Organic light-emitting diode

Patent metadata

Field	Value
Publication number	US-9590184-B2
Application number	US-201314021022-A
Country	US
Kind code	B2
Filing date	Sep 9, 2013
Priority date	Dec 27, 2012
Publication date	Mar 7, 2017
Grant date	Mar 7, 2017

Abstract

An organic light-emitting diode (OLED) is provided. The OLED comprises a substrate, a first electrode on the substrate, a second electrode disposed opposite to the first electrode, an emission layer disposed between the first electrode and the second electrode, a hole migration region disposed between the first electrode and the emission layer, and an electron migration region disposed between the emission layer and the second electrode. The hole migration region comprises a tertiary amine having one N-substituent comprising a substituted or unsubstituted carbazole moiety and another N-substituent comprising a substituted or unsubstituted fluorene moiety. At least one of the hole migration region and the emission layer comprises a substituted or unsubstituted compound comprising at least two carbazole moieties.

First claim

What is claimed is:

1. An organic light-emitting diode comprising:
a substrate; a first electrode on the substrate; a second electrode disposed opposite to the first electrode; an emission layer disposed between the first electrode and the second electrode; a hole migration region disposed between the first electrode and the emission layer; and an electron migration region disposed between the emission layer and the second electrode,
the hole migration region comprising a first compound represented by Formula 1 below, at least one of the hole migration region and the emission layer comprising a second compound represented by Formula 2 below:

Ar 101 , Ar 102 , Ar 1 , and Ar 2 in Formulae 1 and 2 each being independently selected from a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 2 -C 10 heterocycloalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a substituted or unsubstituted C 2 -C 10 heterocycloalkenylene group, a substituted or unsubstituted C 6 -C 60 arylene group, and a substituted or unsubstituted C 2 -C 60 heteroarylene group;
xa, xb, a, and b in Formulae 1 and 2 each being independently an integer from 0 to 5;
R 101 , R 109 , R 1 , and R 2 in Formulae 1 and 2 each being independently selected from 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, and a substituted or unsubstituted C 2 -C 60 heteroaryl group;
R 102 to R 108 , R 111 to R 119 , and R 11 to R 14 in Formulae 1 and 2 each being independently selected from: a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl 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 60 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 2 -C 60 heteroaryl group, —N(Q 1 )(Q 2 ), and —Si(Q 3 )(Q 4 )(Q 5 ) (where Q 1 to Q 5 are each independently one of a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a C 6 -C 60 aryl group, and a C 2 -C 60 heteroaryl group);
c1 and c4 in Formula 2 each being independently an integer from 1 to 4; and
c2 and c3 in Formula 2 each being independently an integer from 1 to 3.

2. The organic light-emitting diode of claim 1 , Ar 101 , Ar 102 , Ar 1 , and Ar 2 in Formulae 1 and 2 each being independently a group represented by one of Formulae 3-1 to 3-24 below:

Y 1 in Formulae 3-3 and 3-4 being one of O, S, C(R 21 )(R 22 ) and N(R 23 );
Z 1 , Z 2 , and R 21 to R 23 in Formula 3-1 to 3-24 each being independently selected from among:
a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl 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, and a C 1 -C 20 alkoxy group;
a C 1 -C 20 alkyl group and a C 1 -C 20 alkoxy group, substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof;
a C 6 -C 20 aryl group and a C 2 -C 20 heteroaryl group;
a C 6 -C 20 aryl group and a C 2 -C 20 heteroaryl group, substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl 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 phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, and an isoquinolyl group; and
—N(Q 11 )(Q 12 ) and —Si(Q 13 )(Q 14 )(Q 15 ) (where Q 11 to Q 15 are each independently one of a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a C 6 -C 20 aryl group and a C 2 -C 20 heteroaryl group);
d1 in Formula 3-1 to 3-24 being an integer from 1 to 4;
d2 in Formula 3-1 to 3-24 being an integer from 1 to 3;
d3 in Formula 3-1 to 3-24 being an integer from 1 to 6;
d4 in Formula 3-1 to 3-24 being an integer from 1 to 8; and
d5 in Formula 3-1 to 3-24 being an integer of 1 or 2.

3. The organic light-emitting diode of claim 2 , Z 1 , Z 2 , and R 21 to R 23 each being independently selected from among:
a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl 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, and a C 1 -C 20 alkoxy group;
a C 1 -C 20 alkyl group, and a C 1 -C 20 alkoxy group, substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, and a phoshoric acid group or a salt thereof;
a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a carbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, and an isoquinolyl group;
a phenyl group, a naphthyl group, an anthryl group, a fluorenyl group, a carbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, and an isoquinolyl group, substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl 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, an anthryl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridinyl group, a pyrimidiny

Assignees

• Samsung Display Co Ltd

Inventors

• Lee Sun-Young
• Kwak Yoon-Hyun
• Park Bum-Woo
• Choi Jong-Won
• Choi Wha-Ii
• Kim So-Yeon
• Lee Ji-Youn

Classifications

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C09K2211/1059

  containing three nitrogen atoms as heteroatoms · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C09K2211/1022

  bridged by heteroatoms, e.g. N, P, Si or B · CPC title