# US 2019/0315718 A1 · Electrochromic compounds and optical articles containing them

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- Number: US 2019/0315718 A1
- Document ID: US20190315718A1
- Status: Published application
- Kind: A1
- Application number: 16/471,050
- Filed: 2018-01-04
- Published: 2019-10-17
- Earliest claimed: 2017-01-09
- Assignees: Essilor International
- Applicants: Essilor International
- Inventors: Claudine BIVER; Fabien BERIT-DEBAT; Samuel ARCHAMBEAU; Christopher GABBUTT; Stuart AIKEN; Bernard Mark HERON; Thomas David BROADBENT
- Web page: https://patentgrep.com/patent/US20190315718A1

## CPC

- C07D 401/14: containing three or more hetero rings
- C07D 213/22: containing two or more pyridine rings directly linked together, e.g. bipyridyl
- C09K 9/02: Organic tenebrescent materials
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## 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.

## Claims

### Claim at position 1

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.

### Claim at position 2 (depends on 1)

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.

### Claim at position 3 (depends on 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.

### Claim at position 4 (depends on 1)

4: The compound of formula (I) according to claim 1, wherein Z is a 2,3 branched pyridinediyl radical.

### Claim at position 5 (depends on 1)

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.

### Claim at position 6 (depends on 1)

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.

### Claim at position 7 (depends on 1)

7: The compound of formula (I) according to claim 1, wherein each one of R1 is selected from H, alkyl, and heteroaryl.

### Claim at position 8 (depends on 1)

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.

### Claim at position 9 (depends on 1)

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.

### Claim at position 10 (depends on 1)

10: The compound of formula (I) according to claim 1, wherein said compound is selected from the group consisting of:

### Claim at position 11 (depends on 1)

11: An electrochromic composition comprising at least one compound according to claim 1.

### Claim at position 12 (depends on 11)

12: The electrochromic composition according to claim 11, wherein said composition further comprises a host medium.

### Claim at position 13 (depends on 1)

13: An electrochromic device comprising a compound according to claim 1.

### Claim at position 14 (depends on 13)

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.