Liquid crystal dielectric
First Claim
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1. A liquid-crystal dielectric useful for electrooptical display elements comprising at least two liquid crystal components, wherein at least one component is a compound of the formula ##STR4## wherein G is H2 or ═
- O;
R1 and R2 each independently is alkyl of 1-10 C-atoms;
alkyl of 1-10 C atoms wherein one or two non-adjacent CH2 groups are replaced by O atoms;
F;
Cl;
Br;
or CN; and
R2 can also be H;
A1 and A2 each independently is 1,4-phenylene, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, piperidine-1,4-diyl, 1,4-bicyclo[2.2.2]octylene or pyrimidine-2,5-diyl or one of these groups substituted by 1-4 F atoms;
Z1 and Z2 each independently is --CO--O--, --O--CO--, CH2 CH2 --, --OCH2 --, --CH2 O--, or a single bond; and
m and n each is 0, 1, 2, or 3, but (m+n) is at least 1 and at most 3, it being possible, when m is 2 or 3, for the groups A1 and, when n is 2 or 3, for the groups A2 each to be identical or different from one another, with the proviso that when --(A2)n --R2 is OR, wherein R is H or alkyl, Z1 and Z2 are single bonds, and G is H2, then R1 -(A1)m -- is not 4-cyanophenyl, 4-alkylphenyl and 4-alkylcyclohexyl.
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Abstract
New tetrahydropyran derivatives of the formula I ##STR1## in which G is H2 or ═O, R1 and R2 are each an alkyl group having 1-10 C atoms, it also being possible for one or two CH2 groups to be replaced by O atoms, or are F, Cl, Br or CN, R2 is also H, A1 and A2 are each 1,4-phenylene, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, piperidine-1,4-diyl, 1,4-bicyclo[2.2.2]octylene or pyrimidine-2,5-diyl groups which are unsubstituted or substituted by 1-4 F atoms, Z1 and Z2 are each --CO--O--, --O--CO--, --CH2 CH2 --, --OCH2 --, --CH2 O--, or a single bond, m and n are each 0, 1, 2 or 3, but (m+n) is at least 1 and at most 3, it being possible, when m is 2 or 3, for the group A1 and, when n is 2 or 3, for the groups A2 each to be identical or different from one another, and the acid addition salts of those among these compounds which are basic, are suitable for use as components in liquid-crystal dielectrics.
51 Citations
17 Claims
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1. A liquid-crystal dielectric useful for electrooptical display elements comprising at least two liquid crystal components, wherein at least one component is a compound of the formula ##STR4## wherein G is H2 or ═
- O;
R1 and R2 each independently is alkyl of 1-10 C-atoms;
alkyl of 1-10 C atoms wherein one or two non-adjacent CH2 groups are replaced by O atoms;
F;
Cl;
Br;
or CN; and
R2 can also be H;A1 and A2 each independently is 1,4-phenylene, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, piperidine-1,4-diyl, 1,4-bicyclo[2.2.2]octylene or pyrimidine-2,5-diyl or one of these groups substituted by 1-4 F atoms; Z1 and Z2 each independently is --CO--O--, --O--CO--, CH2 CH2 --, --OCH2 --, --CH2 O--, or a single bond; and m and n each is 0, 1, 2, or 3, but (m+n) is at least 1 and at most 3, it being possible, when m is 2 or 3, for the groups A1 and, when n is 2 or 3, for the groups A2 each to be identical or different from one another, with the proviso that when --(A2)n --R2 is OR, wherein R is H or alkyl, Z1 and Z2 are single bonds, and G is H2, then R1 -(A1)m -- is not 4-cyanophenyl, 4-alkylphenyl and 4-alkylcyclohexyl. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16)
- 3. A dielectric of claim 1 wherein said compound is of the formula
- space="preserve" listing-type="equation">R.sup.1 --Z.sup.1 --A--Z.sup.2 --Phe--R.sup.2
space="preserve" listing-type="equation">R.sup.1 --Z.sup.1 --A--Z.sup.2 --Cy--R.sup.2
space="preserve" listing-type="equation">R.sup.1 --Z.sup.1 --A--Z.sup.2 --Dio--R.sup.2
space="preserve" listing-type="equation">R.sup.1 --Z.sup.1 --A--Z.sup.2 --Pip--R.sup.2
space="preserve" listing-type="equation">R.sup.1 --Z.sup.1 --A--Z.sup.2 --Bi--R.sup.2, or
space="preserve" listing-type="equation">R.sup.1 --Z.sup.1 --A--Z.sup.2 --Pyr--R.sup.2wherein "A" deontes 2-G-tetrahydropyran-3,6-diyl;
"Phe" denotes 1,4-phenylene;
"Cy" denotes 1,4-cyclohexylene;
"Dio" denotes 1,3-dioxane-2,5-diyl;
"Bi" denotes bicyclo[2.2.2]octylene;
"Pip" denotes piperidine-1,4-diyl; and
"Pyr" denotes pyrimidine-2-5-diyl.
- O;
-
4. A dielectric of claim 1 wherein said compound is of the formula R1 --Z1 --A--Z2 --Phe--R2.
- 5. A dielectric of claim 1 wherein said compound is of the formula
- space="preserve" listing-type="equation">R.sup.1 --Phe--Phe--Z.sup.1 --A--Z.sup.2 --R.sup.2
space="preserve" listing-type="equation">R.sup.1 --Phe--Cy--Z.sup.1 --A--Z.sup.2 --R.sup.2
space="preserve" listing-type="equation">R.sup.1 --Cy--Phe--Z.sup.1 --A--Z.sup.2 --R.sup.2, or
space="preserve" listing-type="equation">R.sup.1 --Cy--Cy--Z.sup.1 --A--Z.sup.2 --R.sup.2wherein "A" denotes 2-G-tetrahydropyan-3,6-diyl;
"Phe" denotes 1,4-phenylene;
"Cy" denotes 1,4-cyclohexylene.
- space="preserve" listing-type="equation">R.sup.1 --Phe--Z.sup.1 --A--Z.sup.2 --Phe--R.sup.2
space="preserve" listing-type="equation">R.sup.1 --Phe--Z.sup.1 --A--Z.sup.2 --Cy--R.sup.2
space="preserve" listing-type="equation">R.sup.1 --Cy--Z.sup.1 --A--Z.sup.2 --Phe--R.sup.2, or
space="preserve" listing-type="equation">R.sup.1 --Cy--Z.sup.1 --A--Z--Cy--R.sup.2
"Phe" denotes 1,4-phenylene and;
"Cy" denotes 1,4-cyclohexylene.
- space="preserve" listing-type="equation">R.sup.1 --Z.sup.1 --A--Z.sup.2 --Phe--Phe--R.sup.2
space="preserve" listing-type="equation">R.sup.1 --Z.sup.1 --A--Z.sup.2 --Phe--Cy--R.sup.2
space="preserve" listing-type="equation">R.sup.1 --Z.sup.1 --A--Z.sup.2 --Cy--Phe--R.sup.2, or
space="preserve" listing-type="equation">R.sup.1 --Z.sup.1 --A--Z.sup.2 --Cy--Cy--R.sup.2
"Phe" denotes 1,4-phenylene and;
"Cy" denotes 1,4-cyclohexylene.
- space="preserve" listing-type="equation">R.sup.1 --Phe--Phe--Phe--Z.sup.1 --A--Z.sup.2 --R.sup.2
space="preserve" listing-type="equation">R.sup.1 --Phe--Phe--Cy--Z.sup.1 --A--Z.sup.2 --R.sup.2
space="preserve" listing-type="equation">R.sup.1 --Phe--Cy--Phe--Z.sup.1 --A--Z.sup.2 --R.sup.2
space="preserve" listing-type="equation">R.sup.1 --Phe--Cy--Cy--Z.sup.1 --A--Z.sup.2 --R.sup.2
space="preserve" listing-type="equation">R.sup.1 --Cy--Phe--Phe--Z.sup.1 --A--Z.sup.2 --R.sup.2
space="preserve" listing-type="equation">R.sup.1 --Cy--Phe--Cy--Z.sup.1 --A--Z.sup.2 --R.sup.2
space="preserve" listing-type="equation">R.sup.1 --Cy--Cy--Phe--Z.sup.1 --A--Z.sup.2 --R.sup.2, or
space="preserve" listing-type="equation">R.sup.1 --Cy--Cy--Cy--Z.sup.1 --A--Z.sup.2 --R.sup.2
"Phe" denotes 1,4-phenylene and;
"Cy" denotes 1,4-cyclohexylene.
- space="preserve" listing-type="equation">R.sup.1 --Phe--Phe--Z.sup.1 --A--Z.sup.2 --Phe--R.sup.2
space="preserve" listing-type="equation">R.sup.1 --Phe--Phe--Z.sup.1 --A--Z.sup.2 --Cy--R.sup.2
space="preserve" listing-type="equation">R.sup.1 --Phe--Cy--Z.sup.1 --A--Z.sup.2 --Phe--R.sup.2
space="preserve" listing-type="equation">R.sup.1 --Phe--Cy--Z.sup.1 --A--Z.sup.2 --Cy--R.sup.2
space="preserve" listing-type="equation">R.sup.1 --Cy--Phe--Z.sup.1 --A--R.sup.2 --Phe--R.sup.2
space="preserve" listing-type="equation">R.sup.1 --Cy--Phe--Z.sup.1 --A--Z.sup.2 --Cy--R.sup.2
space="preserve" listing-type="equation">R.sup.1 --Cy--Cy--Z.sup.1 --A--Z.sup.2 --Phe--R.sup.2, or
space="preserve" listing-type="equation">R.sup.1 --Cy--Cy--Z.sup.1 --A--Z.sup.2 --Cy--R.sup.2
"Phe" denotes 1,4-phenylene and;
"Cy" denotes 1,4-cyclohexylene.
- space="preserve" listing-type="equation">R.sup.1 --Phe--Z.sup.1 --A--Z.sup.2 --Phe--Phe--R.sup.2
space="preserve" listing-type="equation">R.sup.1 --Phe--Z.sup.1 --A--Z.sup.2 --Phe--Cy--R.sup.2
space="preserve" listing-type="equation">R.sup.1 --Phe--Z.sup.1 --A--Z.sup.2 --Cy--Phe--R.sup.2
space="preserve" listing-type="equation">R.sup.1 --Phe--Z.sup.1 --A--Z.sup.2d --Cy--Cy--R.sup.2
space="preserve" listing-type="equation">R.sup.1 --Cy--Z.sup.1 --A--Z.sup.2 --Phe--Phe--R.sup.2
space="preserve" listing-type="equation">R.sup.1 --Cy--Z.sup.1 --A--Z.sup.2 --Phe--Cy--R.sup.2
space="preserve" listing-type="equation">R.sup.1 --Cy--Z.sup.1 --A--Z.sup.2 --Cy--Phe--R.sup.2, or
space="preserve" listing-type="equation">R.sup.1 --Cy--Z.sup.1 --A--Z.sup.2 --Cy--Cy--R.sup.2
"Phe" denotes 1,4-phenylene and;
"Cy" denotes 1,4-cyclohexylene.
- space="preserve" listing-type="equation">R.sup.1 --Z.sup.1 --A--Z.sup.2 --Phe--Phe--Phe--R.sup.2
space="preserve" listing-type="equation">R.sup.1 --Z.sup.1 --A--Z.sup.2 --Phe--Phe--Cy--R.sup.2
space="preserve" listing-type="equation">R.sup.1 --Z.sup.1 --A--Z.sup.2 --Phe--Cy--Phe--R.sup.2
space="preserve" listing-type="equation">R.sup.1 ;
13 Z.sup.1 --A--Z.sup.2 --Phe--Cy--Cy--R.sup.2
space="preserve" listing-type="equation">R.sup.1 --Z.sup.1 --A--Z.sup.2 --Cy--Phe--Phe--R.sup.2
space="preserve" listing-type="equation">R.sup.1 --Z.sup.1 --A--Z.sup.2 --Cy--Phe--Cy--R.sup.2
space="preserve" listing-type="equation">R.sup.1 --Z.sup.1 --A--Z.sup.2 --Cy--Cy--Phe--R.sup.2, or
space="preserve" listing-type="equation">R.sup.1 --Z.sup.1 --A--Z.sup.2 --Cy--Cy--Cy--R.sup.2
"Phe" denotes 1,4-phenylene and;
"Cy" denotes 1,4-cyclohexylene.
- space="preserve" listing-type="equation">R.sup.1 --Z.sup.1 --A--Z.sup.2 Phe--Phe--R.sup.2, or
space="preserve" listing-type="equation">R.sup.1 --Z.sup.1 --A--Z.sup.2 Phe--Phe--Cy--R.sup.2,
"Phe" denotes 1,4-phenylene and;
"Cy" denotes 1,4-cyclohexylene.
- space="preserve" listing-type="equation">R.sup.1 --A--Phe--CN
space="preserve" listing-type="equation">R.sup.1 --A--Phe--Phe--R.sup.2 or
space="preserve" listing-type="equation">R.sup.1 --A--Phe--Phe--Cy--R.sup.2
"Phe" denotes 1,4-phenylene and;
"Cy" denotes 1,4-cyclohexylene.
- 17. A liquid crystal dielectric useful for electrooptical display elements comprising at least two liquid crystal components, wherein at least one component is a compound of the formula
- space="preserve" listing-type="equation">R.sup.1 --A--Ph--COO--A.sup.2 --R.sup.2
wherein R1 and R2 each independently is alkyl of 1-10 C-atoms;
alkyl of 1-10 C atoms wherein one or two non-adjacent CH2 groups are replaced by O atoms, F;
Cl;
Br;
or CN; and
R2 can also be H;A is 1-G-2-tetrahydropyran-3,6-diyl; G is H2 or ═
O;Ph is 1,4-phenylene or 1,4-phenylene substituted by 1-4 F atoms; and A2 is 1,4-phenylene, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, piperidine-1,4-diyl, 1,4-bicyclo[2.2.2]octylene or pyrimidine-2,5-diyl or one of these groups substituted by 1-4 F atoms.
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Current AssigneeMerck Patent GmbH (Merck & Co., Inc.)
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Original AssigneeMerck Patent GmbH (Merck & Co., Inc.)
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InventorsFuss, Peter, Eidenschink, Rudolf, Krause, Joachim
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Primary Examiner(s)Gron, Teddy S.
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Application NumberUS06/933,953Time in Patent Office862 DaysField of Search549/291, 549/292, 549/293, 549/273, 549/414, 549/415, 549/416, 549/417, 549/419, 549/420, 549/423, 549/426, 549/427, 549/428, 549/356, 250/350 R, 250/350 S, 252/299.61, 252/299.5US Class Current252/299.61CPC Class CodesC07D 309/04 with only hydrogen atoms, h...C07D 309/06 Radicals substituted by oxy...C07D 309/30 Oxygen atoms, e.g. delta-la...C07D 407/04 directly linked by a ring-m...C09K 19/3402 having oxygen as hetero ato...C09K 19/3441 having nitrogen as hetero atomC09K 19/3472 Pyrimidine condensed or bri...C09K 2019/3422 the heterocyclic ring being...
