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US 12,398,325 B2Granted
Liquid-crystal display
AssigneeMerck Patent GmbH
InventorsShih-Hung Wang, Chi-Shun Huang, Jer-Lin Chen, Kuang-Ting Chou
Life of this patent
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Abstract
The present invention relates to a method of manufacturing a liquid crystal display (LCD) of the polymer stabilized ultra fast (PS-UF) twisted nematic (TN) mode, to an LCD obtained by this method and to an LC medium used therein.
Claims19
A liquid crystal display comprising:
- a) a first substrate and a second substrate, the first substrate being equipped with a first electrode layer and optionally a first alignment layer, the second substrate being equipped with a second electrode layer and optionally a second alignment layer,
- b) a layer of a nematic liquid crystal medium containing liquid crystal molecules and a chiral additive and having positive dielectric anisotropy being dispensed between the first and the second substrate,
- c) optionally a first polarizer on the side of the first substrate facing away from the liquid crystal layer and a second polarizer on the side of the second substrate facing away from the liquid crystal layer,
- wherein the longitudinal axes of the liquid crystal molecules are oriented parallel or tilted relative to the planes of the substrates, and the chiral additive induces in the liquid crystal molecules of the liquid crystal medium a helical twist along an axis perpendicular to the substrates with a given pitch p,
- wherein layer of the liquid crystal medium has a thickness d, and the ratio of the thickness d of the liquid crystal medium and the pitch p of the helical twist induced by the chiral additive is from 0.6 to 0.8,
- wherein the twist angle of the helical twist of the liquid crystal molecules is from 60 to 120°,
- wherein the display further comprises a polymer layer deposited on one or both of said first and second electrode or, if present, on one or both of said first and second alignment layer,
- wherein said polymer layers are formed from one or more polymerizable mesogenic compounds, which are contained in the liquid crystal medium at a concentration from 1 to <3% by weight, and which are polymerized in situ after the liquid crystal medium has been dispensed between the two substrates,
- wherein the polymerizable mesogenic compounds are selected from formula I
- Ra—B1—(Zb—B2)m—Rb I
- in which the individual radicals, on each occurrence identically or differently, and each, independently of one another, have the following meaning:
- Ra and Rb P, P-Sp-, H, F, Cl, Br, I, —CN, —NO2, —NCO, —NCS, —OCN, —SCN, SF5 or 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(R0)═C(R00)—, —C≡C—, —N(R00)—, —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 each be replaced by F, Cl, 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-,
- P a polymerizable group,
- Sp a spacer group or a single bond,
- B1 and B2 an aromatic, heteroaromatic, alicyclic or heterocyclic group, having 4 to 25 ring atoms, which may also contain fused rings, and which is unsubstituted, or mono- or polysubstituted by L,
- Zb —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—, —C≡C—, —CH═CH—COO—, —OCO—CH═CH—, CR0R00 or a single bond,
- R0 and 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 or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having up to 25 C atoms, in which, in addition, one or more H atoms may each be replaced by F, Cl, P or P-Sp-,
- Y1 halogen, and
- Rx P, P-Sp-, H, halogen, straight-chain, branched or cyclic alkyl having up to 25 C atoms, in which, in addition, one or more non-adjacent CH2 groups may each 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 each 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,
- wherein liquid crystal medium comprises one or more compounds selected from formulae A1a2, A1b1, A1d1, A1f1, A2a1, A2h1, A2l1 A2l2, A2k1, B2d1, B2g2, B2h3, B2i1, B2k1, B2l1, and F1a, in an amount of from 4 to 40% by weight
- wherein
- R21, R31 each, independently of one another, alkyl, alkoxy, oxaalkyl or alkoxyalkyl having up to 9 C atoms or alkenyl or alkenyloxy having 2 to 9 C atoms, all of which are optionally fluorinated,
- and
- wherein the liquid crystal mixture comprises one or more compounds selected from formulae E1, E3 and E6 in an amount of from 5 to 75%
- in which alkyl denotes a straight-chain alkyl radical having 1-6 C atoms, and alkenyl denotes a straight-chain alkenyl radical having 2-7 C atoms.
26 more elements
A liquid crystal medium comprising
- A) a liquid crystal component A comprising
- (a) one or more compounds selected from formulae A and B
- in which the individual radicals have, independently of each other and on each occurrence identically or differently, the following meanings:
- each, independently of one another, and on each occurrence, identically or differently
- R21, R31 each, independently of one another, alkyl, alkoxy, oxaalkyl or alkoxyalkyl having up to 9 C atoms or alkenyl or alkenyloxy having 2 to 9 C atoms, all of which are optionally fluorinated,
- X0 F, Cl, halogenated alkyl or alkoxy having 1 to 6 C atoms or halogenated alkenyl or alkenyloxy having 2 to 6 C atoms,
- Z31 —CH2CH2—, —CF2CF2—, —COO—, trans-CH═CH—, trans-CF═CF—, —CH2O— or a single bond,
- L21, L22, L31, L32 each, independently of one another, H or F,
- LS H or CH3, and
- g 0, 1, 2 or 3;
- (b) one or more compounds selected from formulae C and D
- in which the individual radicals have the following meanings:
- each, independently of one another, and
- on each occurrence, identically or differently
- R41, R42 each, independently of one another, alkyl, alkoxy, oxaalkyl or alkoxyalkyl having up to 9 C atoms or alkenyl or alkenyloxy having 2 to 9 C atoms, all of which are optionally fluorinated,
- Z41, Z42 each, independently of one another, —CH2CH2—, —COO—, trans-CH═CH—, trans-CF═CF—, —CH2O—, —CF2O—, —C≡C— or a single bond, and
- h 0, 1, 2 or 3;
- and
- (c) optionally one or more compounds of formula E
- in which the individual radicals, on each occurrence identically or differently, each, independently of one another, have the following meaning:
- RA1 alkenyl having 2 to 9 C atoms or, if at least one of the rings X and Y denotes cyclohexenyl, also one of the meanings of RA2,
- RA2 alkyl having 1 to 12 C atoms, in which, in addition, one or two non-adjacent CH2 groups may each be replaced by —O—, —CH═CH—, —CO—, —OCO— or —COO— in such a way that O atoms are not linked directly to one another, and
- x 1 or 2;
- B) a polymerizable component B comprising one or more polymerizable mesogenic compounds of formula I
- Ra—B1—(Zb—B2)m—Rb I
- in which the individual radicals, on each occurrence identically or differently, and each, independently of one another, have the following meaning:
- Ra and Rb P, P-Sp-, H, F, Cl, Br, I, —CN, —NO2, —NCO, —NCS, —OCN,
- —SCN, SF5 or 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(R0)═C(R00)—, —C≡C—, —N(R00)—, —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 each be replaced by F, Cl, 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-,
- P a polymerizable group,
- Sp a spacer group or a single bond,
- B1 and B2 an aromatic, heteroaromatic, alicyclic or heterocyclic group, having 4 to 25 ring atoms, which may also contain fused rings, and which is unsubstituted, or mono- or polysubstituted by L,
- Zb —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—, —C≡C—, —CH═CH—COO—, —OCO—CH═CH—, CR0R00 or a single bond,
- R0 and 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 or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having up to 25 C atoms, in which, in addition, one or more H atoms may each be replaced by F, Cl, P or P-Sp-,
- Y1 halogen, and
- Rx P, P-Sp-, H, halogen, straight-chain, branched or cyclic alkyl having up to 25 C atoms, in which, in addition, one or more non-adjacent CH2 groups may each 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 each 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;
- C) one or more chiral additives;
- and
- D) one or more polymerization initiators, and optionally one or more stabilizers and/or self-aligning additives;
- wherein the concentration of the polymerizable mesogenic compounds in the liquid crystal medium is from 2 to 2.8% by weight,
- wherein the liquid crystal medium contains a photoinitiator,
- wherein the liquid crystal medium has a dielectric anisotropy from +4 to +15 at 20° C. and 1 kHz,
- and
- wherein the concentration of the chiral additives is selected such that the twist angle of the helical twist of the liquid crystal molecules induced by the chiral additives in the liquid crystal medium is 210-330°.
44 more elements
Dependencies are inferred from the claim text.