Organic Light-Emitting Diode With High Efficiency And Long Lifetime

Patent metadata

Field	Value
Publication number	US-2016204355-A1
Application number	US-201514981659-A
Country	US
Kind code	A1
Filing date	Dec 28, 2015
Priority date	Jan 13, 2015
Publication date	Jul 14, 2016
Grant date	—

Abstract

An organic light-emitting diode with high efficiency and long lifetime includes a first electrode, a second electrode facing the first electrode and an emissive layer between the first electrode and the second electrode, wherein the emissive layer includes a luminescent material that allows for the emission of deep blue light at high efficiency with a long lifetime.

First claim

What is claimed is:

1 . An organic light-emitting diode, comprising:
a first electrode; a second electrode facing the first electrode; and an emissive layer intercalated between the first electrode and the second electrode, wherein the emissive layer comprises at least one of the amine compounds represented by the following Chemical Formula A, and emits light with a color coordinate CIEy on a chromaticity diagram of 0.1 or less:

wherein Q 1 is

Q 2 is

A 1 , A 2 , E, and F may be the same or different, and are each independently a substituted or unsubstituted aromatic hydrocarbon ring of 6 to 50 carbon atoms, or a substituted or unsubstituted heteroaromatic ring of 2 to 40 carbon atoms wherein two adjacent carbon atoms of the aromatic ring A 1 and two adjacent carbon atoms of the aromatic ring A 2 form a 5-membered fused ring together with a carbon atom to which substitutents R 1 and R 2 are bonded;
linkers L 1 to L 12 may be the same or different, and are each independently selected from among a direct bond, a substituted or unsubstituted alkylene of 1 to 60 carbon atoms, a substituted or unsubstituted alkenylene of 2 to 60 carbon atoms, a substituted or unsubstituted alkynylene of 2 to 60 carbon atoms, a substituted or unsubstituted cycloalkylene of 3 to 60 carbon atoms, a substituted or unsubstituted heterocycloalkylene of 2 to 60 carbon atoms, a substituted or unsubstituted arylene of 6 to 60 carbon atoms, and a substituted or unsubstituted heteroarylene of 2 to 60 carbon atoms;
M is any one selected from among N—R 3 , CR 4 R 5 , SiR 6 R 7 , GeR 8 R 9 , O, S, and Se;
R 1 to R 9 , and Ar 1 to Ar 8 may be the same or different, and are each independently any one selected from among hydrogen, deuterium, a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted aryl of 6 to 50 carbon atoms, a substituted or unsubstituted alkenyl of 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl of 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl of 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl of 5 to 30 carbon atoms, a substituted or unsubstituted heteroaryl of to 50 carbon atoms, a substituted or unsubstituted heterocycloalkyl of 2 to 30 carbon atoms, a substituted or unsubstituted alkoxy of 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy of 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy of 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy of 6 to 30 carbon atoms, a substituted or unsubstituted alkylamine of 1 to 30 carbon atoms, a substituted or unsubstituted arylamine of 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl of 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl of 6 to 30 carbon atoms, a substituted or unsubstituted alkylgermanium of 1 to 30 carbon atoms, a substituted or unsubstituted arylgermanium of 6 to 30 carbon atoms, a cyano, a nitro, and a halogen, with a proviso that R 1 and R 2 together may form a mono- or polycyclic aliphatic or aromatic ring that may be a heterocyclic ring with a heteroatom selected from among N, O, P, Si, S, Ge, Se, and Te as a ring member;
p1 to p4, r1 to r4, and s1 to s4 are each independently an integer of 1 to 3, with a proviso that when any of them is 2 or greater, the corresponding linkers may be the same or different,
x is an integer of 1 or 2, and y and z may be the same or different and are each independently an integer of 0 to 3; and
Ar 1 may form a ring with Ar 2 , Ar 3 may form a ring with Ar 4 , Ar 5 may form a ring with Ar 6 , and Ar 7 may form a ring with Ar 8 ,
two adjacent carbon atoms of the A 1 ring occupy respective positions * of Q 2 to form a fused ring, and two adjacent carbon atoms of the A 2 ring occupy respective positions * of Q 1 to form a fused ring,
the term ‘substituted’ in the expression ‘substituted or unsubstituted’ is to have a substituent selected from the group consisting of deuterium, cyano, halogen, hydroxy, nitro, alkyl of 1 to 24 carbon atoms, halogenated alkyl of 1 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms, alkynyl of 2 to 24 carbon atoms, heteroalkyl of 1 to 24 carbon atoms, aryl of 6 to 24 carbon atoms, arylalkyl of 7 to 24 carbon atoms, heteroaryl of 2 to 24 carbon atoms or heteroarylalkyl of 2 to 24 carbon atoms, alkoxy of 1 to 24 carbon atoms, alkylamino of 1 to 24 carbon atoms, arylamino of 6 to 24 carbon atoms, hetero arylamino of 1 to 24 carbon atoms, alkylsilyl of 1 to 24 carbon atoms, arylsilyl of 6 to 24 carbon atoms, and aryloxy of 6 to 24 carbon atoms.

2 . The organic light-emitting diode of claim 1 , wherein the emissive layer comprises a host and a dopant, and the amine compound of Chemical Formula A serves as the dopant.

3 . The organic light-emitting diode of claim 2 , wherein the emissive layer includes as a host an anthracene derivative represented by the following Chemical Formula B:

wherein R 11 to R 18 may be the same or different, and are the same as above defined for R 1 to R 9 ;
Ar 9 , and Ar 10 may be the same or different and are each independently any one selected from among hydrogen, deuterium, a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted aryl of 6 to 50 carbon atoms, a substituted or unsubstituted alkenyl of 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl of 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl of 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl of 5 to 30 carbon atoms, a substituted or unsubstituted heteroaryl of 2 to 50 carbon atoms, a substituted or unsubstituted heterocycloalkyl of 2 to 30 carbon atoms, a substituted or unsubstituted alkoxy of 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy of 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy of 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy of 6 to 30 carbon atoms, a substituted or unsubstituted alkylamine of 1 to 30 carbon atoms, a substituted or unsubstituted arylamine of 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl of 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl of 6 to 30 carbon atoms;
L 13 represents a direct bond, or is a substituted or unsubstituted arylene of 6 to 20 carbon atoms or a substituted or unsubstituted heteroarylene of 2 to 20 carbon atoms; and
k is an integer of 1 to 3, with a proviso that when k is 2 or greater, the corresponding linkers L 13 may be the same or different.

4 . The organic light-emitting diode of claim 1 , wherein A d , A 2 , E, and F of Chemical Formula A may be identical or different, and are each independently a substituted or unsubstituted aromatic hydrocarbon ring of 6 to 50 carbon atoms.

5 . The organic light-emitting diode of claim 4 , wherein the substituted or unsubstituted aromatic hydrocarbon ring of 6 to 50 carbon atoms is selected from among compounds represented by Structural Formula 10 to Structural Formula 21:

wherein, “-*” for moiety A 1 or A 2 denotes a bonding site for forming a 5-membered ring containing the c

Assignees

• Sfc Co Ltd

Inventors

• Kim Hee-Dae
• Park Seok-Bae
• Shin Yoona
• Park Sang-Woo
• Cha Soon-Wook

Classifications

• H10K85/636

  comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• H01L27/3244

  Electricity · mapped topic

• H01L51/0073

  Electricity · mapped topic

• H01L51/0072

  Electricity · mapped topic