Liquid-crystal medium
AssigneeMerck Patent GmbH
InventorsMin Tzu Chuang, I-Wen Chen, I-Hua Huang, Jer-Lin Chen, Sven Christian Laut
Life of this patent
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Abstract
A liquid-crystal (LC) medium (as a subcategory of liquid crystal material), based on a mixture of polar compounds, its use for optical, electro-optical and electronic purposes, in particular in LC displays, especially in LC displays of the vertically aligned mode, an LC display of the vertically aligned mode comprising the LC medium, especially an energy-saving LC display, and a process of manufacturing the LC display.
Claims16
An LC medium having negative dielectric anisotropy and comprising one or more compounds of formulae L1-1 to L1-6:
- wherein RL1 has the following meaning
- RL1 straight chain alkyl having 1 to 15 C atoms or branched or cyclic alkyl having 3 to 15 C atoms, wherein one or more non-adjacent CH2-groups are optionally replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O—, CR0=CR00—, —C═C—,
- in such a manner that O- and/or S-atoms are not directly connected with each other, and wherein one or more H atoms are each optionally replaced by F or Cl,
- and
- wherein it additionally comprises one or more polymerizable compounds of formula M:
- Ra—B1—(Zm—B2)m—Rb M
- wherein the individual radicals, independently of each other and on each occurrence identically or differently, have the following meanings:
- P a polymerizable group,
- Sp a spacer group or a single bond, which is optionally substituted by La,
- Ra, Rb P, P-Sp-, H, F, Cl, Br, I, —CN, —NO2, —NCO, —NCS, —OCN, —SCN, SF5 or straight-chain alkyl having 1 to 25 C atoms or branched alkyl having 3 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(R0)═C(R00)—, —C≡C—, —N(R00)—, —O—, —S—, —CO—, —CO—O—, —O—CO—, —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, C, Br, I, CN, P or P-Sp-, where, if B1 and/or B2 contain a saturated C atom, Ra and/or Rb may also denote a radical which is spiro-linked to this saturated C atom,
- wherein at least one of the radicals Ra and Rb denotes or contains a group P or P-Sp-,
- B1, B2 an aromatic, heteroaromatic, alicyclic or heterocyclic group, which may also contain fused rings, and which is unsubstituted, or mono- or polysubstituted by L,
- Zm —O—, —S—, —CO—, —CO—O—, —OCO—, —O—CO—O—, —OCH2—, —CH2O—, —SCH2—, —CH2S—, —CF2O—, —OCF2—, —CF2S—, —SCF2—, —(CH2)n1—, —CF2CH2—, —CH2CF2—, —(CF2)n1—, —CH═CH—, —CF═CF—, —CH═CF—, —CF═CH—, —C≡C—, —CH═CH—COO—, —OCO—CH═CH—, —CH2CH2—CO—O—, O—CO—CH2—CH2—, —CR0R00— or a single bond,
- R0, R00 H or alkyl having 1 to 12 C atoms,
- m 0, 1, 2, 3 or 4,
- n1 1, 2, 3 or 4,
- L P, P-Sp-, OH, CH2OH, F, Cl, Br, I, —CN, —NO2, —NCO, —NCS, —OCN, —SCN, —C(═O)N(Rx)2, —C(═O)Y1, —C(═O)Rx, —N(Rx)2, optionally substituted silyl, optionally substituted aryl having 6 to 20 C atoms, or straight-chain alkyl or alkoxy having 1 to 25 C atoms, straight-chain alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 2 to 25 C atoms, or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 3 to 25 C atoms, in which, in addition, one or more H atoms may be replaced by F, C, P or P-Sp-,
- Y1 halogen,
- Rx P, P-Sp-, H, halogen, straight-chain alkyl having 1 to 25 C atoms or branched or cyclic alkyl having 3 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—, —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, C, P or P-Sp-, an optionally substituted aryl or aryloxy group having 6 to 40 C atoms, or an optionally substituted heteroaryl or heteroaryloxy group having 2 to 40 C atoms.
A process of preparing an LC medium, comprising the steps of mixing one or more one or more compounds of formulae L1-1 to L1-6:
- wherein RL1 has the following meaning
- RL1 straight chain alkyl having 1 to 15 C atoms or branched or cyclic alkyl having 3 to 15 C atoms, wherein one or more non-adjacent CH2-groups are optionally replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O—, CR0=CR00—, —C≡C—,
- in such a manner that O- and/or S-atoms are not directly connected with each other, and wherein one or more H atoms are each optionally replaced by F or Cl,
- one or more polymerizable compounds of formula M:
- Ra—B1—(Zm—B2)m—Rb M
- wherein the individual radicals, independently of each other and on each occurrence identically or differently, have the following meanings:
- P a polymerizable group,
- Sp a spacer group or a single bond, which is optionally substituted by La,
- Ra, Rb P, P-Sp-, H, F, Cl, Br, I, —CN, —NO2, —NCO, —NCS, —OCN, —SCN, SF3 or straight-chain alkyl having 1 to 25 C atoms or a branched alkyls having 3 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(R0)=C(R00)—, —C≡C—, —N(R00)—, —O—, —S—, —CO—, —CO—O—, —O—CO—, —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, C, Br, I, CN, P or P-Sp-, where, if B1 and/or B2 contain a saturated C atom, Ra and/or Rb may also denote a radical which is spiro-linked to this saturated C atom,
- wherein at least one of the radicals Ra and Rb denotes or contains a group P or P-Sp-,
- B1, B2 an aromatic, heteroaromatic, alicyclic or heterocyclic group, which may also contain fused rings, and which is unsubstituted, or mono- or polysubstituted by L,
- Zm —O—, —S—, —CO—, —CO—O—, —OCO—, —O—CO—O—, —OCH2—, —CH2O—, —SCH2—, —CH2S—, —CF2O—, —OCF2—, —CF2S—, —SCF2—, —(CH2)n1—, —CF2CH2—, —CH2CF2—, —(CF2)n1—, —CH═CH—, —CF═CF—, —CH═CF—, —CF═CH—, —C≡C—, —CH═CH—COO—, —OCO—CH═CH—, —CH2CH2—CO—O—, O—CO—CH2—CH2—, —CR0R00— or a single bond,
- R0, R00 H or alkyl having 1 to 12 C atoms,
- m 0, 1, 2, 3 or 4,
- n1 1, 2, 3 or 4,
- L P, P-Sp-, OH, CH2OH, F, Cl, Br, I, —CN, —NO2, —NCO, —NCS, —OCN, —SCN, —C(═O)N(Rx)2, —C(═O)Y1, —C(═O)Rx, —N(Rx)2, optionally substituted silyl, optionally substituted aryl having 6 to 20 C atoms, or straight-chain alkyl or alkoxy having 1 to 25 C atoms, straight-chain alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 2 to 25 C atoms, or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 3 to 25 C atoms, in which, in addition, one or more H atoms may be replaced by F, C, P or P-Sp-,
- Y1 halogen,
- Rx P, P-Sp-, H, halogen, straight-chain alkyl having 1 to 25 C atoms or branched or cyclic alkyl having 3 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—, —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, P or P-Sp-, an optionally substituted aryl or aryloxy group having 6 to 40 C atoms, or an optionally substituted heteroaryl or heteroaryloxy group having 2 to 40 C atoms, with one or more compounds of formula II, III, IV and/or V:
- wherein the individual radicals, independently of each other and on each occurrence identically or differently, have the following meanings
- R21 and R22H, straight chain, branched or cyclic alkyl or alkoxy having 1 to 20 C atoms, wherein one or more non-adjacent CH2-groups are optionally replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O—, CR0=CR00—, —C═C—,
- in such a manner that O- and/or S-atoms are not directly connected with each other, and wherein one or more H atoms are each optionally replaced by F, Cl, CN or CF3, preferably alkyl or alkoxy having 1 to 6 C atoms,
- R0, R00 H or alkyl having 1 to 12 C atoms,
- A1 and A2 a group selected from the following formulae
- Z1 and Z2 —CH2CH2—, —CH═CH—, —CF2O—, —OCF2—, —CH2O—, —OCH2—, —CO—O—, —O—CO—, —C2F4—, —CF═CF—, —CH═CH—CH2O— or a single bond,
- L1, L2, L3 and L4 F, Cl, OCF3, CF3, CH3, CH2F or CHF2,
- Y H, F, Cl, CF3, CHF2 or CH3,
- Lc CH3 or OCH3,
- a1 0, 1 or 2,
- a2 0 or 1,
- in which
- R31 and R32 each, independently of one another, denote H, an alkyl or alkoxy radical having 1 to 15 C atoms or an alkenyl radical having 2 to 15 C atoms which is unsubstituted, monosubstituted by F, Cl, CN or CF3 or at least monosubstituted by halogen, where, in addition, one or more CH2 groups in R31 or R32 may be replaced by —O—, —S—,
- C≡C—, —CF2O—, —OCF2—, —OC—O— or —O—CO— in such a way that O atoms are not linked directly to one another,
- Y1, Y2 H, F, Cl, CF3, CHF2, CH3 or OCH3,
- A on each occurrence, independently of one another, denotes
- a) 1,4-cyclohexenylene or 1,4-cyclohexylene radical, in which one or two non-adjacent CH2 groups may be replaced by —O— or —S—,
- b) a 1,4-phenylene radical, in which one or two CH groups may be replaced by N, or
- c) a radical selected from the group consisting of spiro[3.3]heptane-2,6-diyl, 1,4-bicyclo[2.2.2]octylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydro-naphthalene-2,6-diyl, phenanthrene-2,7-diyl and fluorene-2,7-diyl,
- wherein the radicals a), b) and c) may be mono- or polysubstituted by halogen atoms,
- n denotes 0, 1 or 2,
- Z1 on each occurrence independently of one another denotes —CO—O—, —O—CO—, —CF2O—, —OCF2—, —CH2O—, —OCH2—, —CH2—, —CH2CH2—, —(CH2)4—, —CH═CH—CH2O—, —C2F4—, —CH2CF2—, —CF2CH2—, —CF═CF—, —CH═CF—, —CF═CH—, —CH═CH—, —C═C— or a single bond, and
- L11 and L12 each, independently of one another, denote F, Cl, CF3 or CHF2, and
- W denotes O or S,
- in which
- R41 denotes an unsubstituted alkyl radical having 1 to 7 C atoms where, in addition, one or more CH2 groups may be replaced by
- or an unsubstituted alkenyl radical having 2 to 7 C atoms, and
- R42 denotes an unsubstituted alkyl radical having 1 to 7 C atoms or an unsubstituted alkoxy radical having 1 to 6 C atoms or an unsubstituted alkenyl radical having 2 to 7 C atoms,
- in which
- R51 and R52 independently of one another, denote H, an alkyl, alkoxy or alkenyl radical having up to 15 C atoms which is unsubstituted, monosubstituted by F, Cl, CN or CF3 or at least monosubstituted by halogen, where, in addition, one or more CH2 groups in R51 or R52 may be replaced by —O—, —S—, —C═C—, —CF2O—, —OCF2—, —OC—O—, —O—CO—
- in such a way that O atoms are not linked directly to one another,
- identically or differently, denote
- Z51, Z52 each, independently of one another, denote —CH2—CH2—, —CH2═O—, —CH═CH—, —C≡C—, —COO— or a single bond, and
- n is 1 or 2,
- and optionally polymerizing the polymerizable compounds.
Dependencies are inferred from the claim text.