IP Library Granted Patent US 7,226,550
Granted Patent B2
US 7,226,550 · App. 10/683,869 · Granted Jun 5, 2007

Electrophoretic dispersions

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Quick Facts
Patent No.
US 7,226,550
App. No.
10/683,869
Granted
Jun 5, 2007
Kind
B2
Abstract

This invention relates to electrophoretic displays having improved performance. The threshold promoter of the present invention may induce or significantly enhance the threshold effect by improving the particle-particle interaction and/or the particle-electrode interaction. The promoter may be present in the system as a soluble or micelle molecule in the electrophoretic fluid or an adsorbed or chemically bonded molecule on the surface of particles. The use of such a threshold promoter does not show a detrimental effect on the display switching rate.

Claims (42)

1. A method for inducing or enhancing the threshold voltage of an electrophoretic display, which method comprises

a) preparing an electrophoretic fluid comprising forming pigment containing microparticles via emulsifying an internal phase comprising primary pigment particles and a reactive monomer or oligomer into a continuous phase comprising a protective colloid and dispersing the pigment-containing microparticles in a dielectric solvent or solvent mixture; and

b) adding to said electrophoretic fluid a threshold promoter represented by the following formula:

R-[Q-L-(X) m ] q   (T-1)

wherein:

m is a natural number which is ≧1;

q is a natural number which is ≧1;

R is a halogenated group or a halogenated polymeric or oligomeric chain;

Q and L together forms a linking chain; and

X is a functional group capable of forming hydrogen bonding, acid-base interaction, donor-acceptor interaction, metal-ligand interaction or Coulombic interaction.

2. The method of claim 1 wherein Q in -Q-L- is absent, —O—, —S—, —CON<, —CONR 12 —, —R 12 NCO—, (—CO) 2 N—, —R 12 NCONR 13 —, —R 12 NCSNR 13 —, —OCONR 12 —, —R 12 NCOO—, —OCSNR 12 —, —R 12 NCSO—, —COO—, —OOC—, —OC(O)O—, ═N— or —NR 12 —, wherein R 12 and R 13 are independently hydrogen, alkyl, aryl, alkylaryl, polyether or a derivative thereof.

3. The method of claim 1 wherein m is 1 or 2.

4. The method of claim 1 wherein q is 1 or 2.

5. The method of claim 1 wherein X is —OH, —SH, —NH 2 , —NH—, ═N—, >N + <, ═N + <, —CO—, —COO—, —OCO—, —COO − , —COOH, —COOCO—, —O—, —CONR 8 —, —CONH 2 , —OCONR 8 —, —NR 8 COR 9 , —R 8 NCONR 9 —, —CONR 8 CO—, —OCOO—, —SO—, —SO 2 —, —SO 2 − , —SO 3 − , —SO 4 − , —SO 2 H, —SO 3 H, —PO 4 H 2 , —PO 4 −2 , —PO 4 H − , —PO 3 H 2 , —PO 3 H − , —SO 2 NH—, —SO 2 NR 8 —, a pyridinium or quaternary ammonium salt, metal or metal ion or a chelated derivative thereof, wherein R8 and R9 independently hydrogen, alkyl or fluorinated alkyl of 1 to 30 carbon atoms.

6. The method of claim 5 wherein X is a pyridinium salt formed with a counter ion selected from the group consisting of F − , Cl − , Br − , I − , NO 3 − , NO 2 − , CO 3 = , SO 3 = , SO 4 = , PO 3 = , PO 4 3− , MnO 4 − , Cr 2 O 7 = , CrO 3 = , BF 4 − , PF 6 − , AsF 6 − , SbF 6 − , optionally fluorinated aliphatic carboxylates, optionally fluorinated sulfonates, anions of optionally fluorinated sulfonyl imides, anions of optionally fluorinated aromatic carboxylates, anions of optionally fluorinated sulfonates, fluoropolyether substituted carboxylate, and fluoropolyether substituted sulfonates.

7. The method of claim 6 wherein said optionally fluorinated aliphatic sulfonate is C a H b F (2a+1−b) SO 3 − wherein a is 1-30 and b is 0-61.

8. The method of claim 6 wherein said optionally fluorinated aliphatic carboxylate is C a H b F (2a+1−b) CO 2 − wherein a is 1-30 and b is 0-61.

9. The method of claim 6 wherein said counter ion is F(C 3 F 6 O) d CF(CF 3 )CO 2 − , F(C 3 F 6 O) d CF 2 CF 2 CO 2 − , CF 3 O(C 2 F 4 O) d CF 2 CO 2 − , F(C 2 F 4 O) d CF 2 CO 2 − , F(C 3 F 6 O) d CF(CF 3 )SO 3 − , F(C 3 F 6 O) d CF 2 CF 2 SO 3 − , CF 3 O(C 2 F 4 O) d CF 2 SO 3 − or F(C 2 F 4 O) d CF 2 SO 3 − wherein d is 1-20.

10. The method of claim 5 wherein said pyridinium salt is formed with an anion of F(C 3 F 6 O) y CF(CF 3 )COOH.

11. The method of claim 1 wherein R is fluorinated alkyl or fluorinated aryl.

12. The method of claim 1 wherein R is a polymeric or oligomeric chain represented by the following formula (R):

wherein the open and not designated substituent positions on the main chain are independently selected from the group consisting of hydrogen, halogen, alkyl, alkenyl, aryl, alkylaryl, fluoroalkyl, fluoroalkenyl, fluoroaryl, fluoroalkylaryl, —OR 10 , OCRO 10 , —COOR 10 , —CONR 10 R 11 and substituted derivatives thereof, wherein R 10 and R 11 are independently hydrogen, alkyl, aryl, alkylaryl, fluoroalkyl, fluoroaryl, fluoroalkylaryl or fluorinated polyether;

Z 1 , Z 2 , and Z 3 are independently oxygen or absent; and

a′, b′ and c′ are the weight fractions of the corresponding repeating units and are independently in the range of 0-1 with their sum no greater than 1.

13. The method of claim 12 wherein the open substituent positions are independently fluorine or fluorinated alkyl.

14. The method of claim 1 wherein said threshold promoter is represented by Formula T-1:

wherein

m is 1 or2;

q is 1 or2;

Q is absent, an amide, urea or urethane moiety;

L is a straight or branched alkylene, alkylphenylene, fluorinated alkylene or fluorinated alkylphenylene chain optionally interrupted by one or more heteroatoms; and

X is hydroxyl, amino or —NR 8 COR 9 wherein R 8 and R 9 are independently hydrogen, alkyl or fluorinated alkyl.

15. The method of claim 14 wherein R is a fluorinated alkyl.

16. The method of claim 14 wherein R is a fluoropolyether.

17. The method of claim 14 wherein R is a polymeric or oligomeric chain of Formula (R).

18. The method of claim 17 wherein the open substituent positions on the main chain of Formula (R) are independently fluorine or fluorinated alkyl.

19. The method of claim 14 wherein m is 2, q is 1, L is a straight or branched alkylene or alkylphenylene chain optionally interrupted by one or more nitrogen atoms.

20. The method of claim 19 wherein L is a straight or branched alkylene chain optionally interrupted by one or more nitrogen atoms.

21. The method of claim 1 wherein said threshold promoter is a pyridinium salt.

22. The method of claim 21 wherein said pyridinium salt has a counter ion selected from the group consisting of C a F 2a+1 SO 3 − , F(C 3 F 6 O) d CF(CF 3 )CO 2 — and F(C 2 F 4 O) d CF 2 CO 2 — in which a is 1-12 and d is 1-20.

23. The method of claim 1 wherein said protective colloid is an amino- or hydroxy-functionalized fluorinated polymer or oligomer.

24. The method of claim 23 wherein said polymer or oligomer is derived from a fluorinated hydrocarbon, hydrofluoropolyether or perfluoropolyether.

Assignments (2)
CHANGE OF NAME Recorded Jul 7, 2014
From: SIPIX IMAGING, INC.
To: E INK CALIFORNIA, LLC
Reel/Frame 033280/0408 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 5, 2004
From: HOU, JACK; ZANG, HONGMEI; CHEN, YAJUAN; CHEN, JING-DEN; LIAO, CHIH-YUAN; LIANG, RONG-CHANG
To: SIPIX IMAGING, INC.
Reel/Frame 015051/0792 →