IP Library Granted Patent US 10,283,715
Granted Patent B2
US 10,283,715 · App. 15/554,345 · Granted May 7, 2019

Conductive polymer in organic solvent with fluorinated compound

Inventors: Stefan Schumann (Köln, DE); Nina Kausch-Busies (Bergisch Gladbach, DE); Wilfried Lövenich (Bergisch-Gladbach, DE); Jan Sütterlin (Köln, DE); Andreas Elschner (Mülheim, DE); Arnulf Scheel (Köln, DE)
Assignee: HERAEUS DEUTSCHLAND GMBH & CO. KG
H01L51/0035B32B27/06B32B27/281B32B27/286B32B27/30B32B27/302B32B27/304B32B27/32B32B27/325B32B27/34B32B27/36B32B27/365C08L53/025C09D5/24C09D141/00H01L51/0037H01L51/0043H01L51/0094B32B2250/44B32B2255/10B32B2255/26B32B2307/202B32B2457/12B32B2457/20B32B2457/206B32B2457/208H01L51/5088Y02E10/549
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Quick Facts
Patent No.
US 10,283,715
App. No.
15/554,345
Granted
May 7, 2019
Kind
B2
Abstract

The present invention relates to a composition comprising: a) at least one organic solvent; b) at least one conductive polymer, preferably a cationic polymer; c) at least one fluorinated compound; d) at least one polymeric anion, wherein the at least one polymeric anion is a copolymer comprising ionic and non-ionic repeating units. The present invention also relates to a layered structure comprising the composition, to a process for the production of the composition, to a process for the production of the layered structure and to devices comprising the layered structure as well as to the use of the composition in devices to achieve a prolongation of lifetime.

Claims (40)

1. A composition comprising:

a) at least one organic solvent;

b) at least one conductive polymer;

c) at least one fluorinated compound, wherein the at least one fluorinated compound is a non-ionic compound;

d) at least one polymeric anion, wherein the at least one polymeric anion is a copolymer comprising ionic and non-ionic repeating units.

2. The composition according to claim 1 , wherein copolymer comprises polymerized styrene monomer units at least a part of which is sulfonated and polymerized non-sulfonated monomer units and wherein molar ratio of the non-sulfonated monomer units is at least 5%, based on the total amount of monomer units in the copolymer.

3. The composition according to claim 1 , wherein the copolymer is a hydrogenated styrene-isoprene block copolymer with the structure A-B-C-B-A, in which the block A corresponds to a polystyrene block which is at least partially substituted with tert-butyl groups, the block B corresponds to a block of alternating copolymerised ethylen-propylene units and the block C corresponds to a sulphonated polystyrene block.

4. The composition according to claim 1 , wherein the at least one organic solvent a) is selected from the group consisting of an aprotic, a polar, a non-polar and a non-polar, aprotic organic solvent or a mixture of at least two of these.

5. The composition according to claim 1 , wherein the composition comprises as the at least one fluorinated compound c) a compound comprising at least one aliphatic or aromatic residue in which at least 10% of the hydrogen atoms are substituted by fluorine atoms.

6. The composition according to claim 1 , wherein the composition comprises as the at least one fluorinated compound c) a fluorinated compound having a molecular weight of less than 2,100 g/mol.

7. The composition according to claim 1 , wherein the at least one fluorinated compound c) is a mono-, di- or trialkoxysilane, in which at least one fluorinated aliphatic or a fluorinated aromatic group is bond to the Si atom.

8. The composition according to claim 1 , wherein the at least one fluorinated compound c) is a polymeric fluorinated compound.

9. The composition according to claim 1 , wherein the at least one fluorinated compound c) has a vapor pressure of less than 40 mbar at 100° C. (determined at a pressure of 1 bar).

10. The composition according to claim 1 , wherein the at least one conductive polymer b) is a cationic polythiophene.

11. The composition according to claim 10 , wherein the cationic polythiophene and the at least one polymeric anion d) are present in the form of a polythiophene: polymeric anion-complex.

12. The composition according to claim 1 , wherein the composition comprises:

a) 70 to 99.5 wt.-% of the at least one organic solvent;

b) 0.05 to 4 wt.-% of the at least one conductive polymer;

c) 0.05 to 10 wt.-% of the at least one fluorinated compound;

d) 0.05 to 13 wt.-% of the at least one polymeric anion;

e) 0 to 6 wt.-% of at least one further additive;

wherein the sum of components a) to e) is 100 wt.-%.

13. The composition according to claim 1 , wherein the water content of the composition is not more than 2 wt.-%, based on the total weight of the composition.

14. A process for the production of a layered structure, comprising the process steps:

I) providing of a substrate with a first surface;

II) superimposing the substrate at least partially on its first surface with a composition according to claim 1 ;

III) at least partially removing the at least one organic solvent a) from the composition, thereby obtaining an electrically conductive layer superimposed on the substrate.

15. A layered structure obtainable by the process according to claim 14 .

16. A layered structure comprising the following layers:

i. a substrate with a first surface;

ii. a first layer superimposing at least a part of the substrate surface; wherein the first layer comprises:

a) at least one conductive polymer;

b) at least one fluorinated compound, wherein the at least one fluorinated compound is a non-ionic compound;

c) at least one polymeric anion, wherein the at least one polymeric anion is a copolymer comprising ionic and non-ionic repeating units.

17. The layered structure according to claim 16 , wherein

(i) the at least one conductive polymer is a cationic polythiophene;

(ii) the at least one fluorinated compound is a compound comprising at least one aliphatic or aromatic residue in which at least 10% of the hydrogen atoms are substituted by fluorine atoms; and

(iii) the at least one polymeric anion is a copolymer comprising polymerized styrene monomer units at least a part of which is sulfonated and polymerized non-sulfonated monomer units, and wherein the molar ratio of the non-sulfonated monomer units is at least 5%, based on the total amount of monomer units in the copolymer.

18. A device comprising a layered structure according to claim 16 .

19. The device according to claim 18 , wherein the device is selected from the group consisting of an OLED, a display, an organic solar cell, a hybrid solar cell, a field effect transistor, a touchscreen or a thermoelectric generator or a combination of at least two thereof.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 7, 2024
From: HERAEUS DEUTSCHLAND GMBH & CO. KG
To: HERAEUS EPURIO GMBH
Reel/Frame 067330/0850 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 29, 2017
From: SCHUMANN, STEFAN; KAUSCH-BUSIES, NINA; LÖVENICH, WILFRIED; SÜTTERLING, JAN; ELSCHNER, ANDREAS; SCHEEL, ARNULF
To: HERAEUS DEUTSCHLAND GMBH & CO. KG
Reel/Frame 044531/0415 →
Priority Claims (1)
EP 15158257 · Mar 9, 2015 · regional
Continuity (1)
Related Publication 20180182965A1 · Jun 28, 2018
Cited By (1)
US 12,500,039