Preparation of conjugated dimer and products formed therefrom

Patent metadata

Field	Value
Publication number	US-9928964-B1
Application number	US-201414470319-A
Country	US
Kind code	B1
Filing date	Aug 27, 2014
Priority date	Aug 28, 2013
Publication date	Mar 27, 2018
Grant date	Mar 27, 2018

Abstract

An improved process for forming a conjugated thiophene precursor is described as in the formation of an improved polymer prepared from the conjugated thiophene and an improved capacitor formed from the improved polymer. The improved process includes forming a thiophene mixture comprising thiophene monomer, unconjugated thiophene oligomer, optionally a solvent and heating the thiophene mixture at a temperature of at least 100° C. to no more than the lower of 250° C. or the boiling point of a component of said thiophene mixture with the lowest boiling point temperature.

First claim

The invention claimed is:

1. A process for forming a capacitor comprising:
forming an anode with a dielectric on said anode;
forming a conjugated thiophene precursor comprising:
forming a thiophene mixture comprising thiophene monomer, unconjugated thiophene oligomer; and
heating said thiophene mixture at a temperature of at least 100° C. to no more than the lower of 250° C.;

forming a layer of a conductive polythiophene polymer of said conjugated thiophene precursor on said dielectric by in-situ polymerization.

2. The process for forming a capacitor of claim 1 wherein said thiophene monomer is defined by Formula I:

wherein R 1 and R 2 are independently α-directors; and
X is Sulphur.

3. The process for forming a capacitor of claim 2 wherein R 1 and R 2 independently represent hydrogen, linear or branched C 1 -C 16 alkyl or C 1 -C 18 alkoxyalkyl; C 3 -C 8 cycloalkyl; phenyl or benzyl which are unsubstituted or substituted by C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halogen or —OR 3 ; or R 1 and R 2 , taken together, are linear C 1 -C 6 alkylene which is unsubstituted or substituted by C 1 -C 5 alkyl, C 1 -C 6 alkoxy, halogen, C 3 -C 8 cycloalkyl, phenyl, benzyl, C 1 -C 4 alkylphenyl, C 1 -C 4 alkoxyphenyl, halophenyl, C 1 -C 4 alkylbenzyl, C 1 -C 4 alkoxybenzyl or halobenzyl, 5-, 6-, or 7-membered heterocyclic structure containing two oxygen elements; and
R 3 represents hydrogen, linear or branched C 1 -C 16 alkyl; C 1 -C 16 alkoxyalkyl; C 3 -C 8 cycloalkyl, phenyl; benzyl which are unsubstituted or substituted by C 1 -C 8 alkyl.

4. The process for forming a capacitor of claim 2 wherein R 1 and R 2 are not hydrogen.

5. The process for forming a capacitor of claim 2 wherein R 1 and R 2 are ether linkages.

6. The process for forming a capacitor of claim 2 wherein R 1 and R 2 are taken together as —O—(CH 2 ) 2 —O—.

7. The process for forming a capacitor of claim 1 wherein said unconjugated thiophene oligomer is defined by Formula III:

wherein:
X is an integer selected from 0-3;
R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are independently α-directors; and
Y is sulphur.

8. The process for forming a capacitor of claim 7 wherein X is 0 or 1.

9. The process for forming a capacitor of claim 7 wherein R 4 , R 5 , R 6 , R 7 , R 8 and R 9 independently represent hydrogen, linear or branched C 1 -C 16 alkyl or C 1 -C 18 alkoxyalkyl; C 3 -C 8 cycloalkyl, phenyl or benzyl which are unsubstituted or substituted by C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halogen or —OR 3 ; or R 4 and R 5 , R 6 and R 7 or R 8 and R 9 , taken together, are linear C 1 -C 6 alkylene which is unsubstituted or substituted by C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halogen, C 3 -C 8 cycloalkyl, phenyl, benzyl, C 1 -C 4 alkylphenyl, C 1 -C 4 alkoxyphenyl, halophenyl, C 1 -C 4 alkylbenzyl, C 1 -C 4 alkoxybenzyl or halobenzyl, 5-, 6-, or 7-membered heterocyclic structure containing two oxygen elements; and
R 3 represents hydrogen, linear or branched C 1 -C 16 alkyl; C 1 -C 18 alkoxyalkyl; C 3 -C 8 cycloalkyl, phenyl; benzyl which are unsubstituted or substituted by C 1 -C 6 alkyl.

10. The process for forming a capacitor of claim 7 wherein R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are not hydrogen.

11. The process for forming a capacitor of claim 7 wherein R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are ether linkages.

12. The process for forming a capacitor of claim 2 wherein R 4 and R 5 , R 6 and R 7 , and R 8 and R 9 are taken together as —O—(CH 2 ) 2 —O—.

13. The process for forming a capacitor of claim 1 wherein said thiophene mixture further comprises a solvent.

14. The process for forming a capacitor of claim 13 wherein said solvent is selected from the group consisting of alcohols, ketones, esters and ethers.

15. The process for forming a capacitor of claim 13 comprising 10-90% by weight solvent.

16. The process for forming a capacitor of claim 1 wherein said thiophene mixture comprising 75-99.9 wt % thiophene monomer and 0.1 to 25 wt % unconjugated thiophene oligomer.

17. The process for forming a capacitor of claim 16 wherein said thiophene mixture comprising 90-99.9 wt % thiophene monomer and 0.1 to 10 wt % unconjugated thiophene oligomer.

18. The process for forming a capacitor of claim 1 wherein said forming of said layer comprises dipping in a solution of said polymer of said conjugated thiophene precursor.

19. The process for forming a capacitor of claim 1 wherein said polymerizing is by electrochemical polymerization.

20. The process for forming a capacitor of claim 1 wherein said polymerizing is by chemical polymerization.

21. The process for forming a capacitor of claim 20 wherein said chemical polymerization is oxidative chemical polymerization.

22. The process for forming a capacitor of claim 1 wherein said anode comprises a conductor.

23. The process for forming a capacitor of claim 22 wherein said conductor comprises at least one material selected from niobium, aluminum, tantalum, titanium, zirconium, hafnium, tungsten and NbO.

24. The process for forming a capacitor of claim 23 wherein said anode comprises at least one material selected from niobium, tantalum and NbO.

Assignees

• Kemet Electronics Corp

Inventors

• Jin Yang
• Chen Qingping

Classifications

• C23C28/00 Primary

  Coating for obtaining at least two superposed coatings either by methods not provided for in a single one of groups C23C2/00 - C23C26/00 or by combinations of methods provided for in subclasses C23C and C25C or C25D · CPC title

• C07D409/14 Primary

  containing three or more hetero rings · CPC title

• C08G75/06

  from cyclic thioethers · CPC title

• C25B3/00

  Electrolytic production of organic compounds · CPC title

• H01G9/15

  Solid electrolytic capacitors (H01G11/00 takes precedence) · CPC title