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US 6,475,595 B1Granted
Fluorocyclohexene derivatives, and liquid-crystalline medium
AssigneeMerck & Co., Inc.
InventorsMatthias Bremer, Detlef Pauluth, Joachim Krause, Michael Heckmeier, Peer Kirsch
Life of this patent
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Abstract
Fluorocyclohexene derivatives of formula I R1—(A1—Z1)n—A—(Z2—A2)m—Z3—B—(Z4—A3)p—R2 I, in which n, m, p, R1, R2, Z1, Z2, Z3, Z4, A1, A2, A3, A and B are as defined herein, are suitable for use in liquid crystal mediums. Also, difluorocyclohexanes of formula III R3—A*—(Z6—A7)m—Z7—Qr—R7 III, where R3, A*, Z6, A7, m, Z7, Q, r, and R4 are as defined herein, are suitable for use in liquid crystal mediums.
Claims24
A fluorocyclohexene compound of formula I
- R1—(A1—Z1)n—A—(Z2—A2)m—Z3—B—(Z4—A3)p—R2 I
- wherein
- R1 and R2, independently of one another, are each H, —CN, —F, —OCHF2, —OCF3, —OCHFCF3, —OCH2CF3 or —OCF2CF3, alkyl having 1-12 carbon atoms which is unsubstituted or at least monosubstituted by halogen or CN, wherein one or more CH2 groups of the alkyl groups may in each case, independently of one another, be replaced by —O—, —S—, —CO—,
- —CO—O—, —O—CO—, —O—CO—O— or —CH═CH— in such a way that heteroatoms are not connected directly;
- A is
- A1, A2 and A3 are in each case independently of one another,
- a) a trans-1,4-cyclohexylene wherein one or more non adjacent CH2 groups may in each case, independently of one another, be replaced by —O—or —S—,
- b) a 1,4-phenylene wherein one or two CH groups may in each case, independently of one another, be replaced by N, and which is unsubstituted or substituted by CN, Cl or F,
- c) 1,4-bicyclo[2.2.2]octylene, piperidine-1,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, or 1,2,3,4-tetrahydronaphthalene-2,6-diyl,
- d) 1,4-cyclohexenylene,
- B can also be trans-1,4-cyclohexylene, in which one or more non-adjacent CH2 groups may in each case, independently of one another, be replaced by —O—or —S—, when -n is 0 and Z3 is not a single bond, -n is 1 and Z1 is not a single bond, or -n is 1 and A1 has a meaning according to a), c) or d);
- X1 and X2, independently of one another, are each F, Cl, CN, CF3 or CHF2;
- Z1, Z2, Z3
- and Z4 are each, independently of one another, —CO—O—, —O—CO—, —CH2O—, —O—, —O—CH2—, —CH2CH2—, —CH═CH—, —C≡C—, —CF2CF2—, —OCF2—, —CF2O—, —CH═CF—, —CF═CH— or a single bond;
- n, m
- and p, independently of one another, are each 0, 1, 2 or 3;
- and
- m+n+p is 0, 1, 2 or 3.
15 more elements
A difluorocyclohexane compound of formula III
- R3—A*—(Z6—A7)m—Z7—Qr—R4 III
- wherein
- R3 and R4, independently of one another, are each H, alkyl having 1-12 carbon atoms, or alkyl having 1-12 carbon atoms in which one or more CH2 groups are each, independently of one another, replaced by —O—or —CH═CH— in such a way that heteroatoms are not connected directly;
- A7 is in each case, independently of one another, trans-1,4-cyclohexylene radical, wherein one or more non-adjacent CH2 groups may in each case, independently, be replaced by —O—or —S—, and where the radical may be monosubstituted by Cl or F,
- Z6 and Z7 are each, independently of one another, —CO—O—, —O—CO—, —CH2O—, —O—, —O—CH2—, —CH2CH2—, —CH═CH—, —C≡C—, —CF2CF2—, —OCF2, —CF2O—, —CH2CF2—, —CF2CH2— or a single bond;
- m is 0, 1, 2 or 3;
- r is 0 or 1;
- and
- m+r is 1, 2 or 3;
- with the proviso that compounds in which
- m is 1,
- r is 0,
- Z6 is a single bond,
- A7 is cyclohexane-1,4-diyl and
- R3 and R4 are alkyl, or alkyl in which, one CH2 group is replaced by —O—,
- are excluded.
13 more elements
A fluorocyclohexene compound of formula I
- R1—(A1—Z1)n—A—(Z2—A2)m—Z3—B—(Z4—A3)p—R2 I
- wherein
- R1 and R2, independently of one another, are each H, —CN, —F, —OCHF2, —OCF3, —OCHFCF3, —OCH2CF3 or —OCF2CF3, alkyl having 1-12 carbon atoms which is unsubstituted or at least monosubstituted by halogen or CN, wherein one or more CH2 groups of the alkyl groups may in each case, independently of one another, be replaced by —O—, —S—, —CO—,
- —CO—O—, —O—CO—, —O—CO—O— or —CH═CH— in such a way that heteroatoms are not connected directly;
- A is
- A1, A2 and A3 are in each case independently of one another,
- a) a trans-1,4-cyclohexylene wherein one or more non-adjacent CH2 groups may in each case, independently of one another, be replaced by —O—or —S—,
- b) a 1,4-phenylene wherein one or two CH groups may in each case, independently of one another, be replaced by N, and which is unsubstituted or substituted by CN, Cl or F,
- c) 1,4-bicyclo[2.2.2]octylene, piperidine-1,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, or 1,2,3,4-tetrahydronaphthalene-2,6-diyl,
- d) 1,4-cyclohexenylene,
- B, is trans-1,4-cyclohexylene, in which one or more non-adjacent CH2 groups may in each case, independently of one another, be replaced by —O—or —S—,
- X1 and X2, independently of one another, are each F, Cl, CN, CF3 or CHF2;
- Z1, Z2,
- and Z4 are each, independently of one another, —CO—O—, —O—CO—, —CH2O—, —O—, —O—CH2—, —CH2CH2—, —CH═CH—, —C≡C—, —CF2CF2—, —OCF2—, —CF2O—, —CH═CF—, —CF═CH— or a single bond;
- Z3 is —CO—O—, —O—CO—, —CH2O—, —O—, —O—CH2—, —CH2CH2—, —CH═CH—, —C≡C—, —CF2CF2—, —OCF2—, —CF2O—, —CH═CF—, or —CF═CH—;
- n is 0;
- m is 0, 1, 2, or 3;
- p is 0, 1, 2, or 3;
- and
- m+n+p is 0, 1, 2 or 3.
17 more elements
Dependencies are inferred from the claim text.