Organic light-emitting device

Patent metadata

Field	Value
Publication number	US-2016111663-A1
Application number	US-201514885913-A
Country	US
Kind code	A1
Filing date	Oct 16, 2015
Priority date	Oct 17, 2014
Publication date	Apr 21, 2016
Grant date	—

Abstract

An organic light-emitting device includes a first electrode; a second electrode facing the first electrode; an emission layer between the first electrode and the second electrode; and a hole transport region between the first electrode and the emission layer. The emission layer includes an organometallic compound represented by Formula 1, and the hole transport region includes a first compound represented by Formula 2.

First claim

What is claimed is:

1 . An organic light-emitting device comprising
a first electrode; a second electrode facing the first electrode; an emission layer between the first electrode and the second electrode; a hole transport region between the first electrode and the emission layer, wherein the emission layer comprises an organometallic compound represented by Formula 1, and the hole transport region comprises a first compound represented by Formula 2:
M(L1) n1 (L2) n2   Formula 1

wherein, in Formula 1, M is selected from iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), and rhodium (Rd); L1 is a ligand represented by Formula 1A; L2 is a ligand represented by Formula 1 B; L1 and L2 are different from each other; n1 and n2 are each independently 1 or 2, n1+n2=2 or n1+n2=3, when n1 is 2, two L1s are identical to or different from each other, and when n2 is 2, two L2s are identical to or different from each other;

wherein, in the formulae above,
CY 1 and CY 2 are each independently selected from a C 5 -C 60 cyclic group and a C 2 -C 60 heterocyclic group, wherein CY 1 and CY 2 are linked to each other by a single bond;
Y 1 to Y 4 are each independently carbon (C) or nitrogen (N), wherein Y 1 and Y 2 are linked to each other by a single bond or a double bond, and Y 3 and Y 4 are linked to each other by a single bond or a double bond;
CY 3 to CY 6 are each independently selected from a C 5 -C 40 cyclic group, a C 2 -C 40 heterocyclic group, and Formula 2-1;
in Formula 2-1, A 1 and A 2 are each independently selected from a C 5 -C 20 cyclic group and a C 2 -C 20 heterocyclic group;
X 1 is selected from N-(L 3 ) Ib3 -Ar 2 , oxygen atom (O), sulfur atom (S), C(R 13 )(R 14 ),
and Si(R 15 )(R 16 );
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 6 -C 60 arylene group, a substituted or unsubstituted C 1 -C 60 heteroarylene group, —N(Q 1a )-, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic;
Ar 1 and Ar 2 are each independently a substituted or unsubstituted C 6 -C 60 aryl group or a substituted or unsubstituted C 1 -C 60 heteroaryl group;
R 1 to R 5 , and R 9 to R 16 are each independently selected from a hydrogen atom, a deuterium atom, —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, 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 ),
R 6 to R 8 are each independently selected from:
a C 1 -C 10 alkyl group; and
a C 1 -C 10 alkyl group substituted with at least one selected from a deuterium atom, —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, and a phosphoric acid group or a salt thereof,
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 1 -C 10 heterocycloalkyl group, substituted C 3 -C 10 cycloalkenyl group, substituted C 1 -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 C 3 -C 10 cycloalkylene group, substituted C 6 -C 60 arylene group, substituted C 1 -C 60 heteroarylene group, substituted monovalent non-aromatic condensed polycyclic group, substituted monovalent non-aromatic condensed heteropolycyclic, substituted divalent non-aromatic condensed polycyclic group, and substituted divalent non-aromatic condensed heteropolycyclic is selected from:
a deuterium atom, —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 a deuterium atom, —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 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, —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 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 polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from a deuterium atom, —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 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

Assignees

• Samsung Display Co Ltd

Inventors

• Kim Myeong-Suk
• Kim Sung-Wook
• Cho Hwan-Hee
• Chu Chang-Woong
• Kim Youn-Sun
• Ito Naoyuki

Classifications

• H01L51/0054

  Electricity · mapped topic

• H01L51/0061

  Electricity · mapped topic

• H01L51/0094 Primary

  Electricity · mapped topic

• H01L51/5012

  Electricity · mapped topic

• H01L51/0058

  Electricity · mapped topic