IP Library Granted Patent US 7,951,938
Granted Patent B2
US 7,951,938 · App. 12/053,492 · Granted May 31, 2011

Fluorinated dyes or colorants and their uses

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Quick Facts
Patent No.
US 7,951,938
App. No.
12/053,492
Granted
May 31, 2011
Kind
B2
Abstract

The present invention relates to novel fluorinated dyes or colorants having high solubility and low viscosity in halogenated, especially fluorinated, solvents. The dyes or colorants of the present invention have shown to improve the performance of electrophoretic displays. The invention is particularly directed to a fluorinated porphyrin dye or colorant expressed by Formula (VII).

Claims (25)

1. An electrophoretic dispersion comprising charged pigment particles dispersed in a fluorinated solvent, wherein said fluorinated solvent comprises the fluorinated porphyrin dye or colorant expressed by Formula (VII):

wherein:

m, n, p and q are independently 0-5;

M is a divalent metal, an oxometal group, a halogenometal group or a hydroxymetal group;

R 1 and R 2 are independently hydrogen, halogen, alkyl, heteroalkyl, aryl, heteroC 6-18 aryl, a halogenated alkyl, a halogenated heteroalkyl, a halogenated aryl, a halogenated derivative of heteroC 6-18 aryl, R′O—, R′S—, R′R″N—, R′C(O)—, R′OC(O), R′C(O)O—, R′C(O)NR″, R′R″NC(O), R′NHC(O)NR″—, R′SO 2 NR″—, R′R″NSO 2 —, wherein R′ and R″ are independently hydrogen, alkyl, heteroalkyl, aryl, heteroC 6-18 aryl, a halogenated alkyl, a halogenated heteroalkyl, a halogenated aryl, or a halogenated heteroC 6-18 aryl; or

R 1 and R 2 are independently R f -A-;

R f is a fluorinated alkyl, fluorinated heteroalkyl, fluorinated aryl, fluorinated heteroC 6-18 aryl, or a fluorinated polymeric or oligomeric moiety; and

A is absent or a linking chain comprising one or more of the following, connected together: —O—, —S—, —SO—, —SO 2 —, —SO 2 NR′—, —NR'—, —NR′CO—, —NR′COO—, —NR′CONR″—, —NR′CS—, —NR′CSO—, —NR′CSNR″—, —OC(O)—, —OCO 2 —, —C(O)O—, —OC(O)N′R—, alkylene, arylene, a halogenated alkylene, and a halogenated arylene;

provided that the dyes or colorants Formula (VII) comprise at least about 25% by weight of fluorine.

2. The electrophoretic dispersion of claim 1 , wherein R f is represented by Formula (A):

wherein the open and undesignated substituent positions on the main chain of Formula (A) are the same or different and are independently selected from the group consisting of hydrogen, halogen, alkyl, heteroalkyl, aryl, heteroC 6-18 aryl, a halogenated alkyl, a halogenated heteroalkyl, a halogenated aryl, a halogenated heteroC 6-18 aryl, —OR a , —OC(O)R a , —C(O)OR a , —C(O)NR a R b ; wherein R a and R b are independently hydrogen, alkyl, heteroalkyl, aryl, heteroC 6-18 aryl, a halogenated alkyl, a halogenated heteroalkyl, a halogenated aryl, a halogenated heteroC 6-18 aryl, provided R f is a fluorinated alkyl, fluorinated heteroalkyl, fluorinated aryl, fluorinated heteroC 6-18 aryl, or a fluorinated polymeric or oligomeric moiety;

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

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.

3. The electrophoretic dispersion of claim 1 , wherein m, n, p and q are all 0.

4. The electrophoretic dispersion of claim 1 , wherein at least one of R 1 s is R f -A-, R f is a fluorinated alkyl of Formula (A) or a fluoropolyether of Formula (A), and A is a linking chain comprising —O— and alkylene(s).

5. The electrophoretic dispersion of claim 1 , wherein R 2 is independently hydrogen or R f -A-, R f is a fluorinated alkyl of Formula (A) or a fluoropolyether of Formula (A).

6. The electrophoretic dispersion of claim 5 , wherein A is selected from the group consisting of absent, a linking moiety comprising alkylene(s) and —O—, and a linking moiety comprising alkylene(s) and —S—.

7. The electrophoretic dispersion of claim 1 , wherein R 2 is hydrogen or R f -A-, R f is a fluorinated alkyl of Formula (A) or a fluoropolyether of Formula (A).

8. The electrophoretic dispersion of claim 7 , wherein A is absent or a linking moiety comprising optionally substituted arylene and —NH—.

9. The electrophoretic dispersion of claim 1 , wherein the fluorinated porphyrin dye or colorant is

10. The electrophoretic dispersion of claim 1 , wherein the fluorinated porphyrin dye or colorant is

11. A compound of

12. An electrophoretic dispersion comprising charged pigment particles dispersed in a fluorinated solvent, wherein said fluorinated solvent comprises the compound of claim 11 .

13. A compound of

14. An electrophoretic dispersion comprising charged pigment particles dispersed in a fluorinated solvent, wherein said fluorinated solvent comprises the compound of claim 13 .

Assignments (1)
CHANGE OF NAME Recorded Jul 7, 2014
From: SIPIX IMAGING, INC.
To: E INK CALIFORNIA, LLC
Reel/Frame 033280/0408 →