Organic light-emitting diode

Patent metadata

Field	Value
Publication number	US-9520568-B2
Application number	US-201314077506-A
Country	US
Kind code	B2
Filing date	Nov 12, 2013
Priority date	May 23, 2013
Publication date	Dec 13, 2016
Grant date	Dec 13, 2016

Abstract

An organic light-emitting diode including a substrate; a first electrode on the substrate; a second electrode facing the first electrode; and an emission layer between the first electrode and the second electrode, the emission layer including an anthracene-based compound represented by Formula 1, below, and a condensed ring compound represented by Formula 20, below:

First claim

What is claimed is:

1. An organic light-emitting diode, comprising:
a substrate;
a first electrode on the substrate;
a second electrode facing the first electrode; and
an emission layer between the first electrode and the second electrode, the emission layer including an anthracene-based compound represented by Formula 1, below, and a condensed ring compound represented by Formula 20, below:

wherein, in Formulae 1 and 20:
n is 0 or 1;
R 1 to R 6 are each independently selected from a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted non-condensed ring group in which a number of ring forming atoms is in a range of 3 to 10, and a substituted or unsubstituted condensed ring group in which two or more rings are condensed, and when n is 0, at least one of R 1 to R 3 is a substituted or unsubstituted condensed ring group in which two or more rings are condensed, and when n is 1, at least one of R 1 to R 6 is a substituted or unsubstituted condensed ring group in which two or more rings are condensed;
L 1 , L 2 , Ar 1 , and Ar 2 are each independently selected from a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a substituted or unsubstituted C 3 -C 10 heterocycloalkylene group, a substituted or unsubstituted C 3 -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;
c and d are each independently an integer of 1 to 3;
R 11 , R 12 , R 43 , and R 44 are each 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 group, a hydrazone group, a carboxyl group 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 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 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 3 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -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 ), wherein Q 1 to Q 5 are each independently a hydrogen atom, a C 1 -C 10 alkyl group, a C 6 -C 20 aryl group, or a C 2 -C 20 heteroaryl group;
a and b are each independently an integer of 1 to 4;
R 41 and R 42 are each 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 group, a hydrazone group, a carboxyl group 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 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 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 3 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -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, and a substituted or unsubstituted C 2 -C 60 heteroaryl group;
i and j are each independently an integer of 0 to 3; and
Ar 3 and Ar 4 are each independently represented by one of Formulae 7B, 7D, or 7F below:

in Formulae 7B, 7D, and 7F,
Z 31 to Z 44 are each 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 group, a hydrazone group, a carboxyl group 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 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 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 3 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -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 51 )(Q 52 ), and —Si(Q 53 )(Q 54 )(Q 55 ), wherein Q 51 to Q 55 are each independently a hydrogen atom, a C 1 -C 10 alkyl group, a C 6 -C 20 aryl group, or a C 2 -C 20 heteroaryl group, and two or more of Z 31 to Z 44 are bindable to each other to selectively form a saturated or unsaturated ring having 6 to 20 carton atoms;
w1 is an integer of 1 to 4; and
w2 is an integer of 1 to 5.

2. The organic light-emitting diode as claimed in claim 1 , wherein a weight ratio of the anthracene-based compound to the condensed ring compound in the emission layer is in a range of about 99.9:0.01 to 80:20.

3. The organic light-emitting diode as claimed in claim 1 , wherein:
R 1 to R 6 in Formula 1 are each independently selected from:
a C 1 -C 20 alkyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclopentenyl group, a cyclopentadienyl group, a cyclohexenyl group, a cyclohexadienyl group, a cycloheptadienyl group, a thiophenyl group, a furanyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, an isothiazolyl group, an isoxazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a triazolyl group, a phenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, a biphenylenyl group, an indacenyl group, an acenaphthylenyl group, a fluorenyl group, a spiro-fluorenyl group, a carbazolyl group, an anthracenyl group, a phenalenyl group, a phenanthrenyl group, a perylenyl group, a fluorantenyl group, a naphthacenyl group, a pycenyl group, a pentaphenyl group, a hexacenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a phenothiazinyl group, a phenoxazinyl group, a dihydrophenazinyl group, a phenoxathiinyl group, and a phenanthridinyl group; and
a C 1 -C 20 alkyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclopentenyl group, a cyclopentadienyl group, a cyclohexenyl group, a cyclohexadienyl group, a cycloheptadienyl group, a thiophenyl group, a furanyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, an isothiazolyl group, an i

Assignees

• Samsung Display Co Ltd
• Industry-Academic Coop Found Gyeongsang Nat Univ

Inventors

• Kim Se-Hun
• Kim Dong-Hyun
• Cho Hwan-Hee
• Kim Mi-Kyung
• Chu Chang-Woong
• Lee Yun-Ji
• Kim Yun-Hi
• Kwon Soon-Ki

Classifications

• H01L51/0052

  Electricity · mapped topic

• H01L51/0094

  Electricity · mapped topic

• H01L51/006

  Electricity · mapped topic

• H01L51/0072

  Electricity · mapped topic

• H01L51/5012

  Electricity · mapped topic