Polymerised liquid crystal film with retardation or orientation pattern

• US 7,435,357 B2
• Filed: 04/02/2004
• Issued: 10/14/2008
• Est. Priority Date: 04/08/2003
• Status: Active Grant

• Current Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Original Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Inventors: Harding, Richard, Skjonnemand, Karl, Marden, Shirley Ann, Hassall, Ian Victor Edward, McCreary, Janice
• Primary Examiner(s): Visconti; Geraldina
• Application Number:
  US10/552,710
• Publication Number:
  US 20060193998A1
• Time in Patent Office: 1,656 Days
• Field of Search: 2522991-2997, 430/20, 430/270.1, 428/1.1, 428/1.2, 349/176
• US Class Current: 252/299.1
• CPC Class Codes: C08J 5/18 Manufacture of films or sheets
• CPC Class Codes: C09K 19/2014 containing additionally a linking group other than -COO- or -OCO-, e.g. -CH2-CH2-, -CH=CH-, -C=C-; containing at least one additional carbon atom in the chain containing -COO- or -OCO- groups, e.g. -(CH2)m-COO-(CH2)n-
• CPC Class Codes: C09K 2219/03 in the form of films, e.g. films after polymerisation of LC precursor
• CPC Class Codes: C09K 2323/00 Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
• CPC Class Codes: C09K 2323/02 Alignment layer characterised by chemical composition
• CPC Class Codes: C09K 2323/03 Viewing layer characterised by chemical composition
• CPC Class Codes: G02B 5/3083 Birefringent or phase retarding elements G02B5/3008, G02B5/3016 take precedence; systems for polarisation control G02B27/286; manufacturing phase modulating patterns by lithographic processes G03F7/001
• CPC Class Codes: G02F 1/13363 Birefringent elements, e.g. for optical compensation
• CPC Class Codes: G02F 1/133631 with a spatial distribution of the retardation value
• CPC Class Codes: G02F 1/133633 using mesogenic materials
• CPC Class Codes: G02F 2413/01 Number of plates being 1

Abstract

The invention relates to a polymerised liquid crystal (LC) film comprising at least one photoisomerisable compound and having a pattern of regions with different retardation and/or different orientation of the LC material, to methods of preparing such a film, and to its use as alignment layer, optical retardation film or optical waveguide in liquid crystal displays or other optical or electrooptical components or devices, or for decorative or security applications.

Claims

1. A film comprising a polymerised nematic or smectic liquid crystal material, said polymerised liquid crystal material comprising at least one photoisomerisable compound, and wherein said film comprises at least two regions with different retardation of liquid crystal material, and/or at least two regions with different orientation of the liquid crystal material.

2. A film according to claim 1, wherein said film comprises at least two regions with different retardation of the liquid crystal material.

3. A film according to claim 1, wherein said film is obtained by polymerisation or crosslinking of a polymerisable liquid crystal material comprising at least one polymerisable and photoisomerisable compound.

4. A film according to claim 1, wherein the orientation of the liquid crystal material is controlled by varying the irradiation time and/or intensity of the photoradiation used to cause photoisomerisation in the liquid crystal material.

5. A film according to claim 1, wherein the polymerisable liquid crystal material comprises one or more photoisomerisable compounds selected from azobenzenes, benzaldoximes, azomethines, stilbenes, spiropyrans, spirooxadines, fulgides, diarylethenes, cinnamates, 2-methyleneindane-1-ones and bis-benzylidenecycloalkanones.

6. A film according to claim 5, wherein the polymerisable liquid crystal material comprises one or more photoisomerisable compounds selected from polymerisable mesogenic cinnamates.

7. A film according to claim 1, wherein the polymerisable liquid crystal material comprises one or more photoisomerisable compounds selected from the following formulae

8. A film according to claim 1, wherein said polymerised material is obtained from a polymerisable liquid crystal material having a polymerisable component, and said polymerisable component comprises at least 12 mol % of photoisomerisable compounds.

9. A film according to claim 8, wherein the polymerisable component of the polymerisable liquid crystal material comprises from 40 to 100 mol % of photoisomerisable compounds.

10. A film according to claim 8, wherein the polymerisable component of the polymerisable liquid crystal material comprises 100% of photoisomerisable compounds.

11. A polymerisable liquid crystal material for preparing a film comprising a polymerised nematic or smectic liquid crystal according to claim 1, said polymeris able liquid crystal material having a polymerisable component, and said polymerisable component comprising at least 12 mol % of photoisomerisable compounds.

13. A method of preparing a film according to claim 1, said method comprising:

a) providing a layer of a polymerisable liquid crystal material comprising at least one photoisomerisable compound onto a substrate,

b) aligning said layer of liquid crystal material into planar orientation,

c) exposing the liquid crystal material in said layer, or in selected regions thereof, to photoradiation to cause isomerisation of said isomerisable compound,

d) polymerising the liquid crystal material in at least a part of the exposed regions the material, thereby fixing the orientation, and

e) optionally removing the polymerised film from the substrate.

14. A method according to claim 13, wherein the retardation and/or orientation of the liquid crystal material is controlled by varying the amount and/or type of the photoisomerisable compound, and/or by varying the intensity of the photoradiation and/or the exposure time.

16. A method according to claim 13, wherein the liquid crystal material is exposed to radiation that causes photoisomerisation and photopolymerisation, and photoisomerisation is carried out in the presence of oxygen and photopolymerisation is carried out in the absence of oxygen.

18. A film according to claim 13, wherein said film comprises at least one region having planar orientation and at least one region having splayed orientation.

22. In a liquid crystal display containing an optical retardation film, the improvement wherein said film is an optical retardation film according to claim 1.

23. A display according to claim 22, wherein said film is positioned between the substrates of the switchable liquid crystal cell.

24. A liquid crystal display comprising a liquid crystal cell formed by two plane parallel substrates at least one of which is transparent to incident light,

an electrode layer provided on the inside of at least one of said two transparent substrates and optionally superposed with an alignment layer,

a liquid crystal medium located between the two substrates, and said medium is switchable between at least two different states by application of an electric field, and

at least one film according to claim 1 positioned between the two plane parallel substrates forming the liquid crystal cell.

25. A liquid crystal display comprising:

1) a liquid crystal cell comprising the following elements

     11)-17), starting from the edges to the center of the cell in the following sequence

11) a first and a second substrate plane parallel to each other, at least one of which is transparent to incident light,

12) an array of nonlinear electric elements on one of said substrates which can be used to individually switch individual pixels of said liquid crystal cell,

13) a color filter array provided on one of said substrates, said color filter optionally being covered by a planarisation layer,

14) a first electrode layer provided on the inside of said first substrate,

15) optionally a second electrode layer provided on the inside of said second substrate,

16) optionally first and second alignment layers provided on said first and second electrodes, and

17) an liquid crystal medium that is switchable between at least two different states by application of an electric field;

2) a first linear polariser on one side of the liquid crystal cell,

3) optionally a second linear polariser on the side of the liquid crystal cell opposite to that of the first linear polariser, and

4) at least one optical retardation film according to claim 1, said optical retardation film

     4) being positioned between the color filter and the liquid crystal medium.

26. A liquid crystal display according to claim 25, wherein said color filter has a pattern of different pixels transmitting one of the primary colors red, green and blue (R, G, B), and the optical retardation film exhibits a pattern of pixels with three different retardations, each of which is adjusted such that its efficiency of convening linearly polarised light into circularly polarised light is optimized for one of the colors R, G and B, and the optical retardation film is positioned on the color filter such that each R-, G- or B-pixel of the color filter is covered by a corresponding pixel of the optical retardation film having a retardation optimized for this color.

27. An optical waveguide comprising a film according to claim 1.

28. An optical waveguide according to claim 27, wherein said waveguide has constant thickness and a refractive index gradient wherein the refractive index continuously decreases in a direction parallel to the film plane from one edge of the waveguide to its opposite edge.

29. A film according to claim 1, wherein said film:

(a) has a pattern of a first and a second region, wherein the first and said second region differ in both retardation and orientation;

(b) has a pattern of a first, a second and a third region, wherein said first and second region differ in either retardation or orientation, and said third region differs in at least one of retardation and orientation from at least one of said first and said second regions;

or

(c) has a pattern of a first, a second, a third and a fourth region, each of which has a retardation different from each other region, and two of said regions have the same orientation.

30. A film according to claim 1, wherein said polymerised liquid crystal material is obtained by polymerizing a mixture containing at least one polymerisable mesogenic compound selected from the following formulas:

31. A film according to claim 7, wherein said polymerised material is obtained from a polymerisable liquid crystal material having a polymerisable component, and said polymerisable component comprises at least 12 mol % of photoisomerisable compounds selected from formulas III, IV and V.

32. A film according to claim 31, wherein said polymerisable component comprises 80 to 100 mol % of photoisomerisable compounds selected from formulas III, IV and V.

33. A film according to claim 31, wherein said polymerisable component comprises 50 to 70 mol % of photoisomerisable compounds selected from formulas III, IV and V.

34. A film according to claim 1, wherein said film has a thickness of 0.6 to 2 microns.

35. A film according to claim 1, wherein said film has a thickness of 0.7 to 1.5 microns.

36. A film according to claim 1, wherein said film has an on-axis retardation, at 0°

viewing angle, of from 60 nm to 400 nm.

37. A film according to claim 1, wherein said film has an on-axis retardation, at 0°

viewing angle, of from 100 nm to 350 nm.

38. A film according to claim 8, wherein said polymerised material is obtained from a polymerisable nematic or smectic liquid crystal material and said polymerisable liquid crystal material comprises at least one di- or multireactive achiral, polymerisable mesogenic or liquid crystal compound and optionally one or more than one monoreactive achiral polymerisable mesogenic or liquid crystal compound.

12. A patterned film comprising polymerised nematic or smectic liquid crystal material, wherein said film comprises at least two regions with different retardation and at least two regions with different orientation of the liquid crystal material.

15. A method of preparing a multilayer structure comprising at least two layers of polymerised nematic or smectic liquid crystal material having different orientation, comprising:

A) providing a first layer of a polymerisable liquid crystal material comprising at least one photoisomerisable compound onto a substrate,

B) aligning the first layer of liquid crystal material into planar orientation and polymerising the material, thereby fixing the orientation,

C) providing a second layer of liquid crystal material as described in A) and B), wherein the first layer serves as substrate,

wherein the liquid crystal material in at least one of said first and second layers, or in selected regions thereof, before polymerisation, is exposed to photoradiation to cause isomerisation of the isomerisable compound.

17. A multilayer structure obtained by a method according to claim 15.

19. A multilayer structure according to claim 17, wherein said structure comprises at least one layer having planar orientation and at least one layer having splayed orientation.

20. A multilayer structure according to claim 17, wherein said structure comprises at least one layer having splayed orientation and at least one region having homeotropic orientation.

21. In an active matrix color liquid crystal display containing an optical retardation film, the improvement wherein said film comprises a patterned film having at least two regions having different retardation.