Condensed cyclic compound and organic light-emitting device including condensed cyclic compound

Patent metadata

Field	Value
Publication number	US-11299502-B2
Application number	US-201816218670-A
Country	US
Kind code	B2
Filing date	Dec 13, 2018
Priority date	Jun 12, 2018
Publication date	Apr 12, 2022
Grant date	Apr 12, 2022

Abstract

A condensed cyclic compound and an organic light-emitting device including the same are provided. When the condensed cyclic compound is used as an emission layer material in a device, the device may have excellent driving voltage, efficiency, and colorimetric purity. An organic light-emitting device including the condensed cyclic compound may have a low driving voltage, excellent efficiency, and a long lifespan.

First claim

What is claimed is:

1. An organic light-emitting device comprising:
a first electrode;
a second electrode facing the first electrode; and
an organic layer between the first electrode and the second electrode and comprising an emission layer and at least one condensed cyclic compound represented by Formula 1:

wherein in Formulae 1, 2A, and 2B,
X 11 is selected from C(R 12 )(R 13 ), Si(R 12 )(R 13 ), O, and S, and X 12 is selected from C(R 14 )(R 16 ), Si(R 14 )(R 16 ), O, and S,
when X 11 is O or S, X 12 is selected from C(R 14 )(R 15 ) and Si(R 14 )(R 15 ),
when X 12 is O or S, X 11 is selected from C(R 12 )(R 13 ) and Si(R 12 )(R 13 ),
X 21 and X 22 are each independently selected from a single bond, C(R 24 )(R 25 ), Si(R 24 )(R 25 ), N(R 24 ), O, and S,
X 23 is selected from a single bond, C(R 26 )(R 27 ), Si(R 26 )(R 27 ), N(R 26 ), O, and S, and X 24 is selected from a single bond, C(R 28 )(R 29 ), Si(R 28 )(R 29 ), N(R 28 ), O, and S, provided that X 23 and X 24 are not each a single bond at the same time,
A 21 to A 25 are each independently selected from a C 5 -C 30 carbocyclic group and a C 1 -C 30 heterocyclic group,
L 21 is selected from a single bond, a substituted or unsubstituted C 5 -C 60 carbocyclic group, and a substituted or unsubstituted C 1 -C 60 heterocyclic group,
a21 is an integer from 1 to 5,
R 1 to R 3 are each independently selected from a group represented by Formula 2A, a group represented by Formula 2B, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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 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 C 1 -C 60 heteroaryloxy group, a substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), and —P(═O)(Q 1 )(Q 2 ), provided that at least one selected from R 1 to R 3 is selected from the group represented by Formula 2A and the group represented by Formula 2B,
R 4 to R 15 and R 21 to R 29 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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 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 C 1 -C 60 heteroaryloxy group, a substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), and —P(═O)(Q 1 )(Q 2 ),
two adjacent groups selected from R 1 to R 6 and R 9 to R 15 and/or two adjacent groups selected from R 21 to R 29 are optionally bound to form a saturated ring or an unsaturated ring,
b21 to b23 are each independently an integer from 1 to 10,
provided that in Formula 1, i) when X 11 is C(R 12 )(R 13 ), X 12 is C(R 14 )(R 15 ), O, or S, and R 12 and R 13 and/or R 14 and R 15 are not bound to each other, or ii) when X 11 is C(R 12 )(R 13 ), O, or S, X 12 is C(R 14 )(R 15 ), and R 12 and R 13 and/or R 14 and R 15 are not bound to each other, R 1 to R 3 does not comprise a group represented by Formula 2A-a:

wherein in Formula 2A-a, X 201 is a single bond, C(R 24 )(R 25 ), N(R 24 ), O, or S, R 24 and R 25 are not bound, and
at least one substituent of the substituted C 5 -C 60 carbocyclic group, the substituted C 1 -C 60 heterocyclic group, the substituted C 1 -C 60 alkyl group, the substituted C 2 -C 60 alkenyl group, the substituted C 2 -C 60 alkynyl group, the substituted C 1 -C 60 alkoxy group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 1 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 1 -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 1 -C 60 heteroaryl group, the substituted C 1 -C 60 heteroaryloxy group, the substituted C 1 -C 60 heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 11 )(Q 12 ), —B(Q 11 )(Q 12 ), —C(═O)(Q 11 ), —S(═O) 2 (Q 11 ), and —P(═O)(Q 11 )(Q 12 );
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 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic 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 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycycli

Assignees

• Samsung Display Co Ltd

Inventors

• Kim Sehun
• Lyu Jaejin

Classifications

• H10K85/658 Primary

  Organoboranes · CPC title

• C07F5/02 Primary

  Boron compounds · CPC title

• C07F5/027 Primary

  Organoboranes and organoborohydrides · CPC title

• C07F7/0816

  said ring comprising Si as a ring atom · CPC title

• C09K2211/1096

  containing other heteroatoms · CPC title