Heterocyclic compound and organic light-emitting device including the same

Patent metadata

Field	Value
Publication number	US-12069948-B2
Application number	US-202117489613-A
Country	US
Kind code	B2
Filing date	Sep 29, 2021
Priority date	Apr 14, 2017
Publication date	Aug 20, 2024
Grant date	Aug 20, 2024

Abstract

An organic light-emitting device includes 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 including an emission layer. The emission layer includes at least one heterocyclic compound of Formula 1. The heterocyclic compound may be a host or a delayed fluorescent dopant. The organic light-emitting device including the heterocyclic compound may have a low driving voltage, high efficiency, high luminance, and a long lifespan.

First claim

What is claimed is:

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:
| E H, HOMO −E D, HOMO |≤0.5 eV  Equation 2

| E H, LOMO −E D, LOMO |≤0.5 eV,  Equation 3

wherein, in Equations 2 and 3,
E H, HOMO is a highest occupied molecular orbital level of the second compound,
E D, HOMO is a highest occupied molecular orbital level of the first compound,
E H, LUMO is a lowest unoccupied molecular orbital level of the second compound, and
E D, LUMO is a lowest unoccupied molecular orbital level of the first compound:

wherein, in Formulae 1, 2-1, 2-2, 3-1, and 3-2,
X 1 is O or S,
Ar 1 and Ar 2 are each independently a substituted or unsubstituted C 5 -C 60 carbocyclic group or a substituted or unsubstituted C 2 -C 60 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,
R 1 and R 2 are each independently a group represented by Formula 2-1,
R 3 is a group represented by Formula 2-2,
A 1 to A 4 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,
A 5 to A 8 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,
Y 1 is a single bond, O, S, SO 2 , N(R 19 ), C(R 19 )(R 20 ), Si(R 19 )(R 20 ), S(═O)(R 19 ), S(═O) 2 (R 19 ), or P(═O)(R 19 ),
Y 2 is a single bond, O, S, SO 2 , N(R 19 ), C(R 19 )(R 20 ), Si(R 19 )(R 20 ), S(═O)(R 19 ), S(═O) 2 (R 19 ), or P(═O)(R 19 ),
Y 3 is a single bond, O, S, SO 2 , N(R 19 ), C(R 19 )(R 20 ), Si(R 19 )(R 20 ), S(═O)(R 19 ), S(═O) 2 (R 19 ), or P(═O)(R 19 ),
Y 4 is a single bond, O, S, SO 2 , N(R 19 ), C(R 19 )(R 20 ), Si(R 19 )(R 20 ), S(═O)(R 19 ), S(═O) 2 (R 19 ), or P(═O)(R 19 ),
Y 5 is a single bond, O, S, SO 2 , N(R 19 ), C(R 19 )(R 20 ), Si(R 19 )(R 20 ), S(═O)(R 19 ), S(═O) 2 (R 19 ), or P(═O)(R 19 ),
wherein (i) when Y 2 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 —(Ar 1 ) a1 —(R 1 ) b1 and —(Ar 2 ) a2 —(R 2 ) b2 each represent a phenyl group, either Y 2 is S(═O)(R 19 ) or S(═O) 2 (R 19 ), or at least one of R 13 and R 14 is selected from a group represented by Formula 3-1 and a group represented by Formula 3-2,
R 11 to R 14 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 C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —S(═O)(Q 1 ), and —P(═O)(Q 1 )(Q 2 ),
wherein two or more R 11 (s) are optionally linked to form a substituted or unsubstituted C 5 -C 60 carbocyclic group or a substituted or unsubstituted C 2 -C 60 heterocyclic group, two or more R 12 (s) are optionally linked to form a substituted or unsubstituted C 5 -C 60 carbocyclic group or a substituted or unsubstituted C 2 -C 60 heterocyclic group, two or more R 13 (s) are optionally linked to form a substituted or unsubstituted C 5 -C 60 carbocyclic group or a substituted or unsubstituted C 2 -C 60 heterocyclic group, and two or more R 14 (s) are optionally linked to form a substituted or unsubstituted C 5 -C 60 carbocyclic group or a substituted or unsubstituted C 2 -C 60 heterocyclic group,
b11 to b14 are each independently an integer from 1 to 8,
when X 1 is O, at least one of R 13 and R 14 is a group represented by Formula 3-1 or a group represented by Formula 3-2, provided that Y 2 and Y 3 are not both a single bond at the same time, and Y 2 and Y 4 or Y 2 and Y 5 are not both a single bond at the same time,
R 15 to R 20 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 C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic, —S(═O)(Q 1 ), and —P(═O)(Q 1 )(Q 2 ),
b15 to b18 are each independently an integer from 1 to 8,
at least one substituent of the substituted C 5 -C 60 carbocyclic group, the substituted C 2 -C 60 heterocyclic group, the substituted C 1 -C 60 alkyl group, the substituted C 2 -C 60 alkenyl group, the substituted C 2 -C 60 alkynyl group, the substituted C 1 -C 60 alkoxy group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 1 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 1 -C 10 heterocycloalkenyl group, the substituted C 6 -C 60 aryl group, the substituted C 6 -C 60 aryloxy group, the substituted C 6 -C 60 arylthio group, the substituted C 1 -C 60 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 C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group;
a C 1 -C

Assignees

• Samsung Display Co Ltd

Inventors

• Ahn Heechoon
• Ko Soobyung
• Jun Mieun
• Kim Sungbum
• Jeon Mina
• Kim Youngkook
• Hwang Seokhwan

Classifications

• H10K2101/20

  Delayed fluorescence emission · CPC title

• H10K85/6572 Primary

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• C07F9/65616 Primary

  containing the ring system [IMAGE cpc-sch-C07F-1006.gif] having three or more than three double bonds between ring members or between ring members and non-ring members, e.g. purine or analogs · CPC title

• H10K2101/30

  Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values · CPC title

• H10K2101/27

  Combination of fluorescent and phosphorescent emission · CPC title