Colored fluids for electrowetting, electrofluidic, and electrophoretic technologies

• US 8,520,286 B2
• Filed: 12/20/2010
• Issued: 08/27/2013
• Est. Priority Date: 12/18/2009
• Status: Active Grant

• Current Assignee: Sun Chemical Corporation
• Original Assignee: Sun Chemical Corporation
• Inventors: Schwartz, Russell, Vilner, Stan, Clapp, Lisa
• Primary Examiner(s): Lester, Evelyn A.
• Application Number:
  US13/516,995
• Publication Number:
  US 20120307347A1
• Time in Patent Office: 981 Days
• Field of Search: 359265-275, 359665-667, 252/586
• US Class Current: 359/270
• CPC Class Codes: C09B 69/10 Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds addition products of alkylene oxide to dyes, C09B69/00; dyeing with polymeric dyes D06P1/0056
• CPC Class Codes: C09B 69/102 containing a perylene dye
• CPC Class Codes: C09B 69/106 containing an azo dye
• CPC Class Codes: C09B 69/108 containing a phthalocyanine dye
• CPC Class Codes: C09B 69/109 containing other specific dyes
• CPC Class Codes: G02B 26/005 based on electrowetting
• CPC Class Codes: G02F 1/167 by electrophoresis
• CPC Class Codes: G02F 1/1685 Operation of cells; Circuit arrangements affecting the entire cell
• CPC Class Codes: G02F 1/172 based on a suspension of orientable dipolar particles, e.g. suspended particles displays
• CPC Class Codes: G02F 2001/1678 characterised by the composition or particle type

Abstract

Colored fluids for electrowetting, electrofluidic, and electrophoretic chromatophore devices are disclosed. In one embodiment, the colored fluid includes at least one solvent and at least one oligomeric and/or polymeric dye in the solvent. The oligomeric dye has at least one chromophore attached to one or more oligomeric chains, and the polymeric dye has at least one chromophore attached to one or more oligomeric and/or polymeric chains. The dye also has a molecular weight from 400 to 100,000, solubility in the solvent of at least 5% wt at 25° C., and a dynamic viscosity from 0.5 cPs to 2,000 cPs at 25° C. The solvent may be polar or non-polar each having specific properties defined.

Claims

1. A colored fluid comprising:

at least one polar or non-polar solvent and at least one oligomeric and/or polymeric dye in the solvent, the oligomeric dye having at least one chromophore attached to one or more oligomeric chains and the polymeric dye having at least one chromophore attached to one or more oligomeric and/or polymeric chains, the dye further having a molecular weight from 400 to 100,000, solubility in the solvent of at least 5% by wt at 25°

C., and a dynamic viscosity from 0.5 cPs to 2,000 cPs at 25°

C., and wherein, if the solvent is the polar solvent, the colored fluid has a conductivity from about O·

^S/cm to 3000 μ

8Λ

;

η

, a surface tension of 15 dynes/cm to 90 dynes/cm at 25°

C., and a total content of monatomic ions with radii smaller than 2.0 A and polyatomic ions with radii smaller than 1.45 A less than 500 ppm, and, if the solvent is the non-polar solvent, the colored fluid has a conductivity less than 5×

10^˜

S/cm and a surface tension of 10 dynes/cm to 40 dynes/cm at 25°

C.

2. The colored fluid of claim 1 wherein the oligomeric or polymeric dye is defined by at least one of the following formulas:

Q[X—

(Y) i]_m 

 

(1)

(Q-X)_p—

Z—

(X—

Y)_q 

 

(2)

(Q-X)_P(X—

Y)_qZ—

Y—

Z(X—

Y)_q(X-Q)_p 

 

(3)

(Q-X)_P(X—

Y)_qZ-L-Z(X—

Y)_q(X-Q)_p 

 

(4)

Q-X—

Y—

X-Q 

 

(5)

Z(X—

Y—

X-Q)_p 

 

(6)

[(Y) iX]_mQ-X—

Y—

X-Q[X(Y)i]_m 

 

(7)

X-Q-X—

Y—

[X-Q-X—

Y]_k—

X-Q-X—

Y 

 

(8)

Y(—

X-Q)[Y(—

X-Q)]_kY(—

X-Q)Y 

 

(9)

Q[X₁⁻

Y₁⁺]_m 

 

(10)

Q[X₂⁺Y₂⁻

]_m 

 

(11)

[Yi⁺Xf]m Q-X—

Y—

X-Q[X fYi⁺]m 

 

(12)

[Y₂—

X₂⁺]_mQ-X—

Y—

X-Q[X₂⁺Y₂⁻

]_m 

 

(13)

Z{X—

Y—

X-Q[XfY₁⁺]_m}_p 

 

(14)

Z{X—

Y—

X-Q[X₂⁺Y₂—

]_m}_p 

 

(15)

where Q is a chromophore;

X is R;

RC(0)0;

ROC(O);

RC(0)NRi;

RNRiC(O);

S0₂NRi;

S0₂;

RO;

RS;

═

N—

;

RNHC(0)NRi;

RNHC(0)0;

ROC(0)NH;

RC(0)OCH₂CH(OH)CH₂;

ROCH₂CH(OH)CH₂;

or RNRiCH₂CH(OH)CH₂, where R is a single bond, alkyl, aryl, alkylaryl, or a heterocycle, and Ri is H, alkyl, aryl, or alkylaryl;

Y is an oligomer or polymer selected from a polyvinyl, polyvinylidene, polydiene, polyanhydride, polyalkyleneglycol, polyester, polyepoxy, polyurethane, polyamide, polyimide, polyuria, polycarbonate, polyacetal, polysulfone, polyaldehyde, polyketone, or random or block co-polymer thereof;

Z is a radical of 1,3,5- and 1,2,4-triazine, benzene-1,3,5-tricarboxylic acid, benzene-1,2,4-tricarboxy lie acid, benzene-2,3,5,6-tetracarboxylic acid, glycerol, pentaerythritol, dimethylol propionic acid, citric acid, isocitric acid, propane-1,2,3-tricarboxylic acid, mucic acid, malic acid, tartaric acid, 2,4-dihydroxybenzoic acid, 1,3,5-triaminobenzene, 1,3,5-trihydroxybenzene, gallic acid, 2-amino-1,3-propanediol, or triethanolamine;

L is a single bond or a bifunctional linking group;

X is an anionic group of the chromophore;

X₂⁺ is a cationic group of the chromophore;

Yi⁺ is a cationic group of the oligomer or polymer;

Y₂⁻

is an anionic group of the oligomer or polymer; and

l is 1-2;

m is 1-8;

p and q are 1-4;

p+q<

5; and

k is 0-500.

3. The colored fluid of claim 1 wherein the solvent is the polar solvent.

4. The colored fluid of claim 3 wherein the polar solvent has a dielectric constant greater than 10, a surface tension of 25 dynes/cm to 90 dynes/cm, a dynamic viscosity from 0.1 to 2,000 cPs at 25°

C., and an electrowetting relative response (EWRR) to direct or alternating current of 30V in the range of 20-80%.

5. The colored fluid of claim 3 wherein the polar solvent is selected from water, glycols, polyglycols, alcohols, polyols, ethers, esters, ketals, lactones, ketones, lactams, pyrrolidones and polyvinylpyrrolidones, pyrrolidines, carbonates, ureas, sulfones, sulfoxides, amines, imines, amides, nitriles, carboxylic acids, acetals, carbamates, aldehydes, halogenated, thio, or nitro compounds, ionic fluids, or any mixtures thereof.

6. The colored fluid of claim 3 wherein the polar solvent is water, 1,2-propylene glycol, 1,3-propylene glycol, 1,4-butylene glycol, propylene carbonate, beta-propiolactone, beta-valerolactone, gamma-butyrolactone, gamma-valerorolactone, or any combination thereof.

7. The colored fluid of claim 2 wherein the solvent is the non-polar solvent.

8. The colored fluid of claim 7 wherein the non-polar solvent has a dielectric constant less than 10, a dynamic viscosity at 25°

C. from 0.1 to 2,000 cPs, and a surface tension of 10 dynes/cm to 40 dynes/cm.

9. The colored fluid of claim 7 wherein the non-polar solvent is selected from linear or branched aliphatic or aromatic hydrocarbons, partially hydrogenated aromatic hydrocarbons, alicyclic or aromatic heterocyclic compounds or their derivatives containing a halogen, nitro, nitrozo, or cyano groups, fatty alcohols and carboxylic acids, esters, amides, or any mixtures thereof.

10. The colored fluid of claim 7 wherein the non-polar solvent is octane, nonane, decane, undecane, dodecane, tetradecane, tetralin, or decalin.

11. The colored fluid of claim 1 wherein the oligomeric and/or polymeric dye is present in an amount from about 0.01 weight to about 50% weight of the fluid and the polar or non-polar solvent is present in an amount from about 50% to about 99.99% weight of the fluid.

12. The colored fluid of claim 1 further comprising a pigment.

13. The colored fluid of claim 12 wherein the pigment has a particle size from 10 to 200 nm.

14. The colored fluid of claim 12 wherein the oligomeric and/or polymeric dye is present in an amount from 0.01% to 40% weight of the fluid, the pigment is present in an amount from 0.01% to 30% by weight of the fluid, and the polar or non-polar solvent is present in an amount from 40% to 99.98% weight of the fluid.

15. The colored fluid of claim 1 wherein the dye is a fluorescent dye.

16. An electro wetting or electrofluidic device including the colored fluid of claim 1.

17. The device of claim 16 further comprising a clear polar or non-polar fluid.

18. The device of claim 16 wherein the colored fluid includes the polar solvent to define a colored polar fluid and further comprising another colored fluid of claim 1, which includes the non-polar solvent thereby defining a colored non-polar fluid.

19. An electrophoretic device including the colored fluid of claim 1, which includes the non-polar solvent thereby defining a non-polar fluid.

20. A pixel for a display including the colored fluid of claim 1.

21. A method for changing a display state of a pixel for a display, the method comprising:

applying a potential difference to a reservoir of the pixel that includes the colored fluid of claim 1 via a plurality of electrodes to create a change in the display state of the pixel by moving or changing the shape of the colored fluid.