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

Patent metadata

Field	Value
Publication number	US-9705090-B2
Application number	US-201514596574-A
Country	US
Kind code	B2
Filing date	Jan 14, 2015
Priority date	Jun 16, 2014
Publication date	Jul 11, 2017
Grant date	Jul 11, 2017

Abstract

An organic light-emitting device includes a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode and including at least one condensed cyclic compound represented by Formula 1:

The organic light-emitting device including the condensed cyclic compound represented by Formula 1 may have low driving voltage, high efficiency, high brightness, and long lifespan.

First claim

What is claimed is:

1. A condensed cyclic compound represented by Formula 1:
Formula 1

 wherein
X is an oxygen (O) atom or a sulfur (S) atom;
R 1 to R 10 are each independently selected from a hydrogen, a deuterium, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a carboxylic acid, 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 1 -C 30 heteroaryl group, a substituted or unsubstituted C 6 -C 30 aryloxy group, a substituted or unsubstituted C 6 -C 30 arylthio group, and a substituted or unsubstituted monovalent C 6 -C 30 non-aromatic condensed polycyclic group,
each R 1 in a plurality of R 1 and each R 2 in a plurality of R 2 are independent of one another,
at least one of the plurality of R 1 and the plurality of R 2 is optionally linked to an adjacent R 1 and/or R 2 to form a condensed ring with at least one selected from ‘a’ benzene ring and ‘b’ benzene ring;
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 1 -C 30 heteroaryl group, substituted C 6 -C 30 aryloxy group, substituted C 6 -C 30 arylthio group, and substituted monovalent C 6 -C 30 non-aromatic condensed polycyclic group is selected from
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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 10 alkyl group, a C 2 -C 10 alkenyl group, a C 2 -C 10 alkynyl, and a C 1 -C 10 alkoxy group;
a C 1 -C 10 alkyl group, a C 2 -C 10 alkenyl group, a C 2 -C 10 alkynyl group, and a C 1 -C 10 alkoxy group, each substituted with at least one selected from 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid 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 ), and —B(Q 16 )(Q 17 );
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, and a monovalent C 6 -C 30 non-aromatic condensed polycyclic group;
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, and a C 6 -C 30 arylthio group, and a monovalent C 6 -C 30 non-aromatic condensed polycyclic group, each substituted with at least one selected from 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid 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, C 3 -C 10 a 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 ), and —B(Q 26 )(Q 27 ); and
—Si(Q 31 )(Q 32 )(Q 33 ) and —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 selected from 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, and a monovalent C 6 -C 30 non-aromatic condensed polycyclic group.

2. The condensed cyclic compound of claim 1 ,
wherein the plurality of R 1 are each independently selected from a hydrogen and a C 1 -C 10 alkyl group,
or at least one R 1 of the plurality of R 1 is selected from a hydrogen and a C 1 -C 10 alkyl group, and two or more R 1 of the plurality of R 1 different from the at least one R 1 of the plurality of R 1 are linked to each other to form a substituted or unsubstituted naphthylene group or a substituted or unsubstituted anthrylene group with the ‘a’ benzene ring, and
wherein at least one substituent of the substituted naphthylene group and the substituted anthrylene group is selected from a deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 10 alkyl group, and a C 6 -C 30 aryl group.

3. The condensed cyclic compound of claim 1 ,
wherein the plurality of R 2 are each independently selected from a hydrogen and a C 1 -C 10 alkyl group,
or at least one R 2 of the plurality of R 2 is selected from a hydrogen and a C 1 -C 10 alkyl group, and two or more R 2 of the plurality of R 2 different from the at least one R 2 of the plurality of R 2 are linked to each other to form a substituted or unsubstituted naphthylene group or a substituted or unsubstituted anthrylene group with the ‘b’ benzene ring, and
wherein at least one substituent of the substituted naphthylene group and the substituted anthrylene group is selected from a deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 10 alkyl group, and a C 6 -C 30 aryl group.

4. The condensed cyclic compound of claim 1 ,
wherein at least one of the plurality of R 1 and the plurality of R 2 is selected from a hydrogen and a C 1 -C 10 alkyl group,
and at least another one R 1 of the plurality of R 1 and at least another one R 2 of the plurality of R 2 are linked to each other to form a substituted or unsubstituted C 13 -C 30 condensed ring with the ‘a’ and ‘b’ benzene rings, and
wherein at least one substituent of the substituted C 13 -C 30 condensed ring is selected from a deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 10 alkyl group, and a C 6 -C 30 a

Assignees

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

Inventors

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

Classifications

• H01L51/0071 Primary

  Electricity · mapped topic

• H01L51/0052

  Electricity · mapped topic

• H01L51/0059

  Electricity · mapped topic

• H01L51/5056

  Electricity · mapped topic

• C07D519/00 Primary

  Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00 · CPC title