IP Library Granted Patent US 12668737
Granted Patent B2
US 12668737 · App. 18/170,587 · Granted Jun 30, 2026

Multilayer low current electro-optic assembly

Inventors: Garret C. DeNolf (Grand Rapids, MI); Caleb Knust (Holland, MI); Leroy J. Kloeppner (Jenison, MI); Punam Giri (Holland, MI)
Assignee: GENTEX CORPORATION
C09K9/02G02F1/1524
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Quick Facts
Patent No.
US 12668737
App. No.
18/170,587
Granted
Jun 30, 2026
Kind
B2
Abstract

An electro-optic assembly includes a first substrate and a second substrate that is disposed in a substantially parallel spaced apart relationship with the first substrate. A first conductive layer is disposed on the first substrate, and a second conductive layer is disposed on the second substrate. A cathodic electro-optic film is in contact with the second conductive layer and includes a cathodic species. An anodic electro-optic film is in contact with the first conductive layer. The anodic electro-optic film includes a plurality of anodic species mixed at a molar ratio that is configured to generally maintain an a* value and a b* value of the electro-optic assembly both staying between −8 and 8 between a high-end transmission state and a fully darkened state caused by an applied voltage range. An electrolyte medium is disposed between the cathodic and anodic electro-optic films.

Claims (56)

1 . An electro-optic assembly, comprising:

a first substrate having a first and a second surface disposed on opposite sides thereof;

a second substrate having a third and a fourth surface disposed on opposite sides thereof, the second substrate disposed in a substantially parallel spaced apart relationship with the first substrate such that the second and third surfaces face one another;

a first conductive layer disposed on the second surface;

a second conductive layer disposed on the third surface;

a cathodic electro-optic film in contact with the second conductive layer and including a cathodic species;

an anodic electro-optic film in contact with the first conductive layer, the anodic electro-optic film including a homogenous layer with uniform concentrations of a plurality of anodic species, the plurality of anodic species mixed at a molar ratio that is configured to generally maintain an a* value and a b* value of the electro-optic assembly both staying between −8 and 8 between a high-end transmission state and a fully darkened state caused by an applied voltage range; and

an electrolyte medium disposed between the cathodic and anodic electro-optic films; and

wherein the first anodic species is selected from a variety one group of non-substituted anodic species selected from a group consisting of:

(a) 5,10-bis[(hydroxyalkyl dimethylammonio)alkyl]-5,10-dihydrophenazine including a non-substituted phenazine compound;

(b) 5,10-bis(hydroxyalkyl)-5,10-dihydrophenazine including a non-substituted phenazine compound;

(c) 5,10-bis[4-(3-hydroxypropyl dimethylammonio)butyl]-5,10-dihydrophenazine; and

(d) 5,10-bis(6-hydroxyhexl)-5,10-dihydrophenazine.

2 . The electro-optic assembly of claim 1 , wherein the plurality of anodic species includes a first anodic species and a second anodic species, wherein the first anodic species comprises the molar percentage between 80% and 60% of an aggregation of the first anodic species and the second anodic species.

3 . The electro-optic assembly of claim 2 , wherein the second anodic species is selected from a variety two group of substituted anodic species comprising substituted alkyl groups in the 2 and 7 or 2 and 8 position of a non-substituted phenazine compound, the variety two group of substituted anodic species selected from a group consisting:

(a) 5,10-bis[(hydroxyalkyl dimethylammonio)alkyl] 2,7-bis(alkyl)-5,10-dihydrophenazine;

(b) 5,10-bis(hydroxyalkyl)-2,7-bis(alkyl)-5,10-dihydrophenazine;

(c) 5,10-bis[(hydroxyalkyl dimethylammonio)alkyl] 2,8-bis(alkyl)-5,10-dihydrophenazine; and

(d) 5,10-bis(hydroxyalkyl)-2,8-bis(alkyl)-5,10-dihydrophenazine.

4 . The electro-optic assembly of claim 3 , wherein the phenazine compound is an ammonium salt with an anion selected from a group consisting of F − , Cl − , Br − , I − , BF 4 − , PF 6 − , SbF 6 − , AsF 6 − , ClO 4 − , SO 3 CF 3 − , N(CF 3 SO 2 ) 2 − , C(CF 3 SO 2 ) 3 − , N(SO 2 C 2 F 5 ) 2 − , Al(OC(CF 3 ) 3 ) 4 , BAr 4 − , PF 6 − and SO3CF3, and a mixture of anions thereof where Ar is an aryl or fluorinated aryl group.

5 . The electro-optic assembly of claim 2 , wherein the second anodic species is selected from a variety two group of substituted anodic species comprising substituted butyl groups in the 2 and 7 or 2 and 8 position of a non-substituted phenazine compound, the variety two group of substituted anodic species selected from a group consisting of:

(a) 5,10-bis[4-(3-hydroxypropyl dimethylammonio)butyl] 2,7-di(tert-butyl)-5,10-dihydrophenazine;

(b) 5,10-bis[4-(3-hydroxypropyl dimethylammonio)butyl] 2,8-di(tert-butyl)-5,10-dihydrophenazine;

(c) 5,10-bis(6-hydroxyhexyl)-2,7-di(tert-butyl)-5,10-dihydrophenazine; and

(d) 5,10-bis(6-hydroxyhexyl)-2,8-di(tert-butyl)-5,10-dihydrophenazine.

6 . The electro-optic assembly of claim 5 , wherein the phenazine compound is an ammonium salt with an anion selected from a group consisting of F − , Cl − , Br − , I − , BF 4 − , PF 6 − , SbF 6 − , AsF 6 − , ClO 4 − , SO 3 CF 3 − , N(CF 3 SO 2 ) 2 − , C(CF 3 SO 2 ) 3 − , N(SO 2 C 2 F 5 ) 2 − , Al(OC(CF 3 ) 3 ) 4 − , BAr 4 − , PF 6 − and SO3CF3, and a mixture of anions thereof, where Ar is an aryl or fluorinated aryl group.

7 . The electro-optic assembly of claim 2 , wherein the anodic electro-optic film includes a crosslinker bonding molecules of the first anodic species and molecules of the second anodic species into a polymer matrix.

8 . The electro-optic assembly of claim 2 , wherein the first anodic species and the second anodic species each include a first redox potential that is within a 200 mV range.

9 . The electro-optic assembly of claim 1 , wherein the cathodic electro-optic film includes a crosslinker bonding molecules of the cathodic species into a polymer matrix.

10 . The electro-optic assembly of claim 1 , wherein the applied voltage range is between 0.0 V and 1.0 V.

11 . The electro-optic assembly of claim 1 , wherein a transmission state of the electro-optic assembly changes between at least 75% at the high-end transmission state to less than 30% at the fully darkened state.

12 . The electro-optic assembly of claim 1 , wherein the molar ratio is further configured to maintain a total color excursion of the a* value and the b* value both between −8 and 8 throughout the applied voltage range.

13 . The electro-optic assembly of claim 12 , wherein the molar ratio is further configured to maintain the total color excursion of the a* value and the b* value both between −6 and 6 throughout the applied voltage range.

14 . The electro-optic assembly of claim 13 , wherein the molar ratio is further configured to maintain the total color excursion of the a* value and the b* value both between −4 and 4 throughout the applied voltage range.

15 . The electro-optic assembly of claim 1 , wherein the anodic electro-optic film contains a first crosslinker, the cathodic electro-optic film includes a second crosslinker, and the electrolyte medium contains an electrolyte crosslinker and an electrolyte polymer.

16 . The electro-optic assembly of claim 1 , wherein the cathodic species is a viologen.

17 . An electro-optic assembly, comprising:

a first substrate having a first and a second surface disposed on opposite sides thereof;

a second substrate having a third and a fourth surface disposed on opposite sides thereof, the second substrate disposed in a substantially parallel spaced apart relationship with the first substrate such that the second and third surfaces face one another;

a first conductive layer disposed on the second surface;

a second conductive layer disposed on the third surface;

a cathodic electro-optic film in contact with the second conductive layer and including a cathodic species;

an anodic electro-optic film in contact with the first conductive layer, the anodic electro-optic film including a plurality of anodic species, the plurality of anodic species mixed at a molar ratio that is configured to generally maintain an a* value and a b* value of the electro-optic assembly both staying between −8 and 8 between a high-end transmission state and a fully darkened state caused by an applied voltage range;

the plurality of anodic species includes a first anodic species and a second anodic species, wherein the first anodic species comprises the molar percentage between 80% and 60% of an aggregation of the first anodic species and the second anodic species; and

an electrolyte medium disposed between the cathodic and anodic electro-optic films; and

wherein the second anodic species is selected from a variety two group of substituted anodic species comprising substituted alkyl groups in the 2 and 7 or 2 and 8 position of a non-substituted phenazine compound or substituted butyl groups in the 2 and 7 or 2 and 8 position of a non-substituted phenazine compound, the variety two group of substituted anodic species selected from a group consisting:

(a) 5,10-bis[(hydroxyalkyl dimethylammonio)alkyl] 2,7-bis(alkyl)-5,10-dihydrophenazine;

(b) 5,10-bis(hydroxyalkyl)-2,7-bis(alkyl)-5,10-dihydrophenazine;

(c) 5,10-bis[(hydroxyalkyl dimethylammonio)alkyl] 2,8-bis(alkyl)-5,10-dihydrophenazine;

(d) 5,10-bis(hydroxyalkyl)-2,8-bis(alkyl)-5,10-dihydrophenazine;

(e) 5,10-bis[4-(3-hydroxypropyl dimethylammonio)butyl] 2,7-di(tert-butyl)-5,10-dihydrophenazine;

(f) 5,10-bis[4-(3-hydroxypropyl dimethylammonio)butyl] 2,8-di(tert-butyl)-5,10-dihydrophenazine;

(g) 5,10-bis(6-hydroxyhexyl)-2,7-di(tert-butyl)-5,10-dihydrophenazine; and

(h) 5,10-bis(6-hydroxyhexyl)-2,8-di(tert-butyl)-5,10-dihydrophenazine.

18 . The electro-optic assembly of claim 17 , wherein the first anodic species includes 5,10-bis[4-(3-hydroxypropyl dimethylammonio)butyl]-5,10-dihydrophenazine with a counterion.

19 . The electro-optic assembly of claim 18 , wherein the second anodic species includes 5,10-bis[4-(3-hydroxypropyldimethylammonio)butyl] 2,7-di(tert-butyl)-5,10-dihydrophenazine with a counterion.