Photo-alignment polymer material

Abstract

The present invention relates to a novel photo-alignment polymer material, the use thereof as an alignment layer for liquid crystals, for the preparation of unstructured and structured optical elements, electro-optical elements, multilayer systems or for use in nanoelectronic devices.

Description

[0001] This application is a divisional application of application number 201880051357.9. Technical Field

[0002] The present invention relates to a novel photoaligned polymer material, a composition comprising such a photoaligned polymer material, the use of the photoaligned polymer material or the composition as an alignment layer for liquid crystals for the preparation of unstructured and structured optical elements or electro-optical elements and multilayer systems, and unstructured and structured optical elements or electro-optical elements or nanoelectronic elements and multilayer systems comprising the novel photoaligned polymer material or a composition comprising such a photoaligned polymer material. Background Art

[0003] Optical or electro-optical elements are used, for example, as security devices, liquid crystal devices (LCDs), and optical films, such as retarders (e.g., 3D retarders) or as variable transmission films. For example, US 6,107,427 describes photo-aligned polymer materials that can be used in alignment layers. WO 2013 / 0281564 describes other photo-aligned polymer materials that can be used in alignment layers and that require less energy and more quickly align liquid crystals.

[0004] However, there is still an increasing demand for advanced alignment materials that allow efficient manufacturing methods (e.g. roll-to-roll methods), can be coated on different substrates and require less energy than prior art compounds while still providing good liquid crystal alignment and having excellent optical properties. Summary of the Invention

[0005] Therefore, the object of the present invention is to provide a novel photo-aligned polymer material that provides excellent liquid crystal orientation and allows the use of efficient manufacturing processes while maintaining good optical contrast and optical properties. The novel photo-aligned material of the present invention has excellent compatibility with various solvents, thereby allowing high flexibility in coating and printing methods. It can be applied at room temperature, so that various temperature-sensitive substrates can be used. The novel photo-aligned polymer material shows extremely high compatibility with organic materials (such as curable compositions or polymerizable liquid crystals) that can be used for various applications. In addition, it has improved adhesion to different substrates.

[0006] The present invention relates to a photo-aligned polymer material comprising repeating structural units of formula (I):

[0007]

[0008] in

[0009] M 1 、M 1’represents, independently of one another, the following repeating monomer units: acrylate, methacrylate, 2-chloroacrylate, 2-phenylacrylate, acrylamide, methacrylamide, 2-chloroacrylamide, 2-phenylacrylamide, N-lower alkyl-substituted acrylamide, N-lower alkyl-substituted methacrylamide, N-lower alkyl-substituted 2-chloroacrylamide, N-lower alkyl-substituted 2-phenylacrylamide, vinyl ether, vinyl ester, styrene, diamine, amide, imide, siloxane, amic acid ester and amic acid;

[0010] S 1 is a spacer unit, wherein, if m and n are 0, the spacer unit is S 2 , and if at least one of m or n is 1, the spacer unit is S 3 ;

[0011] S 1’ is a spacer unit, wherein, if m' and n' are 0, the spacer unit is S 2’ , and if at least one of m' or n' is 1, the spacer unit is S 3’ .

[0012] Among them S 2 、S 2’ 、S 3 、S 3’ is a substituted or unsubstituted straight or branched chain -(CH2) r - and -(CH2) r -O-, -(CH2) r -O-(CH2) s -、-(CH2) r -O-(CH2) s -O-, -(CH2) r -CO-, -(CH2) r -CO-O-, -(CH2) r -O-CO-, -(CH2) r -NR 2 -、-(CH2) r -CO-NR 2 -、-(CH2) r -NR 2 -CO-, -(CH2) r -NR 2 -CO-O- or -(CH2) r -NR 2 -CO-NR 3 -, which is optionally replaced by C1-C 24Alkyl, hydroxy, fluorine, chlorine, cyano, ether, ester, amino, amide monosubstituted or polysubstituted; and wherein one or more -CH2- groups may be substituted by a linking group, an alicyclic or aromatic group; and wherein r and s are each an integer from 1 to 20, provided that for S 2 , 3≤r+s≤24; and for S 3 , 6≤r+s≤24; and R 2 and R 3 each independently represents hydrogen or lower alkyl; and

[0013] Rings A and A' each independently represent phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl, 1,3-dioxane-2,5-diyl, cyclohexane-1,4-diyl, piperidine-1,4-diyl or piperazine-1,4-diyl which is unsubstituted or optionally substituted by fluorine, chlorine, cyano, alkyl or alkoxy;

[0014] Rings B and B' each independently represent phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl, 1,4- or 2,6-naphthylene, 1,3-dioxane-2,5-diyl, or cyclohexane-1,4-diyl, which is unsubstituted or optionally substituted by fluorine, chlorine, cyano, alkyl or alkoxy;

[0015] Y 1 、Y 2 、Y 1’ 、Y 2’ Each independently represents a covalent single bond, -(CH2) t , -O-, -CO-, -CO-O-, -O-OC-, -CF2O-, -OCF2-, -NR 4 -、-CO-NR 4 -、-R 4 N-CO-, -(CH2) u -O-, -O-(CH2) u -、-(CH2) u -NR 4 -or-NR 4 -(CH2) u -,in

[0016] R 4 represents hydrogen or lower alkyl;

[0017] t represents an integer from 1 to 4;

[0018] u represents an integer from 1 to 3;

[0019] Ring C, C' each independently represent a phenylene, pyrimidine-2,5-diyl, pyridine-2,5-diyl, 2,5-thiophenylene, 2,5-furanylene, 1,4- or 2,6-naphthylene group which is unsubstituted or optionally substituted by fluorine, chlorine, cyano, alkyl or alkoxy;

[0020] Z, Z' each independently represent -O- or -NR 5 -,

[0021] where R 5 represents hydrogen or lower alkyl, or a second group of formula D or D'; and

[0022] D is a C1-C3 straight-chain or branched alkylene chain which is halogenated at least once or contains one or more siloxane moieties; and

[0023] D' represents hydrogen, or a straight-chain or branched alkylene having 1-20 carbon atoms which is optionally substituted by halogen, or a cycloalkyl residue having 3-8 ring atoms which is optionally monosubstituted or polysubstituted by halogen, alkyl, alkoxy or one or more siloxane moieties; and w and w' are the molar fractions of the comonomers and 0 < w ≤ 1 and 0 ≤ w 1 <1.

[0024] In the context of the present invention, the term "linking group" is preferably selected from -O-, -CO, -CO-O-, -O-CO-, -NR 1 -, -NR 1 -CO-, -CO-NR 1 -, -NR 1 -CO-O-, -O-CO-NR 1 -, -NR 1 -CO-NR 1 -, -CH=CH-, -C≡C-, -O-CO-O- and -Si(CH3)2-O-Si(CH3)2-, where:

[0025] R 1 represents a hydrogen atom or a C1-C6 alkyl;

[0026] provided that the oxygen atoms of the linking group are not directly connected to each other.

[0027] Preferably, S 2 、S 2’ 、S 3 、S 3’ in the straight-chain or branched -(CH2) r - and -(CH2) r -、-(CH2) r O-(CH2) s -、-(CH2)r O-(CH2) s -O-, -(CH2) r -CO-, -(CH2) r -CO-O-, -(CH2) r -O-CO-, -(CH2) r -NR 2 -、-(CH2) r -CO-NR 2 -、-(CH2) r -NR 2 -CO-, -(CH2) r -NR 2 -CO-O- or -(CH2) r -NR 2 -CO-NR 3 -(where R 2 and R 3 Each independently represents hydrogen or lower alkyl) is a C1-C 24 Alkyl, preferably C1-C 12 The alkyl group is more preferably a C1-C8 alkyl group, a hydroxyl group, a fluorine group, a chlorine group, a cyano group, an ether group, an ester group, an amino group or an amide group.

[0028] The term "alkyl" in the context of the present invention is a substituted or unsubstituted straight-chain or branched saturated hydrocarbon residue having up to 20 carbon atoms, wherein one or more -CH2- or -CH3- groups may be unsubstituted or substituted by at least one linking group as described above, or / and alicyclic and / or aromatic groups.

[0029] The term "lower alkyl" above and below and similarly "lower alkoxy", "hydroxy-lower alkyl", "phenoxy-lower alkyl", "phenyl-lower alkyl" means a straight-chain or branched saturated hydrocarbon residue having 1 to 6, preferably 1 to 3, carbon atoms, such as methyl, ethyl, propyl or isopropyl.

[0030] The term "alkyl" and similarly "alkoxy" above and below denotes a straight-chain or branched saturated hydrocarbon residue having up to 20 carbon atoms.

[0031] The substituents of "alkyl" or "alkoxy" are hydroxy, fluoro, chloro, cyano, ether, ester, amino, amide, alicyclic or aromatic groups, wherein one or more -CH2- or -CH3- groups may each be substituted by at least one linking group.

[0032] In the context of the present invention, "straight-chain alkyl" is, for example, but not limited to, methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, heneicosyl, docosyl, tricosyl or tetracosyl.

[0033] In the context of the present invention, "alicyclic group" means, for example, a substituted or unsubstituted non-aromatic carbocyclic or heterocyclic group having 3 to 30 carbon atoms, and means, for example, a ring system such as cyclopropane, cyclobutane, cyclopentane, cyclopentene, cyclohexane, cyclohexene, cyclohexadiene, decalin, adamantane, tetrahydrofuran, dioxane, dioxolane, pyrrolidine, piperidine or a steroid backbone such as cholesterol, wherein the substituents are preferably methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, more preferably methyl, ethyl, propyl, butyl, pentyl, hexyl, and most preferably methyl, ethyl, propyl. Preferred alicyclic groups are cyclopentane, cyclopentene, cyclohexane, cyclohexene, and more preferably cyclopentane or cyclohexane.

[0034] In the context of the present invention, an "aromatic group" preferably means five, six, ten or fourteen ring atoms, for example furan, benzene or phenylene, pyridine, pyrimidine, naphthalene, which may form a ring structure, such as diphenylene or triphenylene, which is uninterrupted or interrupted by at least one heteroatom and / or at least one linking group; or a fused polycyclic ring system, for example phenanthrene or tetralin. Preferably, the aromatic group is benzene, phenylene, diphenylene or triphenylene. More preferably, the aromatic group is benzene, phenylene and diphenylene. Most preferably, it is phenylene.

[0035] For the purposes of the present invention, the term “phenylene which is unsubstituted or optionally substituted by fluorine, chlorine, cyano, alkyl or alkoxy” encompasses 1,2-, 1,3- or 1,4-phenylene, but in particular 1,3- or 1,4-phenylene, which is unsubstituted or mono- or polysubstituted by fluorine, chlorine, cyano, alkyl or alkoxy, preferably mono- or polysubstituted by fluorine, methyl, ethyl, propyl, butyl, methoxy, ethoxy, propoxy, butoxy or cyano. Particular preference is given to 1,4-phenylene residues. Examples of preferred phenylene residues are 1,3- or 1,4-phenylene, 4- or 5-methyl-1,3-phenylene, 4- or 5-methoxy-1,3-phenylene, 4- or 5-ethyl-1,3-phenylene, 4- or 5-ethoxy-1,3-phenylene, 2- or 3-methyl-1,4-phenylene, 2- or 3-ethyl-1,4-phenylene, 2- or 3-propyl-1,4-phenylene, 2- or 3-butyl-1,4-phenylene, 2- or 3-methoxy-1,3-phenylene, 4-phenylene, 2- or 3-ethoxy-1,4-phenylene, 2- or 3-propoxy-1,4-phenylene, 2- or 3-butoxy-1,4-phenylene, 2,3-, 2,6- or 3,5-dimethyl-1,4-phenylene, 2,6- or 3,5-dimethoxy-1,4-phenylene, 2- or 3-fluoro-1,4-phenylene, 2,3-, 2,6- or 3,5-difluoro-1,4-phenylene, 2- or 3-chloro-1,4-phenylene, 2,3-, 2,6- or 3,5-dichloro-1,4-phenylene, 2- or 3-cyano-1,4-phenylene, and the like.

[0036] In a more preferred embodiment of the present invention, S 2 、S 2′ 、S 3 、S 3’ is a substituted or unsubstituted straight or branched chain -(CH2) r , and -(CH2) r -O-, -(CH2) r -O-(CH2) S -、-(CH2) r -O-(CH2) s -O-, -(CH2) r -CO-, -(CH2) r -CO-O-, -(CH2) r -O-CO-, -(CH2) r -NR 2 -、-(CH2) r -CO-NR 2 -、-(CH2)-NR 2 -CO-、-(CH2)-NR 2 -CO-O- or -(CH2)r -NR 2 -CO-NR 3 -, where R 2 and R 3 Each independently represents hydrogen or lower alkyl; preferably S 2 、S 2’ 、S 3 、S 3’ Optionally C1-C 24 Alkyl, preferably C1-C 12 Alkyl, more preferably C1-C8 alkyl, mono- or polysubstituted, wherein alkyl has the meanings and preferences given above; or S 2 、S 2′ 、S 3 、S 3’ Optionally substituted or polysubstituted by hydroxyl, fluorine, chlorine, cyano, ether, ester, amino, amide; and wherein one or more -CH2- groups may be substituted by linking groups, alicyclic or / and aromatic groups; wherein for S 2 、S 2′ The single suffix "r" is an integer between 4 and 24, preferably between 5 and 12, more preferably between 5 and 8, especially 6 or 8; 3 、S 3’ The single suffix "r" is an integer between 6 and 24, preferably between 6 and 12, especially 6, 7, 8, 9, 10, 11 or 12;

[0037] and where for S 2 、S 2' The sum of the suffixes "r and s" is an integer between 1 and 24, preferably between 2 and 12, more preferably between 5 and 8;

[0038] and where for S 3 、S 3’ The sum of the suffixes "r and s" is an integer between 6 and 24, preferably between 6 and 12, in particular 6, 7, 8, 9, 10, 11 or 12; and R 2 and R 3 Each independently represents hydrogen or lower alkyl.

[0039] In a most preferred embodiment of the present invention, S 2 、S 2′ 、S 3 、S 3’ is a substituted or unsubstituted straight or branched chain -(CH2) r , and -(CH2) r -O-, -(CH2) r -O-(CH2) S -、-(CH2) r-O-(CH2) s -O-, -(CH2) r -CO-, -(CH2) r -CO-O-, -(CH2) r -O-CO-, especially -(CH2) r -O-, -(CH2) r -O-(CH2) S -、-(CH2) r -O-(CH2) s -O-, -(CH2) r -CO-, -(CH2) r -CO-O-, -(CH2) r -O-CO-, more especially -(CH2) r -O-, which is optionally replaced by C1-C 24 Alkyl, preferably C1-C 12 alkyl, more preferably C1-C8 alkyl, or hydroxy, fluorine, chlorine, cyano, ether, ester, amino, amide monosubstituted or polysubstituted; and wherein one or more -CH2- groups may be substituted by a linking group or an alicyclic or aromatic group; and wherein the individual suffixes r and s and the sum of the suffixes s and r have the meanings and preferences given above; and R 2 and R 3 Each independently represents hydrogen or lower alkyl.

[0040] Preferred "spacer unit" S 2 、S 2' Examples are 1,6-hexylene, 1,7-heptylene, 2-methyl-1,2-propylene, 1,3-butylene, ethyleneoxycarbonyl, acetylene, propyleneoxy, propyleneoxycarbonyl, propionyloxy, butyleneoxy, butyleneoxycarbonyl, butyryleneoxy, propyleneamino, butyleneamino, pentylamino, hexylamino, heptylamino, ethyleneaminocarbonyl, propyleneaminocarbonyl, butyleneaminocarbonyl, ethylenecarbonylamino, propylenecarbonylamino, butylenecarbonylamino, pentylaminocarbonyl, hexylaminocarbonyl, heptylcarbonylamino, pentylaminocarbonyl, hexylaminocarbonyl, heptylaminocarbonyl, pentyloxy, pentyloxycarbonyl, pentyloxy, hexyloxy, hexyloxycarbonyl, heptyloxy, heptyloxycarbonyl, heptyloxy, and particularly preferably hexyloxy.

[0041] Preferred "spacer unit" S 3 、S 3’Examples are 1,6-hexylene, 1,7-heptylene, 1,8-octylene, 1,9-nonylene, 1,10-decylene, 1,11-undecylene, 1,12-dodecylene, 9-nonyleneoxy, 11-undecyleneoxy, 12-dodecyleneoxy, 11-undecyleneoxycarbonyl, 12-dodecyleneoxycarbonyl, nonyleneoxycarbonyl, 11-undecanoyleneoxy, 12-dodecanoyleneoxy, 9-nonyleneoxy, 11-undecyleneamino, 12-dodecyleneamino, 9-nonyleneamino, 11-undecyleneaminocarbonyl, 12-dodecyleneaminocarbonyl, 9-nonyleneaminocarbonyl, 11-undecylenecarbonylamino, 12-dodecylenecarbonylamino, nonylenecarbonylamino and the like.

[0042] Particularly preferred "spacer unit" S 2 、S 2’ For -(CH2) r -(wherein r is 6 or 8) and -(CH2) r -O-, -(CH2) r -CO-O- and -(CH2) r A straight-chain alkylene group represented by -O-CO-.

[0043] In addition, a particularly preferred "spacer unit" S 3 、S 3’ It is composed of -(CH2)r- (wherein r is 6, 7, 8, 9, 10, 11, 12) and -(CH2) r -O-, -(CH2) r -CO-O- and -(CH2) r A straight-chain alkylene group represented by -O-CO-.

[0044] The term "halogenated" in the context of the present invention means that the repeating structural unit or monomer contains one or more halogen atoms, preferably two halogen atoms, more preferably three halogen atoms. The present invention contemplates that the halogen atoms are all bonded to the same carbon atom or to different carbon atoms. It is also contemplated that the same molecule can be halogenated with different halogen atoms. The halogen atom is fluorine, chlorine, bromine or iodine.

[0045] In the context of the present invention, "siloxane moiety" refers to any linear or branched substituent comprising at least one functional group having a Si-O-Si bond. The photo-aligned polymeric material of the present invention may contain one or more siloxane moieties.

[0046] The present invention, if w 1 is 0, the photo-aligned polymer material is a homopolymer, and if w 1 >0, the photo-aligned polymer material is a copolymer.

[0047] In the present invention, if the photo-aligned polymer material contains other repeating structural units, the repeating structural units include photo-aligned groups. Photo-aligned groups include photoactive functional groups, such as α,β-unsaturated nitrile groups; α,β-unsaturated carbonyl groups, wherein the carbonyl group may also be part of an ester, amide, imide, hydrazine, or thioester functional group, including cinnamate and chalcone;

[0048] coumarins and quinolones;

[0049] stilbene and cyanostilbene;

[0050] Azo group;

[0051] chromones and chromenes;

[0052] Mono- and di-acetylene groups, such as tolanyl;

[0053] Benzylphthalimide, benzylacetylphenyl, phenylenediacryl; or photodegradable polymer,

[0054] These photoactive functional groups may be unsubstituted or contain substituents such as:

[0055] Halogen (fluorine, chlorine, bromine), cyano, C1-C4 alkoxy, carboxylic acid, linear or branched C1-C4 optionally substituted by fluorine or cyano 12 An ester group of an alkyl group, a linear or branched alkyl group and a cycloalkyl group having 1 to 12 carbon atoms optionally substituted by a fluorine group or a cyano group, and an aromatic group having 6 to 18 carbon atoms optionally substituted by the above groups.

[0056] Preferred photoactive functional groups are α,β-unsaturated nitrile groups; α,β-unsaturated carbonyl groups, wherein the carbonyl group may also be part of an ester, amide or thioester functional group, including cinnamate and chalcone;

[0057] Coumarin;

[0058] Stilbene; and

[0059] Azo group,

[0060] These photoactive functional groups may be unsubstituted or contain substituents such as:

[0061] Halogen (fluorine, chlorine, bromine), cyano, C1-C4 alkoxy, carboxylic acid, linear or branched C1-C4 optionally substituted by fluorine or cyano 12 An ester group of an alkyl group, a linear or branched alkyl group and a cycloalkyl group having 1 to 12 carbon atoms optionally substituted by a fluorine group or a cyano group, and an aromatic group having 6 to 18 carbon atoms optionally substituted by the above groups.

[0062] The present invention encompasses that if w of formula (I) 1is zero, the photo-aligned polymer material comprises at least one monomer of formula (II)

[0063]

[0064] in

[0065] M 1 、S 1 , Ring A, Ring B, Y 1 、Y 2 , m, n, Ring C, z and D have the same meanings as defined above.

[0066] More preferably, it is a photo-aligned polymer material comprising at least one repeating structural unit of formula (I) or a monomer of formula (II), wherein:

[0067] M 1 is a monomer unit selected from acrylate and methacrylate;

[0068] Ring A is an unsubstituted phenylene group or a phenylene group substituted by an alkyl group or an alkoxy group;

[0069] Ring B is an unsubstituted phenylene group or a phenylene group substituted by fluorine, an alkyl group or an alkoxy group;

[0070] Y 1 、Y 2 Each is independently a covalent single bond, -CO-O-, or -O-OC-;

[0071] m and n are each independently 0 or 1;

[0072] Ring C is an unsubstituted phenylene group or a phenylene group substituted by an alkyl group or an alkoxy group;

[0073] S 1 is a spacer unit, wherein if m and n are 0, the spacer unit is S 2 , and if at least one of m or n is 1, preferably if m is 1 and n is 0, the spacer unit is S 3 ; where S 2 C4-C 24 Alkylene, preferably alkyleneoxy or alkyleneoxycarbonyl, in particular propyleneoxy, butyleneoxy, pentyleneoxy, hexyleneoxy, heptyleneoxy, octyleneoxy, nonyleneoxy, undecyleneoxy or propyleneoxycarbonyl, butyleneoxycarbonyl, pentyleneoxycarbonyl, hexyleneoxycarbonyl, heptyleneoxycarbonyl, octyleneoxycarbonyl, nonyleneoxycarbonyl, undecyleneoxycarbonyl, and S 3 C8-C 24 Alkylene, and wherein alkylene is unsubstituted or substituted linear or branched alkylene, wherein one or more -CH2- groups may be substituted by at least one linking group, alicyclic or / and aromatic group;

[0074] Z is -O-;

[0075] D is a C1-C3 linear or branched alkylene chain which is halogenated at least once or contains one or more siloxane moieties.

[0076] The present invention also relates to a method for preparing a photo-aligned polymer material, wherein the photo-aligned polymer material comprises a repeating structural unit of formula (I) or a monomer of formula (II), and the method comprises polymerizing the repeating structural unit of formula (I) or the monomer of formula (II).

[0077] The present invention also relates to compositions, in particular formulations and / or blends, comprising a photoalignable polymer material comprising repeating structural units of formula (I) or monomers of formula (II), and optionally solvents and / or additives.

[0078] Preferably, the composition comprises further solvents, such as, in particular, aprotic or protic polar solvents such as γ-butyrolactone, N,N-dimethylacetamide, N-methylpyrrolidone or N,N-dimethylformamide, methyl ethyl ketone (MEK), methyl isobutyl ketone (MIBK), 3-pentanone, cyclopentanone, cyclohexanone, ethyl acetate, n-butyl acetate, 1-methoxypropyl acetate (MPA), alcohols, isopropanol, n-butanol, butan-2-ol, in particular 1-methoxypropanol (MP). Preference is given to aprotic polar solvents, in particular γ-butyrolactone, N,N-dimethylacetamide, N-methylpyrrolidone or N,N-dimethylformamide, methyl ethyl ketone (MEK), methyl isobutyl ketone (MIBK), 3-pentanone, cyclopentanone, cyclohexanone, ethyl acetate, n-butyl acetate, 1-methoxypropyl acetate (MPA).

[0079] The molecular weight MW of the photo-alignment polymer material of the present invention is between 10,000 and 1,000,000, preferably between 20,000 and 900,000, more preferably between 50,000 and 500,000, even more preferably between 75,000 and 400,000, and even more preferably between 100,000 and 300,000.

[0080] (M 1 ) or (M 1’ ) is an acrylate, for example:

[0081]

[0082] Acrylamide, such as:

[0083]

[0084] Vinyl ethers and esters, such as:

[0085]

[0086] Styrene derivatives, such as:

[0087]

[0088] Silicones, such as:

[0089]

[0090] where R 1 represents hydrogen or lower alkyl.

[0091] (M 1 ) or (M 1’ Preferred examples of ) are acrylates, methacrylates, 2-chloroacrylates, acrylamides, methacrylamides, 2-chloroacrylamide, styrene derivatives and siloxanes. Acrylates, methacrylates, styrene derivatives and siloxanes are particularly preferred (M 1 ) or (M 1’ ).

[0092] Particularly preferred (M 1 ) or (M 1’ ) are acrylate, methacrylate and styrene derivatives. More preferably (M 1 ) or (M 1’ ) is methacrylate or a methacrylate derivative.

[0093] Furthermore, the preferred photo-alignment polymer material of the present invention comprises a repeating structural unit of formula (I) or a monomer of formula (II), wherein:

[0094] M 1 or M 1’ are acrylate, methacrylate and styrene derivatives;

[0095] Ring A represents phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl, or cyclohexane-1,4-diyl, which is unsubstituted or optionally substituted by fluorine, chlorine, cyano, alkyl, or alkoxy;

[0096] Ring B represents phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl, 1,4- or 2,6-naphthylene, or cyclohexane-1,4-diyl which is unsubstituted or optionally substituted by fluorine, chlorine, cyano, alkyl or alkoxy;

[0097] Y 1 、Y 2 Each independently represents a covalent single bond, -CH2CH2-, -O-, -CF20, -OCF2-, -CH2-O-, -O-CH2-, -CO-O- or -O-OC-;

[0098] Ring C represents phenylene, pyrimidine-2,5-diyl, pyridine-2,5-diyl, 2,5-furylene, 1,4- or 2,6-naphthylene which is unsubstituted or optionally substituted by fluorine, chlorine, cyano, alkyl or alkoxy;

[0099] Z means -O- and

[0100] S 1 、S 1’ 、A'、B'、n'、m'、Y 1’ 、Y 2’ ,C',Z',D,D',w,w 1 , m and n have the meanings given above.

[0101] Particularly preferred photoaligned polymeric materials comprise repeating structural units of formula (I) wherein n=0 and w 1 is 0, where:

[0102] M 1 Acrylate, methacrylate and styrene derivatives

[0103] Ring B represents phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl, or cyclohexane-1,4-diyl, which is unsubstituted or optionally substituted by fluorine, chlorine, cyano, alkyl, or alkoxy;

[0104] Y 2 represents a covalent single bond, -CO-O- or -O-OC-;

[0105] S 2 、S 3 is a substituted or unsubstituted straight or branched chain -(CH2) r , and -(CH2) r -O-, -(CH2) r -O-(CH2) S -、-(CH2) r -O-(CH2) s -O-, -(CH2) r -CO-, -(CH2) r -CO-O-, -(CH2) r -O-CO-, -(CH2) r -NR 2 -、-(CH2) r -CO-NR 2 -、-(CH2) r -NR 2 -CO-, -(CH2) r -NR 2 -CO-O- or -(CH2) r-NR 2 -CO-NR 3 -, wherein the suffix "r" is an integer between 4 and 24, preferably between 5 and 12, more preferably between 5 and 10, even more preferably between 5 and 8, especially between 6 and 8; and

[0106] m represents 0 or 1;

[0107] Ring C represents a phenylene group which is unsubstituted or optionally substituted by fluorine, chlorine, cyano, alkyl or alkoxy, or a 1,4- or 2,6-naphthylene group;

[0108] Z means -O- and

[0109] D is a C1-C3 linear or branched alkylene chain which is halogenated at least once or contains one or more siloxane moieties.

[0110] Even more preferred photoaligned polymeric materials comprise repeating structural units of formula (I) wherein n=m=0 and w 1 is 0, where:

[0111] M 1 are acrylate, methacrylate and styrene derivatives;

[0112] S 2 is a substituted or unsubstituted straight or branched chain -(CH2) r , and -(CH2) r -O-, -(CH2) r -O-(CH2) S -、-(CH2) r -O-(CH2) s -O-, -(CH2) r- CO-, -(CH2) r -CO-O-, -(CH2) r -O-CO-, -(CH2) r -NR 2 -、-(CH2) r -CO-NR 2 -、-(CH2) r -NR 2 -CO-, -(CH2) r -NR 2 -CO-O- or -(CH2) r -NR 2 -CO-NR 3 -, wherein the suffix "r" is an integer between 4 and 24, preferably between 5 and 12, more preferably between 5 and 8, especially between 6 and 8; and

[0113] Ring C represents a phenylene group which is unsubstituted or optionally substituted by fluorine, chlorine, cyano, alkyl or alkoxy, or a 1,4- or 2,6-naphthylene group;

[0114] Z means -O- and

[0115] D is a C1-C3 linear or branched alkylene chain which is halogenated at least once or contains one or more siloxane moieties.

[0116] Even more preferred photoaligned polymeric materials comprise repeating structural units of formula (I) wherein n=m=0 and w 1 is 0, where:

[0117] M 1 is methacrylate;

[0118] S 2 is a substituted or unsubstituted straight or branched chain -(CH2) r , and -(CH2) r -O-, -(CH2) r -O-(CH2) S -、-(CH2) r -O-(CH2) s -O-, -(CH2) r- CO-, -(CH2) r -CO-O-, -(CH2) r -O-CO-, -(CH2) r -NR 2 -、-(CH2) r -CO-NR 2 -、-(CH2) r -NR 2 -CO-, -(CH2) r -NR 2 -CO-O- or -(CH2) r -NR 2 -CO-NR 3 -, wherein the suffix "r" is an integer between 4 and 24, preferably between 5 and 12, more preferably between 5 and 8, especially between 6 and 8; and

[0119] Ring C represents a phenylene group which is unsubstituted or optionally substituted by fluorine, chlorine, cyano, alkyl or alkoxy, or a 1,4- or 2,6-naphthylene group;

[0120] Z means -O-, and

[0121] D is a C1-C3 linear or branched alkylene chain which is halogenated at least once or contains one or more siloxane moieties.

[0122] Even more preferred photoaligned polymeric materials comprise repeating structural units of formula (I) wherein n=m=0 and w 1 is 0, where:

[0123] M 1 is methacrylate;

[0124] S 2 is a substituted or unsubstituted straight or branched chain -(CH2) r , and -(CH2) r -O-, -(CH2) r -O-(CH2) S -、-(CH2) r -O-(CH2) s -O-, -(CH2) r- CO-, -(CH2) r -CO-O-, -(CH2) r -O-CO-, -(CH2) r -NR 2 -、-(CH2) r -CO-NR 2 -、-(CH2) r -NR 2 -CO-, -(CH2) r -NR 2 -CO-O- or -(CH2) r -NR 2 -CO-NR 3 -, wherein the suffix "r" is an integer between 4 and 24, preferably between 5 and 12, more preferably between 5 and 8, especially between 6 and 8; and

[0125] Ring C represents a phenylene group which is unsubstituted or optionally substituted by fluorine, chlorine, cyano or methoxy, or a 1,4- or 2,6-naphthylene group;

[0126] Z means -O-, and

[0127] D is a C1-C3 linear or branched alkylene chain which is halogenated at least once or contains one or more siloxane moieties.

[0128] Even more preferred photoaligned polymeric materials comprise repeating structural units of formula (I) wherein n=m=0 and w 1 is 0, where:

[0129] M 1 is methacrylate;

[0130] S 2 is a substituted or unsubstituted straight or branched chain -(CH2) r, and -(CH2) r -O-, -(CH2) r -O-(CH2) S -、-(CH2) r -O-(CH2) s -O-, -(CH2) r- CO-, -(CH2) r -CO-O-, -(CH2) r -O-CO-, -(CH2) r -NR 2 -、-(CH2) r -CO-NR 2 -、-(CH2) r -NR 2 -CO-, -(CH2) r -NR 2 -CO-O- or -(CH2) r -NR 2 -CO-NR 3 -, wherein the suffix "r" is an integer between 4 and 24, preferably between 5 and 12, more preferably between 5 and 8, especially between 6 and 8; and

[0131] Ring C represents a phenylene group which is unsubstituted or optionally substituted by fluorine, chlorine, cyano or methoxy;

[0132] Z means -O-, and

[0133] D is a C1-C3 linear or branched alkylene chain which is halogenated with fluorine at least once or contains one or more siloxane moieties.

[0134] Even more preferred photoaligned polymeric materials comprise repeating structural units of formula (I) wherein n=m=0 and w 1 is 0, where:

[0135] M 1 is methacrylate;

[0136] S 2 is a substituted or unsubstituted straight or branched chain -(CH2) r , and -(CH2) r -O-, -(CH2) r -O-(CH2) S -、-(CH2) r -O-(CH2) s -O-, -(CH2) r- CO-, -(CH2) r -CO-O-, -(CH2) r -O-CO-, -(CH2)r -NR 2 -、-(CH2) r -CO-NR 2 -、-(CH2) r -NR 2 -CO-, -(CH2) r -NR 2 -CO-O- or -(CH2) r -NR 2 -CO-NR 3 -, wherein the suffix "r" is an integer between 4 and 24, preferably between 5 and 12, more preferably between 5 and 8, especially between 6 and 8; and

[0137] Ring C represents a phenylene group which is unsubstituted or optionally substituted by fluorine, chlorine, cyano or methoxy;

[0138] Z means -O-, and

[0139] D is a C1-C3 linear or branched alkylene chain which is halogenated with fluorine at least once or contains a siloxane.

[0140] If w 1 >0, the photo-aligned polymer material of the present invention is a copolymer. The preferred photo-aligned copolymer material comprises a repeating structural unit of formula (I), wherein M 1 and S 1 and M 1’ and S 1’ and m, n, m', n' are as defined above; and

[0141] Rings A and A' each independently represent a phenylene group which is unsubstituted or optionally substituted with fluorine, chlorine, cyano, alkyl or alkoxy, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group or a cyclohexane-1,4-diyl group;

[0142] Rings B and B' each independently represent phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl, 1,4- or 2,6-naphthylene or cyclohexane-1,4-diyl which is unsubstituted or optionally substituted by fluorine, chlorine, cyano, alkyl or alkoxy;

[0143] Y 1 、Y 2 、Y 1’ 、Y 2’ each independently represents a covalent single bond, -CH2CH2-, -O-, -CH2-O-, -O-CH2-, -OCF2-, -CF2O-, CO-O- or -O-OC-;

[0144] Rings C and C' each independently represent a phenylene group which is unsubstituted or optionally substituted by fluorine, chlorine, cyano, alkyl or alkoxy, or a pyrimidine-2,5-diyl group, a pyridine-2,5-diyl group, a 2,5-furylene group or a 1,4- or 2,6-naphthylene group;

[0145] Z, Z′ represent -O-, and

[0146] D is a C1-C3 linear or branched alkylene chain that is halogenated at least once or contains one or more siloxane moieties; and

[0147] D' is a straight-chain or branched alkylene radical having 1-20 carbon atoms, preferably 1-12 carbon atoms, or a cycloalkyl radical having 5-6 ring atoms, optionally mono- or polysubstituted by alkyl, alkoxy (especially methyl or methoxy) or one or more siloxane moieties.

[0148] Particularly preferred are photo-aligned copolymer materials comprising repeating structural units of formula (I), wherein n and n' represent 0, M 1 and S 1 and M 1’ and S 1’ and m, m' are as defined above; and

[0149] Rings B and B' each independently represent a phenylene group which is unsubstituted or optionally substituted by fluorine, chlorine, cyano, alkyl or alkoxy, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group or a cyclohexane-1,4-diyl group;

[0150] Y 2 、Y 2’ each independently represents a covalent single bond, -CO-O- or -O-OC-;

[0151] Rings C and C' each independently represent a phenylene group which is unsubstituted or optionally substituted by fluorine, chlorine, cyano, alkyl or alkoxy, or a 1,4- or 2,6-naphthylene group;

[0152] Z, Z' represents -O-, and

[0153] D is a C1-C3 linear or branched alkylene chain that is halogenated at least once or contains one or more siloxane moieties; and

[0154] D' is a straight-chain or branched alkylene radical having 1-20 carbon atoms, preferably 1-12 carbon atoms, or a cycloalkyl radical having 5-6 ring atoms, optionally mono- or polysubstituted by alkyl, alkoxy (especially methyl or methoxy) or one or more siloxane moieties.

[0155] Particularly preferred are photo-aligned copolymer materials comprising repeating structural units of formula (I), wherein n, n', m and m' represent 0, M1 and S 1 and M 1’ and S 1’ As defined above; and

[0156] Rings C and C' each independently represent a phenylene group which is unsubstituted or optionally substituted by fluorine, chlorine, cyano, alkyl or alkoxy, or a 1,4- or 2,6-naphthylene group;

[0157] Z, Z' represents -O-; and

[0158] D is a C1-C3 linear or branched alkylene chain that is halogenated at least once or contains one or more siloxane moieties; and

[0159] D' is a straight-chain or branched alkylene radical having 1-12 carbon atoms, preferably 1-12 carbon atoms, or a cycloalkyl radical having 5-6 ring atoms, optionally mono- or polysubstituted by alkyl, alkoxy (especially methyl or methoxy) or one or more siloxane moieties.

[0160] Particularly preferred are photo-aligned copolymer materials comprising repeating structural units of formula (I), wherein n, n', m and m' represent 0, M 1 and S 1 and M 1’ and S 1’ As defined above; and

[0161] Rings C and C' each independently represent a phenylene group which is unsubstituted or optionally substituted by fluorine, chlorine, cyano or methoxy;

[0162] Z, Z' represents -O-; and

[0163] D is a C1-C3 linear or branched alkylene chain that is halogenated at least once or contains one or more siloxane moieties; and

[0164] D' is a straight-chain or branched alkylene radical having 1-12 carbon atoms, preferably 1-12 carbon atoms, or a cycloalkyl radical having 5-6 ring atoms, optionally mono- or polysubstituted by alkyl, alkoxy (especially methyl or methoxy) or one or more siloxane moieties.

[0165] Particularly preferred are photo-aligned copolymer materials comprising repeating structural units of formula (I), wherein n, n', m and m' represent 0, M 1 and S 1 and M 1’ and S 1’ As defined above; and

[0166] Rings C and C' each independently represent a phenylene group which is unsubstituted or optionally substituted by fluorine, chlorine, cyano or methoxy;

[0167] Z, Z' represents -O-; and

[0168] D is a C1-C3 linear or branched alkylene chain which is fluorinated at least once or contains one or more siloxane moieties; and

[0169] D' is a straight-chain or branched alkylene radical having 1-12 carbon atoms, preferably 1-12 carbon atoms, or a cycloalkyl radical having 5-6 ring atoms, optionally mono- or polysubstituted by alkyl, alkoxy (especially methyl or methoxy) or one or more siloxane moieties.

[0170] Homopolymeric materials comprising monomers of formula (II) are particularly preferred.

[0171] Preferred is a homopolymer photoalignment polymer material comprising a monomer of formula (II):

[0172]

[0173] in

[0174] M 1 、S 1 , Ring A, Ring B, Ring C, D, Z, Y 1 、Y 2 , m and n are as defined above.

[0175] Especially preferred are homopolymeric materials comprising repeating structural units of formula (II) wherein

[0176] M 1 、S 1 and m and n are as defined above; and

[0177] Ring A represents phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl, or cyclohexane-1,4-diyl, which is unsubstituted or optionally substituted by fluorine, chlorine, cyano, alkyl, or alkoxy;

[0178] Ring B represents phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl, 1,4- or 2,6-naphthylene or cyclohexane-1,4-diyl which is unsubstituted or optionally substituted by fluorine, chlorine, cyano, alkyl or alkoxy;

[0179] Y 1 、Y 2 Each independently represents a covalent single bond, -CH2CH2-, -O-, -CH2-O-, -O-CH2-, -CO-O-, -O-OC-, -CF2O- or -OCF2-;

[0180] Ring C represents phenylene, pyrimidine-2,5-diyl, pyridine-2,5-diyl, 2,5-furylene or 1,4- or 2,6-naphthylene which is unsubstituted or optionally substituted by fluorine, chlorine, cyano, alkyl or alkoxy;

[0181] Z means -O-, and

[0182] D is a C1-C3 linear or branched alkylene chain which is halogenated at least once or contains one or more siloxane moieties; more preferably the halogen is fluorine.

[0183] Particularly preferred are homopolymer compositions having repeating structural units of formula I, wherein n represents 0 and

[0184] M 1 and S 1 As defined above; and

[0185] Ring B represents phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl or cyclohexane-1,4-diyl which is unsubstituted or optionally substituted by fluorine, chlorine, cyano, alkyl or alkoxy;

[0186] Y 2 Represents a covalent single bond, -CO-O- or -O-OC-;

[0187] m represents 0 or 1;

[0188] Ring C represents a phenylene group which is unsubstituted or optionally substituted by fluorine, chlorine, cyano, alkyl or alkoxy, or a 1,4- or 2,6-naphthylene group;

[0189] Z means -O-, and

[0190] D is a C1-C3 linear or branched alkylene chain which is halogenated at least once or contains one or more siloxane moieties, in particular D is fluorinated at least once, more in particular D is a fluorinated C2 alkylene chain, even more in particular D is 2,2,2-trifluoro-ethyl.

[0191] Especially preferred are homopolymer compositions having repeating structural units of formula I, wherein n represents 0 and

[0192] M 1 and S 1 As defined above; and

[0193] Ring B represents phenylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl or cyclohexane-1,4-diyl which is unsubstituted or optionally substituted by fluorine, chlorine, cyano, alkyl or alkoxy;

[0194] Y 2 Represents a covalent single bond, -CO-O- or -O-OC-;

[0195] m represents 0 or 1;

[0196] Ring C represents a phenylene group which is unsubstituted or optionally substituted by fluorine, chlorine, cyano or methoxy;

[0197] Z means -O-, and

[0198] D is a C1-C3 linear or branched alkylene chain which is optionally halogenated at least once or contains one or more siloxane moieties, in particular D is fluorinated at least once, more in particular D is a fluorinated C2 alkylene chain, even more in particular D is 2,2,2-trifluoro-ethyl.

[0199] Especially preferred are homopolymer compositions having repeating structural units of formula I, wherein n and m represent 0 and

[0200] M 1 and S 1 As defined above; and

[0201] Ring C represents a phenylene group which is unsubstituted or optionally substituted by fluorine, chlorine, cyano, alkyl or alkoxy, or a 1,4- or 2,6-naphthylene group;

[0202] Z means -O-, and

[0203] D is a C1-C3 linear or branched alkylene chain which is halogenated at least once or contains one or more siloxane moieties, in particular D is fluorinated at least once, more in particular D is a fluorinated C2 alkylene chain, even more in particular D is 2,2,2-trifluoro-ethyl.

[0204] Especially preferred are homopolymer compositions having repeating structural units of formula I, wherein n and m represent 0 and

[0205] M 1 and S 1 As defined above; and

[0206] Ring C represents a phenylene group which is unsubstituted or optionally substituted by fluorine, chlorine, cyano or methoxy;

[0207] Z means -O-, and

[0208] D is a C1-C3 linear or branched alkylene chain which is halogenated at least once or contains one or more siloxane moieties, in particular D is fluorinated at least once, more in particular D is a fluorinated C2 alkylene chain, even more in particular D is 2,2,2-trifluoro-ethyl.

[0209] The photo-aligned polymer material comprising the repeating structural unit of formula (I) or the monomer of formula (II) is characterized by being easily obtainable. The method for preparing the photo-aligned polymer material of the present invention is known to those skilled in the art.

[0210] The present invention relates to a method for preparing a photo-aligned polymer material comprising a repeating structural unit of formula (I) or a monomer of formula (II), which comprises polymerizing the repeating structural unit.

[0211] Photoalignable polymer materials comprising repeating structural units of formula (I) or monomers of formula (II) can in principle be prepared according to two different methods. In addition to the direct polymerization of preformed monomers, there is the possibility of polymer-analogous reactions of reactive cinnamic acid derivatives with functional polymers.

[0212] For direct polymerization, the repeating structural units of formula (I) or the monomers of formula (II) are first prepared from the individual components. The formation of the polymer is then achieved in a manner known per se under the influence of UV radiation or heat or by the action of free radical initiators or inorganic or organic peroxides or ionic initiators. The free radical initiators may be azos, for example azobisisobutyronitrile (AIBN), azobismethylbutyronitrile (AMBN), 2,2'-azo(2-methylpropylamidine) dihydrochloride (AAPH), 1,1'-azobis(cyanocyclohexane) (ACHN), 4,4'-azobis(4-cyanovaleric acid) (ACVA) and similar compounds. Examples of inorganic peroxides are sodium persulfate, potassium persulfate or ammonium persulfate. Examples of organic peroxides are tert-butyl peroxide, dicumyl peroxide, lauroyl peroxide or peroxycarbonate. Examples of commercially available peroxides are (but are not limited to) LP (lauroyl peroxide), D1 (di-tert-butyl peroxide) or IPP (diisopropyl peroxydicarbonate). Ionic initiators are basic organic compounds, such as phenyllithium or sodium naphthyl, or Lewis acids, such as BF3, AlCl3, SnCl3, or TiCl4. This list is not exhaustive, and other initiators are contemplated within the context of the present invention. The monomers can be polymerized, but are not limited to, in solution, suspension, emulsion, or by precipitation polymerization.

[0213] The solvents used in the preparation of the polymers of the present invention are as defined above.

[0214] In a second approach, photoaligned polymer materials comprising repeating structural units of formula (I) or monomers of formula (II) can also be prepared in a polymer-analogous reaction of a preformed functional polymer with a suitable functionalized cinnamic acid derivative. Various known methods, such as esterification, transesterification, amidation or etherification, are suitable for the polymer-analogous reaction.

[0215] It has been found that the etherification of hydroxycinnamic acid derivatives in solution with polyhydroxyalkyl acrylates or polyhydroxyalkyl methacrylates under the conditions of the Mitsunobu reaction is advantageous. Thus, the reaction can be carried out in such a way that, for example, all hydroxyl groups react (homopolymers) or hydroxyl groups remain free on the polymer after the reaction, which can then be further functionalized in further polymer-like reactions, meaning that copolymers can be synthesized. Another possible approach for preparing copolymers according to the described method involves using mixtures of different cinnamic acid derivatives.

[0216] Cinnamic acid is partially commercially available or can be obtained by methods known in the literature, for example from commercially available aldehydes or from the Knoevenagel reaction or Wittig reaction of cyano compounds obtained by prior reduction to the corresponding aldehydes. Cinnamic esters or amides can subsequently be prepared from cinnamic acid by known esterification methods.

[0217] The photo-alignable polymer material comprising the repeating structural unit of formula (I) or the monomer of formula (II) is usually used in the form of a composition, especially a formulation or a blend.

[0218] The present invention therefore further comprises a composition comprising a photoalignable polymer material comprising repeating structural units of formula (I) or monomers of formula (II), and optionally a solvent within the meanings and preferred ranges given above for the solvent, and further optionally further additives or compounds, for example:

[0219] - silane-containing compounds, or / and

[0220] - epoxy-containing crosslinking agent, or / and

[0221] - photoactive additives, such as photosensitizers or photoradical generators, or / and

[0222] - cationic photoinitiator, or / and

[0223] - surfactants, or / and

[0224] - emulsifier, or / and

[0225] - antioxidants, or / and

[0226] - Leveling agent, or / and

[0227] - polymerizable liquid crystal, or / and

[0228] - Curable compounds.

[0229] Suitable silane-containing additives are described in Plast. Eng. 36 (1996), (Polyimides, fundamentals and applications), Marcel Dekker.

[0230] Suitable epoxy-containing crosslinking additives include 4,4′-methylene-bis-(N,N-diglycidylaniline), trimethylolpropane triglycidyl ether, benzene-1,2,4,5-tetracarboxylic acid 1,2,4,5-N,N′-diglycidyl diimide, polyethylene glycol diglycidyl ether, N,N-diglycidylcyclohexylamine, and the like.

[0231] Suitable photoactive additives include 2,2-dimethoxyphenyl acetone, mixtures of diphenyl ketone with N,N-dimethylaniline or ethyl 4-(dimethylamino)benzoate, xanthone, thioxanthone, 184, 369, 500, 651 and 907 (BASF), Michler's ketone, triarylsulfonium salts, etc.

[0232] Curable compounds are organic and inorganic compounds, and they do not include any photo-alignable portions. Curable compounds are used to flatten the surface or carrier to reduce surface unevenness, so that the surface or carrier is harder, more scratch-resistant, or more resistant to mechanical or chemical wear. Such curable compounds include polymers, dendrimers, oligomers, prepolymers, and monomers, which can be polymerized by radiation or by heat. Examples of suitable polymer classes are (but are not limited to): polyolefins (e.g., polyethylene, polypropylene), polycycloolefins COP / COC, polybutadiene, poly(meth)acrylates, polyesters, polystyrene, polyamides, polyethers, polyurethanes, polyimides, polyamic acid, polycarbonates, polyvinyl alcohol, polyvinyl chloride, cellulose, and cellulose derivatives (e.g., cellulose triacetate). Examples of suitable monomer classes are: monofunctional and multifunctional (meth)acrylates, epoxy resins, isocyanates, allyl derivatives, and vinyl ethers.

[0233] The present invention contemplates that the curable compound may be added to a composition comprising a photo-alignable polymeric material comprising repeating structural units of formula (I) or monomers of formula (II). It is also contemplated that the curable compound may be added as a layer below or above the alignment layer of the present invention.

[0234] The present invention also relates to the use of a photoalignment polymer material comprising a repeating structural unit of formula (I) or a monomer of formula (II) as an alignment layer for liquid crystals.

[0235] In addition, the present invention relates to a method for preparing an alignment layer for liquid crystals, which comprises irradiating a photo-aligned polymer material containing a repeating structural unit of formula (I) or a monomer of formula (II) or a composition containing a photo-aligned polymer material containing a repeating structural unit of formula (I) or a monomer of formula (II) with alignment light.

[0236] Preferably, the method comprises:

[0237] - applying a composition comprising a photoalignable polymer material comprising repeating structural units of formula (I) or monomers of formula (II) within the meanings and preferences as described above to a support,

[0238] - and irradiating the photo-alignable polymer material comprising the repeating structural unit of formula (I) or the monomer of formula (II) or the composition comprising the photo-alignable polymer material comprising the repeating structural unit of formula (I) or the monomer of formula (II) with aligning light.

[0239] Particularly preferred is a method in which two irradiation processes are carried out, one with aligning light and another with or without aligning light, for example isotropic light.

[0240] The term "support" as used in the context of the present invention is preferably transparent or opaque, birefringent or non-birefringent, preferably a glass or plastic substrate, a polymer film, such as polyethylene naphthalate (PEN), polyethylene terephthalate (PET), triacetyl cellulose (TAC), polypropylene, polycarbonate (PC), polymethyl methacrylate (PMMA), cyclic olefin copolymer (COP) or a silicon wafer, but is not limited thereto. The support can be rigid or flexible and in any form or shape, such as concave or convex. The support can have other layers, such as organic, dielectric or metallic layers. These layers can have different functions, for example, an organic layer can be coated as a primer layer, which increases the compatibility of the material to be coated with the support. A metal layer (such as indium tin oxide (ITO)) can be used as an electrode (for example, when used in an electro-optical device such as a display) or can act as a reflector. The support can also be an optical element or device with certain functions, such as a substrate for an LCD, which may, for example, contain thin film transistors, electrodes or color filters. In another example, the support is a device comprising an OLED layer structure. The support may also be a retarder film, a polarizer, such as a polarizing film or sheet polarizer, a reflective polarizer, such as the commercially available Vikuity™ DBEF film, but is not limited thereto.

[0241] Typically, the composition is applied by conventional coating and printing methods known in the art. Coating methods are, for example, spin coating, air knife coating, blade coating, doctor blade coating, contact roll coating, cast coating, slot coating, calendar coating, die coating, dip coating, brush coating, rod casting, roller coating, flow coating, wire coating, spray coating, dip coating, spin coating, cascade coating, curtain coating, air knife coating, gap coating, drum screen, reverse roll coating, gravure coating, metering rod (Meyerbar) coating, slot die (extrusion) coating, hot melt coating, roller coating, flexographic coating, electrodeposition coating.

[0242] The printing method is, for example, screen printing, relief printing such as flexographic printing, inkjet printing, gravure printing such as direct gravure printing or offset gravure printing, planographic printing such as offset printing, or stencil printing such as screen printing.

[0243] The support may be moved during deposition of the photo-alignable polymeric material or the composition comprising the photo-alignable polymeric material and / or the photo-alignable material, for example when the production is performed in a continuous roll-to-roll process.

[0244] In the context of the present invention, the term "aligning light" shall mean light that can induce anisotropy in the photo-alignable material and that is at least partially linearly or elliptically polarized and / or incident on the surface of the alignment layer from an oblique direction. Preferably, the degree of polarization of the linear polarization of the aligning light is greater than 5:1. The wavelength, intensity, and energy of the aligning light are selected based on the photosensitivity of the photo-alignable material and the photo-aligning group.

[0245] Typically, the wavelength is in the UV-A, UV-B and / or UV-C range or in the visible light range. Preferably, the aligning light comprises light with a wavelength of less than 450 nm. More preferably, the aligning light comprises light with a wavelength of less than 420 nm.

[0246] UV light is preferably selected based on the absorption of the photoalignment groups, i.e., the absorption of the film should overlap with the emission spectrum of the lamp used for LP-UV irradiation, and linearly polarized UV light is more preferably used. The intensity and energy are selected based on the photosensitivity of the material and the target orientation properties. In most cases, very low energy (a few mJ / cm 2 ) has produced high orientation quality.

[0247] More preferably, "aligning light" is at least partially linearly polarized, elliptically polarized (e.g., circularly polarized), or unpolarized, most preferably circularly polarized, or unpolarized light exposed obliquely, or at least partially linearly polarized light. In particular, it is most preferred that the aligning light refers to substantially polarized light, especially linearly polarized light; or the aligning light refers to unpolarized light applied by oblique illumination.

[0248] If the aligning light is linearly polarized, the polarization plane of the aligning light shall mean the plane defined by the propagation direction and polarization direction of the aligning light. If the aligning light is elliptically polarized, the polarization plane shall mean the plane defined by the propagation direction of the light and the major axis of the polarization ellipse.

[0249] More preferably, the aligning light is UV light, preferably linearly polarized UV light.

[0250] Therefore, when preparing an alignment layer in an area where selectivity is limited due to area, a solution of the photoaligned polymer material of the present invention can be applied. For example, it is first generated and can be spun onto a support optionally coated with an electrode (e.g., a glass plate coated with indium tin oxide, ITO) in a spin coating apparatus to produce a uniform layer with a thickness of 0.05-50 μm. Subsequently, using a polarizer and an optional mask, the area to be aligned is exposed to, for example, a mercury high-pressure lamp, a xenon lamp, or a pulsed UV laser to form a structure. The duration of the exposure depends on the output of each lamp and can vary from a few minutes to several hours. However, the photoreaction can also be achieved by irradiating the uniform layer using, for example, a filter that only allows radiation suitable for the photoreaction to pass.

[0251] A preferred method of the present invention relates to a method for producing an alignment layer, wherein time is a critical parameter, in particular wherein irradiation time is a critical parameter, such as in particular for a roll-to-roll process.

[0252] The present invention also relates to an alignment layer comprising a photo-aligned polymer material comprising a repeating structural unit of formula (I) or a monomer of formula (II) or a composition comprising the photo-aligned polymer material.

[0253] The use of the photoaligned polymer materials of the invention as alignment layers for liquid crystals and their use in unstructured and structured optical and electro-optical components, in particular for the production of hybrid layer elements, is also an object of the present invention.

[0254] The term "structuring" refers to a change in azimuthal orientation caused by a local change in the direction of polarized aligned light.

[0255] In addition, the present invention relates to an optical, electro-optical or nanoelectronic component or a multilayer system comprising a photoaligned polymer material comprising repeating structural elements of formula (I) or a monomer of formula (II) or / and a composition comprising a photoaligned polymer material comprising repeating structural elements of formula (I) or a monomer of formula (II) or / and an alignment layer prepared by using a photoaligned polymer material comprising repeating structural elements of formula (I) or a monomer of formula (II).

[0256] Such optical, electro-optical, multilayer systems or nanoelectronic components are also referred to as photo-alignable objects. Such photo-alignable objects have been described in the unpublished application EP16182085.7 and the published application WO2015 / 024810, which are incorporated herein by reference.

[0257] Furthermore, the present invention relates to the use of the photo-aligned polymer material of the present invention as an alignment layer for aligning organic or inorganic compounds, in particular for aligning liquid crystals and liquid crystal polymers.

[0258] The present invention also relates to the use of the alignment layer according to the invention for producing optical or electro-optical components and systems (in particular multilayer systems) or devices: display waveguides, security or trademark protection elements, bar codes, gratings, filters, retarders (e.g. 3D retarder films), compensation films, reflective polarizing films, absorbing polarizing films, anisotropic scattering films, compensators and retardation films, twisted retarder films, cholesteric liquid crystal films, guest-host liquid crystal films, monomeric corrugated films, smectic liquid crystal films, polarizers, piezoelectric cells, films exhibiting nonlinear optical properties, decorative optical elements, brightness enhancing films, components for wavelength-band selective compensation, components for multi-zone compensation, components for multi-view liquid crystal displays, achromatic retarders, polarization state correction / adjustment films, variable transmission films, optical or electro-optical Components of sensors, components of brightness enhancement films, components of light-based telecommunication devices, G / H polarizers with anisotropic absorbers, reflective circular polarizers, reflective linear polarizers, monomeric corrugated films (MC), liquid crystal displays, in particular twisted nematic (TN) liquid crystal displays, hybrid aligned nematic (HAN) liquid crystal displays, electrically controlled birefringence (ECB) liquid crystal displays, super twisted nematic (STN) liquid crystal displays, optically compensated birefringence (OCB) liquid crystal displays, pi-cell liquid crystal displays, in-plane switching (IPS) liquid crystal displays, fringe field switching (FFS) liquid crystal displays, vertically aligned (VA) liquid crystal displays; all of the above display types are used in transmission, reflection or transflective mode.

[0259] Optical or electro-optical components and systems (especially multilayer systems) and devices can be patterned or unpatterned.

[0260] The term "patterning" preferably means birefringence patterning and / or thickness patterning and / or optical axis orientation patterning and / or patterning of the degree of polymerization. Birefringence means the difference between the extraordinary refractive index and the ordinary refractive index.

[0261] Therefore, the present invention further relates to optical or electro-optical components, systems and devices comprising a photoalignable polymer material within the meanings and preferences given above or a composition comprising said photoalignable polymer material.

[0262] Preferred are optical or electro-optical elements, systems and devices comprising an alignment layer according to the invention and at least one orientable layer, such as a liquid crystal layer or a liquid crystal polymer layer.

[0263] Optical components, systems, or devices create, manipulate, or measure electromagnetic radiation.

[0264] Electro-optical elements, systems, or devices operate by modifying the optical properties of a material through an electric field. Therefore, it focuses on the interaction between the electromagnetic (optical) state and the electrical (electronic) state of a material.

[0265] The alignment layer has the ability to align a slave material (eg, liquid crystal, such as nematic liquid crystal) with its long axis along a preferred direction.

[0266] The present invention also relates to the use of the alignment layer of the present invention for aligning a subordinate material. "Subordinate material" shall mean any material that has the ability to establish anisotropy when in contact with a photo-aligned material. The nature of the anisotropy in the photo-aligned material and the subordinate material may be different from each other. An example of a subordinate material is a liquid crystal. Such a subordinate material is applied above the alignment layer. The subordinate material can be applied by coating and / or printing with or without a solvent and can be applied to the entire alignment layer or only to a portion thereof. The subordinate material can be polymerized by heat treatment or exposure to actinic light. The polymerization can be carried out under an inert atmosphere (e.g. nitrogen) or under vacuum. The subordinate material may further contain isotropic or anisotropic dyes and / or fluorescent dyes.

[0267] The slave material may comprise polymerizable and / or non-polymerizable compounds. In the context of the present invention, the terms "polymerizable" and "polymerized" shall include the meanings of "cross-linkable" and "cross-linked", respectively. Likewise, "polymerization" shall include the meaning of "cross-linking".

[0268] As used in the context of this application, liquid crystal polymer (LCP) material shall mean a liquid crystal material comprising liquid crystal monomers and / or liquid crystal oligomers and / or liquid crystal polymers and / or cross-linked liquid crystals. Where the liquid crystal material comprises liquid crystal monomers, such monomers may be polymerized, typically after anisotropy has been generated in the LCP material due to contact with a photo-aligned polymer material in a composition comprising the photo-aligned polymer material of the present invention. Polymerization may be initiated by heat treatment or by exposure to actinic light (preferably including ultraviolet light). LCP materials may consist of a single type of liquid crystal compound, but may also be a composition of different polymerizable and / or non-polymerizable compounds, not all of which are necessarily liquid crystal compounds. In addition, LCP materials may contain additives such as photoinitiators or isotropic or anisotropic fluorescent and / or non-fluorescent dyes.

[0269] The term "anisotropy" refers to a property that is directionally dependent. Anisotropic substances exhibit different or varying characteristics in different directions. These terms may refer, for example, to light absorption, birefringence, electrical conductivity, molecular orientation, alignment properties of other materials (e.g., liquid crystals), or mechanical properties such as elastic modulus. In the context of this application, the term "alignment direction" shall refer to the axis of symmetry of the anisotropic property.

[0270] Preferably, the method is used to induce planar alignment, tilted alignment or vertical alignment in adjacent liquid crystal layers; more preferably, the method is used to induce planar alignment or vertical alignment in adjacent liquid crystal layers.

[0271] It was unexpectedly found in the present invention that the photo-aligned polymer material comprising a repeating structural unit of formula (I) or a monomer of formula (II) of the present invention has rapid orientation, and therefore can use an efficient manufacturing method, such as a roll-to-roll method in particular. The material shows good orientation properties, such as high contrast. It also allows a short irradiation time when aligned at very low energy. Advantageously, it was found that these materials can be coated on several substrates, such as glass or flexible substrates, such as PET or TAC, and the application possibilities are greatly expanded. It was also found that the photo-aligned material of the present invention has excellent compatibility with various solvents, thereby allowing the coating and printing methods to be highly flexible. The novel photo-aligned polymer material exhibits extremely high compatibility with organic materials (such as curable compositions or polymerizable liquid crystals) that can be used in various optical elements or electro-optical elements, such as security devices, liquid crystal devices (LCDs), optical films, such as retarders (such as 3D retarders) and nanoelectronic devices.

[0272] Furthermore, the photo-aligned polymeric materials of the present invention show substantially better liquid crystal alignment. Example

[0273] The polymers of the present invention are illustrated in more detail by the following examples.

[0274] Example 1: Synthesis of Compound 1

[0275] Preparation of 6-[4-[(E)-3-oxo-3-(2,2,2-trifluoroethoxy)prop-1-enyl]phenoxy]hexyl 2-methylprop-2-enoate

[0276]

[0277] 400.1g of 4-hydroxybenzaldehyde, 588.4g of potassium carbonate (powder), 40.0g of potassium iodide and 0.4g of phenothiazine were suspended in 1600g of DMF. 710.7g of 6-chlorohexyl 2-methylprop-2-enoate was added to the suspension. The resulting mixture was then heated to 85°C under a nitrogen atmosphere. After 18 hours at 85°C, the reaction mixture was cooled to 20°C and filtered through Hyflo. The remaining solid was washed with 400g of DMF. The resulting DMF solution was transferred to a reactor. 0.6g of phenothiazine, 0.6g of BHT, 727.98g of 1-(2,2,2-trifluoroethyl) malonate in 250g of DMF and 114g of morpholine were added to the solution. The reaction mixture was then stirred at 50°C under nitrogen. After 6 hours, the reaction was cooled to room temperature and isopropyl alcohol was then added. Water was then added dropwise to precipitate the product from the orange solution. After filtration and washing, 1080 g of compound 2 was obtained as a white solid with an HPLC purity of >97%.

[0278] 1H NMR (300 MHz) of compound 2 in CDCI 3 : 7.75 (d, 1H), 7.51 (d, 2H), 6.91 (d, 2H), 6.35 (d, 1H), 6.1 1 (m, 1H), 5.56 (m, 1H), 4.60 (dd, 2H), 4.18 (t, 2H), 4.02 (t, 2H), 1.96 (m, 3H), 1.84 (m, 2H), 1.74 (m, 2H), 1.51 (m, 4H).

[0279] Example 2: Synthesis of Compound 2

[0280] Preparation of 6-[2-methoxy-4-[(E)-3-oxo-3-(2,2,2-trifluoroethoxy)prop-1-enyl]phenoxy]hexyl 2-methylprop-2-enoate

[0281]

[0282] Analogously to the previous example, 6-chlorohexyl 2-methylprop-2-enoate was condensed with vanillin and then with 1-(2,2,2-trifluoroethyl)malonate, resulting in the synthesis of compound 2 in 78% yield with HPLC purity >97%.

[0283] 1H NMR (300 MHz) of compound 3 in DMSO-d6: 7.70 (d, 1H), 7.42 (d, 1H), 7.26 (d, 1H), 6.98 (d, 1H), 6.68 (d, 1H), 6.02 (m, 1H), 5.66 (m, 1H), 4.85 (dd, 2H), 4.10 (t, 2H), 4.03 (t, 2H), 3.81 (s, 3H), 1.88 (m, 3H), 1.72 (m, 2H), 1.64 (m, 2H), 1.43 (m, 4H).

[0284] Example 3: Synthesis of Compound 3

[0285] Preparation of 8-[2-methoxy-4-[(E)-3-oxo-3-(2,2,2-trifluoroethoxy)prop-1-enyl]phenoxy]octyl 2-methylprop-2-enoate

[0286]

[0287] Analogously to Examples 1 and 2, 8-chlorooctyl 2-methylprop-2-enoate was condensed with 4-hydroxybenzaldehyde and then with 1-(2,2,2-trifluoroethyl)malonate, resulting in the synthesis of compound 3 in 70% yield with HPLC purity >97%.

[0288] 1H NMR (300 MHz) of compound 4 in CDCI3: 7.73 (d, 1H), 7.47 (d, 2H), 6.91 (d, 2H), 6.35 (d, 1H), 6.09 (m, 1H), 5.56 (m, 1H), 4.57 (dd, 2H), 4.14 (t, 2H), 3.98 (t, 2H), 1.94 (m, 3H), 1.77 (m, 2H), 1.68 (m, 2H), 1.45 (m, 8H).

[0289] Example 4: Synthesis of Compound 4

[0290] Preparation of 8-[2-methoxy-4-[(E)-3-oxo-3-(2,2,2-trifluoroethoxy)prop-1-enyl]phenoxy]octyl 2-methylprop-2-enoate

[0291]

[0292] As described for compound 2, 8-chlorooctyl 2-methylprop-2-enoate was condensed with vanillin and then with 1-(2,2,2-trifluoroethyl)malonate to afford compound 4 in 60% yield with HPLC purity >95%.

[0293] 1H NMR (300 MHz) of compound 5 in DMSO-d6: 7.70 (d, 1H), 7.42 (d, 1H), 7.30 (d, 1H), 7.00 (d, 1H), 6.70 (d, 1H), 6.01 (m, 1H), 5.66 (m, 1H), 4.85 (dd, 2H), 4.10 (t, 2H), 3.99 (t, 2H), 3.80 (s, 3H), 1.87 (m, 3H), 1.72 (m, 2H), 1.61 (m, 2H), 1.33 (m, 8H).

[0294] Example 5: Synthesis of Compound 5

[0295] Preparation of 4-(6-prop-2-enoyloxyhexyloxy)benzoic acid [2-methoxy-4-[(E)-3-oxo-3-(2,2,2-trifluoroethoxy)-prop-1-enyl]phenyl] ester

[0296]

[0297] As described for compound 2, 8-chlorooctyl 2-methylprop-2-enoate was condensed with (4-formyl-2-methoxy-phenyl) 4-hydroxybenzoate and then with 1-(2,2,2-trifluoroethyl) malonate to afford compound 5 in 76% yield with HPLC purity >93%.

[0298] 1H NMR (300 MHz) of compound 6 in DMSO-d6: 8.06 (d, 2H), 7.83 (d, 1H), 7.78 (s, 1H), 7.40 (d, 1H), 7.30 (d, 1H), 7.11 (d, 2H), 6.90 (d, 1H), 6.30 (d, 1H), 6.20 (dd, 1H), 5.95 (d, 1H), 4.90 (dd, 2H), 4.10 (m, 4H), 3.83 (s, 3H), 1.77 (m, 2H), 1.65 (m, 2H), 1.44 (m, 4H).

[0299] Example 6: Synthesis of poly 2-methylprop-2-enoic acid-6-[4-[(E)-3-oxo-3-(2,2,2-trifluoroethoxy)prop-1-enyl]phenoxy]hexyl ester:

[0300]

[0301] 25 g of the monomer compound 1 synthesized as in Example 1 was dissolved in cyclohexanone (CHN) under stirring in a nitrogen atmosphere. The reaction mixture was then heated to 75° C., and 0.4 g of LP (lauryl peroxide). The reaction mixture was then maintained at 75°C for 5 hours, and then the temperature was raised to 100°C. After 1 hour at 100°C, the reaction mixture was cooled to room temperature and then filtered to obtain a polymer in CHN solution (Mw = 151,000 and Mn = 41,800). The photoaligned polymer material was designated PAM1.

[0302] Example 7: Synthesis of a copolymer of 6-[4-[(E)-3-oxo-3-(2,2,2-trifluoroethoxy)prop-1-enyl]phenoxy]hexyl 2-methylprop-2-enoate and 6-[4-[(E)-3-methoxy-3-oxo-prop-1-enyl]phenoxyhexyl 2-methylprop-2-enoate

[0303]

[0304] According to the method described for Example 1, 14 g of compound 1, 11 g of 2-methylprop-2-enoic acid 6-[4-[(E)-3-methoxy-3-oxo-prop-1-enyl]phenoxyhexyl ester in 100 g of CHN, and 0.4 g of LP, preparation of copolymer. This copolymer was obtained in CHN solution (Mw=123200 and Mn=39500). The photoaligned polymer material is called PAM2.

[0305] Example 8: Synthesis of comparative photoalignment polymers

[0306] As described in patent application WO 2012 / 085048 A1 , a photoaligned polymer material 3 (PAM3) was synthesized.

[0307]

[0308] As described in Example A4 of patent application WO 2015 / 024810 A1, a photoaligned polymer material 4 (PAM4) was synthesized.

[0309]

[0310] As described in patent application JP2005-326439A, a photo-aligned polymer material 5 (PAM5) was synthesized.

[0311]

[0312] Photoaligned polymer material 6 (PAM6) was synthesized in a similar manner as described in Example 2 of patent application WO 2012 / 085048 A1.

[0313]

[0314] Example 9: Synthesis of poly 2-methylprop-2-enoic acid 6-[2-methoxy-4-[(E)-3-oxo-3-(2,2,2-trifluoroethoxy)prop-1-enyl]phenoxy]hexyl ester

[0315]

[0316] A polymer (Mw=160700 and Mn=59500) was obtained in a CHN solution by using monomer compound 2 according to the method described for Example 6. The photoaligned polymer material was named PAM7.

[0317] Example 10: Synthesis of poly 2-methylprop-2-enoic acid 8-[2-methoxy-4-[(E)-3-oxo-3-(2,2,2-trifluoroethoxy)prop-1-enyl]phenoxy]octyl ester

[0318]

[0319] A polymer (Mw=131600 and Mn=53200) was obtained in a CHN solution by using monomer compound 3 according to the method described for Example 6. The photoaligned polymer material was named PAM8.

[0320] Example 11: Synthesis of poly 2-methylprop-2-enoic acid 8-[2-methoxy-4-[(E)-3-oxo-3-(2,2,2-trifluoroethoxy)prop-1-enyl]phenoxy]octyl ester

[0321]

[0322] A polymer (Mw=212100 and Mn=66100) was obtained in a CHN solution by using monomer compound 4 according to the method described for Example 6. The photoaligned polymer material was named PAM9.

[0323] Example 12: Synthesis of poly (2-methoxy-4-[(E)-3-oxo-3-(2,2,2-trifluoroethoxy)prop-1-enyl]phenyl) 4-(6-prop-2-enoyloxyhexyloxy)benzoate

[0324]

[0325] The polymer (Mw=228000 and Mn=32900) was obtained in CHN solution by using monomer compound 5 according to the method described for Example 6. The photoaligned polymer material was named PAM10.

[0326] Example 13: Preparation of Photoalignment Composition 1 (PAC1)

[0327] Solution PAC1 was prepared by adding 3 wt % of the photoalignment material PAM1 in 97 wt % of methoxypropyl acetate, and stirring the mixture at room temperature for 30 minutes.

[0328] Example 14: Preparation of Photoalignment Composition 2 (PAC2)

[0329] Solution PAC2 was prepared by adding 3 wt % of the photoalignment material PAM3 in 97 wt % of methoxypropyl acetate and stirring the mixture at room temperature for 30 minutes.

[0330] Example 15: Preparation of Photoalignment Composition 3 (PAC3)

[0331] Solution PAC3 was prepared by adding 2 wt % of the photoalignment material PAM6 in 98 wt % of methoxypropyl acetate and stirring the mixture at room temperature for 30 minutes.

[0332] Example 16: Preparation of Photoalignment Composition 4 (PAC4)

[0333] Solution PAC4 was prepared by adding 3 wt % of the photoalignment material PAM4 in 97 wt % of methoxypropyl acetate, and stirring the mixture at room temperature for 30 minutes.

[0334] Example 17: Preparation of Photoalignment Composition 5 (PAC5)

[0335] Solution PAC5 was prepared by adding 3 wt % of the photoalignment material PAM5 in 97 wt % of methoxypropyl acetate, and stirring the mixture at room temperature for 30 minutes.

[0336] Example 18: Preparation of Photoalignment Composition 6 (PAC6)

[0337] Solution PAC6 was prepared by adding 3 wt % of the photoalignment material PAM7 in 97 wt % of methoxypropyl acetate and stirring the mixture at room temperature for 30 minutes.

[0338] Example 19: Preparation of Photoalignment Composition 7 (PAC7)

[0339] Solution PAC7 was prepared by adding 3 wt % of the photoalignment material PAM8 in 97 wt % of methoxypropyl acetate, and stirring the mixture at room temperature for 30 minutes.

[0340] Example 20: Preparation of Photoalignment Composition 8 (PAC8)

[0341] Solution PAC8 was prepared by adding 3 wt % of the photoalignment material PAM9 in 97 wt % of methoxypropyl acetate and stirring the mixture at room temperature for 30 minutes.

[0342] Example 21: Preparation of Photoalignment Composition 9 (PAC9)

[0343] Solution PAC9 was prepared by adding 3 wt % of the photoalignment material PAM10 in 97 wt % of methoxypropyl acetate, and stirring the mixture at room temperature for 30 minutes.

[0344] Examples 22-33: Preparation of Photo-Orientable Materials

[0345] The following curable compositions were prepared.

[0346] Curable composition 1 (CC1) was prepared by mixing 20 wt% of the following in n-butyl acetate (BA):

[0347] 55.95%Laromer 9050 (BASF)

[0348] 37.90% 1,6-Hexanediol diacrylate (Sigma Aldrich)

[0349] 5.05% Irgacure 907 (BASF)

[0350] 1.00% Tinuvin 144 (BASF)

[0351] 0.10% BHT (Sigma Aldrich),

[0352] and stirred at room temperature for 30 minutes.

[0353] Curable composition 2 (CC2) was prepared by mixing 20 wt% of OC-4021 (DYMAX) in n-butyl acetate (BA) and stirring at room temperature for 30 minutes.

[0354] Example 22: Preparation of Photo-Orientable Material 1 (POM1)

[0355] The photoalignment solution POM1 was prepared by mixing 1 wt % of the photoalignment material PAM1 in CC1 and stirring the mixture at room temperature for 30 minutes.

[0356] Example 23: Preparation of Photo-Orientable Material 2 (POM2)

[0357] The photoalignment solution POM2 was prepared by mixing 1 wt % of the photoalignment material PAM5 in CC1 and stirring the mixture at room temperature for 30 minutes.

[0358] Example 24: Preparation of Photo-Orientable Material 3 (POM3)

[0359] The photoalignment solution POM3 was prepared by mixing 1 wt % of the photoalignment material PAM4 in CC1 and stirring the mixture at room temperature for 30 minutes.

[0360] Example 25: Preparation of Photo-Orientable Material 4 (POM4)

[0361] The photoalignment solution POM4 was prepared by mixing 1 wt % of the photoalignment material PAM2 in CC1 and stirring the mixture at room temperature for 30 minutes.

[0362] Example 26: Preparation of Photo-Orientable Material 5 (POM5)

[0363] The photoalignment solution POM5 was prepared by mixing 1 wt % of the photoalignment material PAM1 in CC2 and stirring the mixture at room temperature for 30 minutes.

[0364] Example 27: Preparation of Photo-Orientable Material 6 (POM6)

[0365] The photoalignment solution POM6 was prepared by mixing 1 wt % of the photoalignment material PAM4 in CC2 and stirring the mixture at room temperature for 30 minutes.

[0366] Example 28: Preparation of Photo-Orientable Material 7 (POM7)

[0367] The photoalignment solution POM7 was prepared by mixing 1 wt % of the photoalignment material PAM8 in CC2 and stirring the mixture at room temperature for 30 minutes.

[0368] Example 29: Preparation of Photo-Orientable Material 8 (POM8)

[0369] The photoalignment solution POM8 was prepared by mixing 1 wt % of the photoalignment material PAM7 in CC2 and stirring the mixture at room temperature for 30 minutes.

[0370] Example 30: Preparation of Photo-Orientable Material 9 (POM9)

[0371] The photoalignment solution POM9 was prepared by mixing 2 wt % of the photoalignment material PAM7 in CC2 and stirring the mixture at room temperature for 30 minutes.

[0372] Example 31: Preparation of Photo-Orientable Material 10 (POM10)

[0373] The photoalignment solution POM10 was prepared by mixing 1 wt % of the photoalignment material PAM9 in CC2 and stirring the mixture at room temperature for 30 minutes.

[0374] Example 32: Preparation of Photo-Orientable Material 11 (POM11)

[0375] The photoalignment solution POM11 was prepared by mixing 2 wt % of the photoalignment material PAM9 in CC2 and stirring the mixture at room temperature for 30 minutes.

[0376] Example 33: Preparation of Photo-Orientable Material 12 (POM12)

[0377] The photoalignment solution POM12 was prepared by mixing 1 wt % of the photoalignment material PAM10 in CC2 and stirring the mixture at room temperature for 30 minutes.

[0378] Examples 34-40: Preparation of compositions comprising a polymerizable liquid crystal and a photo-alignable material (PLCPO-M1 to PCLPO-M7).

[0379] All compositions contain:

[0380]

[0381] LCC2:

[0382] Glutaric acid O5-[4-[3-methyl-4-[4-[5-oxo-5-(2-prop-2-enoyloxyethoxy)pentanoyl]oxybenzoyl]oxy-phenoxy]carbonylphenyl]O1-(2-prop-2-enoyloxyethyl) ester

[0383]

[0384] Example 34: PLCPO-M1 contains 1% PAM1.

[0385] Example 35: PLCPO-M2 contains 1% PAM4.

[0386] Example 36: PLCPO-M3 contains 1% PAM5.

[0387] Example 37: PLCPO-M4 contains 1% PAM8.

[0388] Example 38: PLCPO-M5 contains 1% PAM7.

[0389] Example 39: PLCPO-M6 contains 1% PAM9.

[0390] Example 40: PLCPO-M7 contains 1% PAM10.

[0391] Different PLCPO-Ms were dissolved in a solvent mixture of 20% butyl acetate and 80% cyclohexanone at a ratio of 35:65, and the mixture was stirred at room temperature for 30 minutes.

[0392] Application Examples

[0393] Example 41: Preparation of Primed Substrates

[0394] A triacetyl cellulose (TAC) foil was coated with a primer (DYMAX OC-4021) using a Kbar coater (bar size 1). The film was dried at 80°C for 30 seconds and the resulting film thickness was approximately 2 μm. The film was then exposed to UV light (1500 mJ in a nitrogen atmosphere).

[0395] Example 42: Preparation of an alignment layer using a photo-alignment material

[0396] The primed TAC substrate of Application Example 1 was coated with a photoalignment composition (PAC) Kbar (bar size 0). The film was dried at 80°C for 30 seconds, and the resulting film thickness was approximately 100 nm. The film was then exposed to alignment light, which was collimated and linearly polarized UV (LPUV) light (280-320 nm) at an exposure energy of 10-100 mJ / cm 2 The polarization plane is 0° relative to the reference edge on the TAC substrate.

[0397] Example 43: Preparation of an alignment layer using a photo-alignable material

[0398] A triacetyl cellulose (TAC) foil was coated with the POM solution using a Kbar coater (bar size 0). The film was dried at 80°C for 60 seconds; the resulting film had a thickness of approximately 2 μm. The film was then exposed to UV light (500 mJ in a nitrogen atmosphere for curable composition CC1 and 1500 mJ in a nitrogen atmosphere for curable composition CC2). The film was then exposed to aligning light, which was collimated and linearly polarized UV (LPUV) light (280-320 nm) at an exposure energy of 10-100 mJ / cm 2 The polarization plane is 0° relative to the reference edge on the TAC substrate.

[0399] Example 44: Preparation of an alignment layer using a polymerizable liquid crystal and a photo-alignable material

[0400] An alignment layer of Application Example 2 was prepared with a polarization plane at 20° relative to the reference edge of the primed substrate (Application Example 1). This layer was coated (bar size 2) with a PLCPO-M solution (prepared as described above). The layer was dried at 50° C. for 60 s and then exposed to UV-A at 200 mJ / cm2 in a nitrogen atmosphere at room temperature. 2 The PLCPO-M layer is then exposed to collimated LPUV light (280-320 nm) with an exposure energy of 10-100 mJ / cm 2 The polarization plane is 80° relative to the reference edge on the TAC substrate.

[0401] Example 45: Preparation of LCP layer aligned by an alignment layer

[0402] An LCP layer was prepared by Kbar coating (rod size 1) of the LCP solution S-LCC1 on the alignment layer of Example 42, 43 or 44. The wet layer was dried at 50° C. for 60 s and subsequently exposed to UV-A at 30 mW / cm2 in a nitrogen atmosphere at room temperature. 2 50 seconds to crosslink the liquid crystal.

[0403] The following cross-linkable liquid crystal compounds (LCCs) were used:

[0404] LCC1: 2,5-bis[[4-(6-prop-2-enoyloxyhexyloxy)benzoyl]oxy]benzoic acid pentyl ester

[0405]

[0406] Solution S-LCC1 was prepared by mixing 35 wt% of the following:

[0407]

[0408] It was prepared by dissolving in 65 wt% of a solvent mixture of 80% n-butyl acetate and 20% cyclohexanone, and stirring the mixture at room temperature for 30 minutes.

[0409] Examples 46-48: Evaluating Orientation Quality

[0410] An interest for an efficient manufacturing process is to understand how much exposure energy is needed for the photo-alignment layer to obtain a good visible and uniform (without any visible defects) contrast within the aligned LCP layer.The prepared films were analyzed between crossed polarizers.

[0411] The alignment quality ratings are as follows:

[0412] ▲▲Excellent alignment and uniform orientation

[0413] ▲Good orientation (disclination line (DL) area < 2% of coating area)

[0414] Very little DL (<10% of coating area)

[0415] x DL visible (>10% of coating area)

[0416] xx uneven orientation or no orientation

[0417] Example 46

[0418] Optical devices were prepared by coating a primed substrate (prepared in Application Example 41) and an aligned LCP layer (as shown in Application Example 45) with an alignment layer of a PAM material (as described in Application Example 42). The PAM material was aligned using various exposure energies. The results are summarized in Table 1 below. The results show that the compounds of the present invention align liquid crystals at lower energies than, for example, compounds according to the prior art.

[0419] Table 1:

[0420]

[0421] Example 47

[0422] Optical devices were prepared by preparing an alignment layer using a POM material as described in Example 43, followed by coating and aligning an LCP layer (as shown in Example 45). The PAM material was aligned using various exposure energies. The results are summarized in Table 2 below. The results show that the compounds of the present invention align liquid crystals at lower energies than, for example, compounds according to the prior art. Furthermore, the results show that the compounds of the present invention (homopolymers or copolymers) are suitable for alignment in various curable compositions.

[0423] Table 2:

[0424]

[0425] Example 48

[0426] The optical device was prepared by the following procedure: by using PAM2 material (as described in Application Example 42 and at 100 mJ / cm 2 A primed substrate (as prepared in Application Example 41) was coated with an alignment layer (LPUV dose) using a PLCPO material as described in Example 44, followed by the coating and alignment of an LCP layer (as shown in Example 45). The PLCPO layer was aligned using various exposure energies. The results are summarized in Table 3 below. The results demonstrate that the compounds of the present invention achieve better alignment than prior art compounds.

[0427] Table 3:

[0428]

[0429] Example 49

[0430] A liquid crystal cell was prepared in which the liquid crystal was aligned by a photo-alignment material PAM1 and an electric field was applied between two planar electrodes on either side of the cell gap.

[0431] A 6 wt% solution was prepared by mixing the photoalignment material PAM in CHN (cyclohexanone). The above polymer solution was spin coated on two ITO coated glass substrates at a rotation speed of 1000 rpm for 30 seconds. After spin coating, the substrates were baked at a temperature of 100°C for 4 minutes. The resulting layer thickness was about 300 nm. The substrates with the coated polymer layer were exposed to linearly polarized UV light (LPUV) at an incident angle of 60° relative to the normal to the substrate surface. The polarization plane was in a plane that spanned the substrate normal and the direction of propagation of the light. The applied exposure dose was 200 mJ / cm 2 or 250 mJ / cm 2 . After LPUV exposure, the cell is assembled with 2 substrates, with the exposed polymer layer facing the inside of the cell. The substrates are adjusted relative to each other so that the induced alignment directions are antiparallel to each other. The cell is a capillary filled with liquid crystal MLC7067 (Merck KGA), which has a positive dielectric anisotropy. Thereafter, the cell is annealed at 100°C for 30 minutes and then cooled to room temperature. The alignment quality of the liquid crystal in the cell is checked and adjusted by placing the cell between two orthogonal polarizers to obtain a dark state. If the dark state shows no defects and the liquid crystal orientation is good, the alignment quality is defined as good (rating 5). If there is light leakage in the dark state due to slightly uneven orientation of the liquid crystal in some areas of the cell, the alignment quality is defined as medium (rating 3). If the liquid crystal is not oriented in the absence of a dark state, the alignment quality is defined as poor (rating 0).

[0432] Cells were prepared using PAM1, PAM7, PAM8, PAM9, and PAM10 according to the method described above. The liquid crystals in all cells exhibited well-defined and uniform planar orientation after thermal annealing of the cells. Pretilt angles of less than 1° were measured using Shintech's rotational analyzer method. The results are summarized in Table 4 below.

[0433] Table 4:

[0434]

[0435] The results show that all compounds of the present invention have excellent alignment quality compared to compounds of the prior art.

[0436] Example 50: Adhesion Test

[0437] The PET-ITO substrate was removed from its protective liner. The surface was activated by Coronna treatment (300 W, 120 m / min 6x). Immediately after the activation step, the alignment material was applied to the substrate by spin coating (1000 rpm, 30 s) to obtain a 300 nm thick layer.

[0438] The samples were baked at 100°C for 4 minutes and then exposed to LPUV at an incident angle of 50° relative to the substrate surface normal. The applied exposure doses were 200 and 250 mJ / cm 2 .

[0439] Adhesion was measured according to the cross-cut test described in DIN EN ISO 2409. The adhesive tape used was from Nichiban.

[0440] The results are summarized in Table 5 below:

[0441] Table 5:

[0442]

[0443] The results show that all fluorinated compounds have better adhesion parameters compared to prior art compounds.

[0444] The present invention provides the following technical solutions.

[0445] 1. A photo-aligned polymer material comprising repeating structural units of formula (I):

[0446]

[0447] in:

[0448] M 1 、M 1’ represents, independently of one another, the following repeating monomer units: acrylate, methacrylate, 2-chloroacrylate, 2-phenylacrylate, acrylamide, methacrylamide, 2-chloroacrylamide, 2-phenylacrylamide, N-lower alkyl-substituted acrylamide, N-lower alkyl-substituted methacrylamide, N-lower alkyl-substituted 2-chloroacrylamide, N-lower alkyl-substituted 2-phenylacrylamide, vinyl ether, vinyl ester, styrene, diamine, amide, imide, siloxane, amic acid ester and amic acid;

[0449] S 1 is a spacer unit, wherein, if m and n are 0, the spacer unit is S 2 , and if at least one of m or n is 1, the spacer unit is S 3 ;

[0450] S 1’ is a spacer unit, wherein, if m' and n' are 0, the spacer unit is S 2’ , and if at least one of m' or n' is 1, the spacer unit is S 3’ ;

[0451] Among them S 2 、S 2’ 、S 3、S 3’ is an unsubstituted or substituted straight or branched chain -(CH2) r -and-(CH2) r -O-, -(CH2) r -O-(CH2) s -、-(CH2) r -O-(CH2) s -O-, -(CH2) r -CO-, -(CH2) r -CO-O-, -(CH2) r -O-CO-, -(CH2) r -NR 2 -、-(CH2) r -CO-NR 2 -、-(CH2) r -NR 2 -CO-, -(CH2) r -NR 2 -CO-O- or -(CH2) r -NR 2 -CO-NR 3 -, which is optionally replaced by C1-C 24 Alkyl, hydroxy, fluorine, chlorine, cyano, ether, ester, amino, amide monosubstituted or polysubstituted; and wherein one or more -CH2- groups may be substituted by a linking group, an alicyclic or aromatic group; and wherein r and s are each an integer from 1 to 20, provided that: for S 2 , 3≤r+s≤24; for S 3 , 6≤r+s≤24; and R 2 and R 3 each independently represents hydrogen or lower alkyl; and

[0452] Rings A and A' each independently represent a phenylene group which is unsubstituted or optionally substituted by fluorine, chlorine, cyano, alkyl or alkoxy, pyridine-2,5-diyl, pyrimidine-2,5-diyl, 1,3-dioxane-2,5-diyl, cyclohexane-1,4-diyl, piperidine-1,4-diyl or piperazine-1,4-diyl;

[0453] Rings B and B' each independently represent a phenylene group which is unsubstituted or optionally substituted by fluorine, chlorine, cyano, alkyl or alkoxy, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a 1,4- or 2,6-naphthylene group, a 1,3-dioxane-2,5-diyl group or a cyclohexane-1,4-diyl group;

[0454] Y 1 、Y 2 、Y 1’ 、Y 2’each independently represents a covalent single bond, -(CH2) t -, -O-, -CO-, -CO-O-, -O-OC-, -CF2O-, -OCF2-, -NR 4 -, -CO-NR 4 -, -R 4 N-CO-, -(CH2) u -O-, -O-(CH2) u -, -(CH2) u -NR 4 - or -NR 4 -(CH2) u -, wherein:

[0455] R 4 represents hydrogen or a lower alkyl;

[0456] t represents an integer from 1 to 4;

[0457] u represents an integer from 1 to 3;

[0458] Ring C and C' each independently represent an unsubstituted or optionally fluorine-, chlorine-, cyano-, alkyl- or alkoxy-substituted phenylene, pyrimidine-2,5-diyl, pyridine-2,5-diyl, 2,5-thiophenediyl, 2,5-furandiyl, 1,4- or 2,6-naphthylene;

[0459] Z and Z' each independently represent -O- or -NR 5 -, wherein R 5 represents hydrogen or a lower alkyl, or a second group of formula D or D', wherein

[0460] D is a C1-C3 straight-chain or branched alkylene chain halogenated at least once or containing one or more siloxane moieties; and

[0461] D' represents hydrogen, or a straight-chain or branched alkylene having 1-20 carbon atoms optionally substituted by halogen, or a cycloalkyl residue having 3-8 ring atoms optionally substituted by halogen, alkyl or alkoxy; and

[0462] w and w 1 are the mole fractions of the comonomers and 0 < w ≤ 1 and 0 ≤ w 1 < 1.

[0463] 2. The photo-alignment polymer material according to Technical Solution 1, wherein the photo-alignment material is a homopolymer.

[0464] 3. The photo-alignment polymer material according to Technical Solution 1, wherein the photo-alignment material is a copolymer.

[0465] 4. The photo-aligned polymer material according to any one of technical solutions 1 to 3, wherein:

[0466] M 1 、M 1’ are independently selected from the group consisting of acrylates and methacrylates;

[0467] Ring A and A' are unsubstituted phenylene groups, or phenylene groups substituted by alkyl or alkoxy groups;

[0468] Ring B and B' are unsubstituted phenylene groups, or phenylene groups substituted by fluorine, alkyl or alkoxy groups;

[0469] Y 1 、Y 2 、Y 1’ 、Y 2’ Each is independently a covalent single bond, -CO-O-, or -O-OC-;

[0470] m, n, m', n' are each independently 0 or 1;

[0471] Ring C and C' are unsubstituted phenylene groups, or phenylene groups substituted by alkyl or alkoxy groups;

[0472] S 1 、S 1’ is a spacer unit, wherein, if m and n are 0, the spacer unit is S 2 or S 2’ , and if at least one of m or n is 1, the spacer unit is S 3 or S 3’ ;

[0473] Among them S 2 or S 2’ C4-C 24 Alkylene, preferably alkyleneoxy or alkyleneoxycarbonyl, in particular propyleneoxy, butyleneoxy, pentyleneoxy, hexyleneoxy, heptyleneoxy, octyleneoxy, nonyleneoxy, undecyleneoxy, or propyleneoxycarbonyl, butyleneoxycarbonyl, pentyleneoxycarbonyl, hexyleneoxycarbonyl, heptyleneoxycarbonyl, octyleneoxycarbonyl, nonyleneoxycarbonyl, undecyleneoxycarbonyl; and

[0474] Among them S 3 or S 3’ C8-C 24 Alkylene, and wherein alkylene is unsubstituted or substituted linear or branched alkylene, wherein one or more -CH2- groups may be substituted by at least one linking group, alicyclic or / and aromatic group;

[0475] Z, Z 1 is -O-;

[0476] D is a C1-C3 linear or branched alkylene chain that is halogenated at least once or contains one or more siloxane moieties; and

[0477] D' represents hydrogen, or a linear or branched alkylene radical having 1 to 20 carbon atoms which is optionally substituted by halogen, or a cycloalkyl residue having 3 to 8 ring atoms which is optionally substituted by halogen, alkyl or alkoxy.

[0478] 5. The photo-aligned polymer material according to any one of technical solutions 1 to 4, wherein:

[0479] Rings C and C' each independently represent phenylene, which is unsubstituted or optionally substituted by fluorine, chlorine, cyano, alkyl or methoxy, pyrimidine-2,5-diyl, pyridine-2,5-diyl, 2,5-thienylene, 2,5-furylene, or 1,4- or 2,6-naphthylene;

[0480] 6. The photo-aligned polymer material according to any one of technical solutions 1 to 5, wherein:

[0481] S 1 is a spacer unit, wherein, if m and n are 0, the spacer unit is S 2 , and if at least one of m or n is 1, the spacer unit is S 3 ;

[0482] S 1’ is a spacer unit, wherein, if m' and n' are 0, the spacer unit is S 2’ , if at least one of m' or n' is 1, the spacer unit is S 3’ ;

[0483] Among them S 2 、S 2’ 、S 3 、S 3’ is a substituted or unsubstituted straight or branched chain -(CH2) r -and-(CH2) r -O-, -(CH2) r -O-(CH2) s -、-(CH2) r -O-(CH2) s -O-, -(CH2) r -CO-, -(CH2) r -CO-O-, -(CH2) r -O-CO-, -(CH2) r -NR 2 -、-(CH2) r -CO-NR 2 -、-(CH2)r -NR 2 -CO-, -(CH2) r -NR 2 -CO-O- or -(CH2) r -NR 2 -CO-NR 3 -, wherein the suffix "r" is an integer between 4 and 24, preferably between 5 and 12, more preferably between 5 and 10, even more preferably between 5 and 8, especially between 6 and 8; R 2 and R 3 Each independently represents hydrogen or lower alkyl.

[0484] 7. The photo-aligned polymer material according to any one of technical solutions 1 to 6, wherein D is 2,2,2-trifluoro-ethyl.

[0485] 8. The photo-aligned polymer material according to any one of technical solutions 1 to 7, wherein M 1 and M 1’ It is methacrylate.

[0486] 9. A composition comprising the photo-aligned polymer material according to any one of technical solutions 1 to 8, at least one solvent and at least one additive.

[0487] 10. The composition according to technical solution 9, wherein the additive is selected from polymerizable liquid crystals, UV-curable compounds, crosslinkers, silane-containing compounds, photoactive additives, photoinitiators, surfactants, emulsifiers, antioxidants, leveling agents, dyes, epoxy-containing crosslinkers and curable compounds.

[0488] 11. Use of the photo-aligned polymer material described in any one of Technical Solutions 1 to 8 or the composition described in Technical Solution 9 or 10 as an alignment layer for liquid crystals.

[0489] 12. A method for preparing an alignment layer for liquid crystal, comprising irradiating the photo-alignment polymer material described in any one of technical solutions 1 to 8 or the composition described in technical solution 9 or 10 with alignment light.

[0490] 13. An oriented layer obtained by the method described in Technical Solution 12.

[0491] 14. An alignment layer comprising the photo-aligned polymer material according to any one of technical solutions 1 to 8 or the composition according to technical solution 9 or 10.

[0492] 15. An optical, electro-optical or nanoelectronic component comprising the photo-aligned polymer material of any one of technical solutions 1 to 8, or the composition of technical solution 9 or 10, or the alignment layer of technical solution 13 or 14.

Claims

1. A composition comprising: A photo-aligned polymer material having the formula: and At least one additive selected from the group consisting of a crosslinking agent, a silane-containing compound, a photoactive additive, a photoinitiator, a surfactant, an emulsifier, an antioxidant, a leveling agent, a dye, and a curable compound.

2. The composition according to claim 1, further comprising a solvent.

3. The composition according to claim 1 or 2, further comprising a slave material having the ability to establish anisotropy when in contact with the photoaligned polymeric material.

4. The composition of claim 3, wherein the slave material comprises a non-polymerizable liquid crystal.

5. The composition of claim 3, wherein the slave material comprises a polymerizable liquid crystal. The composition of claim 5 , wherein the polymerizable liquid crystal comprises a nematic polymerizable liquid crystal.

7. Use of the composition according to any one of claims 1 to 6 as an alignment layer for liquid crystals.

8. A method for preparing an alignment layer for liquid crystals, comprising irradiating the composition according to any one of claims 1 to 6 with alignment light.

9. An alignment layer obtained by the method according to claim 8.

10. An alignment layer comprising the composition of any one of claims 1 to 6.

11. An optical, electro-optical or nanoelectronic component comprising the composition according to any one of claims 1 to 6, or comprising the alignment layer according to claim 9 or 10.

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