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US 7,442,475 B2Granted
Cyanopyridone derivatives as liquid crystals
AssigneeMerck Patent GmbH
InventorsLouise Diane Farrand, Michael Heckmeier
Life of this patent
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Abstract
The invention relates to cyanopyridone derivatives, to their use in liquid crystal media, liquid crystal devices, anisotropic polymers, optical, electrooptical, decorative, security, cosmetic, diagnostic, pharmaceutic, electric, electronic, charge transport, semiconductor, optical recording, electroluminescent, photoconductor and electrophotographic applications, and to liquid crystal media, polymers and displays comprising them.
Claims19
A liquid crystalline medium, comprising at least two liquid crystalline compounds, wherein at least one of said compounds comprises a 5-cyanophridon-2-yl group is of formula I
- wherein R1, R2 and R3 are independently of each other H or an optionally substituted aliphatic, cycloaliphatic or aromatic group with up to 20 C atoms that optionally comprises one or more hetero atoms and optionally comprises fused rings,
- A1 and A2 are independently of each other an aromatic or alicyclic ring, or a group comprising two or more fused aromatic or alicyclic rings, wherein these rings optionally contain one or more hetero atoms selected from N, O, and S, and are optionally mono- or polysubstituted by R,
- Z1 and Z2 are independently of each other —O—, —S—, —CO—, —COO—, —OCO—, —S—CO—, —CO—S—, —O—COO—, —CO—NR0—, —NR0—CO—, —OCH2—, —CH2O—, —SCH2—, —CH2S—, —CF2O—, —OCF2—, —CF2S—, —SCF2—, —CH2CH2—, —CF2CH2—, —CH2CF2—, —CF2CF2—, —CH═N—, —N═CH—, —N═N—, —CH═CR0—, —CY1═CY2—, —C≡C—, —CH═CH—COO—, —OCO—CH═CH— or a single bond,
- Y1 and Y2 are independently of each other H, F, CI or CN,
- R is H, F, Cl, Br, I, CN, NO2, NCS, SF5 or alkyl which is straight chain or branched, has 1 to 20 C-atoms, is unsubstituted, mono- or poly-substituted by F, CI, Br, I or CN, and in which 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—, —CY1═CY2— or —C═C— in such a manner that O and/or S atoms are not linked directly to one another, or R denotes P-Sp
- R0 and R00 are independently of each other H or alkyl with 1 to 12 C-atoms,
- P is a polymerisable or reactive group,
- Sp is a spacer group or a single bond, and
- m is 0, 1 or 2.
8 more elements
A cyanopyridone compound of formula I,
- wherein R1, R2 and R3 are independently of each other H or an optionally substituted aliphatic, cycloaliphatic or aromatic group with up to 20 C atoms that optionally comprises one or more hetero atoms and optionally comprises fused rings,
- A1 and A2 are independently of each other an aromatic or alicyclic ring, or a group comprising two or more fused aromatic or alicyclic rings, wherein these rings optionally contain one or more hetero atoms selected from N, O and S, and are optionally mono- or polysubstituted by R,
- Z1 and Z2 are independently of each other —O—,—S—,—CO—,
- —COO—, —OCO—, —S—CO—,—CO—S—, —O—COO—, —CO—NR0—,
- —NR0—CO—, —OCH2—, —CH2O—, —SCH2—, —CH2S—, —CF2O—,
- —OCF2—, —CF2S—, —SCF2—, —CH2CH2−, —CF2CH2—,
- —CH2CF2—, —CF2CF2—, —CH═N—, —N═CH—, —N═N—,
- —CH═CR0—, —CY1═CY2—, —C═C—, —CH═CH—COO—, —OCO—CH═CH— or a single bond,
- Y1 and Y2 are independently of each other H, F, Cl or CN,
- R is H, CN, NO2, NCS, SF5 or alkyl which is straight chain or branched, has 1 to 20 C-atoms, is unsubstituted, mono- or poly-substituted by F, CI, Br, I or CN, and in which one or more non-adjacent CH2 groups are replaced, in each case independently from one another, by —S—, —NH—, —NR0—, —SiR0R00—, —CO—, —COO—, —OCO—, —OCO—O—,
- —S—CO—, —CO—S—, —CY1═CY2 or —C═C— in such a manner that O and/or S atoms are not linked directly to one another, or R denotes P-Sp,
- R0 and R00 are independently of each other H or alkyl with 1 to 12 C-atoms,
- P is a polymerisable or reactive group,
- Sp is a spacer group or a single bond, and
- m is 0, 1 or 2, with the proviso that if m is 0, R1 and R3 are H, R2 is carboxyethyl and Z1 is CH═CH, CH═C(CH3) or CH═C(C6H5), then A1—R is different from phenyl or 4-methoxyphenyl.
12 more elements
A cyanopyridone compound of formula I,
- wherein R1, R2 and R3 are independently of each other H or an optionally substituted aliphatic, cycloaliphatic or aromatic group with up to 20 C atoms that optionally comprises one or more hetero atoms and optionally comprises fused rings,
- A1 and A2 are independently of each other an aromatic or alicyclic ring, or a group comprising two or more fused aromatic or alicyclic rings, wherein these rings optionally contain one or more hetero atoms selected from N, O and S, and are optionally mono- or polysubstituted by R,
- Z1 Z2 are independently of each other —O—, —S—, —CO—,
- —COO—, —OCO—, —S—CO—, —CO—S—, —O—COO—, —CO—NR0—,
- —NR0—CO—, —OCH2—, —CH2O—, —SCH2—, —CH2S—,—CF2O—,
- —OCF2—, —CF2S—, —SCF2—, —CH2CH2—, —CF2CH2—,
- —CH2CF2—, —CF2CF2—, —CH═N—, —N═CH—, —N═N—,
- —CH═CR0—, —CY1═CY2—, —C═C—, —CH═CH—COO—, —OCO—CH═CH— or a single bond,
- Y1 and Y2 are independently of each other H, F, Cl or CN,
- R is H, CN, NO2, NCS, SF5 or P-Sp,
- R0 and R00 are independently of each other H or alkyl with 1 to 12 C-atoms,
- P is a polymerisable or reactive group,
- Sp is a spacer group or a single bond, and
- m is 0, 1 or 2.
11 more elements
Dependencies are inferred from the claim text.