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

Patent metadata

Field	Value
Publication number	US-2016308142-A1
Application number	US-201515102642-A
Country	US
Kind code	A1
Filing date	Jan 6, 2015
Priority date	Jan 10, 2014
Publication date	Oct 20, 2016
Grant date	—

Abstract

A condensed cyclic compound and an organic light-emitting device including the condensed cyclic compound are provided.

First claim

1 . A condensed cyclic compound represented by Formula 1:

wherein, in Formula 1, ring A 1 is represented by Formula 1A, where X 1 is N-[(L 1 ) a1 -(R 1 ) b1 ], S, O, or Si(R 4 )(R 5 );

L 1 to L 3 are each independently selected from a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a substituted or unsubstituted C 6 -C 60 arylene group, a substituted or unsubstituted C 2 -C 60 heteroarylene group, and a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, wherein L 2 and L 3 are not a substituted or unsubstituted carbazolylene group,
a1 to a3 are each independently an integer selected from 0 to 5,
R 1 to R 5 are each independently selected from a hydrogen, a deuterium, a fluoro group (—F), a chloro group (—Cl), a bromo group (—Br), an iodo group (—I), a hydroxyl group, a cyano 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 2 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 2 -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 2 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q 1 )(Q 2 ), —Si(Q 3 )(Q 4 )(Q 5 ), and —B(Q 6 )(Q 7 ), wherein at least one of R 2 and R 3 is a substituted or unsubstituted N-containing C 2 -C 60 heteroaryl group,
R 11 to R 14 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 2 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, —Si(Q 3 )(Q 4 )(Q 5 ), and —B(Q 6 )(Q 7 ), and
b1 to b3 are each independently an integer selected from 1 to 3,
wherein R 3 is not a substituted or unsubstituted morpholinyl group;
when R 3 is a pyridinyl group, pyridazinyl group, or a pyrimidinyl group, R 2 is selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, and a substituted or unsubstituted triphenylenyl group;
at least one of substituents of the substituted C 3 -C 10 cycloalkylene group, the substituted C 3 -C 10 cycloalkenylene group, the substituted C 6 -C 60 arylene group, the substituted C 2 -C 60 heteroarylene group, the substituted divalent non-aromatic condensed polycyclic group, the substituted C 1 -C 60 alkyl group, the substituted C 1 -C 60 alkoxy group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 2 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 2 -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 2 -C 60 heteroaryl group, and the substituted monovalent non-aromatic condensed polycyclic group is selected from
a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a C 1 -C 60 alkyl group, and a C 1 -C 60 alkoxy group,
a C 1 -C 60 alkyl group, and a C 1 -C 60 alkoxy group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a C 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 2 -C 60 heteroaryl group, and a monovalent non-aromatic condensed polycyclic group, —Si(Q 13 )(Q 14 )(Q 15 ), and —B(Q 16 )(Q 17 ),
a C 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 2 -C 60 heteroaryl group, and a monovalent non-aromatic condensed polycyclic group,
a C 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 2 -C 60 heteroaryl group, and a monovalent non-aromatic condensed polycyclic group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 2 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, —Si(Q 23 )(Q 24 )(Q 25 ), and —B(Q 26 )(Q 27 ), and
—Si(Q 33 )(Q 34 )(Q 35 ), and —B(Q 36 )(Q 37 );
Q 3 to Q 7 , Q 13 to Q 17 , Q 23 to Q 27 , and Q 33 to Q 37 are each independently selected from a hydrogen, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 2 -C 60 heteroaryl group, and a monovalent non-aromatic condensed polycyclic group; and
a substituent of R 2 and R 3 is not a carbazolyl group substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 2 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, —Si(Q 23 )(Q 24 )(Q 25 ), and —B(Q 26 )(Q 27 ).

2 . The condensed cyclic compound of claim 1 , wherein the condensed cyclic compound is represented by one of Formulae 1-1 and 1-2:

wherein, in Formulae 1-1 to 1-2, X 1 , L 2 , L 3 , a2, a3, R 2 , R 3 , R 11 to R 14 , b2 and b3 are the same as those defined in claim 1 .

3 . The condensed cyclic compound of claim 1 , wherein X 1 is S or O.

4 . The condensed cyclic compound of claim 1 , wherein L 1 to L 3 are each independently represented by one of Formulae 2-1 to 2-15:

wherein, in Formulae 2-1 to 2-15,
Z 1 to Z 4 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, a naphthyl group, an anthracenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl gr

Assignees

• Samsung Electronics Co Ltd

Inventors

• Kim Byung-Ku
• Lee Sang-Shin
• Shin Chang-Ju
• Jung Sung-Hyun
• Kwon O Hyun
• Kim Young-Kwon
• Kim Chang-Woo
• Kim Hyung-Sun
• Seo Joo-Hee
• Yu Eun-Sun
• Lee Seung-Jae
• Choi Byoung Ki
• Hwang Kyu Young

Classifications

• C07F7/0816

  said ring comprising Si as a ring atom · CPC title

• C07D401/14

  containing three or more hetero rings · CPC title

• H05B33/22

  characterised by the chemical or physical composition or the arrangement of auxiliary dielectric or reflective layers · CPC title

• C07D491/048 Primary

  the oxygen-containing ring being five-membered · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title