Conductive thin film, method for producing same, and electronic element comprising same

Patent metadata

Field	Value
Publication number	US-9583725-B2
Application number	US-201414771479-A
Country	US
Kind code	B2
Filing date	Feb 21, 2014
Priority date	Feb 28, 2013
Publication date	Feb 28, 2017
Grant date	Feb 28, 2017

Abstract

Provided are a conductive thin film, a method for producing same, and an electronic element comprising same. The conductive thin film has excellent conductivity, allows the easy adjustment of a work function, also allows easy film formation, and thus can be advantageously used in various electronic elements, such as organic light-emitting devices and organic solar cells.

First claim

The invention claimed is:

1. A conductive thin film comprising a conductive layer and a surface energy-tuning layer,
wherein the conductive layer comprises a conductive polymer and a first fluorine-based material,
the surface energy-tuning layer comprises a second fluorine-based material but does not comprise the conductive polymer, and
the first fluorine-based material and the second fluorine-based material are the same or different from each other.

2. The conductive thin film of claim 1 , wherein the conductive polymer comprises polythiophene, polyaniline, polypyrrole, polystyrene, polyethylenedioxythiophene, polyacetylene, polyphenylene, polyphenylvinylene, polycarbazole, a copolymer comprising two or more different repeating units thereof, a derivative thereof, or a blend of two or more types thereof.

3. The conductive thin film of claim 1 , wherein the conductive polymer comprises a self-doped conductive polymer doped with one or more types of an ionic group and a polymeric acid,
the ionic group comprises an anionic group, and a cationic group disposed to counter the anionic group,
the anionic group is selected from the group consisting of PO 3 2− , SO 3 − , COO − , I − , CH 3 COO − , and BO 2 2− ,
the cationic group comprises one or more types among a metal ion and an organic ion,
the metal ion is selected from the group consisting of Na + , K + , Li + , Mg +2 , Zn +2 , and Al +3 , and
the organic ion is selected from the group consisting of H + , CH 3 (CH 2 ) n NH 3 + (n is an integer ranging from 0 to 50), NH 4 + , NH 2 + , NHSO 2 CF 3 + , CHO + , C 2 H 5 OH + , CH 3 OH + , and RCHO + (R is CH 3 (CH 2 ) n —; and n is an integer ranging from 0 to 50).

4. The conductive thin film of claim 1 , wherein the first fluorine-based material and the second fluorine-based material are each independently an ionomer represented by the following Formula 1:

wherein 0<m≦10,000,000, 0≦n<10,000,000, 0≦a≦20, and 0≦b≦20;
A, B, A′, and B′ are each independently selected from the group consisting of C, Si, Ge, Sn, and Pb;
R 1 , R 2 , R 3 , R 4 , R 1 ′, R 2 ′, R 3 ′, and R 4 ′ are each independently selected from the group consisting of hydrogen, a halogen, a nitro group, a substituted or unsubstituted amino group, a cyano group, a substituted or unsubstituted C 1 -C 30 alkyl group, a substituted or unsubstituted C 1 -C 30 heteroalkyl group, a substituted or unsubstituted C 1 -C 30 alkoxy group, a substituted or unsubstituted C 1 -C 30 heteroalkoxy group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 6 -C 30 arylalkyl group, a substituted or unsubstituted C 6 -C 30 aryloxy group, a substituted or unsubstituted C 2 -C 30 heteroaryl group, a substituted or unsubstituted C 2 -C 30 heteroarylalkyl group, a substituted or unsubstituted C 2 -C 30 heteroaryloxy group, a substituted or unsubstituted C 5 -C 20 cycloalkyl group, a substituted or unsubstituted C 2 -C 30 heterocycloalkyl group, a substituted or unsubstituted C 1 -C 30 alkylester group, a substituted or unsubstituted C 1 -C 30 heteroalkylester group, a substituted or unsubstituted C 6 -C 30 arylester group and, and a substituted or unsubstituted C 2 -C 30 heteroarylester group, provided that at least one of R 1 , R 2 , R 3 , and R 4 is an ionic group, or comprises the ionic group; and
X and X′ are each independently selected from the group consisting of a simple bond, O, S, a substituted or unsubstituted C 1 -C 30 alkylene group, a substituted or unsubstituted C 1 -C 30 heteroalkylene group, a substituted or unsubstituted C 6 -C 30 arylene group, a substituted or unsubstituted C 6 -C 30 arylalkylene group, a substituted or unsubstituted C 2 -C 30 heteroarylene group, a substituted or unsubstituted C 2 -C 30 heteroarylalkylene group, a substituted or unsubstituted C 5 -C 20 cycloalkylene group, a substituted or unsubstituted C 5 -C 30 heterocycloalkylene group, a substituted or unsubstituted C 6 -C 30 arylester group, and a substituted or unsubstituted C 2 -C 30 heteroarylester group,
provided that, when n is 0, at least one of R 1 , R 2 , R 3 , and R 4 is a hydrophobic functional group containing a halogen element, or comprises the hydrophobic functional group.

5. The conductive thin film of claim 4 , wherein the ionic group comprises an anionic group, and a cationic group disposed to counter the anionic group,
the anionic group is selected from the group consisting of PO 3 2− , SO 3 − , COO − , I − , CH 3 COO − , and BO 2 2− ,
the cationic group comprises one or more types among a metal ion and an organic ion,
the metal ion is selected from the group consisting of Na + , K + , Li + , Mg +2 , Zn −2 , and Al +3 , and
the organic ion is selected from the group consisting of H + , CH 3 (CH 2 ) n NH 3 + (n is an integer ranging from 0 to 50), NH 4 + , NH 2 + , NHSO 2 CF 3 + , CHO + , C 2 H 5 OH + , CH 3 OH + , and RCHO + (R is CH 3 (CH 2 ) n —; and n is an integer ranging from 0 to 50).

6. The conductive thin film of claim 4 , wherein the hydrophobic functional group is a halogen element.

7. The conductive thin film of claim 1 , wherein the first fluorine-based material and the second fluorine-based material are each independently an ionomer comprising one or more types among repeating units represented by the following Formulas 2 to 13:

wherein m is an integer ranging from 1 to 10,000,000, x and y are each independently an integer ranging from 0 to 10, and M + represents Na + , K + , Li + , H + , CH 3 (CH 2 ) n NH 3 + (n is an integer ranging from 0 to 50), NH 4 + , NH 2 + , NHSO 2 CF 3 + , CHO + , C 2 H 5 OH + , CH 3 OH + , or RCHO + (R is CH 3 (CH 2 ) n —; and n is an integer ranging from 0 to 50);

wherein m is an integer ranging from 1 to 10,000,000;

wherein m and n are 0<m≦10,000,000, and 0≦n<10,000,000, respectively, x and y are each independently an integer ranging from 0 to 20, and M + represents Na + , K + , Li + , H + , CH 3 (CH 2 ) n NH 3 + (n is an integer ranging from 0 to 50), NH 4 + , NH 2 + , NHSO 2 CF 3 + , CHO + , C 2 H 5 OH + , CH 3 OH + , or RCHO + (R is CH 3 (CH 2 ) n —; and n is an integer ranging from 0 to 50);

wherein m and n are 0<m≦10,000,000, and 0≦n<10,000,000, respectively, x and y are each independently an integer ranging from 0 to 20, and M + represents Na + , K + , Li + , H + , CH 3 (CH 2 ) n NH 3 + (n is an integer ranging from 0 to 50), NH 4 + , NH 2 + , NHSO 2 CF 3 + , CHO + , C 2 H 5 OH + , CH 3 OH + , or RCHO + (R is CH 3 (CH 2 ) n —; and n is an integer ranging from 0 to 50);

wherein m and n are 0<m≦10,000,000, and 0≦n<10,000,000, respectively, z is an integer ranging from 0 to 20, and M + represents Na + , K + , Li + , H + , CH 3 (CH 2 ) n NH 3 + (n is an integer ranging from 0 to 50), NH 4 + , NH 2 + , NHSO 2 CF 3 + , CHO + , C 2 H 5 OH + , CH 3 OH + , or RCHO + (R is CH 3 (CH 2 ) n —; and n is an integer ranging from 0 to 50);

wherein m and n are 0<m≦10,

Assignees

• Postech Academy-Industry Found

Inventors

• Lee Tae-Woo

Classifications

• H10K50/818

  Reflective anodes, e.g. ITO combined with thick metallic layers · CPC title

• H10K30/50

  Photovoltaic [PV] devices · CPC title

• Y02E10/549

  Organic PV cells · CPC title

• C08L101/12

  characterised by physical features, e.g. anisotropy, viscosity or electrical conductivity (liquid crystal materials or compositions C09K19/00) · CPC title

• H01L51/424

  Electricity · mapped topic