US2021009901A1PendingUtilityA1
Liquid-Crystal Display Devices Containing Polymerisable Compounds
Est. expiryDec 8, 2036(~10.4 yrs left)· nominal 20-yr term from priority
C07C 43/23C09K 19/12C09K 19/44G02F 1/13471G02F 1/137G02F 2202/022C09K 2019/3004G02F 1/133711G02F 1/133726C09K 2019/3016C09K 19/3003C09K 2019/0448G02F 1/134309C09K 19/56C09K 2019/123C09K 2019/548C09K 2019/301C09K 2019/122C07C 69/602C09K 2019/3009G02F 1/133397C07C 67/08C09K 2019/3027C09K 19/3857G02F 1/1333G02F 1/13775C09K 19/0208C09K 19/542G02F 1/133703G02F 2001/133397G02F 2001/13775
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Claims
Abstract
Liquid-crystal (LC) display devices comprising polymerisable compounds, processes and intermediates for the preparation of the devices and compounds, LC media comprising the compounds, and the use of the polymerisable compounds and LC media for optical, electro-optical and electronic purposes, in particular in LC displays, especially in LC displays of the polymer sustained alignment type.
Claims
exact text as granted — not AI-modified1 . A liquid crystal (LC) display device, which is a PSA display or a polymer stabilised SA-VA display, and which comprises two substrates, at least one which is transparent to light, an electrode provided on each substrate or two electrodes provided on only one of the substrates, and located between the substrates a layer of an LC medium, wherein the LC medium comprises one or more polymerisable compounds of the following formula I and the polymerisable compounds are polymerised between the substrates of the display:
wherein the individual radicals, independently of each other, and on each occurrence identically or differently, have the following meanings
P are a methacrylate group or an acrylate group, wherein both groups P have the same meaning,
Sp are a single bond or —(CH 2 ) p1 —, —O—(CH 2 ) p1 —, —O—CO—(CH 2 ) p1 —, or —CO—O—(CH 2 ) p1 —, wherein p1 is 2, 3, 4, 5 or 6, and, if Sp is —O—(CH 2 ) p1 —, —O—CO—(CH 2 ) p1 — or —CO—O—(CH 2 ) p1 — the O-atom or CO-group, respectively, is linked to the benzene ring,
L 11 , L 12 are F, CI or OR,
R is straight-chain or branched alkyl with 1 to 4 C atoms that is optionally fluorinated,
L 13 , L 14 are F, Cl, —CN or straight chain, branched or cyclic alkyl having 1 to 25 C atoms, wherein one or more non-adjacent CH 2 -groups are optionally replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O— 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,
r1, r2 are 0, 1, 2, 3 or 4, wherein r1+r2≥2,
r3, r4 are 0, 1, 2, 3 or 4, wherein r1+r3≤4 and r2+r4≤4,
wherein the compounds contain at least group L 11 or L 12 that is F or Cl, and at least one group L 11 or L 12 that is OR, and
with the proviso that the following compounds are excluded
wherein P, Sp, L 11 and L 12 are as defined above.
2 . A liquid crystal (LC) display device, which comprises and an LC medium, wherein the LC medium comprises one or more polymerisable compounds of the following formula I:
wherein the individual radicals, independently of each other, and on each occurrence identically or differently, have the following meanings
P are a methacrylate group or an acrylate group, wherein both groups P have the same meaning,
Sp are a single bond or —(CH 2 ) p1 —, —O—(CH 2 ) p1 —, —O—CO—(CH 2 ) p1 —, or —CO—O—(CH 2 ) p1 —, wherein p1 is 2, 3, 4, 5 or 6, and, if Sp is —O—(CH 2 ) p1 —, —O—CO—(CH 2 ) p1 — or —CO—O—(CH 2 ) p1 — the O-atom or CO-group, respectively, is linked to the benzene ring,
L 11 , L 12 are F, Cl or OR,
R is straight-chain or branched alkyl with 1 to 4 C atoms that is optionally fluorinated,
L 13 , L 14 are F, Cl, —CN or straight chain, branched or cyclic alkyl having 1 to 25 C atoms, wherein one or more non-adjacent CH 2 -groups are optionally replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O— 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,
r1, r2 are 0, 1, 2, 3 or 4, wherein r1+r2≥2,
r3, r4 are 0, 1, 2, 3 or 4, wherein r1+r3≤4 and r2+r4≤4,
wherein the compounds contain at least group L 11 or L 12 that is F or Cl, and at least one group L 11 or L 12 that is OR, and
with the proviso that the following compounds are excluded
wherein P, Sp, L 11 and L 12 are as defined above.
3 . The LC display device of claim 2 , which is a PS-VA, PS-OCB, PS-IPS, PS-FFS, PS-UB-FFS, PS-posi-VA, PS-TN or polymerized SA-VA display.
4 . The LC display device of claim 1 , wherein the compound of formula I is selected from the following subformulae:
wherein P, Sp, R, L 11 , L 12 , L 13 , L 14 , r2, r3, r4 have the meanings given in claim 1 , r5 is 0, 1, 2 or 3, r3+r5≤3, and r2+r5 is ≥1.
5 . The LC display device of claim 1 , wherein the compound of formula I is selected from the following subformulae:
wherein P, Sp and R have the meanings given in claim 1 and L′ is F or Cl.
6 . The LC display device of claim 1 , wherein the compound of formula I is selected from the following subformulae:
wherein P and R have the meanings given in claim 1 , L′ is F or CI and Sp has one of the meanings given in claim 1 which is different from a single bond.
7 . The LC display device of claim 1 , wherein the compound of formula I is selected from the following subformulae:
wherein P, Sp and R have the meanings given in claim 1 , L′ is F or CI and L″ has one of the meanings of L 13 given in claim 1 .
8 . The LC display device of claim 5 , wherein, in the compound of formula I, R is CH 3 and L′ is F.
9 . The LC display device of claim 1 , wherein the LC medium comprises:
a polymerisable component A) comprising one or more polymerisable compounds of formula I, and a liquid-crystalline LC component B) comprising one or more mesogenic or liquid-crystalline compounds.
10 . The LC display device of claim 1 , wherein the LC medium further comprises one or more compounds of the formulae CY and/or PY:
in which the individual radicals have the following meanings:
a denotes 1 or 2,
b denotes 0 or 1,
denotes
R 1 and R 2 each, independently of one another, denote alkyl having 1 to 12 C atoms, where, in addition, 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, preferably a single bond,
L 1-4 each, independently of one another, denote F, Cl, OCF 3 , CF 3 , CH 3 , CH 2 F, CHF 2 .
11 . The LC display device of claim 1 , wherein the LC medium further comprises one or more compounds selected from the following formulae:
in which the individual radicals, on each occurrence identically or differently, each, independently of one another, have the following meaning:
R A1 alkenyl having 2 to 9 C atoms or, if at least one of the rings X, Y and Z denotes cyclohexenyl, also one of the meanings of R A2 ,
R A2 alkyl having 1 to 12 C atoms, in which, in addition, one or two non-adjacent CH 2 groups may be replaced by —O—, —CH═CH—, —CO—, —OCO— or —COO— in such a way that O atoms are not linked directly to one another,
Z x —CH 2 CH 2 —, —CH═CH—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —CO—O—, —O—CO—, —C 2 F 4 —, —CF═CF—, —CH═CH—CH 2 O—, or a single bond
L 1-4 each, independently of one another, H, F, Cl, OCF 3 , CF 3 , CH 3 , CH 2 F or CHF 2 H,
x 1 ort,
z 0 or 1.
12 . The LC display device of claim 1 , wherein the LC medium further comprises one or more compounds of the following formula:
in which the individual radicals have the following meanings:
denotes
denotes
R 3 and R 4 each, independently of one another, denote alkyl having 1 to 12 C atoms, in which, in addition, 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 y denotes —CH 2 CH 2 —, —CH═CH—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —COO—, —OCO—, —C 2 F 4 —, —CF═CF— or a single bond.
13 . A process for the production of an LC display device according to claim 1 , comprising the steps of providing the LC medium comprising one or more polymerisable compounds of formula I between the substrates of the display and polymerising the polymerisable compounds.
14 . The LC display device of claim 2 , wherein the compound of formula I is selected from the following subformulae:
wherein P, Sp, R, L 11 , L 12 , L 13 , L 14 , r2, r3, r4 have the meanings given in claim 1 , r5 is 0, 1, 2 or 3, r3+r5≤3, and r2+r5 is ≥1.
15 . The LC display device of claim 2 , wherein the compound of formula I is selected from the following subformulae:
wherein P, Sp and R have the meanings given in claim 1 and L′ is F or Cl.
16 . The LC display device of claim 2 , wherein the compound of formula I is selected from the following subformulae:
wherein P and R have the meanings given in claim 1 , L′ is F or Cl and Sp has one of the meanings given in claim 1 which is different from a single bond.
17 . The LC display device of claim 2 , wherein the compound of formula I is selected from the following subformulae:
wherein P, Sp and R have the meanings given in claim 1 , L′ is F or CI and V has one of the meanings of L 13 given in claim 1 .
18 . The LC display device of claim 15 , wherein, in the compound of formula I, R is CH 3 and L′ is F.
19 . The LC display device of claim 2 , wherein the LC medium comprises:
a polymerisable component A) comprising one or more polymerisable compounds of formula I, and a liquid-crystalline LC component B) comprising one or more mesogenic or liquid-crystalline compounds.
20 . The LC display device of claim 2 , wherein the LC medium further comprises one or more compounds of the formulae CY and/or PY:
in which the individual radicals have the following meanings:
a denotes 1 or 2,
b denotes 0 or 1,
denotes
R 1 and R 2 each, independently of one another, denote alkyl having 1 to 12 C atoms, where, in addition, 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, preferably a single bond,
L 1-4 each, independently of one another, denote F, Cl, OCF 3 , CF 3 , CH 3 , CH 2 F, CHF 2 .
21 . The LC display device of claim 2 , wherein the LC medium further comprises one or more compounds selected from the following formulae:
in which the individual radicals, on each occurrence identically or differently, each, independently of one another, have the following meaning:
R A1 alkenyl having 2 to 9 C atoms or, if at least one of the rings X, Y and Z denotes cyclohexenyl, also one of the meanings of R A2 ,
R A2 alkyl having 1 to 12 C atoms, in which, in addition, one or two non-adjacent CH 2 groups may be replaced by —O—, —CH═CH—, —CO—, —OCO— or —COO— in such a way that O atoms are not linked directly to one another,
Z x —CH 2 CH 2 —, —CH═CH—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —CO—O—, —O—CO—, —C 2 F 4 —, —CF═CF—, —CH═CH—CH 2 O—, or a single bond
L 1-4 each, independently of one another, H, F, Cl, OCF 3 , CF 3 , CH 3 , CH 2 F or CHF 2 H,
x 1 ort,
z 0 or 1.
22 . The LC display device of claim 2 , wherein the LC medium further comprises one or more compounds of the following formula:
in which the individual radicals have the following meanings:
denotes
denotes
R 3 and R 4 each, independently of one another, denote alkyl having 1 to 12 C atoms, in which, in addition, 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 y denotes —CH 2 CH 2 —, —CH═CH—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —COO—, —OCO—, —C 2 F 4 —, —CF═CF— or a single bond.Join the waitlist — get patent alerts
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