Polymerisable liquid crystal material and polymerised liquid crystal film

1 . A polymerizable LC material comprising at least one di- or multireactive mesogenic compound and one or more compounds of formula UVI,

wherein the individual radicals have the following meanings:

R 1 to R 5 are each independently selected from H, alkyl, —OH, -alkylaryl, -alkylheteroaryl, cycloalkyl, cycloheteroalkyl, alkenyl, aryl, and —SO 3 H, and

R 6 and R 7 together form an optionally substituted cycloalkyl or cycloheteroalkyl ring.

2 . The polymerizable LC material according to claim 1 , wherein the compounds of formula UVI are selected from the following subformulae:

wherein

R 1 to R 5 are each independently selected from H, alkyl, —OH, -alkylaryl, -alkylheteroaryl, cycloalkyl, cycloheteroalkyl, alkenyl, aryl, and —SO 3 H,

R 8 to R 13 are each independently selected from H, alkyl, aryl, heteroaryl, alkylaryl, alkylheteroaryl, alkenyl, and alkynyl,

X 1 denotes O or S, and

R 14 and R 15 are each independently selected from H, —C(═O)R 8 , alkyl, alkenyl, alkynyl, aryl, cycloalkyl, heteroaryl, and cycloheteroalkyl.

3 . The polymerizable LC material according to claim 1 , wherein the compounds of formula UVI are selected from the following subformulae:

wherein

R 2 to R 5 are each independently selected from H, alkyl, —OH,-alkylaryl,-alkylheteroaryl, cycloalkyl, cycloheteroalkyl, alkenyl, aryl, and —SO 3 H,

R 6 and R 7 are as defined in claim 1 ,

R 8 to R 13 are each independently selected from H, alkyl, aryl, heteroaryl, alkylaryl, alkylheteroaryl, alkenyl, and alkynyl,

X 1 denotes O or S, and

R 14 and R 15 are each independently selected from H, —C(═O) R 8 , alkyl, alkenyl, alkynyl, aryl, cycloalkyl, heteroaryl, and cycloheteroalkyl.

4 . The polymerizable LC material according to claim 1 , wherein the compounds of formula UVI are selected from the following subformulae:

wherein

R 2 and R 4 are each independently selected from H, alkyl, —OH,-alkylaryl,-alkylheteroaryl, cycloalkyl, cycloheteroalkyl, alkenyl, aryl, and —SO 3 H,

R 6 and R 7 are as defined in claim 1 ,

R 8 to R 13 are each independently selected from H, alkyl, aryl, heteroaryl, alkylaryl, alkylheteroaryl, alkenyl, and alkynyl,

X 1 denotes O or S, and

R 14 and R 15 are each independently selected from H, —C(═O) R 8 , alkyl, alkenyl, alkynyl, aryl, cycloalkyl, heteroaryl, and cycloheteroalkyl.

5 . The polymerizable LC material according to claim 1 , wherein R 2 and R 4 are each independently alkylaryl or alkyl, wherein one or more —(CH 2 )— groups may each be replaced by —COO— or —OCO— in that way that no two oxygen atoms are linked together.

6 . The polymerizable LC material according to claim 1 , wherein the compound of formula UVI is of the following subformulae

7 . The polymerizable LC material according to claim 1 , wherein at least one di- or multireactive mesogenic compound is selected of formula DRM

P 1 -Sp 1 -MG-Sp 2 -P 2   DRM

wherein

P 1 and P 2 independently of each other denote a polymerizable group,

Sp 1 and Sp 2 independently of each other are a spacer group or a single bond, and

MG is a rod-shaped mesogenic group.

8 . The polymerizable LC material according to claim 1 , further comprising at least one direactive mesogenic compound selected from the following formulae,

wherein

P 0 is, in case of multiple occurrences independently of one another, an acryl, methacryl, oxetane, epoxy, vinyl, heptadiene, vinyloxy, propenyl ether, or styrene group,

L is, on each occurrence identically or differently, P-Sp-, F, Cl, Br, I, —CN, —NO 2 , —NCO, —NCS, —OCN, —SCN, —C(═O) NR 00 R 000 , —C(═O) OR 00 , —C(═O) R 00 , —NR 00 R 000 , —OH, —SF 5 , optionally substituted silyl, aryl having 6 to 12 C atoms, heteroaryl having 2 to 12 C atoms, straight chain alkyl or alkoxy having 1 to 12 C atoms, branched alkyl or alkoxy having 3 to 12 C atoms, straight chain alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, or alkoxycarbonyloxy 2 to 12, C atoms, or branched alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, or alkoxycarbonyloxy 4 to 12, C atoms, wherein one or more H atoms are each optionally replaced by F or Cl,

r is 0, 1, 2, 3 or 4,

x and y are independently of each other 0 or identical or different integers from 1 to 12, and

Z is each and independently, 0 or 1, with z being 0 if the adjacent x or y is 0.

9 . The polymerizable LC material according to claim 1 , further comprising at least one monoreactive mesogenic compound selected from formula MRM,

P 1 -Sp 1 -MG-R  MRM

wherein

P 1 and P 2 independently of each other denote a polymerizable group,

Sp 1 and Sp 2 independently of each other are a spacer group or a single bond, and

MG is a rod-shaped mesogenic group,

R is F, Cl, Br, I, —CN, —NO 2 , —NCO, —NCS, —OCN, —SCN, —C(═O) NR x R y , —C(═O) X, —C(═O) OR x , —C(═O)R y , —NR x R y , —OH, —SF 5 , optionally substituted silyl, straight chain alkyl or alkoxy having 1 to 12 C atoms, branched alkyl or alkoxy having 3 to 12 C atoms, straight chain alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, or alkoxycarbonyloxy having 2 to 12 C atoms, or branched alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, or alkoxycarbonyloxy having 4 to 12 C atoms, wherein one or more H atoms are each optionally replaced by F or Cl,

X is halogen, and

R x and R y are independently of each other H or alkyl with 1 to 12 C-atoms.

10 . The polymerizable LC material according to claim 1 , further comprising at least one monoreactive mesogenic compound is selected from the following formulae,

wherein

P 0 is, in case of multiple occurrences independently of one another, an acryl, methacryl, oxetane, epoxy, vinyl, heptadiene, vinyloxy, propenyl ether, or styrene group,

L is, on each occurrence identically or differently, P-Sp-, F, Cl, Br, I, —CN, —NO 2 , —NCO, —NCS, —OCN, —SCN, —C(═O) NR 00 R 000 , —C(═O)OR 00 , —C(═O) R 00 , —NR 00 R 000 , —OH, —SF 5 , optionally substituted silyl, aryl having 6 to 12 C atoms, heteroaryl having 2 to 12 C atoms, straight chain alkyl or alkoxy having 1 to 12 C atoms, branched alkyl or alkoxy having 3 to 12 C atoms, straight chain alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, or alkoxycarbonyloxy 2 to 12, C atoms, or branched alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, or alkoxycarbonyloxy 4 to 12, C atoms, wherein one or more H atoms are each optionally replaced by F or Cl,

r is 0, 1, 2, 3 or 4,

x and y are independently of each other 0 or identical or different integers from 1 to 12,

z is each and independently, 0 or 1, with z being 0 if the adjacent x or y is 0,

R 0 is alkyl, alkoxy, thioalkyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy with up to 15 C atoms or denotes Y 0 ,

Y 0 is F, Cl, CN, NO 2 , OCH 3 , OCN, SCN, SF 5 , or mono-, oligo-, or polyfluorinated alkyl or alkoxy with 1 to 4 C atoms,

R 01 and R 02 is H, alkyl, alkoxy, thioalkyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy up to 15 C atoms or denotes Y 0 ,

Z 0 is —COO—, —OCO—, —CH 2 CH 2 —, —CF 2 O—, —OCF 2 —, —CH═CH—, —OCO—CH═CH—, —CH═CH—COO—, or a single bond,

A 0 is, in case of multiple occurrences independently of one another, 1,4-phenylene that is unsubstituted or substituted with 1, 2, 3 or 4 groups L, or trans-1,4-cyclohexylene,

u and v are independently of each other 0, 1 or 2,

w is 0 or 1, and

wherein benzene and naphthalene rings of formulae MRM1 to MRM27 can additionally be substituted with one or more identical or different groups L.

11 . The polymerizable LC material according to claim 1 , further comprising one or more compounds of formula ND,

wherein

U 1,2 are independently of each other selected from

including their mirror images, wherein the rings U 1 and U 2 are each bonded to the group-(B) q -via the axial bond, and one or two non-adjacent CH 2 groups in these rings are each optionally replaced by O or S, and the rings U 1 and U 2 are optionally substituted by one or more groups L,

L is, on each occurrence identically or differently, P-Sp-, F, Cl, Br, I, —CN, —NO 2 , —NCO, —NCS, —OCN, —SCN, —C(═O)NR 00 R 000 , —C(═O)OR 00 , —C(═O)R 00 , —NR 00 R 000 , —OH, —SF 5 , optionally substituted silyl, aryl or heteroaryl with up to 12 C atoms, straight chain alkyl having 1 to 12 C atoms, branched alkyl having 3 to 12 C atoms, alkoxy having 1 to 12 C atoms, alkylcarbonyl having 2 to 12 C atoms, alkoxycarbonyl having 2 to 12 C atoms, alkylcarbonyloxy having 2 to 12 C atoms, or alkoxycarbonyloxy having 2 to 12 C atoms, wherein one or more H atoms are each optionally replaced by F or C,

Q 1,2 are independently of each other CH or SiH,

Q 3 is C or Si,

B is in each occurrence independently of one another —C≡C—, —CY 1 ═CY 2 — or an optionally substituted aromatic or heteroaromatic group,

Y 1,2 are independently of each other H, F, Cl, CN, or R 0 ,

q is an integer from 1 to 10,

A 1-4 are independently of each other selected from non-aromatic, aromatic or heteroaromatic carbocyclic or heterocyclic groups, which are optionally substituted by one or more groups R 5 , and wherein each of -(A 1 -Z 1 ) m —U 1 —(Z 2 -A 2 ) n - and -(A 3 -Z 3 ) o —U 2 —(Z 4 -A 4 ) p - does not contain more aromatic groups than non-aromatic groups,

Z 1-4 are independently of each other —O—, —S—, —CO—, —COO—, —OCO—, —O—COO—, —CO—NR 0 —, —NR 0 —CO—, —NR 0 —CO—NR 00 —, —OCH 2 —, —CH 2 O—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH 2 CH 2 —, —(CH 2 ) 3 —, —(CH 2 ) 4 —, —CF 2 CH 2 —, —CH 2 CF 2 —, —CF 2 CF 2 —, —CH═CH—, —CY 1 ═CY 2 —, —CH═N—, —N═CH—, —N═N—, —CH═CR 0 —, —C≡C—, —CH—CH—COO—, —OCO—CH═CH—, CR 0 R 00 or a single bond,

R 0 and R 00 are independently of each other H or alkyl with 1 to 12 C-atoms,

m and n are independently of each other 0, 1, 2, 3 or 4,

and p are independently of each other 0, 1, 2, 3 or 4,

R 1-5 are independently of each other identical or different groups selected from H, halogen, —CN, —NC, —NCO, —NCS, —OCN, —SCN, —C(═O)NR 0 R 00 , —C(═O)X 0 , —C(═O)R 0 , —NH 2 , —NR 0 R 00 , —SH, —SR 0 , —SO 3 H, —SO 2 R 0 , —OH, —NO 2 , —CF 3 , —SF 5 , P—Sp-, optionally substituted silyl, or carbyl or hydrocarbyl with up to 40 C atoms that is optionally substituted and optionally comprises one or more hetero atoms, or denote P or P-Sp-, or are substituted by P or P-Sp-, wherein the compounds comprise at least one group R 1-5 denoting or being substituted by P or P-Sp-,

P is a polymerizable group,

Sp is a spacer group or a single bond.

12 . The polymerizable LC material according to claim 1 , wherein the proportion of di- or multireactive polymerizable mesogenic compounds is in the range from 5 to 99% by weight.

13 . The polymerizable LC material according to claim 1 , wherein the material contains a proportion of monoreactive polymerizable mesogenic compounds in the range from 5 to 80% by weight.

14 . The polymerizable LC material according to claim 1 , further comprising one or more additives selected from surfactants, further stabilizers, catalysts, sensitizers, inhibitors, chain-transfer agents, co-reacting monomers, reactive thinners, surface-active compounds, lubricating agents, wetting agents, dispersing agents, hydrophobing agents, adhesive agents, flow improvers, degassing or defoaming agents, deaerators, diluents, reactive diluents, auxiliaries, colorants, dyes, pigments, and nanoparticles.

15 . A process for the preparation of the polymerizable LC material according to claim 1 comprising: mixing one or more compounds of formula UVI with at least one di- or multireactive mesogenic compound.

16 . A process for the preparation of the of a polymer film comprising:

providing a layer of a polymerizable LC material according to claim 1 onto a substrate,

photopolymerizing the polymerizable LC material, and

optionally removing the polymerized LC material from the substrate and/or optionally providing it onto another substrate.

17 . A polymer film obtainable from a polymerizable LC material according to claim 1 by a process comprising:

providing a layer of the polymerizable LC material onto a substrate,

photopolymerizing the LC material, and

optionally, removing the polymerized LC material from the substrate and/or optionally providing it onto another substrate.

18 . The polymer film according to claim 17 , wherein the LC material is uniformly aligned.

19 . A liquid crystal display, 3D display, projection system, polarizer, compensator, alignment layer, circular polarizer, color filter, decorative image, liquid crystal pigment, reflective film with spatially varying reflection colors, multicolor image, non-forgeable document, identity or credit card, or banknote, comprising a polymer film according to claim 17 .

20 . An optical component or device, polarizer, patterned retarder, compensator, alignment layer, circular polarizer, color filter, decorative image, liquid crystal lens, liquid crystal pigment, reflective film with spatially varying reflection colors, multicolor image for decorative or information storage, comprising a polymerizable LC material according to claim 1 .

21 . The polymerizable LC material according to claim 1 , wherein R 2 and R 4 are each independently alkylphenyl or a straight chain or branched alkyl having 5 to 15 carbon atoms, wherein one or more —(CH 2 )— groups may each be replaced by —COO— or —OCO— in such a way that no two oxygen atoms are linked together.

22 . The polymerizable LC material according to claim 7 , wherein MG is a rod-shaped mesogenic group of formula MG

-(A 1 -Z 1 ) n -A 2 -  MG

wherein

A 1 and A 2 denote, in case of multiple occurrences independently of one another, an aromatic or alicyclic group, which optionally contains one or more heteroatoms selected from N, O and S, and is optionally mono- or polysubstituted by L 1 ,

L 1 is P-Sp-, F, Cl, Br, I, —CN, —NO 2 , —NCO, —NCS, —OCN, —SCN, —C(═O)NR 00 R 000 , —C(═O)OR 00 , —C(═O)R 00 , —NR 00 R 000 , —OH, —SF 5 , optionally substituted silyl, aryl having 6 to 12 C atoms, heteroaryl having 2 to 12 C atoms, straight chain alkyl or alkoxy having 1 to 12 C atoms, branched alkyl or alkoxy having 3 to 12 C atoms, straight chain alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, or alkoxycarbonyloxy 2 to 12, C atoms, or branched alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, or alkoxycarbonyloxy 4 to 12, C atoms, wherein one or more H atoms are each optionally replaced by F or Cl,

R 00 and R 000 independently of each other are H or alkyl with 1 to 12 C-atoms,

Z 1 denotes, in case of multiple occurrences independently of one another, —O—, —S—, —CO—, —COO—, —OCO—, —S—CO—, —CO—S—, —O—COO—, —CO—NR 00 —, —NR 00 —CO—, —NR 00 —CO—NR 000 , —NR 00 —CO—O—, —O—CO—NR 00 , —OCH 2 —, —CH 2 O—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH 2 CH 2 —, —(CH 2 ) n1 , —CF 2 CH 2 —, —CH 2 CF 2 —, —CF 2 CF 2 —, —CH═N—, —N═CH—, —N═N—, —CH═CR 00 , —CY 1 ═CY 2 —, —C≡C—, —CH═CH—COO—, —OCO—CH═CH—, or a single bond,

Y 1 and Y 2 independently of each other denote H, F, Cl, or CN,

n is 1, 2, 3 or 4, and

n1 is an integer from 1 to 10.

23 . The polymerizable LC material according to claim 11 , wherein, in formula ND,

(B) q — is selected from —C≡C—, —C≡C—C≡C—, —C≡C—C≡C—C≡C—, —C≡C—C≡C—C≡C—C≡C—,

r is 0, 1, 2, 3 or 4;

L is selected from P-Sp-, F, Cl, Br, I, —CN, —NO 2 , —NCO, —NCS, —OCN, —SCN, —C(═O)NR 0 R 00 , —C(═O)X, —C(═O)OR 0 , —C(═O)R 0 , —NR 0 R 00 , —OH, —SF 5 , optionally substituted silyl, aryl or heteroaryl, straight chain alkyl or alkoxy having 1 to 12 C atoms, branched alkyl or alkoxy having 3 to 12 C atoms, straight chain alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 2 to 12 C atoms, or branched chain alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 4 to 12 C atoms, wherein one or more H atoms are each optionally replaced by F or Cl; and

X is halogen.