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

Patent metadata

Field	Value
Publication number	US-9634259-B2
Application number	US-201414444895-A
Country	US
Kind code	B2
Filing date	Jul 28, 2014
Priority date	Mar 11, 2014
Publication date	Apr 25, 2017
Grant date	Apr 25, 2017

Abstract

A condensed cyclic compound is represented by Formula 1, and an organic light-emitting device includes the condensed cyclic compound. The organic light-emitting device includes a first electrode, a second electrode facing the first electrode, and an organic layer. The organic layer includes an emission layer and the condensed-cyclic compound.

First claim

What is claimed is:

1. A condensed cyclic compound represented by Formula 1:

wherein, as shown in Formula 1,
A is represented by

B is represented by

and wherein,
X 1 and X 2 are each independently an oxygen (O) atom or a sulfur (S) atom;
R 1 is a C 6 -C 10 aryl group or a C 3 -C 10 heteroaryl group;
R 2 to R 11 are each independently a hydrogen, a deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C 1 -C 10 alkyl group, a substituted or unsubstituted C 2 -C 10 alkenyl group, a substituted or unsubstituted C 2 -C 10 alkynyl group, a substituted or unsubstituted C 1 -C 10 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 3 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, a substituted or unsubstituted C 6 -C 30 aryloxy group, a substituted or unsubstituted C 6 -C 30 arylthio group, or a monovalent C 6 -C 30 non-aromatic condensed polycyclic group;
each of the R 10 s and each of the R ii s are the same or different;
R 2 and R 3 , R 4 and R 5 , R 6 and R 7 , R 8 and R 9 , or two R 10 s optionally combine to form a substituted or unsubstituted ring;
when one or more of R 2 to R 11 includes a substituted group, at least one substituent of the substituted C 1 -C 10 alkyl group, substituted C 2 -C 10 alkenyl group, substituted C 2 -C 10 alkynyl group, substituted C 1 -C 10 alkoxy group, substituted C 3 -C 10 cycloalkyl group, substituted C 3 -C 10 cycloalkenyl group, substituted C 3 -C 10 heterocycloalkyl group, substituted C 3 -C 10 heterocycloalkenyl group, substituted C 6 -C 30 aryl group, substituted C 2 -C 30 heteroaryl group, substituted C 6 -C 30 aryloxy group, or substituted C 6 -C 30 arylthio group is:
a deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 10 alkyl group, a C 2 -C 10 alkenyl group, a C 2 -C 10 alkynyl group, or a C 1 -C 10 alkoxy group; or
a C 1 -C 10 alkyl group, a C 2 -C 10 alkenyl group, a C 2 -C 10 alkynyl group, or a C 1 -C 10 alkoxy group, substituted with at least one of a deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 3 -C 10 cycloalkyl group, a C 3 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 3 -C 10 heterocycloalkenyl group, a C 6 -C 30 aryl group, a C 2 -C 30 heteroaryl group, a C 6 -C 30 aryloxy group, a C 6 -C 30 arylthio group, a monovalent C 6 -C 30 non-aromatic condensed polycyclic group, —N(Q 11 )(Q 12 ), —Si(Q 13 )(Q 14 )(Q 15 ), or —B(Q 16 )(Q 17 ); or
a C 3 -C 10 cycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 3 -C 10 heterocycloalkyl group, a C 3 -C 10 heterocycloalkenyl group, a C 6 -C 30 aryl group, a C 2 -C 30 heteroaryl group, a C 6 -C 30 aryloxy group, a C 6 -C 30 arylthio group, or a monovalent C 2 -C 30 non-aromatic condensed polycyclic group; or
a C 3 -C 10 cycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 3 -C 10 heterocycloalkyl group, a C 3 -C 10 heterocycloalkenyl group, a C 6 -C 30 aryl group, a C 2 -C 30 heteroaryl group, a C 6 -C 30 aryloxy group, a C 6 -C 30 arylthio group, or a monovalent C 6 -C 30 non-aromatic condensed polycyclic group, substituted with at least one of a deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 10 alkyl group, a C 2 -C 10 alkenyl group, a C 2 -C 10 alkynyl group, a C 1 -C 10 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 3 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 3 -C 10 heterocycloalkenyl group, a C 6 -C 30 aryl group, a C 2 -C 30 heteroaryl group, a C 6 -C 30 aryloxy group, a C 6 -C 30 arylthio group, a monovalent C 6 -C 30 non-aromatic condensed polycyclic group, —N(Q 21 )(Q 22 ), —Si(Q 23 )(Q 24 )(Q 25 ), or —B(Q 26 )(Q 27 ); or
—Si(Q 31 )(Q 32 )(Q 33 ) or —B(Q 34 )(Q 35 ),
wherein Q 11 to Q 17 , Q 21 to Q 27 , and Q 31 to Q 35 are each independently a hydrogen, a C 1 -C 10 alkyl group, a C 2 -C 10 alkenyl group, a C 2 -C 10 alkynyl group, a C 1 -C 10 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 3 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 3 -C 10 heterocycloalkenyl group, a C 6 -C 30 aryl group, a C 2 -C 30 heteroaryl group, or a monovalent C 6 -C 30 non-aromatic condensed polycyclic group, and,
* indicates a binding site to the carbazole group.

2. The condensed cyclic compound of claim 1 , wherein X 1 and X 2 are identical to each other.

3. The condensed cyclic compound of claim 1 , wherein R 1 is a phenyl group, a naphthyl group, a pyridyl group, or a triazinyl group.

4. The condensed cyclic compound of claim 1 , wherein R 1 is represented by one of Formulae 2A to 2E:

5. The condensed cyclic compound of claim 1 , wherein R 2 to R 11 are each independently:
a hydrogen, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a biphenyl group, a heptalenyl group, a phenalenyl group, a fluorenyl group, a phenanthrenyl group, an anthryl group, a fluoranthenyl group, a pyrenyl group, a benzofluorenyl group, a naphthacenyl group, a chrysenyl group, a triphenylenyl group, a terphenyl group, a perylenyl group, a picenyl group, a hexacenyl group, a spiro-fluorenyl group, a pyrrolyl group, a furyl group, a pyrazolyl group, an imidazolyl group, an oxazolyl group, an isoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a pyranyl group, a thiophenyl group, a thiazolyl group, an isothiazolyl group, a thiopyranyl group, an indolyl group, an isoindolyl group, an indolizinyl group, a benzofuryl group, an isobenzofuryl group, an indazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzisoxazolyl group, an imidazopyridyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a phthalazinyl group, a quinazolinyl group, a quinoxalinyl group, a naphthyridinyl group, a cinnolinyl group, a benzothiophenyl group, a benzothiazolyl group, a carbazolyl group,

Assignees

• Samsung Display Co Ltd
• Pusan Nat Univ Industry-Univ Coop Found
• Pusan Nat Univ Industry—Univ Coop Found

Inventors

• Kim Sung-Wook
• Kim Myeong-Suk
• Hwang Jin-Soo
• Kho Sam-Il
• Suh Hong-Suk

Classifications

• H01L51/5056

  Electricity · mapped topic

• H01L51/006

  Electricity · mapped topic

• H01L51/0071 Primary

  Electricity · mapped topic

• H01L51/0072

  Electricity · mapped topic

• H10K50/00

  Organic light-emitting devices (integrated devices or assemblies of multiple devices H10K59/00, H10K65/00; organic semiconductor lasers H01S5/36) · CPC title