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1. (WO2004048499) COMBINED ROD-DISC CRYSTALLINE SYSTEMS WITH NEMATIC PROPERTIES
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Claims

1. A compound which is a liquid crystal which comprises a discotic nematic phase promoting moiety and at least two calamitic nematic phase promoting moieties.

2. A compound according to claim 1 characterised in that the discotic nematic phase promoting moiety comprises a disc shaped moiety.

3. A compound according to claim 2 characterised in that each of the at least two calamitic nematic phase promoting moieties comprise rod shaped moieties.

4. A compound according to claim 1 which comprises a compound of formula I comprising a disc-shaped mesogen and a rod-shaped mesogen;


in which R is X or hydrogen or is represented by formula II provided that at least one group is represented by formula II;


wherein D1 is selected from the following rings or fused ring systems:


each of which may optionally be substituted in at least one of the available positions with one or more of a substituent selected from the group F, CI, Br, CN, NO2, L1,

OL2 and SL3;

E1 is selected from the group; single bond, -CO2- -OCO-, -CH2CH2- -CH=CH- -C-≡C-, -CH2O-, -OCH2-, -CH2S-, -SCH2-, -CN=N- -N=CH- -N=N- OCO(CH2)c and CO2(CH2)c;

Y1 is selected from the group; single bond, O, S, CH2, CO2, OCO, CONH, NHCO,

NH and-(C=O)-;

Ti is selected from the group; H, CN, F, CI, CF3, NO2, NCS, SCN, L4, OL5, SL6,

CO2L7, OCOL8;

X is represented by formula III;


wherein [Z], which is a bond or is optionally a branching group, provided that when it is not a branching group then at least one R group in formula I is a group X, and when [Z] is a branching group it is selected from E1 or is an aromatic or aliphatic multifunctional moiety, selected from one of the structures of formula V;


[Y2], [Y3] and [Y4], which may be the same or different, are each selected from the group; single bond, H, O, S, CH2, CO2, OCO, CONH, NHCO, NH, -(C=O)-, CH2O,

CH2CH2O, CH2OCO, CH2CH2OCO;

Q1 and Q2, which may be the same or different, are each selected from the group;

(CH2)g, (CF2)h, (CH2CH2O)iCH2CH2 and (SiZ12O )jSiZ22 ,

Z1 and Z2, which may be the same or different, are each selected from CH3, CF3 and

H;

L1, L2 and L3, which may be the same or different, are each a C1-5 branched or straight alkyl chain;

L4, L5, L6, L7 and L8, which may be the same or different, are each a C1-16 straight or branched alkyl chain;

c is an integer from 1 to 12;

g and h, which may be the same or different, are each an integer from 1 to 20;

i andj, which may be the same or different, are each an integer from 1 to 10; and m is an integer from 1 to 5.

5. A compound according- to claim 4 characterised in that the rod-shaped mesogen is selected from an end-on rod-shaped mesogen or a side on rod-shaped mesogen.

6. A compound according to claim 5 characterised in that the rod-shaped mesogen is an end-on rod-shaped mesogen of formula IV;


wherein D2, D3 and D4, which may be the same or different, are each selected from the following groups;


each of which may optionally be substituted in at least one of the available positions with one or more of the following substituents: F, CI, Br, CN, NO2, L9, OL10 and

SL11;

E2 and E3, which may be the same or different, are each selected from the group; single bond, -CO2- -OCO-, -CH2CH2- -CH=CH- -C≡C-, -CH2O-, -OCH2- -CH2S- -SCH2- -CN=N- -N=CH- -N=N- OCO(CH2)f and

CO2(CH2)f ;

T2 is selected from the group; H, CN, F, CI, CF3, NO2, NCS, SCN, L12, OL13, SL14,

CO2L15 and OCOL16,

L9, L10 and L11, which may be the same or different, are each selected from a C1-5 branched or straight alkyl chain;

L12, L13, L14, L15 and L16, which may be the same or different, are each a C1-16 straight or branched alkyl chain; and

f is an integer from 1 to 4.

7. A compound according to claim 5 characterised in that the rod-shaped mesogen is a side-on on rod-shaped mesogen of formula IVa;


wherein D2, D3, D4 and D5, which may be the same or different, are each selected from the following groups;


each of which may optionally be substituted in at least one of the available positions with one or more of the following substituents: F, CI, Br, CN, NO2, L9, OL10 and

SL11;

E2, E3 and E4, which may be the same or different, are each selected from the group; single bond, -CO2- -OCO- -CH2CH2- -CH=CH- -C=C- -CH2O-, -OCH2- -CH2S- -SCH2-, -CN=N- -N=CH- -N=N- OCO(CH2)f and CO2(CH2)f ;

T2 and T3, which may be the same or different, are each selected from the group; H,

CN, F, CI, CF3, NO2, NCS, SCN, L12, OL13, SL14, CO2L15 and OCOL16,

L9, L10 and L11, which may be the same or different, are each selected from a C1-5 branched or straight alkyl chain;

L12, L13, L14, L15 and L16, which may be the same or different, are each a C1-16 straight or branched alkyl chain; and

f is an integer from 1 to 4.

8. A compound according to claim 7 characterised in that the groups D3 or D5 are substituted by a spacer of type Q2 in one of the available positions.

9. A compound according to claim 6 characterised in that T1 includes one or more non-adjacent CH2 groups that are substituted with CH(CN), CH(CF3), CH(Cl) CH(CH3) in chiral or non-chiral form and/or one or more non-adjacent CH2 groups that are substituted by CH such that there is a double bond present and the terminal CH3 group may be replaced by a CH2 group.

10. A compound according to claim 2 or 4 characterised in that the disc-shaped mesogen is ll-[pentakis(4-methoxyphenyletynyl)phenoxy] undecyl alcohol or 11-[pentakis(4-hexyloxyphenyletynyl)phenoxy] undecyl alcohol.

11. A compound according to 4 characterised in that the compound is a compound of formula X;


in which Rx is selected from one of the following;


in which m is an integer from 6 to 10.

12. A compound according to claim 3 or 4 characterised in that the rod-shaped mesogen is selected from the group comprising; 3,4,5-tris[6-(4'-cyanobiphenyl-4-yloxy)hexyloxy]benzoic acid ethyl ester; 3,4,5-tris[10-(4'-cyanobiphenyl-4-yloxy)decylpxylbenzoic acid ethyl ester; 3,4-bis[6-(4'-cyanobiphenyl-4-yloxy)hexyloxy]benzoic acid ethyl ester; 3,4,5-tris[6-(4-(4-

ρentylphenylazo)phenoxy)decyloxy]benzoic acid ethyl ester; and 3,4,5-tris[6-(2,3- difluoro-4"-octyloxy-[1,1';4',1"]terphenyl-4-yloxy)hexyloxy]benzoic acid ethyl ester.

13. A compound according to claim 4 characterised in that the compound comprises an ester formed between ll-[pentakis(4-methoxyphenyletynyl)phenoxy] undecyl alcohol or 11- [ρentakis(4-hexyloxyphenyletynyl)phenoxy] undecyl alcohol and a compound selected from the group comprising; 3,4,5-tris[6-(4'-cyanobiphenyl- 4-yloxy)hexyloxy]benzoic acid; 3,4,5-tris[10-(4'-cyanobiphenyl-4- yloxy)decyloxy]benzoic acid; 3,4-bis[6-(4'-cyanobiphenyl-4-yloxy)hexyloxy]benzoic acid; 3,4,5-tris[6-(4-(4-pentylphenylazo)phenoxy)decyloxy]benzoic acid; and 3,4,5- tris[6-(2,3-difluoro-4"-octyloxy-[1,1';4',1']terphenyl-4-yloxy)hexyloxy]benzoic acid.

14. A compound according to claim 13 characterised in that the compound is selected from the group consisting of 3,4,5-tris[6-(4'-cyanobiphenyl-4-yloxy)hexyloxy]benzoic acid 11- [pentakis(4-methoxyphenyletynyl)phenoxy] undecyl ester; 3,4,5-tris[10-(4'-cyanobiphenyl-4-yloxy)decyloxy]benzoic acid 11-[pentakis(4-methoxyphenyletynyl)phenoxy] undecyl ester; 3,4,5-tris[6-(4'-cyanobiphenyl-4-yloxy)hexyloxy]benzoic acid 11-[pentakis(4-hexyloxyphenyletynyl)phenoxy] undecyl ester; 3,4,5-tris[10-(4'-cyanobiphenyl-4-yloxy)decyloxy]benzoic acid 11-[pentakis(4-hexyloxyphenyletynyl)phenoxy] undecyl ester; 3,4-bis[10-(4'-cyanobiphenyl-4-yloxy)decyloxy]benzoic acid 11-[pentakis(4-methoxyphenyIetynyl)-phenoxy] undecyl ester; 3,4,5-tris[6-(4-(4-pentylphenylazo)phenoxy)hexyloxy]benzoic acid 11-[pentakis(4-methoxy-phenyletynyl)phenoxy] undecyl ester; and 3,4,5-tris[6-(2,3-difluoro-4"-octyloxy-[1,1';4',1"]terphenyl-4-yloxy)hexyloxy]benzoic acid 11-[pentakis(4-methoxyphenyletynyl)phenoxy] undecyl ester.

15. A compound according to claim 14 characterised in that the compound is a compound of formula D1R5, 3,4,5-tris[6-(2,3-difluoro-4"-octyloxy-[1,1';4',1"]terphenyl-4-loxy)hexyloxy]benzoic acid 11-[pentakis(4-methoxyphenyletynyl)phenoxy] undecyl ester.

16. A compound according to claim 4 characterised in that the compound is admixed with a rod-shaped mesogen or a disc-shaped mesogen.

17. A compound according to claim 4 characterised in that the compound is admixed with a rod-shaped mesogen and a disc-shaped mesogen.

18. A compound according to claims 8, 16 or 17 characterised in that the rod- shaped mesogen is selected from the group comprising; 3,4,5-tris[6-(4'- cyanobiphenyl-4-yloxy)hexyloxy]benzoic acid ethyl ester; 3,4,5-tris[10-(4'- cyanobiphenyl-4-yloxy)decyloxy]benzoic acid ethyl ester; 3,4-bis[6-(4'- cyanobiphenyl-4-yloxy)hexyloxy]benzoic acid ethyl ester; 3,4,5-tris[6-(4-(4- pentylphenylazo)phenoxy)decyloxy]benzoic acid ethyl ester; and 3,4,5-tris[6-(2,3- difluoro-4"-octyloxy-[1,1';4',1'']terphenyl-4-yloxy)hexyloxy]benzoic acid ethyl ester.

19. A compound according to claims 11 or 12 characterised in that the discshaped mesogen is 3,4,5-tris[6-(4'-cyanobiphenyl-4-yloxy)hexyloxy]benzoic acid 11- [pentakis(4-methoxyphenyletynyl)phenoxy] undecyl alcohol.

20. The use of a compound according to claim 4 in the manufacture of a liquid crystal.

21. The use of a compound according to claim 16 in the manufacture of a liquid crystal.

22. The use according to claim 21 characterised in that the mesogen is a discshaped mesogen.

23. The use according to claim 22 characterised in that the disc-shaped mesogen is 3,4,5-tris[6-(4'-cyanobiphenyl-4-yloxy)hexyloxy]benzoic acid ll-[pentakis(4-methoxyphenyletynyl)phenoxy] undecyl alcohol.

24. The use according to claim 21 characterised in that the mesogen is a rod- shaped mesogen.

25. The use according to claim 24 characterised in that the rod-shaped mesogen is selected from the group comprising; 3,4,5-tris[6-(4'-cyanobiphenyl-4- yloxy)hexyloxy]benzoic acid ethyl ester; 3,4,5-tris[10-(4'-cyanobiphenyl-4- yloxy)decyloxy]benzoic acid ethyl ester; 3,4-bis[6-(4'-cyanobiphenyl-4- yloxy)hexyloxy]benzoic acid ethyl ester; 3,4,5-tris[6-(4-(4-pentylphenylazo)phenoxy)decyloxy]benzoic acid ethyl ester; and 3,4,5-tris[6-(2,3- difluoro-4"-octyloxy-[1,1';4',1"]terphenyl-4-yloxy)hexyloxy]benzoic acid ethyl ester.

26. The use according to claim 25 characterised in that the compound is a compound of formula D1R5, 3,4,5-tris[6-(2,3-difluoro-4"-octyloxy-[1,1';4',1']terphenyl-4-yloxy)hexyloxy]benzoic acid 11- [pentakis(4-methoxyphenyletynyl)phenoxy] undecyl ester.

27. The use of a compound according to claim 4 in the manufacture of a liquid crystal that exhibits a nematic phase.

28. The use of a compound according to claim 27 in the manufacture of a liquid crystal that exhibits a uni-axial nematic phase.

29. The use of a compound according to claim 27 in the manufacture of a liquid crystal that exhibits a biaxial nematic phase.

30. The use of a compound according to claim 27 in the manufacture of a liquid crystal that exhibits a chiral nematic phase.

31. The use of a compound according to claim 4 in the manufacture of a liquid crystal containing discotic nematic liquid crystal components.

32. The use of a compound according to claim 4 in the manufacture of a liquid crystal containing discotic nematic and calamitic liquid crystal components.

33. The use of a liquid crystal according to claim 1 or a compound according to claim 4 in the manufacture of a transmissive or reflective device.

34. The use of a liquid crystal according to claim 1 or a compound according to claim 30 in the manufacture of transmissive or reflective devices, where the molecules are in a biaxial nematic phase.

35. The use of a compound according to claim 4 in the manufacture of a liquid crystal which exhibits a smectic A phase.

36. The use of a compound according to claim 4 in the manufacture of a liquid crystal which exhibits a smectic C phase.

37. The use of a compound according to claim 4 in the manufacture of a liquid crystal which exhibits a chiral smectic C phase

38. The use of a compound according to claim 4 in the manufacture of a liquid crystal wherein the two directors of the nematic phase can be oriented selectively and independently.

39. The use of a compound according to claim 4 in the manufacture of a liquid crystal which comprises a polymer so that one of the nematic directors of the mixture is oriented by the polymer the other can be oriented by electromagnetic fields allowing for mechanically flexible devices and for devices where a preferred orientation by a alignment of the polymer matrix; the design of very large area devices without alignment problems.

40. The use of a compound according to claim 1 in the manufacture of a device comprising two spaced cell walls, each bearing electrode structures on at least one facing surface treated with an alignment layer, a layer of liquid crystal material enclosed between the cell walls, characterised that it incorporates a liquid crystal or a liquid crystal mixtures mixture containing nematic liquid crystal.

41. The use of a compound according to claim 1 in the manufacture of a device comprising two spaced cell walls whose transparency in the electromagnetic spectrum is dissimilar, at least one bearing electrode structures on at least one facing surface treated with an alignment layer, a layer of liquid crystal material enclosed between the cell walls, characterised that it incorporates a liquid crystal or a hquid crystal mixtures mixture containing nematic liquid crystal.

42. The use of a compound according to claim 1 in the manufacture of a data storage, memory, or 3D memory device and/or data and processing systems of which optical or holographic devices are examples.

43. The use of a compound according to claim 1 in the manufacture of a laser, where the wavelength of the emitted radiation can be varied by the variation of the pitch of the cholesteric helix performed by the appUcation of an electric field or temperature, or where cholesteric elastomers are used by the application of a mechanical field or temperature.

44. The use of a compound according to claim 1 in the manufacture of a data transmission device.

45. The use of a compound according to claim 1 in the manufacture of an optical switch.

46. The use of a compound according to claim 1 in the manufacture of an optical data transmission device for the alignment of the liquid crystal mixtures.

47. The use of a compound according to claim 1 in the manufacture of a laser.

48. The use of a compound according to claim 1 in the manufacture of an opto- electrical switch.

49. The use of a compound according to claim 1 in the manufacture of an optical computing system.

50. The use of a compound according to claim 1 in the manufacture of a component in protective devices for radiation.

51. The use of a compound according to claim 1 in the manufacture of a paint.

52. The use of a compound according to claim 1 in the manufacture of a medical diagnostic device.

53. The use of a compound according to claim 1 in the manufacture of a light emissive device.

54. The use of a compound according to claim 1 in the manufacture of a lithographic device.

55. The use of a compound according to claim 1 in the manufacture of a molecular logic gate.

56. The use of a compound according to claim 1 in the manufacture of a photovoltaic cell.

57. The use of a compound according to claim 1 as a material as a bulk heterojunction compound.

58. A liquid crystal comprising a compound of claim 1.

59. A liquid crystal or a compound substantially as hereinbefore described with reference to the accompanying examples.