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US 7,597,942 B2Granted
Polymerisable liquid crystal material
AssigneeMerck Patent GmbH
InventorsAlison Linda May, Peter (Fangyun) Hsu, Tara Perrett, Ashley Nathan Smith, Owain Llyr Parri
Life of this patent
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Abstract
The invention relates to a polymerisable liquid crystal (LC) material, to optically biaxial films prepared thereof, to novel polymerisable compounds used therein and to the use of the material and films in optical devices like compensators and LC displays (LCDs).
Claims27
Polymerisable LC material comprising the following components:
- A) at least one compound having a high birefringence selected of formula I
- wherein
- P is a polymerisable or reactive group,
- Sp is a spacer group or a single bond,
- A is in case of multiple occurrence independently of one another an aromatic or aliphatic 5- or 6-ring, or a group comprising two or three fused aromatic or aliphatic 5- or 6-rings, these rings optionally containing one or more hetero atoms selected from N, O and S, and optionally being substituted by one or more identical or different groups L1,
- Z is in case of multiple occurrence independently of one another —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, R00 are independently of each other H or alkyl with 1 to 12 C-atoms,
- Y1, Y2 are independently of each other H, F, Cl or CN,
- m1, m2 are independently of each other 0, 1 or 2, with m1+m2 ≦3,
- L1, L2 are independently of each other F, Cl, Br, I, CN, NO2, P-Sp- or alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonlyoxy or alkoxycarbonyloxy with 1 to 12 C atoms, wherein one or more H atoms are optionally replaced by F or Cl,
- r1, r2 are independently of each other 0, 1, 2, 3 or 4,
- R1 is H, halogen, CN, NO2, NCS, SF5, P-Sp- or straight chain or branched alkyl with 1 to 20 C-atoms that 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—, —NR0—, —SiR0R00—, —CO—, —COO—, —OCO—, —OCO—O—, —NR0—CO—, —CO—NR0—, —NR0—CO—NR0—, —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,
- wherein at least one compound of formula Ia
- wherein P and Sp are as defined in formula I,
- Z0 is —COO—, —OCO— or a single bond,
- L1a,1b,2a,2b are independently of each other F, Cl, CN, (O)aCbFcH2b+1−c or COCH3,
- r1a, r1b, r2a, r2b are independently of each other 0 or 1, with at least one of r1a,
- r1b, r2a, r2b being 1,
- R1a is Cl or optionally mono- or polyfluorinated straight-chain or branched alkyl with 1 to 6 C-atoms wherein one or two non-adjacent CH2-groups are optionally replaced by —O—, —S—, —CO—, —COO—, —OCO—, —OCO—O—, —S—CO— or —CO—S— in such a manner that O and/or S atoms are not linked directly to one another,
- a is 0 or 1,
- b is 1 or 2,
- c is 0, 1, 2, 3, 4 or 5,
- B) at least one polymerisable mesogenic compound having two or more polymerisable groups,
- C) at least one chiral compound having a high helical twisting power (HTP),
- D) optionally at least one monoreactive polymerisable compound having an enantiotropic nematic phase and a clearing point of 75° C. or higher,
- E) at least one dichroic photoinitiator.
23 more elements
Compounds of formula Ia
- wherein
- P is CH2═CW1—COO—, CH2═CW1 —CO—,
- CH2═CW2—(O)k1—, 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)k2—, CH2CH—(CO)k1—Phe—(O)k2—, Phe—CH═CH—, HOOC—, OCN—, or W4W5W6Si—, with W1 being H, Cl, CN, CF3, phenyl or alkyl with 1 to 5 C-atoms, W2 and W3 being independently of each other H or alkyl with 1 to 5 C-atoms, W4, W5and W6 being independently of each other Cl, oxaalkyl or oxacarbonylalkyl with 1 to 5 C-atoms, W7 and W8 being independently of each other H, Cl or alkyl with 1 to 5 C-atoms, Phe being 1,4-phenylene that is optionally substituted by one or more groups L1b, L1a, L2a, or L2b and k1 and k2 being independently of each other 0 or 1,
- Sp is a spacer group or a single bond,
- Z0 is —COO—, —OCO— or a single bond,
- L1a,1b,2a,2b are independently of each other F, Cl, CN, (O)aCbFcH2b+1−c or COCH3,
- r1a, r1b, r2a, r2b are independently of each other 0 or 1, with at least one of r1a, r1b, r2a, r2b being 1,
- R1a is Cl or optionally mono- or polyfluorinated straight-chain or branched alkyl with 1 to 6 C-atoms wherein one or two non-adjacent CH2— groups are optionally replaced by —O—, —S—, —CO—, —COO—, —OCO—, —OCO—O—, —S—CO— or —CO—S— in such a manner that O and/or S atoms are not linked directly to one another,
- a is 0 or 1,
- b is 1 or 2,
- c is 0, 1, 2, 3, 4 or 5.
8 more elements
A compound according to formula Ia
- where P is CH2═CW1—COO—, CH2═CW1 —CO—,
- CH2═CW2—(O)k1—, CH3—CH═CH—O—, (CH2CH)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)k2—, CH2CH—(CO)k1—Phe—(O)k2—, Phe—CH═CH—, HOOC—, OCN—, or W4W5W6Si-, with W1 being H, Cl, CN, CF3, phenyl or alkyl with 1 to 5 C-atoms, W2 and W3 being independently of each other H or alkyl with 1 to 5 C-atoms, W4, W5and W6 being independently of each other Cl, oxaalkyl or oxacarbonylalkyl with 1 to 5 C-atoms, W7 and W8 being independently of each other H, Cl or alkyl with 1 to 5 C-atoms, Phe being 1,4-phenylene that is optionally substituted by one or more groups L1b, L1a, L2a, or L2b and k1 and k2 being independently of each other 0 or 1,
- Sp is a spacer group or a single bond,
- Z0 is —COO—, —OCO— or a single bond,
- L1a,1b,2a,2b are independently of each other F, Cl, CN, (O)aCbFcH2b+1−c or COCH3,
- r1a, r1b, r2a, r2b are independently of each other 0 or 1, with at least one of r1a, r1b, r2a, r2b being 1,
- R1a is Cl, mono- or polyfluorinated alkyl with 1 to 6 C-atoms, optionally mono- or polyfluorinated alkoxy with 1 to 6 C-atoms, or optionally mono- or polyfluorinated alkylsulfanyl with 1 to 6 C-atoms,
- a is 0 or 1,
- b is 1 or 2, and
- c is 0, 1, 2, 3, 4 or 5.
7 more elements
Dependencies are inferred from the claim text.