5 eV,  Equation 3
wherein, in Equations 2 and 3,
EH, HOMO is a highest occupied molecular orbital level of the second compound,
ED, HOMO is a highest occupied molecular orbital level of the first compound,
EH, LUMO is a lowest unoccupied molecular orbital level of the second compound, and
ED, LUMO is a lowest unoccupied molecular orbital level of the first compound:

OG Complex Work Unit Chemistry
wherein, in Formulae 1, 2-1, 2-2, 3-1, and 3-2,
X1 is O or S,
Ar1 and Ar2 are each independently a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C2-C60 heterocyclic group,
a1 and a2 are each independently an integer from 0 to 3,
b1 and b2 are each independently 0 or 1,
a1, a2, b1, and b2 satisfy a1+b1≥1 and a2+b2≥1,
R1 and R2 are each independently a group represented by Formula 2-1,
R3 is a group represented by Formula 2-2,
A1 to A4 are each independently selected from a benzene group, a naphthalene group, a phenanthrene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, and a tetrazine group,
A5 to A8 are each independently selected from a benzene group, a naphthalene group, a phenanthrene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, and a tetrazine group,
Y1 is a single bond, O, S, SO2, N(R19), C(R19)(R20), Si(R19)(R20), S(═O)(R19), S(═O)2(R19), or P(═O)(R19),
Y2 is a single bond, O, S, SO2, N(R19), C(R19)(R20), Si(R19)(R20), S(═O)(R19), S(═O)2(R19), or P(═O)(R19),
Y3 is a single bond, O, S, SO2, N(R19), C(R19)(R20), Si(R19)(R20), S(═O)(R19), S(═O)2(R19), or P(═O)(R19),
Y4 is a single bond, O, S, SO2, N(R19), C(R19)(R20), Si(R19)(R20), S(═O)(R19), S(═O)2(R19), or P(═O)(R19),
Y5 is a single bond, O, S, SO2, N(R19), C(R19)(R20), Si(R19)(R20), S(═O)(R19), S(═O)2(R19), or P(═O)(R19),
wherein (i) when Y2 is a single bond, S, or O, a group represented by Formula 2-1 and a group represented by Formula 2-2 are different from each other, and
(ii) when —(Ar1)a1—(R1)b1 and —(Ar2)a2—(R2)b2 each represent a phenyl group, either Y2 is S(═O)(R19) or S(═O)2(R19), or at least one of R13 and R14 is selected from a group represented by Formula 3-1 and a group represented by Formula 3-2,
R11 to R14 are each independently selected from a group represented by Formula 3-1, a group represented by Formula 3-2, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —S(═O)(Q1), and —P(═O)(Q1)(Q2),
wherein two or more R11(s) are optionally linked to form a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C2-C60 heterocyclic group, two or more R12(s) are optionally linked to form a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C2-C60 heterocyclic group, two or more R13(s) are optionally linked to form a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C2-C60 heterocyclic group, and two or more R14(s) are optionally linked to form a substituted or unsubstituted C5-C60 carbocyclic group or a substituted or unsubstituted C2-C60 heterocyclic group,
b11 to b14 are each independently an integer from 1 to 8,
when X1 is O, at least one of R13 and R14 is a group represented by Formula 3-1 or a group represented by Formula 3-2, provided that Y2 and Y3 are not both a single bond at the same time, and Y2 and Y4 or Y2 and Y5 are not both a single bond at the same time,
R15 to R20 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic, —S(═O)(Q1), and —P(═O)(Q1)(Q2),
b15 to b18 are each independently an integer from 1 to 8,
at least one substituent of the substituted C5-C60 carbocyclic group, the substituted C2-C60 heterocyclic group, the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C1-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C1-C60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from:
deuterium, —F, —Cl —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C0-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), and —P(═O)(Q11)(Q12);
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C0-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), and —P(═O)(Q21)(Q22); and
—Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), and —P(═O)(Q31)(Q32),
Q1, Q2, Q11 to Q13, Q21 to Q23, and Q31 to Q33 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group,
* in Formulae 2-1 and 2-2 indicates a binding site to a corresponding neighboring atom in Formula 1, and
* in Formulae 3-1 and 3-2 indicates a binding site to a corresponding neighboring atom in Formulae 2-1 or 2-2.