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

Patent metadata

Field	Value
Publication number	US-10873034-B2
Application number	US-201715413831-A
Country	US
Kind code	B2
Filing date	Jan 24, 2017
Priority date	Feb 11, 2016
Publication date	Dec 22, 2020
Grant date	Dec 22, 2020

Abstract

A condensed cyclic compound represented by Formula 1:

Ar 1 -(L 1 ) a1 -Ar 2   Formula 1
wherein, in Formula 1, Ar 1 , Ar 2 , L 1 , and a1 are the same as described in the specification.

First claim

What is claimed is:

1. A condensed cyclic compound represented by Formula 1:

wherein, in Formulae 1, 2-2, 2-4, 3-12, 3-15, and 3-16,
Ar 1 is selected from groups represented by Formulae 2-2 and 2-4;
Ar 2 is selected from groups represented by Formulae 3-12, 3-15, and 3-16;
L 1 is selected from a substituted or unsubstituted C 6 -C 60 arylene group and a substituted or unsubstituted C 1 -C 60 heteroarylene group;
a1 is selected from 1, 2, and 3;
X 21 is selected from O, S, C(R 22 )(R 23 ), Si(R 22 )(R 23 ), Ge(R 22 )(R 23 ), and P(═O)(R 22 );
X 31 is selected from O, S, N(R 34 ), C(R 34 )(R 35 ), Si(R 34 )(R 35 ), and Ge(R 34 )(R 35 );
provided that when Ar 1 is Formula 2-4 and Ar 2 is Formula 3-12, when X 21 is S, then X 31 is selected from O, S, C(R 34 )(R 35 ), Si(R 34 )(R 35 ), and Ge(R 34 )(R 35 );
A 21 is selected from a C 5 -C 20 carbocyclic group and a C 4 -C 20 heterocyclic group;
Y 21 is selected from a substituted or unsubstituted C 6 -C 60 aryl group and a substituted or unsubstituted C 1 -C 60 heteroaryl group;

R 21 to R 23 , R 31a to R 31d , R 32a to R 32d , R 33a to R 33d , R 34 , and R 35 are each independently selected from
hydrogen, deuterium, —F, —Cl, —Br, —I, 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 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, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group;
b21 is selected from 1, 2, 3, 4, 5, 6, 7, and 8; and
* denotes a binding site to a neighboring atom.

2. The condensed cyclic compound of claim 1 , wherein L 1 is selected from
a phenylene group, a naphthylene group, a pyridinylene group, a pyrimidinylene group, a pyrazinylene group, a pyridazinylene group, and a triazinylene group; and
a phenylene group, a naphthylene group, a pyridinylene group, a pyrimidinylene group, a pyrazinylene group, a pyridazinylene group, and a triazinylene group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, 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 1 -C 10 alkoxy group, a phenyl group, and a naphthyl group.

3. The condensed cyclic compound of claim 1 , wherein L 1 is selected from a single bond and groups represented by Formulae 4-1 to 4-15:

wherein, in Formulae 4-1 to 4-15,
R 41 is selected from hydrogen, deuterium, —F, —Cl, —Br, —I, 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 1 -C 10 alkoxy group, a phenyl group, and a naphthyl group;
b41 is selected from 1, 2, 3, and 4;
b42 is selected from 1, 2, 3, 4, 5, and 6; and
* and *′ each independently denote a binding site to a neighboring atom.

4. The condensed cyclic compound of claim 1 , wherein a1 is 1.

5. The condensed cyclic compound of claim 1 , wherein (L 1 ) a1 is selected from groups represented by Formulae 5-1 to 5-3:

wherein, in Formulae 5-1 to 5-3,
* and *′ each independently denote a binding site to a neighboring atom.

6. The condensed cyclic compound of claim 1 , wherein A 21 is selected from a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyridine group, a pyrimidine group, a pyrazine group, a quinoline group, an isoquinoline group, 2,6-naphthyridine group, 1,8-naphthyridine group, 1,5-naphthyridine group, 1,6-naphthyridine group, 1,7-naphthyridine group, 2,7-naphthyridine group, a quinoxaline group, a phthalazine group, a quinazoline group, and a cinnoline group.

7. The condensed cyclic compound of claim 1 , wherein A 21 is selected from a benzene group and a naphthalene group.

8. The condensed cyclic compound of claim 1 , wherein Y 21 is selected from
a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pyrrolyl group, an imidazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, and a triazinyl group; and
a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pyrrolyl group, an imidazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, and a triazinyl group, each substituted with at least one selected from deuterium, 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

Assignees

• Samsung Electronics Co Ltd
• Samsung Sdi Co Ltd

Inventors

• LEE Saeyoun
• Numata Masaki
• Miyazaki Hiroshi
• Jeon Soonok
• Kang Hosuk
• Ihn Sooghang
• Chae Miyoung

Classifications

• 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

• H10K2101/20

  Delayed fluorescence emission · CPC title

• H10K85/657

  Polycyclic condensed heteroaromatic hydrocarbons · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K11/025

  non-luminescent particle coatings or suspension media · CPC title