Cross-linking moiety

Patent metadata

Field	Value
Publication number	US-9745252-B2
Application number	US-201013513702-A
Country	US
Kind code	B2
Filing date	Dec 6, 2010
Priority date	Dec 4, 2009
Publication date	Aug 29, 2017
Grant date	Aug 29, 2017

Abstract

A cross-linking moiety having a general formula I: Ar F -W, wherein Ar F comprises a fluorinated phenyl azide group having at least one non-fluorine substituent that is bulkier than fluorine at a meta position relative to the azide group, and W comprises an electron-withdrawing group.

First claim

The invention claimed is:

1. A cross-linking compound having a general formula II:
(Ar F -W) n -L  (II),

wherein:
n is an integer greater than or equal to 2;
each Ar F is the same or different and comprises a fluorinated phenyl azide group having at least one non-fluorine containing substituent that is bulkier than fluorine at a meta position relative to the azide group, the at least one non-fluorine containing substituent is selected from a group consisting of a substituted or unsubstituted: alkyl, cycloalkyl, alkoxy and cycloalkoxy groups;
W comprises an electron-withdrawing group; and
L comprises a linker group, wherein two or more units of (Ar F -W) are linked together by L, provided that the compound of general formula II is not ethylene bis(4-azido-2,3,5-trifluoro-6-isopropylbenzoate).

2. The cross-linking compound according to claim 1 , wherein the non-fluorine containing substituent is a substituted or unsubstituted alkyl group with an alkyl chain length of from 1 to 18 carbon atoms.

3. The cross-linking compound according to claim 1 , wherein the non-fluorine containing substituent is a substituted or unsubstituted alkyl group, where the alkyl group is a linear or branched alkyl group.

4. The cross-linking compound according to claim 1 , wherein the non-fluorine containing substituent is a substituted or unsubstituted alkyl group selected from the group consisting of methyl, ethyl, iso-propyl, secondary butyl, tertiary-butyl, hexyl, octyl, and branched derivatives thereof.

5. The cross-linking compound according to claim 1 , wherein W is in the para position relative to the azide group.

6. The cross-linking compound according to claim 1 , wherein W comprises a sulfonyl group or a carbonyl group.

7. The cross-linking compound according to claim 6 , wherein W comprises an electron-withdrawing group selected from the group consisting of: —CO—, —C(O)O—, —S(O 2 )O—, —C(O)N—, and —S(O 2 )N—.

8. The cross-linking compound according to claim 1 , wherein L comprises a divalent or multivalent linker group selected from the group consisting of substituted or unsubstituted: alkyldioxy, alkyltrioxy, alkyldiamide, alkyltriamide and dialkyltrioxy.

9. The cross-linking compound according to claim 8 , wherein L is selected from the group consisting of: ethylenedioxy, ethylenediamide, diethylenetrioxy and 1,3,5-trioxycyclohexane.

10. The cross-linking compound according to claim 1 , wherein the cross-linking compound is selected from the group consisting of:
ethylene bis(4-azido-2,3,5-trifluoro-6-methylbenzamide);
dodecylene bis(4.azido-2,3,5-trifluoro-6-methylbenzoate);
ethylene bis(4-azido-3,5-difluoro-2,6-diisopropylbenzoate);
ethylene bis(4-azido-3,5-difluoro-2,6-dihexylbenzoate);
diethyleneoxy bis (4-azido-3,5-difluoro-2,6-diisopropylbenzoate); diethyleneoxy bis(4-azido-2,3,5-trifluoro-6-isopropylbenzoate); and
diethyleneoxy bis(4-azido-3,5-difluoro-2,6-dihexylbenzoate).

11. The cross-linking compound according to claim 1 , wherein the cross-linking compound has a formula:
Ar F -W-L-W-Ar F .

12. A solution comprising the cross-linking compound moiety according to claim 1 .

13. The solution according to claim 12 , further comprising a polymer or oligomer.

14. The solution according to claim 13 , wherein the polymer or oligomer is a semiconductive polymer or oligomer.

15. A method of forming a polymer device comprising the steps of:
(a) depositing a solution comprising a polymer or oligomer and a cross-linking compound according to claim 1 , on a substrate to form a layer; and
(b) curing the layer formed in (a) to form an insoluble cross-linked polymer.

16. The method according to claim 15 , wherein the cross-linking compound is sensitive to ultraviolet radiation having a wavelength in the range 200 nm to 400 nm and the curing comprises exposing the layer to UV radiation having a wavelength in the range 200 nm to 400 nm in an inert atmosphere.

17. The method according to claim 15 , wherein the cross-linked polymer is unconjugated, partially conjugated, substantially conjugated or fully conjugated.

18. The method according to claim 15 , further comprising annealing the cross-linked polymer.

19. The method according to claim 15 , wherein the polymer device is selected from the group consisting of: a polymer LED device, a polymer distributed Bragg reflector, a polymer FET device, a polymer photodetector and a polymer photovoltaic device.

20. The method according to claim 19 , wherein the polymer device is a polymer waveguide LED device or a polymer microcavity LED device.

Assignees

• Ho Peter
• Chua Lay-Lay
• Friend Richard Henry
• Tang Jie-Cong
• Png Rui-Qi
• Anto Bibin Thomas
• Chia Perq-Jon
• Tan Zhi Kuang
• Choo Kim Kian
• Nat Univ Singapore

Inventors

• Ho Peter
• Chua Lay-Lay
• Friend Richard Henry
• Tang Jie-Cong
• Png Rui-Qi
• Anto Bibin Thomas
• Chia Perq-Jon
• Tan Zhi Kuang
• Choo Kim Kian

Classifications

• C09D201/04

  containing halogen atoms · CPC title

• C08K5/28

  Azides · CPC title

• C07C247/18 Primary

  being further substituted by carboxyl groups · CPC title

• C08K5/0025

  Crosslinking or vulcanising agents; including accelerators · CPC title