Organic light emitting device and manufacturing method thereof

Patent metadata

Field	Value
Publication number	US-10008685-B2
Application number	US-201514812493-A
Country	US
Kind code	B2
Filing date	Jul 29, 2015
Priority date	Jul 30, 2014
Publication date	Jun 26, 2018
Grant date	Jun 26, 2018

Abstract

An organic light emitting device includes an anode, the anode including a conductive polymer, a fluorine-containing organic material, and metal nanoparticles, a cathode facing the anode, and an emission layer between the anode and the cathode.

First claim

What is claimed is:

1. An organic light emitting device, comprising:
an anode, the anode including a conductive polymer, a fluorine-containing organic material, and metal nanoparticles;
a cathode facing the anode; and
an emission layer between the anode and the cathode, wherein:
concentration of the fluorine-containing organic material in the anode increases toward the emission layer.

2. The organic light emitting device as claimed in claim 1 , wherein the fluorine-containing organic material includes a moiety represented by the following Formula 1:

wherein:
a is a number from 0 to 10,000,000;
b is a number from 1 to 10,000,000;
Q 1 is [O—C(R 1 )(R 2 )—C(R 3 )(R 4 )] c —[OCF 2 CF 2 ] d —R 5 , —COOH, or —O—R f —R 6 ;
R 1 , R 2 , R 3 , and R 4 are independently —F, —CF 3 , —CHF 2 , or —CH 2 F;
c and d are independently a number from 0 to 20;
R f , is —(CF 2 ) z — (where z is an integer from 1 to 50) or —(CF 2 CF 2 O) z —CF 2 CF 2 — (where z is an integer from 1 to 50);
R 5 and R 6 are independently —SO 3 M, —PO 3 M, or —CO 2 M; and
M represents Na + , K + , Li + , H + , CH 3 (CH 2 ) w NH 3 + (where w is an integer from 0 to 50), NH 4 + , NH 2 + , NHSO 2 CF 3 + , CHO + , C 2 H 5 OH + , CH 3 OH + , or CH 3 (CH 2 ) w CHO + (where w is an integer from 0 to 50).

3. The organic light emitting device as claimed in claim 1 , wherein the fluorine-containing organic material includes a moiety represented by the following Formula 2:

wherein:
p is a number from 0 to 10,000,000;
q is a number from 1 to 10,000,000;
Q 2 is hydrogen, a substituted or unsubstituted C 6 -C 60 aryl group, or —COOH;
Q 3 is hydrogen, or a substituted or unsubstituted C 1 -C 20 alkyl group;
Q 4 is —O—(CF 2 ) r —SO 3 M, —O—(CF 2 ) r —PO 3 M 2 , —O—(CF 2 ) r —CO 2 M, or —CO—NH—(CH 2 ) s —(CF 2 ) t —CF 3 ;
r, s, and t are independently a number from 0 to 20; and
M represents Na + , K + , Li + , H + , CH 3 (CH 2 ) w NH 3 + (where w is an integer from 0 to 50), NH 4 + , NH 2 + , NHSO 2 CF 3 + , CHO + , C 2 H 5 OH + , CH 3 OH + , or CH 3 (CH 2 ) w CHO + (where w is an integer from 0 to 50).

4. The organic light emitting device as claimed in claim 1 , wherein the fluorine-containing organic material includes a moiety represented by the following Formula 3:

wherein:
m is a number from 0 to 10,000,000;
n is a number from 1 to 10,000,000;
x is a number from 0 to 20;
y is a number from 0 to 20;
Y is —SO 3 M, —PO 3 M, or —CO 2 M; and
M represents Na + , K + , Li + , H + , CH 3 (CH 2 ) w NH 3 + (where w is an integer from 0 to 50), NH 4 + , NH 2 + , NHSO 2 CF 3 + , CHO + , C 2 H 5 OH + , CH 3 OH + , or CH 3 (CH 2 ) w CHO + (where w is an integer from 0 to 50).

5. The organic light emitting device as claimed in claim 1 , wherein the fluorine-containing organic material is represented by the following Formula 4:
X-M f n -M h m -M a r -(G) p   [Formula 4]

wherein:
X is a terminal group;
M f represents a unit derived from a fluorinated monomer obtained through condensation reaction of perfluoropolyether alcohol, polyisocyanate, and isocyanate reactive-non-fluorinated monomer, or a fluorinated C 1-20 alkylene group;
M h represents a unit derived from a non-fluorinated monomer;
M a represents a unit having a silyl group represented by —Si(Y 4 )(Y 5 )(Y 6 );
Y 4 , Y 5 , and Y 6 are independently a halogen atom, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, or a hydrolysable substituent, at least one of Y 4 , Y 5 , and Y 6 being the hydrolysable substituent;
G is an organic group including a chain transfer agent residue;
n is a number from 1 to 100;
m is a number from 1 to 100;
r is a number from 1 to 100; and
p is a number from 0 to 10.

6. The organic light emitting device as claimed in claim 1 , wherein the conductive polymer includes one or more of polythiophene, polyaniline, polypyrrole, polystyrene, sulfonated polystyrene, poly(3,4-ethylenedioxythiophene), a self-doping conductive polymer, a derivative thereof, or a combination thereof.

7. The organic light emitting device as claimed in claim 6 , wherein the metal nanoparticles are homogeneously dispersed in the anode.

8. The organic light emitting device as claimed in claim 6 , wherein the metal nanoparticles are provided to make contact with an interface of the anode far from the emission layer.

9. The organic light emitting device as claimed in claim 6 , wherein the metal nanoparticles include one or more of Au, Ag, Cu, Pt, Pd, Ru, or Re nanoparticles.

10. The organic light emitting device as claimed in claim 9 , wherein the metal nanoparticles have a size from about 5 to about 50 nm.

11. The organic light emitting device as claimed in claim 9 , wherein the metal nanoparticles have a sphere shape, a cube shape, a plate shape, or a cage shape.

12. The organic light emitting device as claimed in claim 1 , wherein the anode includes:
an electrode part including a transparent conductive material; and
a hole injection part provided between the electrode part and the emission layer.

13. The organic light emitting device as claimed in claim 12 , wherein the hole injection part includes the metal nanoparticles, the conductive polymer, and the fluorine-containing organic material.

14. The organic light emitting device as claimed in claim 13 , wherein the metal nanoparticles are homogeneously dispersed in the hole injection part.

15. The organic light emitting device as claimed in claim 13 , wherein the metal nanoparticles are provided at an interface of the hole injection part adjacent to the anode.

16. A manufacturing method of an organic light emitting device, the method comprising:
forming an anode including metal nanoparticles, a conductive polymer, and a fluorine-containing organic material on a substrate;
forming an emission layer on the anode; and
forming a cathode on the emission layer, wherein:
the forming of the anode includes:
applying a mixture solution that includes the metal nanoparticles, the conductive polymer, and the fluorine-containing organic material on the substrate; and conducting micro-phase separation of the conductive polymer and the fluorine-containing organic material, or
applying the metal nanoparticles on the substrate; applying a mixture solution that includes the conductive polymer, and the fluorine-containing organic material on the substrate; and conducting micro-phase separation of the conductive polymer and the fluorine-containing organic material.

Assignees

• Samsung Display Co Ltd
• Postech Acad Ind Found
• Samsung Dispaly Co Ltd

Inventors

• Lee Tae-Woo
• Jeong Su-Hun
• Lee Kwanhee
• Song Wonjun

Classifications

• H01L2251/5369

  Electricity · mapped topic

• H01L51/0037

  Electricity · mapped topic

• H01L2251/5346

  Electricity · mapped topic

• H01L51/5206 Primary

  Electricity · mapped topic

• H10K59/8051

  Anodes · CPC title