Dye-doped liquid-crystal medium comprising polymerizable compounds
AssigneeMerck Patent GmbH
InventorsHyun-Woo Bae, Jung-Min Lee, Hyun-Jin Yoon, Yong-Kuk Yun
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Abstract
A liquid-crystal (LC) medium containing one or more dyes and one or more polymerizable compounds, its use for optical, electro-optical and electronic purposes, in particular in LC displays, especially in colour LC displays of the PSA (polymer sustained alignment) or SA (self-aligning) mode containing a quantum dot colour filter (QDCF), an LC display of the PSA or SA mode containing the LC medium and containing a QDCF, and to a process of manufacturing the LC display.
Claims21
An LC medium, comprising
- 0.01 to 3.0% by weight of one or more polymerizable compounds of formula I
- P-Sp-Aa-(Za-Ab)z-Rb
- wherein each of the individual radicals, independently of each other and on each occurrence identically or differently, have the following meanings
- Rb is P-Sp- or R,
- R is F, Cl, —CN or a straight chain alkyl having 1 to 25 C atoms or branched or cyclic alkyl having 3 to 25 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 or P-Sp-,
- P is a polymerizable group,
- Sp is a spacer group which is optionally substituted by P, or is a single bond,
- Aa, Ab is an alicyclic, heterocyclic, aromatic or heteroaromatic group with 4 to 20 ring atoms, which is monocyclic or polycyclic and which is optionally substituted by one or more groups L or P-Sp-,
- Za is —O—, —S—, —CO—, —CO—O—, —O—CO—, —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—CO—O—, —O—CO—CH═CH—, —CH2—CH2—CO—O—, —O—CO—CH2—CH2—, —CR0R00—, or a single bond,
- R0, R00 is H or alkyl having 1 to 12 C atoms,
- L is F, Cl, —CN, P-Sp- or a straight chain alkyl having 1 to 25 C atoms or branched or cyclic alkyl having 3 to 25 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 P-Sp-, F or Cl,
- z is 0, 1, 2, 3 or 4,
- n1 is 1, 2, 3 or 4,
- and further comprising one or more compounds of formula II
- wherein each of the individual radicals, independently of each other and on each occurrence identically or differently, have the following meanings
- R1, R2 is H or a straight chain alkyl having 1 to 25 C atoms or branched or cyclic alkyl having 3 to 25 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 CN, CF3, F or Cl,
- A1, A2 is selected from the following formulae
- Z1, Z2 is —CH2CH2—, —CH═CH—, —CF2O—, —OCF2—, —CH2O—, —OCH2—, —CO—O—, —O—CO—, —C2F4—, —CF═CF—, —CH═CH—CH2O— or a single bond,
- L1, L2, L3, L4 is 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, and
- a2 0 or 1,
- and further comprising at least one dichroic dye absorbing green light and/or at least one dichroic dye absorbing red light,
- wherein the LC comprises one or more dichroic dyes of formulae I*
- wherein each of the individual radicals, independently of each other and on each occurrence identically or differently, have the following meanings
- are independently of each other
- and, in case i is 2 or more, the terminal
- may also be
- and, in case j is 2 or more, the terminal
- may also be
- Z11 and Z12 denote a single bond, —N═N—, —OCO— or —COO—,
- R11 and R12 denote alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy with 1 to 20 C-atoms, alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl with 2 to 20 C-atoms, or alkylaminyl, dialkylaminyl, alkylcarbonyl, alkyloxycarbonyl, alkylcarbonyloxy or alkyloxycarbonyloxy with 3 to 20 C-atoms, or alkylcyclohexylalkyl with 8 to 25 C-atoms,
- i and j are independently of each other 1, 2, 3 or 4.
An LC medium, comprising
- 0.01 to 3.0% by weight of one or more polymerizable compounds of formula I
- P-Sp-Aa-(Za-Ab)z-Rb I
- wherein each of the individual radicals, independently of each other and on each occurrence identically or differently, have the following meanings
- Rb is P-Sp- or R,
- R is F, Cl, —CN or a straight chain alkyl having 1 to 25 C atoms or branched or cyclic alkyl having 3 to 25 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 or P-Sp-,
- P is a polymerizable group,
- Sp is a spacer group which is optionally substituted by P, or is a single bond,
- Aa, Ab is an alicyclic, heterocyclic, aromatic or heteroaromatic group with 4 to 20 ring atoms, which is monocyclic or polycyclic and which is optionally substituted by one or more groups L or P-Sp-,
- Za is —O—, —S—, —CO—, —CO—O—, —O—CO—, —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—CO—O—, —O—CO—CH═CH—, —CH2—CH2—CO—O—, —O—CO—CH2—CH2—, —CR0R00—, or a single bond,
- R0, R00 is H or alkyl having 1 to 12 C atoms,
- L is F, Cl, —CN, P-Sp- or a straight chain alkyl having 1 to 25 C atoms or branched or cyclic alkyl having 3 to 25 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 P-Sp-, F or Cl,
- z is 0, 1, 2, 3 or 4,
- n1 is 1, 2, 3 or 4,
- and further comprising one or more compounds of formula II
- wherein each of the individual radicals, independently of each other and on each occurrence identically or differently, have the following meanings
- R1, R2 is H or a straight chain alkyl having 1 to 25 C atoms or branched or cyclic alkyl having 3 to 25 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 CN, CF3, F or Cl,
- A1, A2 is selected from the following formulae
- Z1, Z2 is —CH2CH2—, —CH═CH—, —CF2O—, —OCF2—, —CH2O—, —OCH2—, —CO—O—, —O—CO—, —C2F4—, —CF═CF—, —CH═CH—CH2O— or a single bond,
- L1, L2, L3, L4 is 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, and
- a2 0 or 1,
- and further comprising at least one dichroic dye absorbing green light and/or at least one dichroic dye absorbing red light,
- and one or more compounds of formula III
- in which
- R11 and R12 each, independently of one another, denote H, an alkyl or alkoxy radical having 1 to 15 C atoms, in which one or more CH2 groups may each be replaced, independently of one another, by
- —O—, —S—, —C≡C—, —CF2O—, —OCF2—, —CH═CH—, —OC—O— or —O—CO— in such a way that O atoms are not linked directly to one another, and in which one or more H atoms may be replaced by halogen,
- A3 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-tetrahydronaphthalene-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,
- L11 and L12 each, independently of one another, denote F, Cl, CF3 or CHF2, and
- W denotes O or S.
An LC display comprising a quantum dot colour filter and an LC medium
- wherein the LC medium comprises
- 0.01 to 3.0% by weight of one or more polymerizable compounds of formula I
- P-Sp-Aa-(Za-Ab)z-Rb I
- wherein each of the individual radicals, independently of each other and on each occurrence identically or differently, have the following meanings
- Rb is P-Sp- or R,
- R is F, Cl, —CN or a straight chain alkyl having 1 to 25 C atoms or branched or cyclic alkyl having 3 to 25 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 or P-Sp-,
- P is a polymerizable group,
- Sp is a spacer group which is optionally substituted by P, or is a single bond,
- Aa, Ab is an alicyclic, heterocyclic, aromatic or heteroaromatic group with 4 to 20 ring atoms, which is monocyclic or polycyclic and which is optionally substituted by one or more groups L or P-Sp-,
- Za is —O—, —S—, —CO—, —CO—O—, —O—CO—, —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—CO—O—, —O—CO—CH═CH—, —CH2—CH2—CO—O—, —O—CO—CH2—CH2—, —CR0R00—, or a single bond,
- R0, R00 is H or alkyl having 1 to 12 C atoms,
- L is F, Cl, —CN, P-Sp- or a straight chain alkyl having 1 to 25 C atoms or branched or cyclic alkyl having 3 to 25 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 P-Sp-, F or Cl,
- z is 0, 1, 2, 3 or 4,
- n1 is 1, 2, 3 or 4,
- and further comprising one or more compounds of formula II
- wherein each of the individual radicals, independently of each other and on each occurrence identically or differently, have the following meanings
- R1, R2 is H or a straight chain alkyl having 1 to 25 C atoms or branched or cyclic alkyl having 3 to 25 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 CN, CF3, F or Cl,
- A1, A2 is selected from the following formulae
- Z1, Z2 is —CH2CH2—, —CH═CH—, —CF2O—, —OCF2—, —CH2O—, —OCH2—, —CO—O—, —O—CO—, —C2F4—, —CF═CF—, —CH═CH—CH2O— or a single bond,
- L1, L2, L3, L4 is 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, and
- a2 0 or 1,
- and further comprising at least one dichroic dye absorbing green light and/or at least one dichroic dye absorbing red light.
Dependencies are inferred from the claim text.