Ferroelectric active matrix displays with wide operating temperature range
AssigneeClariant GmbH
InventorsToshiaki Nonaka, Hans-Rolf Dübal, Rainer Wingen
Life of this patent
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Abstract
The active-matrix display contains a chiral smectic liquid-crystal mixture comprising at least one compound of the formula (I) R1—(A1—M1)a—(A2—M2)b—A3—X—B1—(B2)c—R2 (I). where the symbols are as defined in the description.
Claims12
An active-matrix display containing a ferroelectric (chiral smetic) liquid-crystal mixture in a liquid crystal layer in the form of a monodomain having an unambiguously defined direction of the layer normal z of the SmC* phase, where the layer normal z and the preferential direction n of the nematic or cholestreric phase (M* phase) form an angle of more than 5″, wherein the liquid-crystal mixture comprises at least one compound of the formula (I)
- R1—(A1—M1)a-(A2—M2)b-A3—X—B1—(B2)c-R2 (1)
- where the symbols are as defined below:
- R1, R2 are, independently of one another, identical or different and are each
- a) hydrogen, fluorine or CN a straight-chain or branched alkenyl, alkenyloxy, alkyl or alkyloxy radical (with or without asymmetric carbon atoms) having 2 to 16 carbon atoms, where
- b1) one or two nonterminal —CH2— groups may be replaced by —O—, —OC(═O)—, —(C═O), —C(═O)O—, —Si(CH3)2—, CH(Cl)— and/or one or two —CH2— groups may be replaced by —CH═CH— or —C≡C—
- and one or more H atoms may be replaced by F and/or
- b2) one or more —CH2— groups may be replaced by phenylene-1,4-diyl (unsubstituted, monosubstituted or disubstituted by F), phenylene-1,3-diyl (unsubstituted, monosubstituted or disubstituted by F), cyclohexane-1,4-diyl (unsubstituted or monosubstituted by F or CN) or cyclopropane-1,2-diyl
- and one or more H atoms may be replaced by F
- with the provisos that only one of the radicals R1, R2 can be hydrogen, F or CN and that two adjacent —CH2— groups cannot be replaced by —O—
- M1, M2 are, independently of one another, identical or different and are each —C(═O))—, —OC(═O)—, CH2O—, —OCH2—, —CF2O, —OCF2—, —CH2CH2—, CF2CF2—, —CH═CH—, —CH═CF—, —CF═CF—, —C≡C—, —CH2CH2C(═O)O—, —OC(═O)CH2CH2—, —(CH2)4—, —OCH2CH2CH2—, —CH2CH2CH2O—, —OCH2CF2CH2, —CH2CF2CH2O— or a single bond
- A1, A2, A3 are, independently of one another, identical or different and are each cyclohexane-1,4-diyl (unsubstituted or monosubstituted by F, CH3, CN), cyclohex-1-ene-1,4-diyl, cyclohex-2-ene-1,4-diyl, 2-oxocyclohexane-1,4-diyl, 2-cyclohexen-1-one-3,6-diyl, 1-alkyl-1-silacyclohexane-1,4-diyl, bicyclo[2,2,2]octane-1,4-diyl, spiro[4,5]decane-2,8-diyl, spiro[5,5]undecane-3,9-diyl, phenylene-1,4-diyl (unsubstituted, monosubstituted or disubstituted by CN, CN3, CF3, OCH3, unsubstituted, monosubstituted, disubstituted, trisubstituted or tetrasubstituted by F), phenylene-1,3-diyl (unsubstituted monosubstituted or disubstituted by CN, CH3, CF3, OCF3, unsubstituted, monosubstituted, disubstituted, trisubstituted or tetrasubstituted by F), thiophene-2,5-diyl, thiophene-2,4-diyl, (1,3,4)-oxadiazole-2,5-diyl, (1,3,4)-thiadiazole-2,5-diyl, 1,3-thiazole-2,5-diyl, 1,3-thiazole-2,4-diyl, (1,3)-oxazole-2,5-diyl, isoxazole-2,5-diyl, indane-2,6-diyl, naphthalene-2,6-diyl (unsubstituted, monosubstituted or disubstituted by F or CN), 1,2,3,4-tetrahydronaphthalene-2,6-diyl, decaline-2,6-diyl, pyrimidine-2,5-diyl (unsubstituted or monosubstituted by F), pyridine-2,5-diyl (unsubstituted, monosubstituted or disubstituted by F), pyrazine-2,5-diyl (unsubstituted or monosubstituted by F), pyridazine-3,6-diyl, quinoline-2,6-diyl, quioline-3,7-diyl, isoquinoline-3,7-diyl, quinazoline-2,6-diyl, 5,6,7,8-tetrahydroquinazoline-2,6-diyl, quinoxaline-2,6-diyl, 1,3-dioxane-2,5-diyl (unsubstituted or monosubstituted by CN), benzothiazle-2,6-diyl, piperidine-2,4-diyl, piperazine-1,4-diyl
- B1 is cyclohexane-1,4-diyl (unsubstituted, monosubstituted or disubstituted by F, CH3, CN), perfluorocyclohexane-1,4-diyl, cyclohex-1-ene-1,4-diyl, cyclohex-2-ene-1,4-diyl, 1-alkyl-1-silacyclohexane-1,4-diyl, bicyclo[2,2,2]octane-1,4-diyl, cyclopentane-1,3-diyl, cycloheptane-1,4-diyl, tetrahydrofuran-2,5-diyl, tetrahydrofuran-2,4-diyl, phenylene-1,4-diyl (unsubstituted, monosubstituted or disubstituted by CN, CH3, CF3, OCF3, unsubstituted, monosubstituted, disubstituted, trisubstituted or tetrasubstituted by F), phenylene-1,3-diyl (unsubstituted, monosubstituted or disubstituted by CN, CH3, CF3, OCF3, unsubstituted, monosubstituted, disubstituted or trisubstituted by F), thiophene-2,5-diyl (unsubstituted or monosubstituted by F), thiophene-2,4-diyl (unsubstituted or monosubstituted by F), 1,3-thiazol-2,5-diyl (unsubstituted or monosubstituted by F), 1,3-thiazol-2,4-diyl (unsubstituted or monosubstituted by F) (1,3,4)-thiadiazol-2,5-diyl, 1,3-dioxane-2,5-diyl (unsubstituted or monosubstituted by CN), tetrahydropyran-2,5-diyl, 6,6-difluorotetrahydro pyran-2,5-diyl, 6,6-difluoro-2,3-dihydro-6H-pyran-2,5-diyl, 6-fluoro-3,4-dihydro-2H-pyran-2,5-diyl, piperidine-1,4-diyl, piperazine-1,4-diyl, pyrimidine-2,5-diyl (unsubstituted or monosubstituted by F), pyridine-2,5-diyl (unsubstituted or monosubstituted by F), 1,2,3,4-tetrahydronaphthalene-2,6-diyl, decaline-2,6-diyl
- B2 is cyclohexane-1,4-diyl (unsubstituted, monosubstituted or disubstituted by F, CH3, CN), cyclohex-1-ene-1,4-diyl (unsubstituted or monosubstituted by F), cyclohex-2-ene-1,4-diyl, 1-alkyl-1-silacyclohexane-1,4-diyl, bicyclo[2,2,2]octane-1,4-diyl, phenylene-1,4-diyl (unsubstituted, monosubstituted or disubstituted by CN, CH3, CF3, OCF3, unsubstituted, monosubstituted, disubstituted, trisubstituted or tetrasubstituted by F), phenylene-1,3-diyl (unsubstituted, monosubstituted or disubstituted by CN, CH3, CF3, OCF3, unsubstituted, monosubstituted, disubstituted or trisubstituted by F), thiophene-2,5-diyl, thiophene-2,4-diyl, 1,3-thiazole-2,5-diyl, 1,3-thiazole-2,4-diyl, (1,3,4)-thiadiazole-2,5-diyl, 1,3-dioxane-2,5-diyl (unsubstituted or monosubstituted by CN), tetrahydrofuran-2,5-diyl, tetrahydropyran-2,5-diyl, 6,6-difluorotetrahydropyran-2,5-diyl, 6,6-difluoro-2,3-dihydro-6H-pyran-2,5-diyl, 6-fluoro-3,4-dihyfro-2H-pyran-2,5-diyl, pyrimidine-2,5-diyl (unsubstituted or monosubstituted F), pyridine-2,5-diyl (unsubstituted or monosubstituted F), indane-2,6-diyl, piperidine-1,4-diyl, piperazine-1,4-diyl, pyrimidine-2,5-diyl (unsubstituted or monosubstituted by F)
- X is —(CH2)n—, where
- a) one or two —CH2— groups may be replaced by —O— or —C(═O)— and/or
- b) one —CH2CH2— group may be replaced by —CH═CH— and one or more H of the —CH2— groups may be replaced by F
- with the provisos that
- 1) n is 2, 3 or 4
- 2) two adjacent —CH2— groups cannot be replaced by —O—
- a, b, c are each zero, 1 or 2, with the provisos that
- 1) a must be 1 when R1 is hydrogen, F or CN
- 2) the sum of a+b+c is at least 1
- 3) the radicals A and M, respectively, in the brackets may be identical or different when the corresponding index is 2.
A compound selected from compounds of the formula (XXIII), where:
- n 9 9 9 9 9 9 9 9 9 10 10 10 10 10 10 10 10 10 11 11 11 11 11 11 11 m 3 4 5 6 7 8 9 10 11 3 4 6 7 8 9 10 11 12 5 6 7 8 9 10 11 X — — — — — — — — — — — — — — — — — — — — — — — — — n 12 12 12 12 12 12 12 13 13 13 13 13 13 13 13 13 14 14 14 14 14 14 m 4 6 7 8 9 10 11 3 4 5 6 7 8 9 10 11 3 4 5 6 7 8 X — — — — — — — — — — — — — — — — — — — — — — n 14 14 14 14 6 6 6 6 6 6 6 6 6 6 7 7 7 7 7 7 7 7 7 7 8 8 m 9 10 11 12 3 4 5 6 7 8 9 10 11 12 3 4 5 6 7 8 9 10 11 12 3 4 X — — — — O O O O O O O O O O O O O O O O O O O O O O n 8 8 8 8 8 8 8 9 9 9 9 9 9 9 9 9 9 10 10 10 10 10 10 10 10 10 m 5 7 8 9 10 11 12 3 4 5 6 7 8 9 10 11 12 3 4 5 6 7 8 9 10 11 X O O O O O O O O O O O O O O O O O O O O O O O O O O n 11 11 11 11 11 11 11 11 11 11 12 12 12 12 12 12 12 12 12 12 13 13 13 13 13 13 m 3 4 5 6 7 8 9 10 11 12 3 4 5 6 7 8 9 10 11 12 3 4 5 6 7 8 X O O O O O O O O O O O O O O O O O O O O O O O O O O
- compounds of the formula (XXIV), where:
- n is an integer from 8 to 14
- m is an integer from 3 to 11
- X is a single bond
- with the exception of n=11, m=3 or 5, X is a single bond.
- compounds of the formula (XXV), where:
- n is an integer from 2 to 13
- m is an integer from 3 to 11
- X is O or a single bond
- with the exception of n=2, m=11, X=O;
- n=5, m=5, X=O.
- compounds of the formula (XXVI), where:
- n is an integer from 5 to 13
- m is an integer from 3 to 10
- with the exception of n=8, m=5.
- compounds of the formula (XXVII), where:
- n 8 8 8 8 8 8 8 9 9 9 9 9 9 9 9 9 10 10 10 10 10 10 10 10 m 3 4 6 7 8 9 10 3 4 5 6 7 8 9 10 11 3 4 5 6 7 8 9 10 X — — — — — — — — — — — — — — — — — — — — — — — — n 11 11 11 11 11 11 11 11 12 12 12 12 12 12 12 12 12 13 13 13 13 13 13 m 3 4 5 6 7 8 9 10 3 4 5 6 7 8 9 10 11 3 4 5 6 7 8 X — — — — — — — — — — — — — — — — — — — — — — — n 13 13 13 14 14 14 14 14 14 14 14 7 7 7 7 7 7 7 7 7 8 8 8 8 m 9 10 11 3 4 5 6 7 8 9 10 3 4 5 6 7 8 9 10 11 3 4 6 7 X — — — — — — — — — — — O O O O O O O O O O O O O n 8 8 8 8 9 9 9 9 9 9 9 9 9 10 10 10 10 10 10 10 10 11 11 11 m 8 9 10 11 3 4 5 6 7 8 9 10 11 3 4 5 6 7 8 9 10 3 4 5 X O O O O O O O O O O O O O O O O O O O O O O O O n 11 11 11 11 11 11 11 12 12 12 12 12 12 12 12 13 13 13 13 13 13 13 13 13 m 6 7 8 9 10 11 12 3 4 5 6 7 8 9 10 3 4 5 6 7 8 9 10 11 X O O O O O O O O O O O O O O O O O O O O O O O O
- compounds of the formula (XXIX), where:
- n 6 6 6 7 7 7 7 7 m 7 8 9 4 6 8 9 10 X — — — — — — — — n 8 8 9 9 9 9 9 9 9 10 10 10 m 8 10 3 4 6 7 8 9 10 8 9 19 X — — — — — — — — — — — — n 6 6 6 6 6 6 6 7 7 7 7 7 7 7 7 m 3 4 6 7 8 9 10 3 4 5 6 7 8 9 10 X O O O O O O O O O O O O O O O n 8 8 8 8 8 8 8 8 9 9 9 9 9 9 10 10 10 10 10 10 10 m 3 4 5 6 7 8 9 10 5 6 7 8 9 10 4 5 6 7 8 9 10 X O O O O O O O O O O O O O O O O O O O O O
- compounds of the formula (XXX), where:
- n is an integer from 5 to 13
- m is an integer from 3 to 10
- with the exception of n=8, m=4;
- n=9, m=3.
A compound selected from compounds of the formula (XXXI), where:
- n 10 10 10 10 10 10 10 10 10 10 11 11 11 11 11 11 11 11 11 11 12 12 12 12 m 3 4 5 6 7 8 9 10 11 12 3 4 5 6 7 8 9 10 11 12 3 4 5 6 X — — — — — — — — — — — — — — — — — — — — — — — — n 12 12 12 12 12 12 13 14 14 14 14 14 14 14 14 14 6 6 6 6 6 6 6 6 m 7 8 9 10 11 12 3 4 5 6 7 8 9 10 11 12 3 4 5 6 7 8 9 10 X — — — — — — — — — — — — — — — — O O O O O O O O n 6 6 7 7 7 7 7 7 7 7 7 7 8 8 8 8 8 8 8 8 8 9 9 9 m 11 12 3 4 5 6 7 8 9 10 11 12 3 4 5 6 8 9 10 11 12 3 4 5 X O O O O O O O O O O O O O O O O O O O O O O O O n 9 9 9 9 9 9 9 10 10 10 10 10 10 10 10 10 10 11 11 11 11 11 11 11 m 6 7 8 9 10 11 12 3 4 5 6 7 8 9 10 11 12 3 4 5 6 7 8 9 X O O O O O O O O O O O O O O O O O O O O O O O O n 11 11 11 12 12 12 12 12 12 12 12 12 12 13 13 13 13 13 13 13 13 13 13 14 m 10 11 12 3 4 5 6 7 8 9 10 11 12 3 4 5 6 7 8 9 10 11 12 3 X O O O O O O O O O O O O O O O O O O O O O O O O n 14 14 14 14 14 14 14 14 14 m 4 5 6 7 8 9 10 11 12 X O O O O O O O O O
- compounds of the formula (XXVIII), where:
- n 11 12 13 14 13 14 12 13 14 13 14 10 11 12 13 14 13 14 9 10 11 12 13 10 m 5 5 5 5 6 6 7 7 7 8 8 9 9 9 9 9 10 10 11 11 11 11 11 12 X — — — — — — — — — — — — — — — — — — — — — — — — n 11 12 13 14 6 6 6 6 6 6 6 6 6 7 7 7 7 7 7 7 7 7 8 8 m 12 12 12 12 4 5 6 7 8 9 10 11 12 4 5 6 7 8 9 10 11 12 4 6 X — — — — O O O O O O O O O O O O O O O O O O O O n 8 8 8 8 9 9 9 9 9 9 9 9 10 10 10 10 10 10 10 10 11 11 11 11 m 8 10 11 12 4 5 6 8 9 10 11 12 4 5 7 8 9 10 11 12 4 5 6 7 X O O O O O O O O O O O O O O O O O O O O O O O O n 11 11 11 11 11 12 12 12 12 12 12 12 12 m 8 9 10 11 12 5 6 7 8 9 10 11 12 X O O O O O O O O O O O O O
- compounds of the formula (XXXII), where:
- n 5 5 5 5 5 5 5 5 6 6 6 6 6 6 6 6 7 7 7 7 m 2 3 4 5 6 7 8 9 2 3 4 5 6 7 8 9 2 3 4 5 n 7 7 7 7 8 8 8 8 8 8 8 8 9 9 9 9 9 9 9 9 10 10 10 10 10 m 6 7 8 9 2 3 4 5 6 7 8 9 2 3 4 5 6 7 8 9 2 3 4 5 6 n 10 10 10 11 11 11 11 11 11 11 11 12 12 12 12 12 12 12 12 13 13 13 m 7 8 9 2 3 4 5 6 7 8 9 2 3 4 5 6 7 8 9 2 3 4 n 13 13 13 13 13 14 14 14 14 14 14 14 14 m 5 6 7 8 9 2 3 4 5 6 7 8 9
- and where Z is H or F in all cases.
Dependencies are inferred from the claim text.