Fluorinated dyes or colorants and their uses
View Patent ↗This 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.
1. An electrophoretic dispersion comprising charged pigment particles dispersed in a fluorinated solvent, wherein said fluorinated solvent comprises a fluorinated perylene dye or colorant expressed by the following Formula (IV):
wherein:
m, n, p and q are independently 0-2;
X is O, S or NR wherein R is hydrogen, alkyl, heteroalkyl, aryl, heteroaryl or a halogenated derivative of alkyl, heteroalkyl, aryl, heteroaryl or R f -A- in which R f and A are defined below;
R 1 s are independently hydrogen, alkyl, heteroalkyl, aryl, heteroaryl or a halogenated derivative of alkyl, heteroalkyl, aryl or heteroaryl; or R 1 is R f -A- wherein R f and A are defined below;
R 2 s are independently hydrogen, halogen, alkyl, heteroalkyl, aryl, heteroaryl or a halogenated derivative of alkyl, heteroalkyl, aryl or heteroaryl, R′O—, R′S—, R′R″N—, R′C(O)—, R′OC(O)—, R′C(O)—, R′C(O)NR″—, R′R″NC(O)—, R′NHC(O)NR″—, R′SO 2 NR″— or R′R″NSO 2 — in which R′ and R″ are independently hydrogen, alkyl, heteroalkyl, aryl, heteroaryl or a halogenated derivative of alkyl, heteroalkyl, aryl or heteraryl; or
R 2 s are independently R f -A- wherein R f and A are defined below;
R f is a fluorinated alkyl, fluorinated heteroalkyl, fluorinated aryl or fluorinated heteroaryl or a low/medium molecular weight 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)—, —OC 2 —, —C(O)O—, —OC(O)N′R—, alkylene, arylene, and a halogenated derivative of alkylene or arylene, wherein R′ and R″ are as defined above, wherein the fluorinated perylene dye or colorant comprises at least about 25% by weight of fluorine.
2. The electrophoretic dispersion of claim 1 wherein R f is represented by the following 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, heteroaryl or a halogenated derivative of alkyl, heteroalkyl, aryl or heteroaryl, —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, heteroaryl or a halogenated derivative of alkyl, heteroalkyl, aryl or heteraryl;
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 X is O.
4. The electrophoretic dispersion of claim 2 wherein at least one of the R 1 s is R f -A- in which R f is a fluorinated alkyl or a fluoropolyether of Formula (A) and A is absent, an alkylene or a linking chain comprising an alkylene and —NR′C(O)— in which R′ is hydrogen or an alkyl.
5. The electrophoretic dispersion of claim 2 wherein m, n, p and q are all 0.
6. The electrophoretic dispersion of claim 2 wherein R 2 is chlorine and m, n, p and q are all 1.
7. The electrophoretic dispersion of claim 1 wherein at least one of R 2 s is R f -A- wherein R f is a fluorinated alkyl or a fluoropolyether of Formula (A) and A is independently a linking moiety comprising —S— and alkylene or a linking moiety comprising —O— and alkylene.
8. The electrophoretic dispersion of claim 1 wherein the fluorinated perylene dye or colorant comprises at least about 35% by weight of fluorine.
9. The electrophoretic dispersion of claim 1 wherein the fluorinated perylene dye or colorant comprises at least about 50% by weight of fluorine.
10. The electrophoretic dispersion of claim 5 wherein R 1 is R f -A- , R f is a fluoropolyether of Formula (A) and A is —NR′C(O)-alkyelne in which R′ is an alkyl.
11. The electrophoretic dispersion of claim 10 wherein R′ is methyl.
12. The electrophoretic dispersion of claim 6 wherein R 1 is R f -A- in which R f is a fluoroether of Formula (A) and A is —NR′C(O)-alkyene in which R′ is an alkyl.
13. The electrophoretic dispersion of claim 12 wherein R′ is methyl.
14. The electrophoretic dispersion of claim 7 wherein m, n, p and q are 1, R 1 is R f A- in which R f is a fluoroalkyl and A is —CH 2 —, R 2 is R f -A- in which R f is a fluoroalkyl and A is —S-alkylene- or —O-alkylene-.
15. The electrophoretic dispersion of claim 1 , wherein the fluorinated perylene dye or colorant is
16. The electrophoretic dispersion of claim 1 , wherein the fluorinated perylene dye or colorant is
17. The electrophoretic dispersion of claim 1 , wherein the fluorinated perylene dye or colorant is
18. The electrophoretic dispersion of claim 1 wherein said fluorinated solvent is selected from the group consisting of perfluoroarylalkanes, perfluoro-tert-amines, perfluoropolyethers and hydrofluoropolyethers.
19. The electrophoretic dispersion of claim 18 wherein said fluorinated solvent is a perfluoropolyether or hydrofluoropolyether.
20. A fluorinated perylene compound of
21. A fluorinated perylene compound of
22. A fluorinated perylene compound of