IP Library › Granted Patent US 11,133,470
Granted Patent B2
US 11,133,470 · App. 15/048,488 · Granted Sep 28, 2021

Organic electroluminescent device

Inventors: Naotoshi Suganuma (Yokohama, JP); Hiroaki Itoi (Yokohama, JP); Masatsugu Ueno (Yokohama, JP)
Assignee: Samsung Display Co., Ltd.
H01L51/006H01L51/0059H01L51/0061H01L51/0072H01L51/0073H01L51/0081H01L51/5064
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Quick Facts
Patent No.
US 11,133,470
App. No.
15/048,488
Granted
Sep 28, 2021
Kind
B2
Abstract

An organic electroluminescent (EL) device having improved emission efficiency and emission lifetime. An embodiment of the organic EL device of the present disclosure includes a plurality of hole transport layers between an anode and an emission layer. The plurality of the hole transport layers may include an anode-side hole transport layer, a middle hole transport layer, and an emission layer-side hole transport layer. The emission layer-side hole transport layer may include an emission layer-side hole transport material represented by the following Formula 1:

Claims (23)

1. An organic electroluminescent device comprising:

an anode;

an emission layer;

an anode-side hole transport layer between the anode and the emission layer and directly adjacent to the anode, the anode-side hole transport layer comprising an anode-side hole transport material and an electron accepting material doped in the anode-side hole transport material;

a middle hole transport layer between the anode-side hole transport layer and the emission layer, the middle hole transport layer consisting of a middle hole transport material; and

an emission layer-side hole transport layer between the middle hole transport layer and the emission layer, the emission layer-side hole transport layer being directly adjacent to the emission layer,

wherein the middle hole transport layer is directly between the anode-side hole transport layer and the emission layer-side hole transport layer,

the emission layer-side hole transport layer consists of an emission layer-side hole transport material represented by at least one selected from Compounds 1-1 to 1-28,

the middle hole transport material is at least one selected from Compounds 2-1 to 2-17, and

the emission layer-side hole transport material is different from the middle hole transport material:

2. The organic electroluminescent device of claim 1 , wherein the electron accepting material has a lowest unoccupied molecular orbital (LUMO) energy level at about −9.0 eV to about −4.0 eV.

3. The organic electroluminescent device of claim 1 , wherein the electron accepting material is at least one selected from Compounds 4-1 to 4-14:

wherein R is selected from hydrogen, deuterium, a halogen atom, an alkyl fluoride having 1 to 50 carbon atoms, a cyano group, an alkoxy group having 1 to 50 carbon atoms, an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 carbon atoms for forming a ring, and a heteroaryl group having 5 to 50 carbon atoms for forming a ring,

X is one selected from the substituents represented by Formulae X1 to X7:

Y is selected from a methine group (—CH═) and nitrogen (—N═),

Z is selected from a pseudohalogen and sulfur,

Ar is selected from a substituted aryl group with an electron withdrawing group, an unsubstituted aryl group having 6 to 50 carbon atoms for forming a ring, and a substituted or unsubstituted heteroaryl group having 5 to 50 carbon atoms for forming a ring,

n is an integer selected from 0 to 10, and

in Formulae X1 to X7, Ra is selected from hydrogen, deuterium, a halogen atom, an alkyl fluoride having 1 to 50 carbon atoms, a cyano group, an alkoxy group having 1 to 50 carbon atoms, an alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms for forming a ring, and a substituted or unsubstituted heteroaryl group having 5 to 50 carbon atoms for forming a ring.

4. The organic electroluminescent device of claim 1 , wherein the anode-side hole transport material is at least one selected from Compounds 2-1 to 2-17:

5. The organic electroluminescent device of claim 1 , wherein the emission layer comprises a compound represented by Formula 3:

wherein each Ar 1 is independently selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms for forming a ring, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 carbon atoms for forming a ring, a substituted or unsubstituted arylthio group having 6 to 50 carbon atoms for forming a ring, a substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 5 to 50 carbon atoms for forming a ring, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group, and a hydroxyl group, and

n is an integer selected from 1 to 10.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 3, 2016
From: SUGANUMA, NAOTOSHI; ITOI, HIROAKI; UENO, MASATSUGU
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 038445/0986 →
Priority Claims (2)
JP JP2015-120441 · Jun 15, 2015 · national
JP JP2015-120442 · Jun 15, 2015 · national
Continuity (1)
Related Publication 20160365515A1 · Dec 15, 2016
Cited By (3)
US 12,268,092 US 12,559,674 US 12,635,332