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US 2014/0192305 A1Published application
Photoreactive compounds
AssigneeRolic AG
InventorsFrederic Lincker, Izabela Bury S. Pires, Sabrina Chappellet, Patricia Scandiucci De Freitas, Mohammed Ibn-Elhaj, Qian Tang, Satish Palika, Masato Hoshino, Jean-Francois Eckert
Life of this patent
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Abstract
The present invention relates to photoreactive compounds that are particularly useful in materials for the alignment of liquid crystals.
Claims32
A compound comprising a group terminal group of formula (I)
- wherein:
- A1 and A2 each independently are a ring system of 5 to 40 atoms, wherein each ring system includes at least one unsaturation directly connected via electron conjugation (□-□ bonding) to the double bond shown in formula (I);
- and wherein and A2 is linked to a polymerizable group by a single bond or at least one spacer unit;
- R1 is hydrogen, a substituent L, hydroxy or a straight-chain or branched, substituted or unsubstituted C1-C12alkyl, in which one or more C-atom, CH— or CH2— group is unreplaced or replaced by a linking group;
- and wherein if
- W is hydrogen and Z is an electron withdrawing group, then
- R4, R5 are hydrogen, and R2 and R3 are independently from each other an electron-donating single substituent, or R2 and R3 form together the residue of an electron-donating ring which is condensed to ring A1;
- or
- if W is hydrogen and Z is an electron withdrawing group, then
- R4, R5 are independently from each other a substituent L, which is halogen, hydroxy and/or a polar group;
- or, an electron-donating single substituent, or R4, R5 form together the residue of an electron-donating ring which is condensed to ring A2, then R2 and R3 form together the residue of an electron-donating ring which is condensed to ring A1;
- or if W is an electron withdrawing group and Z is hydrogen, then
- R4, R5 are independently from each other hydrogen, a substituent L, an electron-donating single substituent, or R4, R5 form together the residue of an electron-donating ring which is condensed to ring A2 or hydrogen, and R2 and R3 are independently from each other an electron-donating single substituent, or form together the residue of an electron-donating ring which is condensed to ring A1.
10 more elements
A compound comprising a terminal group of formula (Ia)
- wherein:
- the doted line means a linkage of the terminal group to the residue of the compound;
- A1 and A2 each independently are a ring system of 5 to 40 atoms, wherein each ring system includes at least one unsaturation directly connected via electron conjugation (□-□ bonding) to the double bond shown in formula (I);
- and wherein A2 is linked to a polymerizable group by a single bond or at least one spacer unit;
- R1 is hydrogen, a substituent L or a straight-chain or branched, substituted or unsubstituted C1-C12alkyl, in which one or more C-atom, CH— or CH2— group is unreplaced or replaced by a linking group;
- and wherein if
- W is hydrogen and Z is an electron withdrawing group, then
- R4, R5 are hydrogen, and R2 and R3 are independently from each other an electron-donating single substituent, preferably these electron-donating single substituents are in meta-position to each other;
- or
- R2 and R3 form together the residue of an electron-donating ring which is condensed to ring A1;
- or
- if W is hydrogen and Z is an electron withdrawing group, then
- R4, R5 are independently from each other hydrogen, a substituent L, or an electron-donating single substituent, with the proviso that at least one R4 or R5 is a substituent L, or an electron-donating single substituent;
- or R4, R5 form together the residue of an electron-donating ring which is condensed to ring A2;
- and,
- R2 and R3 form together the residue of an electron-donating ring which is condensed to ring A1;
- or
- R4 is —O—C2-C6alkyl, such as —O-ethyl, —O-propyl, —O-butyl, —O-pentyl, —O-hexyl, R5 is hydrogen and R2 and R3 are hydrogen or an electron-donating single substituent, preferably both R2 and R3 are an electron-donating single substituent;
- or
- R4, R5 are independently from each other a substituent L, an electron-donating single substituent, or hydrogen;
- and R2 and R3 are independently from each other —O—C2-C6alkyl, such as —O-ethyl, —O-propyl, —O-isopropyl, —O-butyl, —O-tert-butyl, —O-sec-butyl, —O-pentyl, —O-isopentyl, —O-hexyl;
- or
- R4, R5 are independently from each other a —O—C2-C6alkyl, such as —O-ethyl, —O-propyl, —O-isopropyl, —O-butyl, —O-tert-butyl, —O-sec-butyl, —O-pentyl, —O-isopentyl, —O-hexyl or hydrogen, and R2 and R3 are independently from each other —O—C2-C6alkyl, such as —O-ethyl, —O-propyl, —O-isopropyl, —O-butyl, —O-tert-butyl, —O-sec-butyl,
- —O-pentyl, —O-isopentyl, —O-hexyl;
- or
- R4, R5 are independently from each other a substituent L, an electron-donating single substituent, preferably R4, R5 are O—C1-C6alkyl, more preferably —O-methyl, —O-ethyl, and R2 and R3 are independently from each other —O—C1-C6alkyl, such as —O-methyl,
- —O-ethyl, —O-propyl, —O-isopropyl, —O-butyl, —O-tert-butyl, —O-sec-butyl, —O-pentyl, —O-isopentyl, —O-hexyl;
- or if W is an electron withdrawing group and Z is hydrogen, then
- R4, R5 are independently from each other hydrogen, a substituent L, an electron-donating single substituent, or R4, R5 form together the residue of an electron-donating ring which is condensed to ring A2 or hydrogen, and R2 and R3 are independently from each other an electron-donating single substituent, or form together the residue of an electron-donating ring which is condensed to ring A1;
- most preferred is
- W is hydrogen and Z is an electron withdrawing group, then
- R4, R5 are hydrogen, and R2 and R3 are independently from each other an electron-donating single substituent, preferably these electron-donating single substituents are in meta-position to each other;
- or
- R2 and R3 form together the residue of an electron-donating ring which is condensed to ring A1;
- or
- if W is hydrogen and Z is an electron withdrawing group, then
- R4, R5 are independently from each other hydrogen, a substituent L, or an electron-donating single substituent, with the proviso that at least one R4 or R5 is a substituent L, or an electron-donating single substituent;
- or R4, R5 form together the residue of an electron-donating ring which is condensed to ring A2;
- and,
- R2 and R3 form together the residue of an electron-donating ring which is condensed to ring A1;
- or
- or if W is an electron withdrawing group and Z is hydrogen, then
- R4, R5 are independently from each other hydrogen, a substituent L, an electron-donating single substituent, or R4, R5 form together the residue of an electron-donating ring which is condensed to ring A2 or hydrogen, and R2 and R3 are independently from each other an electron-donating single substituent, or form together the residue of an electron-donating ring which is condensed to ring A1.
40 more elements
Dependencies are inferred from the claim text.