Meterocyclic compounds

Claim 2

A liquid crystalline mixture comprising two or more pyrimidine derivatives of the formula ##STR25## wherein at least one of the rings A and B is a trans-1,4-disubstituted cyclohexane ring and the other optionally is aromatic and R is straight-chain alkyl or alkoxy of 1 to 10 carbon atoms or a branched-chain alkyl of the formula C 2 H 5 --CH(CH 3 )--(CH 2 ) n -- wherein n is 1,2 or 3.

Claim 3

A liquid crystalline mixture comprising one or more pyrimidine derivatives of the formula ##STR26## wherein at least one of the rings A and B is a trans-1,4-disubstituted cyclohexane ring and the other optionally is aromatic and R is straight-chain alkyl or alkoxy of 1 to 10 carbon atoms or a branched-chain alkyl of the formula C 2 H 5 --CH(CH 3 )--(CH 2 ) n -- wherein n is 1,2 or 3, and one or more substances selected from the group consisting of nematic liquid crystal compounds, cholesteric liquid crystal compounds, smectic liquid crystal compounds and dichroic coloring compounds.

Claim 4

A liquid crystalline mixture comprising one or more pyrimidine derivatives of the formula ##STR26## wherein at least one of the rings A and B is a trans-1,4-disubstituted cyclohexane ring and the other optionally is aromatic and R is straight-chain alkyl or alkoxy of 1 to 10 carbon atoms or a branched-chain alkyl of the formula C 2 H 5 --CH(CH 3 )--(CH 2 ) n -- wherein n is 1,2 or 3, and one or more substances selected from the group consisting of nematic liquid crystal compounds, cholesteric liquid crystal compounds, smectic liquid crystal compounds and dichroic coloring compounds.

Claim 5

A liquid crystalline mixture in accordance with claim 2, wherein the dichroic coloring compounds are compounds of the formula: ##STR27## wherein each of n 1 and n 2 is zero, 1 or 2, X 1 is azo or azoxy, Y 1 and Y 2 , which can be the same or different, are one of the groups ##STR28## and Z 1 is hydrogen, cyano, nitro, phenyl, p-substituted phenyl, hydroxy, alkoxy, amino, dialkylamino or pyrrolidyl; or a compound of formula IV wherein one of the benzene rings additionally carries one or more substituents selected from the group consisting of halogen, methyl, halo-substituted methyl and methoxy; ##STR29## wherein n 3 is zero or 1, Y 3 is a group of formula V or VI above, wherein Z 1 is dialkylamino or pyrrolidyl, and X 2 is hydrogen, halogen, cyano, nitro, alkyl, alkoxy, phenyl, p-ethylphenyl, p-n-butylphenyl, benzothiazol-2-yl, alkoxycarbonyl or alkylsulfonyl in the 5- or 6-position; or ##STR30## wherein X 3 is cyano, nitro or alkyl and Z 2 is hydroxy, alkoxy, phenyl, p-ethylphenyl, p-n-butylphenyl, amino, pyrrolidyl, piperidyl, or alkyl-substituted or aryl-substituted amino, pyrrolidyl or piperidyl wherein aryl is phenyl, p-ethylphenyl or p-n-butylphenyl; or a compound of formula VIII wherein the benzene ring additionally carries one or more substituents selected from the group consisting of halogen, hydroxy, methyl and methoxy; or ##STR31## wherein X 4 and X 5 are each hydroxy, Y 4 and Y 5 are each amino and R 1 is a group of formula VI above; or X 4 , Y 5 and R 1 are each hydrogen, X 5 is hydroxy and Y 4 is --NHR 2 or X 4 , X 5 and R 1 are each hydrogen and Y 4 and Y 5 are each --NHR 2 , R 2 is a group of formula VI above wherein Z 1 is alkyl, alkoxy or dialkylamino; or ##STR32## wherein R 3 is alkyl and X 6 is cyano or nitro; or ##STR33## wherein R 4 is alkyl; or ##STR34## wherein R 5 is alkyl.

Claim 6

A liquid crystalline mixture in accordance with claim 3, which contains at least one coloring substance of the formula ##STR35## wherein n 4 is zero or 1, Z 3 is dimethylamino or diethylamino and x 7 is hydrogen, methyl, ethoxy, n-butyloxy, nitro or n-butylsulfonyl.

Claim 7

A liquid crystalline mixture in accordance with claim 3, which contains a dichroic coloring compound of the formula ##STR36## wherein R 6 , R 7 and X 8 are each methyl or R 6 is methyl, X 8 is nitro and R 7 is methyl, phenyl or p-n-butylphenyl.

Claim 8

A liquid crystalline mixture in accordance with claim 3, which contains at least one coloring substance of the formula ##STR37## wherein R 8 is n-alkyl of 1 to 10 carbon atoms.

Claim 9

A liquid crystalline mixture in accordance with claim 3, which contains at least one coloring substance of the formula ##STR38## wherein X 9 is n-butyl, n-nonyloxy or dimethylamino.

Claim 10

A liquid crystalline mixture in accordance with claim 3, which contains at least one coloring substance of the formula ##STR39## wherein X 10 is ethyl, n-butyl, isopropyl, pentyloxy or dimethylamino.

Claim 11

A liquid crystalline mixture in accordance with claim 3, which contains the coloring substance of the formula ##STR40## and/or the coloring substance of formula X wherein R 3 is n-butyl and X 6 is nitro, and/or the coloring substance of formula XI wherein R 4 is ethyl, and/or the coloring substance of formula XII wherein R 5 is ethyl.

Claim 12

A liquid crystalline mixture in accordance with claim 2, which contains 4'-pentyl-4-cyanobiphenyl, trans-4-propylcyclohexane carboxylic acid p-cyanophenyl ester, trans-4-pentylcyclohexane carboxylic acid p-cyanophenyl ester, trans-4-pentylcyclohexane carboxylic acid p-(methoxy)phenyl ester, trans-p-[5-(4-ethylcyclohexyl)-2-pyrimidinyl]benzonitrile, trans-p-[5-(4-pentylcyclohexyl)-2-pyrimidinyl]-benzonitrile and trans-p-[5-(4-heptylcyclohexyl)-2-pyrimidinyl]benzonitrile.

Claim 13

A liquid crystalline mixture in accordance with claim 2, which contains p-butylbenzoic acid p'-cyanophenyl ester, p-(5-pentyl-2-pyrimidinyl)benzonitrile, p-(5-heptyl-2-pyrimidinyl)benzonitrile, trans-4-butylcyclohexane carboxylic acid p-cyanophenyl ester, trans-4-pentylcyclohexane carboxylic acid p-cyanophenyl ester, trans-4-butylcyclohexane carboxylic acid p-(ethoxy)phenyl ester, trans-4-pentylcyclohexane carboxylic acid p-(methoxy)phenyl ester and trans-p-[5-(4-ethylcyclohexyl)-2-pyrimidinyl]benzonitrile.

Claim 14

A liquid crystalline mixture in accordance with claim 2, which contains p-butylbenzoic acid p'-cyanophenyl ester, p-(5-pentyl-2-pyrimidinyl)benzonitrile, p-(5-heptyl-2-pyrimidinyl)benzonitrile, trans-4-propylcyclohexane carboxylic acid p-cyanophenyl ester, trans-4-pentylcyclohexane carboxylic acid p-cyanophenyl ester, trans-4-butylcyclohexane carboxylic acid p-(ethoxy)phenyl ester, trans-4-pentylcyclohexane carboxylic acid p-(methoxy)phenyl ester, trans-p-[5-(4-pentylcyclohexyl)-2-pyrimidinyl]benzonitrile and trans-p-[5-(4-heptylcyclohexyl)-2-pyrimidinyl]benzonitrile.

Claim 15

A liquid crystalline mixture in accordance with claim 2, which contains p-butylbenzoic acid p'-cyanophenyl ester, p-(5-pentyl-2-pyrimidinyl)benzonitrile, p-(5-heptyl-2-pyrimidinyl)benzonitrile, trans-4-propylcyclohexane carboxylic acid p-cyanophenyl ester, trans-4-pentylcyclohexane carboxylic acid p-cyanophenyl ester, trans-4-butylcyclohexane carboxylic acid p-(ethoxy)phenyl ester, trans-4-pentylcyclohexane carboxylic acid p-(methoxy)phenyl ester and trans-p-[5-(4-ethylcyclohexyl)-2-pyrimidinyl]benzonitrile.

Claim 16

A liquid crystalline mixture in accordance with claim 2, which contains 4'-heptyl-4-cyanobiphenyl, p-(5-pentyl-2-pyrimidinyl)benzonitrile, p-(5-heptyl-2-pyrimidinyl)benzonitrile, trans-4-propylcyclohexane carboxylic acid p-cyanophenyl ester, trans-4-butylcyclohexane carboxylic acid p-cyanophenyl ester, trans-4-pentylcyclohexane carboxylic acid p-cyanophenyl ester, trans-4-pentylcyclohexane carboxylic acid p-(methoxy)phenyl ester, trans-4-butylcyclohexane carboxylic acid p-(ethoxy)phenyl ester and trans-p-[5-(4-ethylcyclohexyl)-2-pyrimidinyl]benzonitrile.

Claim 17

A liquid crystalline mixture in accordance with claim 2, which contains p-butylbenzoic acid p'-cyanophenyl ester, p-(5-pentyl-2-pyrimidinyl)benzonitrile, p-(5-heptyl-2-pyrimidinyl)benzonitrile, trans-4-propylcyclohexane carboxylic acid p-cyanophenyl ester, trans-4-butylcyclohexane carboxylic acid p-cyanophenyl ester, trans-4-pentylcyclohexane carboxylic acid p-cyanophenyl ester, trans-4-butylcyclohexane carboxylic acid p-(ethoxy)phenyl ester, 4"-pentyl-4-cyano-p-terphenyl and trans-p-[5-(4-ethylcyclohexyl)-2-pyrimidinyl]benzonitrile.

Claim 18

A liquid crystalline mixture in accordance with claim 2, which contains 4'-pentyl-4-cyanobiphenyl, trans-4-propylcyclohexane carboxylic acid p-cyanophenyl ester, trans-4-pentylcyclohexane carboxylic acid p-cyanophenyl ester, trans-4-butylcyclohexane carboxylic acid p-(ethoxy)phenyl ester, trans-4-pentylcyclohexane carboxylic acid p-(methoxy)-phenyl ester, trans-p-[5-(4-ethylcyclohexyl)-2-pyrimidinyl]benzonitrile, trans-p-[5-(4-pentylcyclohexyl)-2-pyrimidinyl]benzonitrile and trans-p-[5-(4-heptylcyclohexyl)-2-pyrimidinyl]benzonitrile.

Claim 19

A liquid crystalline mixture in accordance with claim 2, which contains 4'-pentyl-4-cyanobiphenyl, p-butylbenzoic acid p'-cyanophenyl ester, p-(5-pentyl-2-pyrimidinyl)benzonitrile, trans-4-propylcyclohexane carboxylic acid p-cyanophenyl ester, trans-4-pentylcyclohexane carboxylic acid p-cyanophenyl ester, trans-4-pentylcyclohexane carboxylic acid p-(methoxy)phenyl ester and trans-p-[5-(4-ethylcyclohexyl)-2-pyrimidinyl]benzonitrile.

Claim 20

A liquid crystalline mixture in accordance with claim 2, which contains 4'-heptyl-4-cyanobiphenyl, p-butylbenzoic acid p'-cyanophenyl ester, p-(5-pentyl-2-pyrimidinyl)benzonitrile, p-(5-heptyl-2-pyrimidinyl)benzonitrile, trans-4-propylcyclohexane carboxylic acid p-cyanophenyl ester, trans-4-pentylcyclohexane carboxylic acid p-cyanophenyl ester, trans-4-butylcyclohexane carboxylic acid p-(ethoxy)-phenyl ester and trans-p-[5-(4-ethylcyclohexyl)-2-pyrimidinyl]benzonitrile.

Claim 21

A liquid crystalline mixture in accordance with claim 2, which contains 4'-pentyl-4-cyanobiphenyl, 4'-heptyl-4-cyanobiphenyl, p-(5-pentyl-2-pyrimidinyl)benzonitrile, p-(5-heptyl-2-pyrimidinyl)benzonitrile, trans-4-butylcyclohexane carboxylic acid p-(ethoxy)phenyl ester and trans-p-[5-(4-pentylcyclohexyl)-2-pyrimidinyl]benzonitrile.

Claim 22

A liquid crystalline mixture in accordance with claim 2, which contains 4'-pentyl-4-cyanobiphenyl, 4'-heptyl-4-cyanobiphenyl, p-(5-pentyl-2-pyrimidinyl)benzonitrile, p-(5-heptyl-2-pyrimidinyl)benzonitrile and trans-p-[5-(4-ethylcyclohexyl)-2-pyrimidinyl]benzonitrile.

Claim 23

A liquid crystalline mixture in accordance with claim 2, which contains 4'-pentyl-4-cyanobiphenyl, 4'-heptyl-4-cyanobiphenyl, p-(5-pentyl-2-pyrimidinyl)benzonitrile, p-(5-heptyl-2-pyrimidinyl)benzonitrile, trans-4-butylcyclohexane carboxylic acid p-(ethoxy)phenyl ester, trans-4-pentylcyclohexane carboxylic acid p-(methoxy)phenyl ester and trans-p-[5-(4-pentylcyclohexyl)-2-pyrimidinyl]benzonitrile.

Claim 24

A liquid crystalline mixture in accordance with claim 2, which contains 4'-pentyl-4-cyanobiphenyl, 4'-octyloxy-4-cyanobiphenyl, p-(5-pentyl-2-pyrimidinyl)benzonitrile, p-(5-heptyl-2-pyrimidinyl)benzonitrile and trans-p-[5-(4-pentylcyclohexyl)-2-pyrimidinyl]benzonitrile.

Claim 25

A liquid crystalline mixture in accordance with claim 2, which contains 4'-pentyl-4-cyanobiphenyl, p-butylbenzoic acid p'-cyanophenyl ester, p-(5-pentyl-2-pyrimidinyl)benzonitrile, p-(5-heptyl-2-pyrimidinyl)benzonitrile, trans-4-butylcyclohexane carboxylic acid p-cyanophenyl ester, trans-4-pentylcyclohexane carboxylic acid p-cyanophenyl ester, trans-4-butylcyclohexane carboxylic acid p-(ethoxy)phenyl ester, trans-4-pentylcyclohexane carboxylic acid p-(methoxy)-phenyl ester and trans-p-[5-(4-ethylcyclohexyl)-2-pyrimidinyl]benzonitrile.

Claim 26

A liquid crystalline mixture in accordance with claim 2, which contains 4'-heptyl-4-cyanobiphenyl, trans-4-propylcyclohexane carboxylic acid p-cyanophenyl ester, trans-4-butylcyclohexane carboxylic acid p-(ethoxy)phenyl ester, trans-4-pentylcyclohexane carboxylic acid p-(methoxy)phenyl ester, trans-4-pentylcyclohexane carboxylic acid p-(propyloxy)phenyl ester and trans-p-[5-(4-pentylcyclohexyl)-2-pyrimidinyl]benzonitrile.