Method for the preparation of photoaligning polymer materials and compositions
AssigneeRolic Technologies AG
InventorsCedric KLEIN, Fabien Xavier DELBAERE, Richard FRANTZ
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Abstract
The present invention relates to a novel method for the preparation of photoaligning polymer materials comprising aryl acrylic acid ester groups, to photoalignment compositions obtained by this process, to the use of the composition as orienting layer for liquid crystals and to non-structured and structured optical elements, electro-optical elements, multi-layer systems or in nanoelectronics comprising the compositions.
Claims19
A process for the preparation of a photoaligning polymer material comprising aryl acrylic acid ester groups comprising the steps of:
- a. reacting a compound of formula (II)
- wherein:
- ring C is phenylene which is unsubstituted or optionally substituted with fluorine, chlorine, cyano, alkyl or alkoxy, pyrimidine-2,5-diyl, pyridine-2,5-diyl, 2,5-thiophenylene, 2,5-furanylene, 1,4- or 2,6-naphthylene,
- Y is either C or O;
- and
- if Y is C then m=1 and R═COOR′,
- wherein R′ is straight-chain or branched alkylene group with 1 to 20 carbon atoms which is optionally at least once substituted with halogen or with at least one siloxane moieties, or a cycloalkyl residue with 3 to 8 ring atoms which is optionally substituted with at least one halogen, alkyl or alkoxy;
- or
- if Y is 0, then m=0;
- with a compound of formula (III)
- M1 signifies a repeating monomer unit from the group consisting of acrylate, methacrylate, 2-chloroacrylate, 2-phenylacrylate, acrylamide, methacrylamide, 2-chloroacrylamide, 2-phenylacrylamide, N-lower alkyl substituted acrylamide, N-lower alkyl substituted methacrylamide, N-lower alkyl substituted 2-chloroacrylamide, N-lower alkyl substituted 2-phenylacrylamide, vinyl ether, vinyl ester, styrene, diamine, amide, imide, siloxane, amic ester, and amic acid;
- S1 is a spacer unit;
- ring A signifies phenylene which is unsubstituted or optionally substituted with fluorine, chlorine, cyano, alkyl or alkoxy, pyridine-2,5-diyl, pyrimidine-2,5-diyl, 1,3-dioxane-2,5-diyl, cyclohexane-1,4-diyl, piperidine-1,4-diyl or piperazine-1,4-diyl;
- ring B signifies phenylene which is unsubstituted or optionally substituted with fluorine, chlorine, cyano, alkyl or alkoxy, pyridine-2,5-diyl, pyrimidine-2,5-diyl, 1,4- or 2,6-naphthylene, 1,3-dioxane-2,5-diyl or cyclohexane-1,4-diyl;
- Y1, Y2 each independently signify a single covalent bond, —(CH2)t—, —O—,
- —CO—, —CO—O—, —O—OC—, —CF2O—,—OCF2—, —NR4—, —CO—NR4—, —R4N—CO—, —(CH2)t—, —O—,
- O—, —O—(CH2)u—, —(CH2)u—NR4— or —NR4—(CH2)u—, in which
- R4 signifies hydrogen or lower alkyl;
- T signifies a whole number of 1 to 4;
- u signifies a whole number of 1 to 3;
- and
- m, n signifies a whole number of 0 to 4;
- and
- optionally with a compound of formula (IV) or (IV′)
- and
- b. optionally reacting the compound obtained under step a. with a compound of formula (V)
- X—(CZqZ′q′)—CZrZ′r′ (V)
- wherein X is OH, F, Cl or I;
- Z and Z′ are independently from each other either H or halogen;
- q and q′ are independently from each other an integer between 0 and 2;
- p is an integer between 0 and 10
- r and r′ are independently from each other an integer between 0 and 3;
- c. polymerizing the compound obtained under step a. or b. with an organic or inorganic peroxide;
- d. stopping the reaction by heating.
A composition comprising the compounds according to claim5.
A composition comprising:
- a homopolymer comprising monomers of formula (I):
- and at least one monomer of formula (I);
- wherein M1, S1, ring A, Y1, ring B, Y2, n, m and ring C have the same meaning as described above;
- and
- wherein Z signifies —O— or —NR5—, in which R5 signifies hydrogen or lower alkyl, or a second group of formula D or D′;
- and
- wherein D signifies a straight-chain or branched alkylene group with 1 to 20 carbon atoms which is optionally at least once substituted with halogen or with at least one siloxane moieties, or a cycloalkyl residue with 3 to 8 ring atoms which is optionally substituted with at least one halogen, alkyl or alkoxy.
Dependencies are inferred from the claim text.