Method for manufacturing a liquid crystal display device and liquid crystal mixture

Patent metadata

Field	Value
Publication number	US-10626330-B2
Application number	US-201616063544-A
Country	US
Kind code	B2
Filing date	Nov 18, 2016
Priority date	Dec 17, 2015
Publication date	Apr 21, 2020
Grant date	Apr 21, 2020

Abstract

The invention relates to a method of manufacturing a liquid crystal display device wherein a liquid crystal mixture having positive dielectric anisotropy or negative dielectric anisotropy is interposed between a first substrate and a second substrate, the liquid crystal mixture comprising liquid crystal molecules, a self assembling photoalignment agent, a polymerisable compound, and wherein said LC mixture is photoaligned by irradiation with linearly polarised ultraviolet light and then cured by irradiation with ultraviolet light.

First claim

The invention claimed is:

1. A method for manufacturing a liquid crystal display device comprising at least the steps of:
providing a first substrate which includes a pixel electrode and a common electrode;
providing a second substrate, the second substrate being disposed opposite to the first substrate;
interposing a liquid crystal mixture between the first substrate and the second substrate, the liquid crystal mixture comprising liquid crystal molecules, at least one self assembling photoalignment compound of formula S below and at least one polymerisable compound of formula P below;
irradiating the liquid crystal mixture with linearly polarised light causing photoalignment of the liquid crystal mixture;
curing the polymerisable compound by irradiation with ultraviolet light causing fixation of alignment;
wherein formula S is

wherein
Y denotes (R b ) 2 N—, R c C(O)O—, or a group L s ,
Sp denotes a spacer group,
G denotes —OH or Si(OR a ) 3 ,
R a , R b , R c each denote, identically or differently, straight chain or branched alkyl with 1 to 6 C atoms,
L s each, identically or differently, denotes F, Cl, CN, SCN, SF 5 , or straight-chain or branched, in each case optionally fluorinated, alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having up to 12 C atoms,
t1, t2 denote 0, 1, 2, 3 or 4,
and formula P is
P a -(Sp a ) s1 -A 2 -(Z 1 -A 1 ) n2 -(Sp b ) s2 -P b   P

wherein
P a , P b each, independently of one another, denote a polymerisable group,
Sp a , Sp b on each occurrence, identically or differently, denote a spacer group,
s1, s2 each, independently of one another, denote 0 or 1,
A 1 , A 2 each, independently of one another, denote a radical selected from the following groups:
a) the group consisting of trans-1,4-cyclohexylene, 1,4-cyclohexenylene and 4,4′-bicyclohexylene, in which one or more non-adjacent CH 2 groups may be replaced by —O— and/or —S— and wherein one or more H atoms may be replaced by F,
b) the group consisting of 1,4-phenylene and 1,3-phenylene, in which one or two CH groups may be replaced by N and wherein one or more H atoms may be replaced by L,
c) the group consisting of tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, tetrahydrofuran-2,5-diyl, cyclobutane-1,3-diyl, piperidine-1,4-diyl, thiophene-2,5-diyl and selenophene-2,5-diyl, each of which may also be mono- or polysubstituted by L,
d) the group consisting of saturated, partially unsaturated or fully unsaturated, and optionally substituted, polycyclic radicals having 5 to 20 cyclic C atoms, one or more of which may be replaced by heteroatoms,

n2 denotes 0, 1, 2 or 3,
Z 1 in each case, independently of one another, denotes —CO—O—, —O—CO—, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 —, or —(CH 2 ) n —, where n is 2, 3 or 4, —O—, —CO—, —C(R 0 R 00 )—, —CH 2 CF 2 —, —CF 2 CF 2 — or a single bond,
L on each occurrence, identically or differently, denotes F, Cl, CN, SCN, SF 5 or straight-chain or branched, in each case optionally fluorinated, alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having up to 12 C atoms,
R 0 , R 00 each, independently of one another, denote H, F or straight-chain or branched alkyl having 1 to 12 C atoms, wherein one or more H atoms may be replaced by F,
M denotes —O—, —S—, —CH 2 —, —CHY 1 — or —CY 1 Y 2 —, and
Y 1 and Y 2 each, independently of one another, have one of the meanings indicated above for R 0 or denote Cl or CN.

2. The method according to claim 1 , wherein the linearly polarised light is linearly polarised ultraviolet light.

3. The method according to claim 1 , wherein the total concentration of the at least one compound of formula S in the liquid crystal mixture is 0.01 to 10%.

4. The method according to claim 1 , wherein the total concentration of the at least one or compound of formula P in the liquid crystal mixture is in the range of from 0.01 to 10%.

5. The method according to claim 1 , wherein the LC mixture comprises at least one compound selected from the group of compounds of formulae P10-1-1 and P10-1-2

wherein
n4 denotes an integer between 2 and 10.

6. The method according to claim 1 , wherein the at least one compound of formula S is of formula S-1

wherein
Y and G have the meaning as defined for formula S, X s denotes O, —C(O)O—, C(O)NH— or a single bond, and
n1 is an integer from 0 to 10.

7. The method according to claim 1 , wherein the LC mixture has negative dielectric anisotropy.

8. The method according to claim 7 , wherein the LC mixture comprises at least one compound selected from the group of the following formulae:

wherein
a denotes 1 or 2,
b denotes 0 or 1,

R 1 and R 2 each, independently of one another, denote alkyl having 1 to 12 C atoms, in which one or two non-adjacent CH 2 groups may be replaced by —O—, —CH═CH—, —CO—, —O—CO— or —CO—O— in such a way that O atoms are not linked directly to one another,
Z x denotes —CH═CH—, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 —, —O—, —CH 2 —, —CH 2 CH 2 — or a single bond, and
L 1-4 each, independently of one another, denote F, Cl, OCF 3 , CF 3 , CH 3 , CH 2 F, or CHF 2 .

9. The method according to claim 1 , wherein the LC mixture has positive dielectric anisotropy.

10. The method according to claim 9 , wherein the LC mixture comprises at least one compound selected from the group of compounds of formulae II and III,

wherein
R 20 each, identically or differently, denotes a halogenated or unsubstituted alkyl or alkoxy radical having 1 to 15 C atoms, in which one or more CH 2 groups may each be replaced, independently of one another, by —C≡C—, —CF 2 O—, —CH═CH—,

 —O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another,
X 20 each, identically or differently, denote F, Cl, CN, SF 5 , SCN, NCS, a halogenated alkyl radical, a halogenated alkenyl radical, a halogenated alkoxy radical or a halogenated alkenyloxy radical, each having up to 6 C atoms,
Y 20-24 each, identically or differently, denote H or F, and

 each, identically or differently, denote

11. The method according to claim 9 , wherein the liquid crystal mixture comprises at least one compound selected from the group of compounds of formulae XI and XII

wherein

 and each, indep

Assignees

• Merck Patent Gmbh

Inventors

• Adlem Kevin
• Davis Alex
• Tuffin Rachel
• Goebel Mark
• Archetti Graziano
• Fortte Rocco
• Skjonnemand Karl
• Sage Ian Charles

Classifications

• C09K19/3003

  Compounds containing at least two rings in which the different rings are directly linked (covalent bond) · CPC title

• C09K2019/2078

  Ph-COO-Ph-COO-Ph · CPC title

• C09K2019/301

  Cy-Cy-Ph · CPC title

• C09K2019/0448

  the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate · CPC title

• C09K2019/3009

  Cy-Ph · CPC title