Metathesis polymers as dielectrics

Patent metadata

Field	Value
Publication number	US-9786409-B2
Application number	US-201414392298-A
Country	US
Kind code	B2
Filing date	Jun 23, 2014
Priority date	Jun 27, 2013
Publication date	Oct 10, 2017
Grant date	Oct 10, 2017

Abstract

Oxacycloolefinic polymers as typically obtained by metathesis polymerization using Ru-catalysts, show good solubility and are well suitable as dielectric material in electronic devices such as capacitors and organic field effect transistors.

First claim

The invention claimed is:

1. An electronic device containing at least one dielectric material which comprises an oxacycloolefinic polymer, which comprises a polymer chain of the formula III

wherein n ranges from 3 to 100 000,
each of R 2 to R 5 is selected from hydrogen and C 1 -C 4 alkyl, and
R is hydrogen, C 1 -C 25 alkyl, C 1 -C 25 haloalkyl, phenyl, phenyl-C 1 -C 4 alkyl, cyclopentyl, or cyclohexyl, wherein phenyl moiety or cyclopentyl or cyclohexyl moiety itself is unsubstituted or substituted by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, OH, halogen.

2. The electronic device according to claim 1 , wherein the oxacycloolefinic polymer is prepared by Ru-carbene catalyzed ring-opening metathesis polymerization of a bicyclic oxaolefin.

3. The electronic device according to claim 1 , wherein the oxacycloolefinic polymer is present as a layer essentially consisting of the oxacycloolefinic polymer.

4. The electronic device according to claim 1 , wherein the oxacycloolefinic polymer has a glass transition temperature, as determined by differential scanning calorimetry, above 90° C.

5. The electronic device according to claim 1 , wherein the electronic device is selected from capacitors, transistors such as organic field effect transistors, and devices comprising said capacitor and/or transistor.

6. The electronic device according to claim 1 , further comprising a substrate and comprising at least one further layer of a functional material in direct contact with the oxacycloolefinic polymer dielectric.

7. The electronic device according to claim 6 , wherein a layer of the oxacycloolefinic polymer as a dielectric material is in direct contact with an electrode layer and/or a semiconductor layer.

8. The electronic device according to claim 6 , wherein a layer of the oxacycloolefinic polymer as a dielectric material is in direct contact with a semiconductor layer that comprises a copolymer of the diketopyrrolopyrrole class.

9. The electronic device according to claim 1 , wherein the dielectric material is a dielectric layer in a printed electronic device.

10. The electronic device according to claim 9 , wherein the printed electronic device is a capacitor or an organic field-effect transistor.

11. A process for the preparation of an electronic device according to claim 1 , the process comprising;
providing a solution or dispersion of the oxacycloolefinic polymer of formula III in a solvent, and
applying the solution or the dispersion in the form of a layer onto a substrate, an electrode material or a semiconductor, and
drying said layer.

12. The process according to claim 11 , wherein the solution or the dispersion includes at least 8% by weight of the oxacycloolefinic polymer in solution.

13. The electronic device according to claim 1 , wherein the oxacycloolefinic polymer has a molecular weight, as determined by gel permeation chromatography, in a range of 10,000 to 1,000,000 g/mol.

14. A gate insulator layer comprising an oxacycloolefinic polymer comprising a polymer chain of formula III

wherein n ranges from 3 to 100 000,
each of R 2 to R 5 is selected from hydrogen and C 1 -C 4 alkyl, and
R is hydrogen, C 1 -C 25 alkyl, C 1 -C 25 haloalkyl, phenyl, phenyl-C 1 -C 4 alkyl, cyclopentyl, or cyclohexyl, wherein phenyl moiety or cyclopentyl or cyclohexyl moiety itself is unsubstituted or substituted by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, OH, halogen.

Assignees

• Basf Se

Inventors

• Flores Jean-Charles
• Martin Emmanuel
• Bujard Patrice

Classifications

• H01B3/448 Primary

  from other vinyl compounds · CPC title

• H01L51/0096

  Electricity · mapped topic

• H01L51/0541

  Electricity · mapped topic

• C08F232/00

  Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system · CPC title

• C08G2261/3342

  derived from cycloolefins containing heteroatoms · CPC title