Condensed cyclic compound, organic light-emitting device including the same, and electronic apparatus including the organic light-emitting device

Patent metadata

Field	Value
Publication number	US-12297214-B2
Application number	US-202117400727-A
Country	US
Kind code	B2
Filing date	Aug 12, 2021
Priority date	Aug 13, 2020
Publication date	May 13, 2025
Grant date	May 13, 2025

Abstract

Provided are a condensed cyclic compound represented by Formula 1-1 or 1-2, an organic light-emitting device including the condensed cyclic compound, and an electronic apparatus including the organic light-emitting device:

wherein Formulae 1-1 and 1-2 are the same as described in the present specification.

First claim

What is claimed is:

1. A condensed cyclic compound represented by Formula 1-1 or 1-2:

wherein, in Formulae 1-1 and 1-2,
CY 1 to CY 3 are each independently a C 5 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group,
at least one of CY 1 and CY 2 is a group represented by Formula 2-1 or 2-2,
X 1 is O, S, Se, Te, N(R 1a ), or C(R 1a )(R 1b ),
X 2 is O, S, Se, Te, N(R 2a ), or C(R 2a )(R 2b ),
Y 1 is O, S, Se, Te, N(R 3a ), or C(R 3a )(R 3b ),
Z 1 is B, Al, Si(R 4a ), Ge(R 4a ), P, P(═O), or P(═S),
R 1 to R 3 , R 1a to R 4a , and R 1b to R 3b are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkenyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkynyl group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 alkoxy group unsubstituted or substituted with at least one R 10a , a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 aryloxy group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 arylthio group unsubstituted or substituted with at least one R 10a , —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), or —P(═O)(Q 1 )(Q 2 ),
R 1 to R 3 , R 1a to R 4a , and R 1b to R 3b are optionally linked to each other or via a single bond to form a C 8 -C 60 polycyclic group that is unsubstituted or substituted with at least one R 10a ,
d1 to d3 are each independently an integer from 0 to 20,
in Formulae 2-1 and 2-2,
CY 11 and CY 12 are each independently a C 5 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, or a group represented by Formula 3,
CY 13 is condensed with CY 1 , CY 2 , or each of CY 1 and CY 2 , wherein one of the bonds marked with a dotted line in CY 13 indicates a binding site to a bond marked with a solid line in CY 1 or CY 2 ,
in Formula 3,
CY 31 to CY 33 are each independently a C 5 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group,
X 31 is O, S, Se, Te, N(R 5a ), or C(R 5a )(R 5b ),
X 32 is O, S, Se, Te, N(R 6a ), or C(R 6a )(R 6b ),
Z 31 is B, Al, Si(R 7a ), Ge(R 7a ), P, P(═O), or P(═S),
R 5a to R 7a , R 5b , and R 6b are each independently the same as described in connection with R 1a ,
R 10a is:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group; a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, or a C 1 -C 60 alkoxy group, each unsubstituted or substituted with deuterium, —F, —C 1 , —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 11 )(Q 12 ), —B(Q 11 )(Q 12 ), —C(═O)(Q 11 ), —S(═O) 2 (Q 11 ), —P(═O)(Q 11 )(Q 12 ), or any combination thereof;
a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, or a C 6 -C 60 arylthio group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, —Si(Q 21 )(Q 22 )(Q 23 ), —N(Q 21 )(Q 22 ), —B(Q 21 )(Q 22 ), —C(═O)(Q 21 ), —S(═O) 2 (Q 21 ), —P(═O)(Q 21 )(Q 22 ), or any combination thereof: or
—Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), or —P(═O)(Q 31 )(Q 32 ), and
Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C 1 -C 60 alkyl group: a C 2 -C 60 alkenyl group: a C 2 -C 60 alkynyl group; a C 1 -C 60 alkoxy group; or a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.

2. The condensed cyclic compound of claim 1 , wherein CY 1 to CY 3 are each independently a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluorene-9-one group, an azadibenzothiophene 5,5-dioxide group, an indolocarbazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isooxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, a 5,6,7,8-tetrahydroquinoline group, or a group represented by Formula 2-1 or 2-2.

3. The condensed cyclic compound of claim 1 , wherein CY 3 is a benzene group, a naphthalene group, a dibenzosilole group, a carbazole group, a dibenzothiophene group, or a dibenzofuran group.

4. The condensed cyclic compound of claim 1 , wherein CY 11 and CY 12 are each independently a benzene group or a group represented by Formula 3.

5. The condensed cyclic compound of claim 1 , wherein the condensed cyclic compound represented by Formula 1-1 or 1-2 satisfies at least one of Conditions 1 to 3:
Condition 1
CY 1 is a group represented by Formula 2-1 or 2-2;
Condition 2
CY 2 is a group represented by Formula 2-1 or 2-2; and
Condition 3
CY 1 and CY 2 are each independently a group represented by Formula 2-1 or 2-2.

6. The condensed cyclic compound of claim 1 , wherein
in Formula 1-1, a moiety represented by

is represented by one of Formulae 3-1 to 3-8, and
in Formula 1-1, a moiety represented by

Assignees

• Samsung Electronics Co Ltd

Inventors

• Sotoyama Wataru
• Jeon Soonok
• Sakurai Rie
• Shibata Katsunori
• Imamura Atsushi
• Kim Juhyun
• Ito Mitsunori
• Miyazaki Eigo
• Kim Joonghyuk

Classifications

• C09K2211/1096

  containing other heteroatoms · CPC title

• H10K50/121

  for assisting energy transfer, e.g. sensitization · CPC title

• H10K85/658

  Organoboranes · CPC title

• H10K85/6572

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

• H10K2101/30

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