Compound and organic light-emitting device including the same

Patent metadata

Field	Value
Publication number	US-11114622-B2
Application number	US-201615152540-A
Country	US
Kind code	B2
Filing date	May 11, 2016
Priority date	Oct 22, 2015
Publication date	Sep 7, 2021
Grant date	Sep 7, 2021

Abstract

An organic light-emitting device includes: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode, the organic layer including an emission layer, wherein the organic layer includes a compound of Formula 1:According to one or more embodiments of the present disclosure, due to the inclusion of the compound of Formula 1, characteristics of an organic light-emitting device may be improved.

First claim

What is claimed is:

1. A compound represented by Formula 1:

wherein, in Formula 1,
R 1 , R 12 , R 13 , and R 17 are each independently hydrogen or deuterium;
R 2 to R 11 and R 14 to R 16 are each independently selected from hydrogen, deuterium, halogen, an amino group, a nitro group, a nitrile group, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C2-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 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, provided that R 14 and R 16 are not both a substituted or unsubstituted C 1 -C 60 heteroaryl group at the same time;
wherein only one selected from R 5 to R 8 comprises a group represented by Formula 1-1:

wherein, in Formula 1-1, Ar 1 and Ar 2 are each independently selected from a group represented by one of Formulae 3a, 3b, and 3d to 3g, and Ar 1 and Ar 2 are not linked to each other to form a ring:

wherein, in Formulae 3a, 3b, and 3d to 3g,
H 1 in Formula 3g is selected from O, S, NR 21 , and CR 22 R 23 ;
R 21 to R 23 , and Z 1 are each independently selected from hydrogen, deuterium, halogen, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 1 -C 20 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and Si(Q 13 )(Q 14 )(Q 15 );
p in Formula 3a is an integer selected from 1 to 5, p in Formula 3b is an integer selected from 1 to 7, p in Formula 3d is an integer selected from 1 to 4 and p in Formulae 3e to 3g is an integer selected from 1 to 6,
wherein when p is 2 or more, 2 or more Z 1 (s) are identical to or different from each other; and
*indicates a binding site,
provided that when Ar 1 and Ar 2 are both represented by Formula 3a at the same time, at least one Z 1 is selected from deuterium, halogen, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and Si(Q 13 )(Q 14 )(Q 15 );
X 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; and
m is an integer selected from 0 to 5, and when m is 2 or more, 2 or more X(s) are identical to or different from each other;
wherein at least one substituent of the substituted C 1 -C 60 alkyl group, substituted C 2 -C 60 alkenyl group, substituted C 2 -C 60 alkynyl group, substituted C 1 -C 60 alkoxy group, substituted C 3 -C 10 cycloalkyl group, substituted C 2 -C 10 heterocycloalkyl group, substituted C 3 -C 10 cycloalkenyl group, substituted C 2 -C 10 heterocycloalkenyl group, substituted C 6 -C 60 aryl group, substituted C 6 -C 60 aryloxy group, substituted C 6 -C 60 arylthio group, substituted C 1 -C 60 heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group, substituted monovalent non-aromatic condensed heteropolycyclic group, substituted C 6 -C 60 arylene group, substituted C 1 -C 60 heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, and substituted divalent non-aromatic condensed heteropolycyclic group is selected from the group consisting of:
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 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 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 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -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, —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 2 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -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 2 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -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, 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 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -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, —N(Q 21 )(Q22), —Si(Q 23 )(Q 24 )(Q 25 ), and —B(Q 26 )(Q 27 ), and
Si(Q 13 )(Q 14 )(Q 15 ),
wherein Q 11 to Q 17 and Q 21 to Q 27 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 carb

Assignees

• Samsung Display Co Ltd

Inventors

• Kim Youngkook
• Kim Sooyon
• Kim Jongwoo
• Hwang Seokhwan
• Oh Jeonga

Classifications

• H10K85/631

  Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine · CPC title

• H10K50/15

  Hole transporting layers · CPC title

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• H10K85/6574

  comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes · CPC title

• H10K85/6576

  comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene · CPC title