Cyclohexylene reactive mesogens and their applications
AssigneeMerck Patent GmbH
InventorsLouise Diane Farrand, Kevin Adlem, Andreas Taugerbeck, John Patrick, Christopher John Dunn, Janice McCreary
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Abstract
The invention relates to new cyclohexylene reactive mesogens (RM), polymers derived thereof, liquid crystal (LC) media comprising them, and the use of the compounds, polymers and liquid crystalline media in optical, electrooptical, electronic, semiconducting or luminescent components or devices, in decorative, security, cosmetic or diagnostic applications, especially in the polymer stabilised blue phase.
Claims29
A compound according to formula I
- R1-A-(B)b—R2 I
- wherein
- R1 and R2 are independently of each other selected from H, F, Cl, Br, I, CN, NCS, SF5, or straight-chain or branched alkyl having 1 to 30 C-atoms that is optionally mono- or polysubstituted by F, Cl, 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 denote P-Sp-, wherein at least one of R1 and R2 is P-Sp,
- R0 and R00 independently of each other denote H or alkyl with 1 to 12 C-atoms,
- Y1 and Y2 independently of each other denote H or F,
- P is a polymerizable group,
- Sp is a Sp′-X′ or a single bond,
- Sp′ 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,
- X′ is —O—, —S—, —CO—, —COO—, —OCO—, —O—COO—,—CO—NR0—, —NR0—CO—, —NR0—CO—NR0—, —OCH2—, —CH2O—, —SCH2—, —CH2S—, —CF2O—, —OCF2—, —CF2S—, —SCF2—, —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,
- A and B are independently of each other 1,4-cyclohexylene wherein one or more —CH2— groups are optionally replaced by —O— and/or —S—, in such a way, that no two O-atoms are linked together and that is optionally substituted, and
- b is 0 or 1;
- wherein at least one of R1 and R2 is P-Sp′-X′ is not a single bond, and if only one of R1 and R2 is P-Sp′-X′— then X′ is not —O— or —CH2O— and Sp ′ is not an alkylene with 1 20 C atoms wherein only one CH2 group is replaced and it is replaced by —O—;
- with the proviso that compounds wherein;
- b is 0,
- R1 and R2 are P-Sp,
- P is arcylate or methacrylate, and
- Sp is a single bond or a —CH2— group
- are excluded.
A liquid-crystal medium comprising one or more compounds of formula I
- R1-A-(B)b—R2 I
- wherein
- R1 and R2 are independently of each other selected from H, F, Cl, Br, I, CN, NCS, SF5, or straight-chain or branched alkyl having 1 to 30 C-atoms that is optionally mono- or polysubstituted by F, Cl, 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 denote P-Sp-, wherein at least one of R1 and R2 is P-Sp,
- R0 and R00 independently of each other denote H or alkyl with 1 to 12 C-atoms,
- Y1 and Y2 independently of each other denote H or F,
- P is a polymerizable group,
- Sp is a SP′-X′ or a single bond,
- Sp′ 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,
- X′ is —O—, —S—, —CO—, —COO—, —OCO—, —O—COO—, —CO—NR0—, —NR0—CO—, —NR0—CO—NR0—, —OCH2—, —CH2O—, —SCH2—, CH2S—, —CF2O—, —OCF2—, —CF2S—, —SCF2—, —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,
- A and B are independently of each other 1,4-cyclohexylene wherein one or more —CH2— groups are optionally replaced by —O— and/or —S—, in such a way, that no two O-atoms are linked together and that is optionally substituted, and
- b is 0 or 1,
- wherein at least one of R1 and R2 is P-Sp′-X′— in which X′ is not a single bond, and if only one of R1 and R2 is P-Sp′-X′— then X′ is not —O— or —CH2O— and Sp′ is not an alkylene with 1 to 20 C atoms wherein only one CH2 group is replaced and it replaced by —O—.
A compound according to formula I
- R1-A-(B)b-R2 I
- wherein
- R1 and R2 are independently of each other P-Sp′-X′—,
- P is a polymerizable group,
- Sp′ 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,
- X′ is —O—, —S—, —CO—, —COO—, —OCO—, —O—COO—, —CO—NR0—, —NR0—CO—, —NR0—CO—NR0—, —OCH2—, —CH2O—, —SCH2—,—CH2S—, —CF2O—, —OCF2—, —CF2S—, —SCF2—, —CF2CH213 , —CH2CF2—, —CF2CF2—, —CH═N—, —N═CH—, —N═N—, —CH═CR0—, —CY1═CY213 , —C≡C—, —CH═CH—COO—, —OCO—CH═CH— or a single bond,
- R0 and R00 independently of each other denote H or alkyl with 1 to 12 C-atoms,
- Y1 and Y2 independently of each other denote H or F,
- A and B are independently of each other 1,4-cyclohexylene wherein one or more —CH2— groups are optionally replaced by —O— and/or —S—, in such a way, that no two O-atoms are linked together and that is optionally substituted, and
- b is 0 or 1;
- with the proviso that compounds wherein:
- b is 0,
- P is acrylate or methacrylate,
- Sp′ is a single bond or a —CH2— group, and
- X′ is a single bond,
- are excluded.
A compound selected from the following formulae IB to ID
- wherein
- R1 is selected from H, F, Cl, Br, I, CN, NCS, SF5, or straight-chain or branched alkyl having 1 to 30 C-atoms that is optionally mono- or polysubstituted by F, Cl, 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,
- Y1 and Y2 independently of each other denote H or F,
- P, P1 and P2 are, independently of each other, a polymerizable group,
- X, X1 and X2 are, independently of each other, —O—, —S—, —CO—, —COO—, —OCO—, —O—COO—, —CO—NR0—, —NR0—CO—, —NR0—CO—NR0—, —OCH2—, —CH2O—, —SCH2—,—CH2S—, —CF2O—, —OCF2—, —CF2S—, —SCF2—, —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, and
- Sp, Sp1 and Sp2 are, independently of each other, 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,
- with the proviso that compounds of Formula IB wherein P1 and P2 are acrylate or methacrylate, and Sp1-X1— and Sp2-X2— are a single bond or a —CH2— group are excluded.
Dependencies are inferred from the claim text.