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US 11,168,257 B2Granted
Liquid crystalline medium
AssigneeMerck Patent GmbH
InventorsPeer Kirsch, Andreas Ruhl, Michael Junge, Ursula Patwal, Mila Fischer
Life of this patent
Estimating the term…
Abstract
The present invention relates to liquid crystalline media comprising one or more benzothiadiazol derivatives of formula I, in which R11, R12, A11, A12, A21, A22, Z11, Z12, Z21, Z22, W, X11, X12, r and s have the meanings indicated in claim 1, to the use of such liquid crystal media for optical, electro-optical and electronic purposes, in particular in devices for regulating the passage of energy from an outside space into an inside space, for example in windows.
Claims18
A liquid crystalline medium comprising
- a dye component A) comprising one or more compounds of formula I,
- and
- a liquid-crystalline component B) comprising one or more mesogenic compounds,
- wherein in formula I of component A)
- W denotes —S—, —Se— or —O—,
- R11, R12, identically or differently, denote H, F, straight-chain or branched alkyl having 1 to 25 C atoms, in which, in addition, one or more non-adjacent CH2 groups may each be replaced, independently of one another, by —C(Rz)═C(Rz)—, —C≡C—, —N(Rz)—, —O—, —S—, —CO—, —CO—O—, —O—CO— or —O—CO—O— in such a way that O and/or S atoms are not linked directly to one another, and in which, in addition, one or more H atoms may be replaced by F, Cl, Br, I or CN,
- Rz on each occurrence, identically or differently, denotes H, halogen, straight-chain, branched or cyclic alkyl having 1 to 25 C atoms, in which, in addition, one or more non-adjacent CH2 groups may be replaced by —O—, —S—, —CO—, —CO—O—, —O—CO— or —O—CO—O— in such a way that O and/or S atoms are not linked directly to one another, and in which, in addition, one or more H atoms may be replaced by F or Cl,
- A11, A12 each, independently of one another, denote an aryl or heteroaryl group, which may be substituted by one or more radicals L,
- A21, A22 are each, independently of one another, defined like A11 or denote a cyclic alkyl group having 3 to 10 C atoms, in which one or more CH2 groups may be replaced by O in such a way that no two, O atoms are adjacent,
- L on each occurrence, identically or differently, denotes OH, CH2OH, F, Cl, Br, I, —CN, —NO2, SF5, —NCO, —NCS, —OCN, —SCN, —C(═O)N(Rz)2, —C(═O)Rz, —N(Rz)2, optionally substituted silyl, optionally substituted aryl having 6 to 20 C atoms, or straight-chain or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 25 C atoms, in which, in addition, one or more H atoms may be replaced by F or Cl, an aryl or heteroaryl group, which may be substituted by one or more radicals L, and alternatively two adjacent groups L together also denote a straight-chain or branched alkylene group having 2 to 10 C atoms, in which one, several or all H atoms may be replaced by F and in which one or more —CH2CH2— groups can be replaced by —CH═CH—,
- Z11, Z12 on each occurrence, identically or differently, denote a single bond, —CRx1═CRx2—, —C≡C— or —C(O)—,
- Z21, Z22 are, on each occurrence identically or differently, defined like Z11 or denote —O—, —S—, —CRy1Ry2—, —CF2O—, —OCF2—, —C(O)—O—, —O—C(O)—, —O—C(O)—O—, —OCH2—, —CH2O—, —SCH2—, —CH2S—, —CF2S—, —SCF2—, —(CH2)n1—, —CF2CH2—, —CH2CF2—, —(CF2)n1—, —CH═CH—COO or —OCO—CH═CH—,
- Rx1, Rx2, independently of one another, denote H, F, Cl, CN or alkyl having 1-12 C atoms,
- Ry1, Ry2 each, independently of one another, denote H or alkyl having 1-12 C atoms,
- r, s, independently of one another, denote 0, 1, 2 or 3,
- n1 denotes 1, 2, 3 or 4.
13 more elements
A compound of formula I
- wherein —W— denotes —O—, and
- R11, R12 identically or differently, denote H, F, straight-chain or branched alkyl having 1 to 25 C atoms, in which, in addition, one or more non-adjacent CH2 groups may each be replaced, independently of one another, by —C(Rz)═C(Rz)—, —C≡C—, —N(Rz)—, —O—, —S—, —CO—, —CO—O—, —O—CO— or —O—CO—O— in such a way that O and/or S atoms are not linked directly to one another, and in which, in addition, one or more H atoms may be replaced by F, Cl, Br, I or CN,
- Rz on each occurrence, identically or differently, denotes H, halogen, straight-chain, branched or cyclic alkyl having 1 to 25 C atoms, in which, in addition, one or more non-adjacent CH2 groups may be replaced by —O—, —S—, —CO—, —CO—O—, —O—CO— or —O—CO—O— in such a way that O and/or S atoms are not linked directly to one another, and in which, in addition, one or more H atoms may be replaced by F or Cl,
- A11, A12 each, independently of one another, denote an aryl or heteroaryl group, which may be substituted by one or more radicals L,
- A21, A22 are each, independently of one another, defined like A11 or denote a cyclic alkyl group having 3 to 10 C atoms, in which one or more CH2 groups may be replaced by O in such a way that no two O atoms are adjacent,
- L on each occurrence, identically or differently, denotes OH, CH2OH, F, Cl, Br, I, —CN, —NO2, SF5, —NCO, —NCS, —OCN, —SCN, —C(═O)N(Rz)2, —C(═O)Rz, —N(Rz)2, optionally substituted silyl, optionally substituted aryl having 6 to 20 C atoms, or straight-chain or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 25 C atoms, in which, in addition, one or more H atoms may be replaced by F or Cl, an aryl or heteroaryl group, which may be substituted by one or more radicals L, and alternatively two adjacent groups L together also denote a straight-chain or branched alkylene group having 2 to 10 C atoms, in which one, several or all H atoms may be replaced by F and in which one or more —CH2CH2— groups can be replaced by —CH═CH—,
- Z11, Z12 on each occurrence, identically or differently, denote a single bond, —CRx1═CRx2—, —C≡C— or —C(O)—,
- Z21, Z22 are, on each occurrence identically or differently, defined like Z11 or denote —O—, —S—, —CRy1Ry2—, —CF2O—, —OCF2—, —C(O)—O—, —O—C(O)—, —O—C(O)—O—, —OCH2—, —CH2O—, —SCH2—, —CH2S—, —CF2S—, —SCF2—, —(CH2)n1—, —CF2CH2—, —CH2CF2—, —(CF2)n1—, —CH═CH—COO or —OCO—CH═CH—,
- Rx1, Rx2 independently of one another, denote H, F, Cl, CN or alkyl having 1-12 C atoms,
- Ry1, Ry2 each, independently of one another, denote H or alkyl having 1-12 C atoms,
- r, s independently of one another, denote 0, 1, 2 or 3,
- n1 denotes 1, 2, 3 or 4,
- or
- wherein the groups
- are different from one another,
- or
- R11 and R12, independently of one another, denote a branched alkyl group having 3 to 25 C atoms, in which one or more H atoms can be replaced by F, one or more CH2 groups can be replaced by O and/or NH and one or more CH groups can be replaced by N.
14 more elements
A compound of formula I
- wherein —W— denotes —O—, and
- R11, R12 identically or differently, denote H, F, straight-chain or branched alkyl having 1 to 25 C atoms, in which, in addition, one or more non-adjacent CH2 groups may each be replaced, independently of one another, by —C(Rz)═C(Rz)—, —C≡C—, —N(Rz)—, —O—, —S—, —CO—, —CO—O—, —O—CO— or —O—CO—O— in such a way that O and/or S atoms are not linked directly to one another, and in which, in addition, one or more H atoms may be replaced by F, Cl, Br, I or CN,
- Rz on each occurrence, identically or differently, denotes H, halogen, straight-chain, branched or cyclic alkyl having 1 to 25 C atoms, in which, in addition, one or more non-adjacent CH2 groups may be replaced by —O—, —S—, —CO—, —CO—O—, —O—CO— or —O—CO—O— in such a way that O and/or S atoms are not linked directly to one another, and in which, in addition, one or more H atoms may be replaced by F or Cl,
- A11, A12 each, independently of one another, denote (1) an aryl group that is benzene, biphenyl, terphenyl, [1,1′:3′,1″]terphenyl, naphthalene, anthracene, binaphthyl, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, tetracene, pentacene, benzopyrene, fluorene, indene, indenofluorene, or spirobifluorene, or (2) a heteroaryl group that is pyrrole, pyrazole, imidazole, 1,2,3-triazole, 1,2,4-triazole, tetrazole, furan, thiophene, selenophene, oxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine, indole, isoindole, indolizine, indazole, benzimidazole, benzotriazole, purine, naphthimidazole, phenanthrimidazole, pyridimidazole, pyrazinimidazole, quinoxalinimidazole, benzoxazole, naphthoxazole, anthroxazole, phenanthroxazole, isoxazole, benzothiazole, benzofuran, isobenzofuran, dibenzofuran, quinoline, isoquinoline, pteridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, benzoisoquinoline, acridine, phenothiazine, phenoxazine, benzopyridazine, benzopyrimidine, quinoxaline, phenazine, naphthyridine, azacarbazole, benzocarboline, phenanthridine, phenanthroline, thieno[2,3b]thiophene, thieno[3,2b]thiophene, dithienothiophene, dihydrothieno [3,4-b]-1,4-dioxin, isobenzothiophene, dibenzothiophene, or benzothiadiazothiophene, which aryl or heteroaryl group may be substituted by one or more radicals L,
- A21, A22 are each, independently of one another, defined like A11 or denote a cyclic alkyl group having 3 to 10 C atoms, in which one or more CH2 groups may be replaced by O in such a way that no two O atoms are adjacent,
- L on each occurrence, identically or differently, denotes OH, CH2OH, F, Cl, Br, I, —CN, —NO2, SF5, —NCO, —NCS, —OCN, —SCN, —C(═O)N(Rz)2, —C(═O)Rz, —N(Rz)2, optionally substituted silyl, optionally substituted aryl having 6 to 20 C atoms, or straight-chain or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 25 C atoms, in which, in addition, one or more H atoms may be replaced by F or Cl, an aryl or heteroaryl group, which may be substituted by one or more radicals L, and alternatively two adjacent groups L together also denote a straight-chain or branched alkylene group having 2 to 10 C atoms, in which one, several or all H atoms may be replaced by F and in which one or more —CH2CH2— groups can be replaced by —CH═CH—,
- Z11, z12 on each occurrence, identically or differently, denote a single bond, —CRx1═CRx2—, —C≡C— or —C(O)—,
- Z21, Z22 are, on each occurrence identically or differently, defined like Z11 or denote —O—, —S—, —CRy1Ry2—, —CF2O—, —OCF2—, —C(O)—O—, —O—C(O)—, —O—C(O)—O—, —OCH2—, —CH2O—, —SCH2—, —CH2S—, —CF2S—, —SCF2—, —(CH2)n1—, —CF2CH2—, —CH2CF2—, —(CF2)n1—, —CH═CH—COO or —OCO—CH═CH—,
- Rx1, Rx2 independently of one another, denote H, F, Cl, CN or alkyl having 1-12 C atoms,
- Ry1, Ry2 each, independently of one another, denote H or alkyl having 1-12 C atoms,
- r, s independently of one another, denote 0, 1, 2 or 3,
- n1 denotes 1, 2, 3 or 4,
- or
- wherein the groups
- are different from one another,
- or
- R11 and R12, independently of one another, denote a branched alkyl group having 3 to 25 C atoms, in which one or more H atoms can be replaced by F, one or more CH2 groups can be replaced by O and/or NH and one or more CH groups can be replaced by N.
14 more elements
Dependencies are inferred from the claim text.