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

Patent metadata

Field	Value
Publication number	US-10396295-B2
Application number	US-201715466087-A
Country	US
Kind code	B2
Filing date	Mar 22, 2017
Priority date	Sep 22, 2016
Publication date	Aug 27, 2019
Grant date	Aug 27, 2019

Abstract

A condensed cyclic compound represented by Formula 1:

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

First claim

What is claimed is:

1. A condensed cyclic compound represented by Formula 1:
Ar 1 -(L 1 ) a1 -Ar 2   Formula 1

wherein, in Formulae 1, 2-3, and 3-1,
Ar 1 is a group represented by Formula 2-3,
Ar 2 is a group represented by Formula 3-1,
L 1 is selected from a substituted or unsubstituted C 6 -C 60 arylene group, a substituted or unsubstituted C 1 -C 60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
a1 is selected from 0, 1, 2, and 3,
X 21 is selected from O, S, and Se,
X 31 is selected from a single bond, O, S, N(R 33 ), C(R 33 )(R 34 ), Si(R 33 )(R 34 ), Ge(R 33 )(R 34 ), and P(═O)(R 33 ),
A 21 , A 31 , and A 32 are each independently selected from a C 5 -C 30 carbocyclic group and a C 1 -C 30 heterocyclic group,
R 21 to R 23 and R 31 to R 34 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro 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 7 -C 60 aryl alkyl 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 C 2 -C 60 heteroaryl alkyl group, a substituted or unsubstituted C 1 -C 60 hetero aryloxy group, a substituted or unsubstituted C 1 -C 60 hetero arylthio 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 1 )(Q 2 )(Q 3 ), and —B(Q 1 )(Q 2 ),
R 22 and R 23 are optionally linked to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,
R 33 and R 34 are optionally linked via a first linking group to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,
b21, b31, and b32 are each independently selected from 1, 2, 3, 4, 5, 6, 7, and 8,
Q 1 to Q 3 are each independently selected from:
hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro 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 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group;
a C 1 -C 60 alkyl group, substituted with at least one selected from deuterium, a C 1 -C 60 alkyl group, and a C 6 -C 60 aryl group;
a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 7 -C 60 arylalkyl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a C 2 -C 60 heteroaryl alkyl group, a C 1 -C 60 hetero aryloxy group, a C 1 -C 60 hetero arylthio group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group; and
a C 6 -C 60 aryl group, substituted with at least one selected from deuterium, a C 1 -C 60 alkyl group, and a C 6 -C 60 aryl group, and
indicates 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 fluorenylene group, a phenanthrenylene group, an anthracenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, and a triazinylene group; and
a phenylene group, a naphthylene group, a fluorenylene group, a phenanthrenylene group, an anthracenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene 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 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, and a triazinyl group.

3. The condensed cyclic compound of claim 1 , wherein
a1 is 0 or 1.

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

5. The condensed cyclic compound of claim 1 , wherein
A 21 is selected from a benzene group, a naphthalene group, a phenanthrene group, a pyrene group, a chrysene group, a triphenylene group, a fluoranthene group, an indene group, a fluorene group, a benzofluorene group, a dibenzofluorene group, a spiro-bifluorene group, a pyridine group, a pyrimidine group, a quinoline group, an isoquinoline group, an indole group, a carbazole group, a benzocarbazole group, a dibenzocarbazole group, a furan group, a benzofuran group, a dibenzofuran group, a naphtho furan group, a benzonaphtho furan group, a dinaphtho furan group, a thiophene group, a benzothiophene group, a dibenzothiophene group, a naphtho thiophene group, a benzonaphtho thiophene group, and a dinaphtho thiophene group.

6. The condensed cyclic compound of claim 1 , wherein
A 21 is selected from a benzene group, a naphthalene group, a phenanthrene group, a pyrimidine group, a quinoline group, and an isoquinoline group.

7. The condensed cyclic compound of claim 1 , wherein
Ar 1 is selected from groups represented by Formulae 2-11 to 2-14:

wherein, in Formulae 2-11 to 2-14,
X 21 , R 22 , and R 23 are the same as described in Formula 2-3,
R 21a to R 21d are each independently the same as described in connection with R 21 in Formula 2-3, and
indicates a binding site to a neighboring atom.

8. The condensed cyclic compound of claim 1 , wherein
X 31 is selected from a single bond, O, S, N(R 33 ), and C(R 33 )(R 34 ).

9. The condensed cyclic compound of claim 1 , wherein
A 31 and A 32 are each independently selected from a benzene group, a naphthalene group, a phenanthrene group, a pyrene group, a chrysene group, a triphenylene group, a fluoranthene group, an indene group, a fluorene group, a benzofluorene group, a dibenzofluorene group, a spiro-bifluorene grou

Assignees

• Samsung Electronics Co Ltd

Inventors

• Numata Masaki
• Miyazaki Hiroshi
• Sim Myungsun
• LEE Saeyoun
• Ihn Sooghang
• Jeon Soonok

Classifications

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K2211/1048

  with oxygen · CPC title

• 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

• H01L51/0072 Primary

  Electricity · mapped topic