US2002011588A1PendingUtilityA1
Naphthyl organic compounds
Priority: Mar 13, 1991Filed: Aug 2, 2001Published: Jan 31, 2002
Est. expiryMar 13, 2011(expired)· nominal 20-yr term from priority
Inventors:Kenneth J. ToyneJohn William GoodbyAlexander SeedGeorge W. GrayDamien Gerad McdonnelEdward P. RaynesSally Elizabeth DayKenneth J. HarrisonMichael Hird
C07D 333/24C09K 19/322C07C 331/28C09K 19/3497C07C 255/52C09K 19/544C09K 2323/00C09K 19/3441C07C 255/54C07D 239/26C09K 19/3461C07D 333/20C07C 323/62C09K 19/3458
47
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Claims
Abstract
A liquid crystalline compounds: R 1 —A—(X) m —(B) n —R 2 are described where A is naphthyl, fluorinated naphthyl or brorninated naphthyl; B is phenyl, methylated phenyl, brominated phenyl, fluorinated phenyl or pyrimidine; R 1 and R 2 are independently C 1-15 alkyl, alkoxy, alkynyl, thioalkyl, perfluoroalkyl, perfluoroalkoxy or Br, CN, SCN, NCS and hydrogen; X is COO or C═C, m is 0 or 1, and n is 1.
Claims
exact text as granted — not AI-modified1 . A liquid crystalline compound characterised by formula I are provided;
R 1 —A—(X) m —(B) n —R 2 Formula I where A is selected from nathyl, fluorinated naphthyl, brominated naphthyl. B is selected from phenyl, methylated phenyl, brominated phenyl, fluorinated phenyl, thiophene, pyrimidine and pyridine, R 1 and R 2 are independently selected from alkyl, alkoxy, alkynyl, thioalkyl, Br, CN, SCN, NCS, perfluoroalkyl, perfluoroalkoxy and hydrogen, X is selected from C≡C, COO and C═C, m is 0 or 1, n is 0 or 1 where m is 1 and n is 0 where m is 0; provided that where A is naphthyl, n is 1 and m is 0 then B is selected from methylated phenyl, brominated phenyl, thiophene, pyrimidne and pyridine; and further provided that where A is naphthyl, X is C≡C, m is 1 and n is 1, then B is selected from thiophene, pyrimidine and pyridine.
2 . A compound according to claim 1 where at least one of terminal groups R 1 and R 2 is selected from alkyl, alkoxy, alkynyl and thioalkyl.
3 . A compound according to claim 2 where at least one of the termianl groups is straight chain.
4 . A compound according to claim 1 where B is thiophene and A is naphthyl.
5 . A compound according to claim 4 where m is 1 and X is C≡C.
6 . A compound according to claim 5 where at least one of the terminal groups is alkynyl.
7 . A compound according to claim 5 where at least one of the terminal groups is NCS.
8 . A compound according to claim 5 where at least one of the terminal groups is thioalkyl.
9 . A compound according to claim 5 where at least one of the terminal groups is CN.
10 . A compound according to claim 6 where one of the terminal groups is NCS and the other is alkynyl.
11 . A compound according to claim 4 where m is 0.
12 . A compound according to claim 11 where at least one of the terminal groups is alkynyl.
13 . A compound according to claim 11 where at least one of the terminal groups is NCS.
14 . A compound according to claim 11 where at least one of the terminal groups is CN.
15 . A compound according to claim 11 where at least one of the terminal groups is thioalkyl.
16 . A compound according to claim 1 where B is pyrimidyl and A is naphtlhyl.
17 . A compound according to claim 16 where m is 1 and X is C≡C.
18 . A compound according to claim 17 where at least one of the terminal groups is NCS.
19 . A compound according to claim 16 where m is 0.
20 . A compound according to claim 19 where at least on of the terminal groups is alkynyl.
21 . A compound according to claim 1 where A is naphthyl, B is phenyl, m is 1, X is C═C and at least one of the terminal groups is NCS.
22 . A compound according to claim 21 where R 2 is NCS and R 1 is alkoxy.
23 . A liquid crystalline material, being a mixture of compounds, and characterised in that it comprises at least one compound according to claim 1 .
24 . A liquid crysatlline material, being a mixture of compounds, and characterised in that it comprises at least on compound of claims 1 to 22 .
25 . A material according to claim 23 and further characterised in that it comprises at least on compound of formula III
here R 1 is selected from a group comprising hydrogen, alkyl, alkoxy, alkynyl, thioalkyl, CN, and Br; R 2 is selected from a group comprising hydrogen, NCS, SCN, CN, alkyl, alkoxy, alkynyl, and thioalkyl; m and n are 1 or 0 such that m is 1 where n is 0 and m is 0 where n is 1 or 0; p is independently 1 or 0; X is selected from a group comprising of naphthyl, fluorinated naphthyl and brominated naphthyl; and Y is selected from a group comprising of phenyl, methylated phenyl, brominated phenyl, thiophene and pyrimidine and pyridine.
26 . A material according to claim 23 and further characterised in that it comprises at least one compound of formula IV
where R A is selected from CN, alkyl and alkoxy.
27 . A material according to claim 23 and further characterised in that it comprisess at least one compound of formula V
where R 1 is C 1-10 n-alkyl or n-alkoxyl and the fluorosubstituent(s) may be in any one or two of the available substitution positions.
28 . A liquid crystal device characterised in that it uses a material according to claim 23 .
29 . A liquid crystal device characterised in that it comprises a material according to claim 24 .
30 . A liquid crystal compound characterised in that it is suitable for inclusion in devices utilising pretransitional characterisitcs of liquid crystalline materials in the isotropic phase and is given by formula II
R 3 —J—(Y) p —(Z) q —R 4 Formula II
where J is selected from nathyl, fluorinated naphthyl, brominated naphthyl, Z is selected from phenyl, methylated phenyl, brominated phenyl, fluorinated phenyl, thiophene, pyrimidine and pyridine, R 1 and R 2 are independently selected from alkyl, alkoxy, alkynyl, thioalkyl, Br, CN, SCN, NCS, perfluoroalkyl, perfluoroalkoxy and hydrogen, Y is selected from C≡C, COO and C═C, p is 0 or 1, q is 0 or 1 where p is 1 and q is 0 where p is 0;
31 . A compound according to claim 30 where at least one of terminal groups R 3 and R 4 is selected from alkyl, alkoxy, alkynyl and thioalkyl.
32 . A compound according to claim 31 where at least one of the termianl groups is straight chain.
33 . A compound according to claim 30 where Z is thiophene and J is naphthyl.
34 . A compound according to claim 33 where p is 1 and X is C≡C.
35 . A compound according to claim 34 where at least one of the terminal groups is alkynyl.
36 . A compound according to claim 34 where at least one of the terminal groups is NCS.
37 . A compound according to claim 34 where at least one of the terminal groups is thioalkyl.
38 . A compound according to claim 34 where at least one of the terminal groups is CN.
39 . A compound according to claim 35 where one of the terminal groups is NCS and the other is alkynyl.
40 . A compound according to claim 33 where p is 0.
41 . A compound according to claim 40 where at least one of the terminal groups is alkynyl.
42 . A compound according to claim 40 where at least one of the terminal groups is NCS.
43 . A compound according to claim 40 where at least one of the terminal groups is CN.
44 . A compound according to claim 40 where at least one of the terminal groups is thioalkyl.
45 . A compound according to claim 30 where Y is pyrimidyl and A is naphthyl.
46 . A compound according to claim 45 where p is 1 and X is C≡C.
47 . A compound according to claim 46 where at least one of the terminal groups is NCS.
48 . A compound according to claim 45 where p is 0.
49 . A compound according to claim 48 where at least on of the terminal groups is alkynyl.
50 . A compound according to claim 30 where J is naphthyl and Y is phenyl.
51 . A compound according to claim 50 where p is 1 and X is C═C.
52 . A compound according to claim 51 where one of the terminal groups is NCS.
53 . A compound according to claim 50 having a formula
54 . A compound according to claim 52 having a formula
55 . A compound according to claim 53 having a formula
56 . A compound according to claim 54 having a formula
57 . A compound according to claim 50 where at least one of the terminal groups is CN.
58 . A liquid crystalline material, being a mixture of compounds, and characterised in that it comprises at least one compound according to claim 29 .
59 . A liquid crysatlline material, being a mixture of compounds, and characterised in that it comprises at least on compound of claims 29 to 57 .
60 . A material according to claim 58 and further characterised in that it comprises at least on compound of formula III
here R 1 is selected from a group comprising hydrogen, alkyl, alkoxy, alkynyl, thioalkyl, CN, and Br; R 2 is selected from a group comprising hydrogen, NCS, SCN, CN, alkyl, alkoxy, alkynyl, and thioalkyl; m and n are 1 or 0 such that m is 1 where n is 0 and m is 0 where n is 1 or 0; p is independently 1 or 0; X is selected from a group comprising of naphthyl, fluorinated naphthyl and brominated naphthyl; and Y is selected from a group comprising of phenyl, methylated phenyl, brominated phenyl, thiophene and pyrimidine and pyridine.
59 . A material according to claim 58 and further characterised in that it comprises at least one compound of formula IV
where R A is selected from CN, alkyl and alkoxy.
60 . A material according to claim 58 and further characterised in that it comprisess at least one compound of formula V
where R 1 is C 1-10 n-alkyl or n-alxoxyl and the fluorosubstituent(s) may be in any one or two of the available substitution positions.
63 . A liquid crystal device characterised in that it uses a material according to claim 58 .Join the waitlist — get patent alerts
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