Organic light-emitting device

Patent metadata

Field	Value
Publication number	US-9882140-B2
Application number	US-201514710729-A
Country	US
Kind code	B2
Filing date	May 13, 2015
Priority date	Dec 2, 2014
Publication date	Jan 30, 2018
Grant date	Jan 30, 2018

Abstract

Provided is an organic light-emitting device including 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 emission layer includes a first compound represented by Formula 1-1 or Formula 1-2 below, a second compound represented by Formula 2 below, and a third compound represented by Formula 3 below:

where Ar1 to Ar8, R1 to R3, A, L1, L2, a1, a2, b1, b2, c1, c2, l1, and l2 are as defined in the specification.

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 including an emission layer,
wherein the emission layer includes a first compound represented by Formula 1-1 or Formula 1-2 below, a second compound represented by Formula 2 below, and a third compound represented by Formula 3 below:

wherein in Formulae 1-1 to 3,
L 1 and L 2 are each independently a substituted or unsubstituted C 6 -C 40 arylene group,
A is a substituted or unsubstituted C 6 -C 40 arylene group, a substituted or unsubstituted divalent C 6 -C 40 non-aromatic hetero condensed polycyclic group, or group made up of a substituted or unsubstituted C 6 -C 40 arylene group, or a substituted or unsubstituted divalent C 6 -C 40 non-aromatic hetero condensed polycyclic group combined with a styrylene group,
Ar 1 to Ar 8 are each independently a substituted or unsubstituted C 6 -C 40 aryl group,
R 1 to R 4 are each independently selected from a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 2 -C 20 alkenyl group, a substituted or unsubstituted C 2 -C 20 alkynyl group, a substituted or unsubstituted C 1 -C 20 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 40 aryl group, a substituted or unsubstituted C 1 -C 40 heteroaryl group, a substituted or unsubstituted C 5 -C 40 aryloxy group, a substituted or unsubstituted C 5 -C 40 arylthio group, a substituted or unsubstituted monovalent C 6 -C 40 non-aromatic condensed polycyclic group(non-aromatic condensed polycyclic group), a substituted or unsubstituted monovalent C 6 -C 40 non-aromatic hetero condensed polycyclic group(non-aromatic hetero condensed polycyclic group), —N(Q 1 )(Q 2 ), —P(═O)(Q 3 )(Q 4 ), —Si(Q 5 )(Q 6 )(Q 7 ), —Ge(Q 5 )(Q 6 )(Q 7 ), and —B(Q 8 )(Q 9 ), wherein Q 1 to Q 9 are each independently a hydrogen atom, a C 1 -C 20 alkyl group, or a C 6 -C 40 aryl group;
at least one substituent of the substituted C 1 -C 20 alkyl group, substituted C 2 -C 20 alkenyl group, substituted C 2 -C 20 alkynyl group, substituted C 1 -C 20 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 40 aryl group, substituted C 1 -C 40 heteroaryl group, substituted C 5 -C 40 aryloxy group, substituted C 5 -C 40 arylthio group, substituted monovalent C 6 -C 40 non-aromatic condensed polycyclic group, substituted monovalent C 6 -C 40 non-aromatic hetero condensed polycyclic group, and substituted C 6 -C 40 arylene group is selected from:
a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, a C 1 -C 20 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 40 aryl group, a C 1 -C 40 heteroaryl group, a C 5 -C 40 aryloxy group, a C 5 -C 40 arylthio group, monovalent C 6 -C 40 non-aromatic condensed polycyclic group, monovalent C 6 -C 40 non-aromatic hetero condensed polycyclic group, —N(Q 11 )(Q 12 ), —Si(Q 13 )(Q 14 )(Q 15 ), —Ge(Q 13 )(Q 14 )(Q 15 ), and B(Q 16 )(Q 17 ), wherein Q 11 to Q 17 are each independently selected from a hydrogen atom, a C 1 -C 20 alkyl group, and a C 6 -C 40 aryl group,
a1 and a2 are each independently an integer from 0 to 4;
b1 and b2 are each independently 1 or 2;
c1 and c2 are each independently an integer from 0 to 7; and
l1 and l2 are each independently an integer from 0 to 3.

2. The organic light-emitting device as claimed in claim 1 , wherein A is selected from the following substituents:
(1) a chrysenylene group, a pyrenylene group, a perylenylene group, a fluorenylene group, and a spiro-fluorenylene group;
(2) a chrysenylene group, a pyrenylene group, a perylenylene group, and a fluorenylene group, each substituted with at least one selected from a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a styryl group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, a C 1 -C 20 alkoxy group, a C 6 -C 40 aryl group, a C 1 -C 40 heteroaryl group, a C 5 -C 40 aryloxy group, a C 5 -C 40 arylthio group, a monovalent C 6 -C 40 non-aromatic condensed polycyclic group, a monovalent C 6 -C 40 non-aromatic hetero condensed polycyclic group, —N(Q 11 )(Q 12 ), —Si(Q 13 )(Q 14 )(Q 15 ), —Ge(Q 13 )(Q 14 )(Q 15 ), and —B(Q 16 )(Q 17 ), wherein Q 11 to Q 17 are each independently selected from a hydrogen atom, a C 1 -C 20 alkyl group, and a C 6 -C 40 aryl group; and
(3) a group made up of at least one styryl group combined with at least one substituent of the substituents (1) and (2).

3. The organic light-emitting device as claimed in claim 1 , wherein A is represented by any one of Formulae 4A to 4F below:

wherein Formulae 4A to 4F,
Z 11 to Z 14 are each independently selected from a deuterium atom, a halogen atom, a C 1 -C 20 alkyl group, a C 6 -C 40 aryl group, a monovalent C 6 -C 40 non-aromatic condensed polycyclic group, —Si(Q 13 )(Q 14 )(Q 15 ), and —Ge(Q 13 )(Q 14 )(Q 15 ), wherein Q 13 to Q 15 are each independently selected from a hydrogen atom, a C 1 -C 20 alkyl group, and a C 6 -C 40 aryl group;
a C 1 -C 20 alkyl group, substituted with at least one selected from a deuterium atom and a halogen atom; and
a C 6 -C 40 aryl group and a monovalent C 6 -C 40 non-aromatic condensed polycyclic group, each substituted with at least one selected from a deuterium atom, a halogen atom, a C 1 -C 20 alkyl group, and a C 6 -C 20 aryl group;
p1 is an integer from 0 to 5;
p2 is an integer from 0 to 4;
p3 is an integer from 0 to 6;
p4 is an integer from 0 to 3;
p5 is an integer from 0 to 8; and
* indicates a binding site to a neighboring atom.

4. The organic light-emitting device as claimed in claim 1 , wherein A is represented by any one of Formulae 5A to 5F below:

wherein in formulae 5A to 5F, * indicates a binding site to a neighboring atom.

5. The organic light-emitting device as claimed in claim 1 , wherein:
L 1 and L 2 are each independently selected from:
a phenylene group, a naphthylene group, a phenanth

Assignees

• Samsung Display Co Ltd

Inventors

• Han Kyul
• Ye Jimyoung
• Lee Bumsuk
• Yoon Jihwan
• Pyo Sangwoo

Classifications

• H01L51/0056

  Electricity · mapped topic

• H01L51/006

  Electricity · mapped topic

• H01L51/0058 Primary

  Electricity · mapped topic

• H01L51/0081

  Electricity · mapped topic

• H01L51/0055

  Electricity · mapped topic