Polymerizable mesogenic cyclohexyl derivatives

A liquid crystalline phase, comprising at least two liquid crystalline compounds, wherein at least one compound is a compound of formula I

• wherein
• P is a polymerizable group of the formula CH2═CW1—COO—,
• (CH2═CH)2CH—OCO—, (CH2═CH—CH2)2CH—OCO—, (CH2═CH)2CH—O—, (CH2═CH—CH2)2N—, (CH2═CH—CH2)2N—CO—, HO—CW2W3—, HS—CW2W3—, HW2N—, HO—CW2W3—NH—, CH2═CW1—CO—NH—, CH2═CH—(COO)k1-Phe-(O)—, Phe-CH═CH—, HOOC—, OCN— or W4W5W6Si—, with W1 being H, Cl, CN, phenyl or alkyl with 1 to 5 C-atoms, W2 and W3 each independently being H or alkyl with 1 to 5 C-atoms, W4, W5 and W6 each independently being Cl, oxaalkyl or oxacarbonylalkyl with 1 to 5 C-atoms, Phe being 1,4-phenylene optionally substituted by one or more groups L, k1 and k2 are each independently 0 or 1, and F, Cl, Br, I, CN, NO2 or alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy with 1 to 20 C atoms, wherein one or more H atoms may be substituted by F or Cl,
• Sp is a spacer group,
• A1 is each independently an aromatic or aliphatic 5- or 6-atom ring, or a group comprising two or three fused aromatic or aliphatic 5- or 6-membered rings, said rings optionally containing one or more N, O or S hetero atoms, and optionally being mono- or polysubstituted,
• Z1 is each independently —O—, —S—, —CO—, —COO—, —OCO—, —S—CO—, —CO—S—, —O—CO—O—, —CO—NR0—, —NR0—CO—, —OCH2—, —CH2O—, —SCH2—, —CH2S—, —CF2O—, —OCF2—, —CF2S—, —SCF2—, —CH2CH2—, —CF2CH2—, —CH2CF2—, —CF2CF2—, —CH═CR0—, —CH═CH—, —CH═CF—, —CY1═CY1—, —C≡C—, —CH═CH—COO—, —OCO—CH═CH— or a single bond,
• R0 and R00 are each independently H or alkyl with 1 to 12 C-atoms,
• Y1 and Y2 are each independently H, F, Cl or CN,
• Q is F, Cl, SF5 or fluorinated alkyl, alkoxy, alkenyl or alkenyl-oxy with 1 to 6 C-atoms,
• X1 and X2 are each independently H or F,
• m is 0, 1 or 2, and
• n is 0 or 1,
• with the proviso that if m is 0, n is 1 and Q is F, then X1 and X2 are F.

A compound of formula I

• wherein
• P is a polymerizable group of the formula CH2═CW1—COO—,
• (CH2═CH)2CH—OCO—, (CH2═CH—CH2)2CH—OCO—, (CH2═CH)2CH—O—, (CH2═CH—CH2)2N—, (CH2═CH—CH2)2N—CO—, HS—CW2W3—, HW2N—, HO—CW2W3—NH—, CH2═CW1—CO—NH—, CH2═CH—(COO)k1-Phe-(O)—, Phe-CH═CH—, or OCN—, with W1 being H, Cl, CN, phenyl or alkyl with 1 to 5 C-atoms, W2 and W3 each independently being H or alkyl with 1 to 5 C-atoms, Phe being 1,4-phenylene optionally substituted by one or more groups L, k1 and k2 are each independently 0 or 1, and F, Cl, Br, I, CN, NO2 or alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy with 1 to 20 C atoms, wherein one or more H atoms may be substituted by F or Cl,
• Sp is a spacer group,
• A1 is each independently an aromatic or aliphatic 5- or 6-atom ring, or a group comprising two or three fused aromatic or aliphatic 5- or 6-membered rings, said rings optionally containing one or more N, O or S hetero atoms, and optionally being mono- or polysubstituted,
• Z1 is each independently —O—, —S—, —CO—, —COO—, —OCO—, —S—CO—, —CO—S—, —O—CO—O—, —CO—NR0—, —NR0—CO—, —OCH2—, —CH2O—, —SCH2—, —CH2S—, —CF2O—, —OCF2—, —CF2S—, —SCF2—, —CH2CH2—, —CF2CH2—, —CH2CF2—, —CF2CF2—, —CH═CR0—, —CH═CH—, —CH═CF—, —CY1═CY1—, —C≡C—, —CH═CH—COO—, —OCO—CH═CH— or a single bond,
• R0 and R00 are each independently H or alkyl with 1 to 12 C-atoms,
• Y1 and Y2 are each independently H, F, Cl or CN,
• Q is F, Cl, SF5 or fluorinated alkyl, alkoxy, alkenyl or alkenyl-oxy with 1 to 6 C-atoms,
• X1 and X2 are each independently H or F,
• m is 0, 1 or 2, and
• n is 0 or 1,
• with the proviso that if the compounds have the structure
• and Q is F, then X1 and X2 are F.

A compound of the formulae

• wherein
• P is a polymerizable group of the formula CH2═CW1—COO—,
• CH2═CW2—(O)—, CH3—CH═CH—O—, (CH2═CH)2CH—OCO—, (CH2═CH—CH2)2CH—OCO—, (CH2═CH)2CH—O—, (CH2═CH—CH2)2N—, (CH2═CH—CH2)2N—CO—, —HS—CW2W3—, HW2N—, HO—CW2W3—NH—, CH2═CW1—CO—NH—, CH2═CH—(COO)k1-Phe-(O)—, Phe-CH═CH—, HOOC—, OCN— or W4W5W6Si—, with W1 being H, Cl, CN, phenyl or alkyl with 1 to 5 C-atoms, W2 and W3 each independently being H or alkyl with 1 to 5 C-atoms, W4, W5 and W6 each independently being Cl, oxaalkyl or oxacarbonylalkyl with 1 to 5 C-atoms, Phe being 1,4-phenylene optionally substituted by one or more groups L, k1 and k2 are each independently 0 or 1, and F, Cl, Br, I, CN, NO2 or alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy with 1 to 20 C atoms, wherein one or more H atoms may be substituted by F or Cl,
• X1 and X2 are each independently H or F,
• Q is F, Cl, SF5 or fluorinated alkyl, alkoxy, alkenyl or alkenyl-oxy with 1 to 6 C-atoms,
• Sp1 is alkylene with 1 to 20 C atoms which is optionally mono- or polysubstituted by F, Cl, Br, I or CN, and wherein one or more non-adjacent CH2 groups are optionally replaced, in each case independently from one another, by —O—, —S—, —NH—, —NR0—, —SiR0R00—, —CO—, —COO—, —OCO—, —OCO—O—, —S—CO—, —CO—S—, —NR0—CO—O—, —O—CO—NR0—, —NR0—CO—NR0—, —CH═CH— or —C≡C— in such a manner that O and/or S atoms are not linked directly to one another, wherein R0 is H or alkyl with 1 to 12 C-atoms, and Sp2 is alkylene with 1 to 12 C-atoms.

An anisotropic polymer or polymer film obtainable from a polymerizable liquid crystal material of formula 1

• wherein
• P is a polymerizable group of the formula CH2═CW1—COO—,
• (CH2═CH)2CH—OCO—, (CH2═CH—CH2)2CH—OCO—, (CH2═CH)2CH—O—, (CH2═CH—CH2)2N—, (CH2═CH—CH2)2N—CO—, HS—CW2W3—, HW2N—, HO—CW2W3—NH—, CH2═CW1—CO—NH—, CH2═CH—(COO)k1-Phe-(O)—, Phe-CH═CH—, HOOC—, OCN— or W4W5W6Si—, with W1 being H, Cl, CN, phenyl or alkyl with 1 to 5 C-atoms, W2 and W3 each independently being H or alkyl with 1 to 5 C-atoms, W4, W5 and W6 each independently being Cl, oxaalkyl or oxacarbonylalkyl with 1 to 5 C-atoms, Phe being 1,4-phenylene optionally substituted by one or more groups L, k1 and k2 are each independently 0 or 1, and F, Cl, Br, I, CN, NO2 or alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy with 1 to 20 C atoms, wherein one or more H atoms may be substituted by F or Cl,
• Sp is a spacer group,
• A1 is each independently an aromatic or aliphatic 5- or 6-atom ring, or a group comprising two or three fused aromatic or aliphatic 5- or 6-membered rings, said rings optionally containing one or more N, O or S hetero atoms, and optionally being mono- or polysubstituted,
• Z1 is each independently —O—, —S—, —CO—, —COO—, —OCO—, —S—CO—, —CO—S—, —O—CO—O—, —CO—NR0—, —NR0—CO—, —OCH2—, —CH2O—, —SCH2—, —CH2S—, —CF2O—, —OCF2—, —CF2S—, —SCF2—, —CH2CH2—, —CF2CH2—, —CH2CF2—, —CF2CF2—, —CH═CR0—, —CH═CH—, —CH═CF—, —CY1═CY1—, —C≡C—, —CH═CH—COO—, —OCO—CH═CH— or a single bond,
• R0 and R00 are each independently H or alkyl with 1 to 12 C-atoms,
• Y1 and Y2 are each independently H, F, Cl or CN,
• Q is F, Cl, SF5 or fluorinated alkyl, alkoxy, alkenyl or alkenyl-oxy with 1 to 6 C-atoms,
• X1 and X2 are each independently H or F,
• m is 0, 1 or 2, and
• n is 0 or 1,
• with the proviso that if the compounds have the structure
• and Q is F, then X1 and X2 are F.

A liquid crystalline phase, comprising at least two liquid crystalline compounds, wherein at least one compound is a compound of formula I

• wherein
• P is a polymerizable group of the formula CH2═CW1—COO—,
• (CH2═CH)2CH—OCO—, (CH2═CH—CH2)2CH—OCO—, (CH2═CH)2CH—O—, (CH2═CH—CH2)2N—, (CH2═CH—CH2)2N—CO—, HO—CW2W3—, HS—CW2W3—, HW2N—, HO—CW2W3—NH—, CH2═CW1—CO—NH—, CH2═CH—(COO)k1-Phe-(O)—, Phe-CH═CH—, HOOC—, OCN— or W4W5W6Si—, with W1 being H, Cl, CN, phenyl or alkyl with 1 to 5 C-atoms, W2 and W3 each independently being H or alkyl with 1 to 5 C-atoms, W4, W5 and W6 each independently being Cl, oxaalkyl or oxacarbonylalkyl with 1 to 5 C-atoms, Phe being 1,4-phenylene optionally substituted by one or more groups L, k1 and k2 are each independently 0 or 1, and F, Cl, Br, I, CN, NO2 or alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy with 1 to 20 C atoms, wherein one or more H atoms may be substituted by F or Cl,
• Sp is a spacer group,
• A1 is each independently an aromatic or aliphatic 5- or 6-atom ring, or a group comprising two or three fused aromatic or aliphatic 5- or 6-membered rings, said rings optionally containing one or more N, O or S hetero atoms, and optionally being mono- or polysubstituted,
• Z1 is each independently —O—, —S—, —CO—, —COO—, —OCO—, —S—CO—, —CO—S—, —O—CO—O—, —CO—NR0—, —NR0—CO—, —OCH2—, —CH2O—, —SCH2—, —CH2S—, —CF2O—, —OCF2—, —CF2S—, —SCF2—, —CH2CH2—, —CF2CH2—, —CH2CF2—, —CF2CF2—, —CH═CR0—, —CH═CH—, —CH═CF—, —CY1═CY1—, —C≡C—, —CH═CH—COO—, —OCO—CH═CH— or a single bond,
• R0 and R00 are each independently H or alkyl with 1 to 12 C-atoms,
• Y1 and Y2 are each independently H, F, Cl or CN,
• Q is F,
• X1 and X2 are each F,
• m is 0, and
• n is 0 or 1.

A compound of formula I

• wherein
• P is a polymerizable group of the formula CH2═CW1—COO—,
• (CH2═CH)2CH—OCO—, (CH2═CH—CH2)2CH—OCO—, (CH2═CH)2CH—O—, (CH2═CH—CH2)2N—, (CH2═CH—CH2)2N—CO—, HS—CW2W3—, HW2N—, HO—CW2W3—NH—, CH2═CW1—CO—NH—, CH2═CH—(COO)k1-Phe-(O)—, Phe-CH═CH—, HOOC— or OCN— with W1 being H, Cl, CN, phenyl or alkyl with 1 to 5 C-atoms, W2 and W3 each independently being H or alkyl with 1 to 5 C-atoms, Phe being 1,4-phenylene optionally substituted by one or more groups L, k1 and k2 are each independently 0 or 1, and F, Cl, Br, I, CN, NO2 or alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy with 1 to 20 C atoms, wherein one or more H atoms may be substituted by F or Cl,
• Sp is a spacer group,
• A1 is each independently an aromatic or aliphatic 5- or 6-atom ring, or a group comprising two or three fused aromatic or aliphatic 5- or 6-membered rings, said rings optionally containing one or more N, O or S hetero atoms, and optionally being mono- or polysubstituted, Z1 is each independently —O—, —S—, —CO—, —COO—, —OCO—, —S—CO—, —CO—S—, —O—CO—O—, —CO—NR0—, —NR0—CO—, —OCH2—, —CH2O—, —SCH2—, —CH2S—, —CF2O—, —OCF2—, —CF2S—, —SCF2—, —CH2CH2—, —CF2CH2—, —CH2CF2—, —CF2CF2—, —CH═CR0—, —CH═CH—, —CH═CF—, —CY1═CY1—, —C≡C—, —CH═CH—COO—, —OCO—CH═CH— or a single bond,
• R0 and R00 are each independently H or alkyl with 1 to 12 C-atoms,
• Y1 and Y2 are each independently H, F, Cl or CN,
• Q is F,
• X1 and X2 are each F,
• m is 0, and
• n is 0 or 1.

An anisotropic polymer or polymer film obtainable from a polymerizable liquid crystal material comprising a compound of formula I

• wherein
• P is a polymerizable group of the formula CH2═CW1—COO—,
• (CH2═CH)2CH—OCO—, (CH2═CH—CH2)2CH—OCO—, (CH2═CH)2CH—O—, (CH2═CH—CH2)2N—, (CH2═CH—CH2)2N—Co—, HS—CW2W3—, HW2N—, HO—CW2W3—NH—, CH2═CW1—CO—NH—, CH2═CH—(COO)k1-Phe-(O)—, Phe-CH═CH—, HOOC—, OCN— or W4W5W6Si—, with W1 being H, Cl, CN, phenyl or alkyl with 1 to 5 C-atoms, W2 and W3 each independently being H or alkyl with 1 to 5 C-atoms, W4, W5 and W6 each independently being Cl, oxaalkyl or oxacarbonylalkyl with 1 to 5 C-atoms, Phe being 1,4-phenylene optionally substituted by one or more groups L, k1 and k2 are each independently 0 or 1, and F, Cl, Br, I, CN, NO2 or alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy with 1 to 20 C atoms, wherein one or more H atoms may be substituted by F or Cl,
• Sp is a spacer group,
• A1 is each independently an aromatic or aliphatic 5- or 6-atom ring, or a group comprising two or three fused aromatic or aliphatic 5- or 6-membered rings, said rings optionally containing one or more N, O or S hetero atoms, and optionally being mono- or polysubstituted,
• Z1 is each independently —O—, —S—, —CO—, —COO—, —OCO—, —S—CO—, —CO—S—, —O—CO—O—, —CO—NR0—, —NR0—CO—, —OCH2—, —CH2O—, —SCH2—, —CH2S—, —CF2O—, —OCF2—, —CF2S—, —SCF2—, —CH2CH2—, —CF2CH2—, —CH2CF2—, —CF2CF2—, —CH═CR0—, —CH═CH—, —CH═CF—, —CY1═CY1—, —C≡C—, —CH═CH—COO—, —OCO—CH═CH— or a single bond,
• R0 and R00 are each independently H or alkyl with 1 to 12 C-atoms,
• Y1 and Y2 are each independently H, F, Cl or CN,
• Q is F,
• X1 and X2 are each F,
• m is 0, and
• n is 0 or 1.