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US 10,868,257 B2Granted
Dithioalkylpyrrolopyrroles and the use thereof as dyes
AssigneeMerck Patent GmbH
InventorsPeer Kirsch, Susann Beck, Michael Junge, Ursula Patwal, Mila Fischer
Life of this patent
Estimating the term…
Abstract
Novel dithiopyrrolopyrrole derivatives having dichroic properties which have very high photostability in solution in a liquid-crystalline host are proposed.
Claims23
A dithiopyrrolopyrrole compound of formula (1)
- in which
- R1 and R2 are each, independently of one another, a linear or branched, optionally halogen-substituted alkyl group having 1 to 20 carbon atoms;
- R3 and R4 are each, independently of one another, a linear or branched, optionally halogen-substituted alkyl group having 1 to 20 carbon atoms or halogen;
- Q1 and Q2 are each, independently of one another, a single bond O, OCF2, CF2, CF2CF2 or CO;
- A1, A2, A3, A4, A5 and A6 are each, independently of one another, a single bond or an aromatic ring, each of which is selected from the group consisting of phenylene, pyridine, pyrimidine, pyridazine, naphthylene, thiophene, selenophene and thiazole,
- with the provisos that
- (i) at least A3 and A4 are aromatic rings, and
- (ii) the aromatic rings are optionally substituted by halide;
- and
- Z1, Z2, Z3, Z4, Z5 and Z6 are each, independently of one another, a single bond, C≡C, CH═CH, CF═CF, CF═CH, CH2CH2, CF2—CF2 or CF2O,
- with the proviso that
- (iii) at least Z3 and Z4 represent either single bonds or a π-conjugated group.
9 more elements
A dithiopyrrolopyrrole compound of formula 2, 3, 4, 5 or 6
- in which
- R are each, independently of one another, a linear or branched, optionally halogen-substituted alkyl group having 1 to 20 carbon atoms or halogen.
A process for the preparation of a dithiopyrrolopyrrole compound of formula (7),
- comprising reacting a compound of formula (6),
- with a compound (6a),
- in which
- R and R′ are each, independently of one another, a linear or branched, optionally halogen-substituted alkyl group having 1 to 20 carbon atoms or halogen,
- in the presence of a catalytic amount of a homogeneous transition-metal complex.
2 more elements
A mixture comprising
- (a) at least one dithiopyrrolopyrrole compound of formula (1)
- in which
- R1 and R2 are each, independently of one another, a linear or branched, optionally halogen-substituted alkyl group having 1 to 20 carbon atoms;
- R3 and R4 are each, independently of one another, a linear or branched, optionally halogen-substituted alkyl group having 1 to 20 carbon atoms or halogen;
- Q1 and Q2 are each, independently of one another, a single bond O, OCF2, CF2, CF2CF2 or CO;
- A1, A2, A3, A4, A5 and A6 are each, independently of one another, a single bond or an aromatic ring, each of which is selected from the group consisting of phenylene, pyridine, pyrimidine, pyridazine, naphthylene, thiophene, selenophene and thiazole,
- with the provisos that
- (i) at least A3 and A4 are aromatic rings, and
- (ii) the aromatic rings are optionally substituted by halide;
- and
- Z1, Z2, Z3, Z4, Z5 and Z6 are each, independently of one another, a single bond, C≡C, CH═CH, CF═CF, CF═CH, CH2CH2, CF2—CF2 or CF2O,
- with the proviso that
- (iii) at least Z3 and Z4 represent either single bonds or a π-conjugated group, and
- (b1) at least one liquid-crystalline compound and/or
- (b2) at least one chiral dopant and/or
- (b3) at least one stabiliser and/or
- (b4) at least one dichroic dye.
14 more elements
A window containing a device for regulating the entry of light into a room, comprising at least one dithiopyrrolopyrrole compound of formula 2, 3, 4, 5 or 6
- in which
- R are each, independently of one another, a linear or branched, optionally halogen-substituted alkyl group having 1 to 20 carbon atoms or halogen.
Dependencies are inferred from the claim text.