Organic light-emitting device

Patent metadata

Field	Value
Publication number	US-11411187-B2
Application number	US-201815870587-A
Country	US
Kind code	B2
Filing date	Jan 12, 2018
Priority date	Jul 19, 2017
Publication date	Aug 9, 2022
Grant date	Aug 9, 2022

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. The organic layer includes a first compound represented by Formula 1 and a second compound represented by Formula 2. The first compound may be included in an emission layer, and the second compound may be included in an electron transport region.

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, the organic layer comprising an emission layer,
wherein the organic layer comprises a first compound represented by Formula 1 and a second compound represented by Formula 2:

wherein, in Formula 1,
M is beryllium (Be), magnesium (Mg), aluminum (Al), calcium (Ca), titanium (Ti), manganese (Mn), cobalt (Co), copper (Cu), zinc (Zn), gallium (Ga), germanium (Ge), zirconium (Zr), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), rhenium (Re), platinum (Pt), or gold (Au),
X 1 is O or S, and a bond between X 1 and M is a covalent bond,
X 2 to X 4 are each independently N or C,
one bond selected from a bond between X 2 and M, a bond between X 3 and M, and a bond between X 4 and M is a covalent bond, and the others thereof are each a coordinate bond,
Y 1 to Y 9 are each independently C or N,
Y 10 and Y 11 are each independently C, N, O, or S,
a bond between Y 1 and Y 10 , a bond between Y 1 and Y 2 , a bond between X 2 and Y 3 , a bond between X 2 and Y 4 , a bond between Y 4 and Y 5 , a bond between Y 4 and Y 6 , a bond between X 3 and Y 7 , a bond between X 3 and Y 8 , a bond between X 4 and Y 9 , and a bond between X 4 and Y 11 are each independently a single bond or a double bond,
a bond between Y 2 and Y 3 , a bond between Y 6 and Y 7 , and a bond between Y 8 and Y 9 are each a single bond,
CY 1 , CY 2 , CY 3 , CY 4 , and CY 5 are each independently a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group,
CY 3 is a naphthalene group, and/or
CY 4 is an isoquinoline group,
CY 5 , CY 2 , CY 3 , and M form a 6-membered ring,
X 51 is selected from O, S, N-[(L 7 ) b7 -(R 7 ) c7 ], C(R 7 )(R 8 ), Si(R 7 )(R 8 ), and C(═O),
R 7 and R 8 are optionally linked via a 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,
L 1 to L 4 and L 7 are each independently a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,
b1 to b4 and b7 are each independently an integer from 0 to 5,
R 1 to R 4 , R 7 , and R 8 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, —SF 5 , 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 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 ), —B(Q 6 )(Q 7 ), and —P(═O)(Q 8 )(Q 9 ),
provided that at least one of R 1 to R 4 , R 7 , or R 8 is independently selected from SF 5 , a hydroxyl group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and —B(Q 6 )(Q 7 ),
c1 to c4 and c7 are each independently an integer from 1 to 5,
a1 to a4 are each independently 1, 2, 3, 4, or 5,
two neighboring R 1 (s) of a plurality of R 1 (s) 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,
two neighboring R 2 (s) of a plurality of R 2 (s) 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,
two neighboring R 3 (s) of a plurality of R 3 (s) 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,
two neighboring R 4 (s) of a plurality of R 4 (s) 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, and
two or more groups selected from R 1 to R 4 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,
wherein, in Formula 2,
X 11 is C(R 11 ) or N,
X 12 is C(R 12 ) or N,
X 13 is C(R 13 ) or N,
at least one of X 11 to X 13 is N,
L 11 to L 13 are each independently a substituted or unsubstituted C 5 -C 60 carbocyclic group or a substituted or unsubstituted C 2 -C 60 heterocyclic group,
m1 to m3 are each independently 0, 1, 2, 3, 4, or 5,
when m1 is two or more, two or more L 11 (s) are identical to or different from each other,
when m2 is two or more, two or more L 12 (s) are identical to or different from each other,
when m3 is two or more, two or more L 13 (s) are identical to or different from each other,
Ar 1 is selected from an unsubstituted C 10 -C 60 aryl group, a substituted C 6 -C 60 aryl group, a substituted or unsubstituted C 10 -C 60 aryloxy group, a substituted or unsubstituted C 10 -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,
Ar 2 and Ar 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 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 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)(Qi), —S(═O) 2 (Q 1 ), and —P(═O)(Q 1 )(Q 2 ),
n1 to n3 are each independently 1, 2, 3, 4, or 5,
when n1 is two or more, two or more Ar 1 (s) are identical to or different from each other,
when n2 i

Assignees

• Samsung Display Co Ltd

Inventors

• Bae Sung-Soo
• Kim Seul-Ong
• Kim Dong-Hyun
• Kim Sung-Wook
• Naijo Tsuyoshi
• Jeong Hye-In
• Cho Hwan-Hee

Classifications

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C09K2211/186

  of the light metals other than alkali metals and alkaline earth metals, i.e. Be, Al or Mg · CPC title

• C09K2211/182

  of the rare earth metals, i.e. Sc, Y or lanthanide · CPC title

• C09K2211/1059

  containing three nitrogen atoms as heteroatoms · CPC title