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US 2019/0315718 A1Published application
Electrochromic compounds and optical articles containing them
AssigneeEssilor International
InventorsClaudine BIVER, Fabien BERIT-DEBAT, Samuel ARCHAMBEAU, Christopher GABBUTT, Stuart AIKEN, Bernard Mark HERON, Thomas David BROADBENT
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Abstract
The present invention relates to a group of novel electrochromic compounds. More specifically, it relates to electrochromic compounds comprising one or several pyridinium rings and the use of these compounds as a variable transmittance medium for the manufacture of an optical article, such as an ophthalmic lens.
Claims14
1:
- An electrochromic compound of formula (I):
- wherein:
- Z is a pyridinediyl radical or a pyridiniumdiyl radical;
- each Y is independently selected from N or (+N—R2)(X−) with R2 a C1-C18 alkyl or R2 an aryl;
- each one of R1 is independently selected from H, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy, haloalkylthio, polyalkylenoxy, alkoxycarbonyl, aryl, or heteroaryl;
- n is 1, 2, 3 or 4;
- a is 4;
- X− is a counterion;
- and
- Z is not simultaneously bound in position 4 of cycle A and in position 4 of cycle B.
7 more elements
2:
- The compound of formula (I) according to claim 1, wherein said compound is represented by formula (II):
- wherein Z, Y, R1, X−, a and n are as defined in claim 1.
3:
- The compound of formula (I) according to claim 1, wherein said compound is represented by formula (III)
- wherein Z, Y, R1, X−, a and n are as defined in claim 1.
4:
- The compound of formula (I) according to claim 1, wherein Z is a 2,3 branched pyridinediyl radical.
5:
- The compound of formula (I) according to claim 1, wherein Z is a pyridiniumdiyl radical selected from:
- 1,4-branched pyridiniumdiyl radical;
- 2,3 branched N-alkylpyridiniumdiyl radical;
- or
- 2,5 branched pyridiniumdiyl radical.
2 more elements
6:
- The compound of formula (I) according to claim 1, wherein Y is independently selected from N and (+N—R2)(X−) with R2 a C1-C8 alkyl or R2 is an aryl.
7:
- The compound of formula (I) according to claim 1, wherein each one of R1 is selected from H, alkyl, and heteroaryl.
8:
- The compound of formula (I) according to claim 1, wherein both Y are N and n is equal to 1 or wherein at least one Y is (+N—R2)(X—) and n is equal to 2, 3 or 4.
9:
- The compound of formula (I) according to claim 1, wherein the counterion X− is selected from the group consisting of halide, tetrafluoroborate, tetraphenylborate, hexafluorophosphate, nitrate, methanesulfonate, trifluoromethane sulfonate, p-toluenesulfonate, hexachloroantimonate, bis(trifluoromethanesulfonyl)imide, perchlorate, acetate and sulfate.
10:
- The compound of formula (I) according to claim 1, wherein said compound is selected from the group consisting of:
11:
- An electrochromic composition comprising at least one compound according to claim 1.
12:
- The electrochromic composition according to claim 11, wherein said composition further comprises a host medium.
13:
- An electrochromic device comprising a compound according to claim 1.
14:
- The electrochromic device according to claim 13, wherein said electrochromic device is selected from the group consisting of an optical article, a window, a visor, a mirror, a head mounted device and a display.