# US 8,999,459 B2 · Liquid crystal display

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- Number: US 8,999,459 B2
- Document ID: US8999459B2
- Status: Granted
- Kind: B2
- Application number: 12/675,478
- Filed: 2008-07-30
- Published: 2010-12-02
- Granted: 2015-04-07
- Earliest claimed: 2007-08-29
- Assignees: Merck Patent GmbH
- Applicants: Georg Bernatz; Melanie Klasen-Memmer; Matthias Bremer
- Inventors: Georg Bernatz; Melanie Klasen-Memmer; Matthias Bremer
- Web page: https://patentgrep.com/patent/US8999459B2

## CPC

- C09K 19/3003: {Compounds containing at least two rings in which the different rings are directly linked (covalent bond)}
- C09K 19/42: Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K 2019/0444: {characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group}
- C09K 2019/0448: {the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate}
- C09K 2019/0451: {the end chain group being a CH3CH=CHCH2CH2- chain}
- C09K 2019/3004: {Cy-Cy}
- C09K 2019/3009: {Cy-Ph}
- C09K 2019/301: {Cy-Cy-Ph}
- C09K 2019/3016: {Cy-Ph-Ph}
- C09K 2019/548: {stabilizing the alignment; Polymer stabilized alignment}
- C09K 2323/00: Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
- C09K 2323/02: Alignment layer characterised by chemical composition
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

The present invention relates to a liquid-crystal (LC) display of the PSA (polymer sustained alignment) type, and to polymerizable compounds and LC media for use in PSA displays.

## Claims

### Claim 1

A polymer stabilised or polymer sustained alignment liquid-crystal display, containing a liquid-crystal cell comprising two substrates, where at least one substrate is transparent to light and at least one substrate has an electrode layer, and a layer of a liquid-crystal medium comprising a polymerised component and a low-molecular-weight component located between the substrates, where the polymerised component is obtainable by polymerisation of one or more polymerisable compounds between the substrates of the liquid-crystal cell in the liquid-crystal medium with application of an electrical voltage,
wherein the low-molecular-weight component comprises one or more compounds of the formula A
in which
a1 denotes 0 or 1,
L1 and L2 each, independently of one another, denote H, F or Cl,
R1 on each occurrence, identically or differently, denotes —(CH2)m—CH═CH—CnH2n+1,
R2 denotes alkyl having 1 to 12 C atoms, in which one or two non-adjacent CH2 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, or, if a1=0 and the ring A1 denotes cyclohexylene, R2 also denotes R1,
m on each occurrence, identically or differently, denotes 0, 1, 2, 3, 4 or 5, and,
n on each occurrence, identically or differently, denotes 1, 2, 3, 4, 5 or 6, where n+m≦6.

### Claim 2 (depends on 1)

A liquid-crystal display according to claim 1, wherein the one or more polymerisable compounds are of formula I or II
Ra-A1-(Z1-A2)m1-Rb I
(R*-(A1Z1)m1)k-Q II
in which
Ra and Rb each, independently of one another, denote P-Sp-, H, L, or straight-chain or branched alkyl having 1 to 25 C atoms, in which one or more non-adjacent CH2 groups are optionally replaced, independently of one another, by —C(Rx)═C(Rx)—, —C≡C—, —N(Rx)—, —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 one or more H atoms are optionally replaced by F, Cl, Br, I, CN or P-Sp-, where at least one of the radicals Ra and Rb denotes P-Sp-,
Rx denotes P-Sp-, H, halogen, straight-chain, branched or cyclic alkyl having 1 to 25 C atoms, in which one or more non-adjacent CH2 groups are optionally 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 one or more H atoms are optionally replaced by F, Cl 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,
P on each occurrence, identically or differently, denotes a polymerisable group,
Sp on each occurrence, identically or differently, denotes a spacer group or a single bond,
A1 and A2 each, independently of one another, denotes an aromatic, heteroaromatic, alicyclic or heterocyclic group which may contain fused rings, and which is optionally mono- or polysubstituted by L,
Z1 on each occurrence, identically or differently, denotes —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,
L denotes P-Sp-, H, OH, CH2OH, halogen, SF5, NO2, a carbon group or hydrocarbon group,
R0 and R00 each, independently of one another, denote H or alkyl having 1 to 12 C atoms,
m1 denotes 0, 1, 2, 3 or 4,
n1 denotes 1, 2, 3 or 4,
R* denotes P-Sp-, H, halogen, SF5, NO2, a carbon group or hydrocarbon group,
Q denotes a k-valent chiral group, which is optionally mono- or polysubstituted by L, and
k denotes 1, 2, 3, 4, 5 or 6.

### Claim 3 (depends on 1)

A liquid-crystal display according to claim 1 wherein the one or more compounds of the formula A are one or more compounds of the following formulae:
in which R1 denotes —(CH2)m—CH═CH—CnH2n+1, o is 0 or 1, and “alkyl” denotes C1-6-alkyl.

### Claim 4 (depends on 1)

A liquid-crystal display according to claim 1, wherein the liquid-crystal medium comprises one or more compounds of the following formulae:
in which
a denotes 1 or 2,
b denotes 0 or 1,
denotes
R1 and R2 each, independently of one another, denote alkyl having 1 to 12 C atoms, in which one or two non-adjacent CH2 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,
Zx and Zy each, independently of one another, denote —CH2CH2—, —CH═CH—, —OCF2—, —CH2O—, —OCH2—, —COO—, —C2F4—, —CF═CF—, —CH═CHCH2O— or a single bond, and
L1-4 each, independently of one another, denote F, Cl, OCF3, CF3, CH3, CH2F, or CHF2.

### Claim 5 (depends on 1)

A liquid-crystal display according to claim 1, wherein the liquid-crystal medium comprises one or more compounds of the following formula:
in which
denotes
denotes
R3 and R4 each, independently of one another, denote alkyl having 1 to 12 C atoms, in which one or two non-adjacent CH2 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, and
Zy denotes —CH2CH2—, —CH═CH—, —CF2O—, —OCF2—, —CH2O—, —OCH2—, —COO—, —OCO—, —C2F4—, —CF═CF—, —CH═CHCH2O— or a single bond.

### Claim 6 (depends on 1)

A liquid-crystal display according to claim 1, wherein the Liquid-crystal medium, apart from the polymerisable compounds of the formula I or II, comprises no compounds which contain a terminal vinyl or vinyloxy group.

### Claim 7 (depends on 1)

A liquid-crystal display according to claim 1, which is a PSA-VA, PSA-OCB, PS-IPS, PS-FFS or PS-TN display.

### Claim 8

A liquid-crystal medium comprising:
a liquid-crystalline component A) comprising one or more compounds of the formula A, and
a polymerisable component B) comprising one or more polymerisable compounds,
in which
denotes
a1 denotes 0 or 1,
L1 and L2 each, independently of one another, denote H, F or Cl,
R1 on each occurrence, identically or differently, denotes —(CH2)m—CH═CH—CnH2n+1,
R2 denotes alkyl having 1 to 12 C atoms, in which one or two non-adjacent CH2 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, or, if al ═O and the ring A1 denotes cyclohexylene, R2 also denotes R1,
m on each occurrence, identically or differently, denotes 0, 1, 2, 3, 4 or 5, and,
n on each occurrence, identically or differently, denotes 1, 2, 3, 4, 5 or 6, where n+m≦6.

### Claim 9 (depends on 8)

A liquid-crystal medium according to claim 8, which comprises one or more compounds of
Ra-A1-(Z1-A2)m1-Rb formula I,
or
(R*-(A1-Z1)m1)k-Q formula II
in which
a denotes 1 or 2,
b denotes 0 or 1,
denotes
denotes
denotes
denotes
R1 denotes (CH2)m, —CH═CH—CnH2n+1,
o is 0 or 1,
alkyl denotes C1-6-alkyl,
R1* and R2 each, independently of one another, denote alkyl having 1 to 12 C atoms, in which one or two non-adjacent CH2 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,
R3 and R4 each, independently of one another, denote alkyl having 1 to 12 C atoms, in which one or two non-adjacent CH2 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,
Zx and Zy each, independently of one another, denote —CH2CH2—, —CH═CH—, —CF2O—, —OCF2—, —CH2O—, —OCH2—, —COO—, —OCO—, —C2F4—, —CF═CF—, —CH═CHCH2O— or a single bond, and
L1-4 each, independently of one another, denote F, Cl, OCF3, CF3, CH3, CH2F, or CHF2,
Ra and Rb each, independently of one another, denote P-Sp-, H, L, or straight-chain or branched alkyl having 1 to 25 C atoms, in which one or more non-adjacent CH2 groups are optionally replaced, independently of one another, by —C(Rx)═C(Rx)—, —C≡C—, —N(Rx)—, —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 one or more H atoms are optionally replaced by F, Cl, Br, I, CN or P-Sp-, where at least one of the radicals Ra and Rb denotes P-Sp-,
Rx denotes P-Sp-, H, halogen, straight-chain, branched or cyclic alkyl having 1 to 25 C atoms, in which one or more non-adjacent CH2 groups are optionally 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 one or more H atoms are optionally replaced by F, Cl 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,
P on each occurrence, identically or differently, denotes a polymerisable group,
Sp on each occurrence, identically or differently, denotes a spacer group or a single bond,
A1 and A2 each, independently of one another, denotes an aromatic, heteroaromatic, alicyclic or heterocyclic group which may contain fused rings, and which is optionally mono- or polysubstituted by L,
Z1 on each occurrence, identically or differently, denotes —O—, —S—, —CO—, —CO—O—, —OCO—, —O—CO—O—, —OCH2—, —CH2O—, —SCH2—, —CH2S—, —OCF2—, —(CH2)n1—, —CF2CH2—, —CH2CF2—, —(CF2)n1—, —CH═CH—, —CF═CF—, —C≡C—, —CH═CH—COO—, —OCO—CH═CH—, CR0R00 or a single bond,
L denotes P-Sp-, H, OH, CH2OH, halogen, SF5, NO2, a carbon group or hydrocarbon group,
R0 and R00 each, independently of one another, denote H or alkyl having 1 to 12 C atoms,
m1 denotes 0, 1, 2, 3 or 4,
n1 denotes 1, 2, 3 or 4,
R* denotes P-Sp-, H, halogen, SF5, NO2, a carbon group or hydrocarbon group,
Q denotes a k-valent chiral group, which is optionally mono- or polysubstituted by L,
k denotes 1, 2, 3, 4, 5 or 6.

### Claim 10 (depends on 8)

A process for the preparation of a liquid-crystal medium according to claim 8 comprising mixing one or more compounds of formula A with one or more polymerisable compounds of formula I or II
Ra-A1-(Z1-A2)m1-Rb I
(R*-(A1-Z1)m1)k-Q II
in which
Ra and Rb each, independently of one another, denote P-Sp-, H, L, or straight-chain or branched alkyl having 1 to 25 C atoms, in which one or more non-adjacent CH2 groups are optionally replaced, independently of one another, by —C(Rx)═C(Rx)—, —C≡C—, —N(Rx)—, —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 one or more H atoms are optionally replaced by F, Cl, Br, I, CN or P-Sp-, where at least one of the radicals Ra and Rb denotes P-Sp-,
Rx denotes P-Sp-, H, halogen, straight-chain, branched or cyclic alkyl having 1 to 25 C atoms, in which one or more non-adjacent CH2 groups are optionally 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 one or more H atoms are optionally replaced by F, Cl 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,
P on each occurrence, identically or differently, denotes a polymerisable group,
Sp on each occurrence, identically or differently, denotes a spacer group or a single bond,
A1 and A2 each, independently of one another, denote an aromatic, heteroaromatic, alicyclic or heterocyclic group, which may contain fused rings, and which is optionally mono- or polysubstituted by L,
Z1 on each occurrence, identically or differently, denotes —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,
L denotes P-Sp-, H, OH, CH2OH, halogen, SF5, NO2, a carbon group or hydrocarbon group,
R0 and R00 each, independently of one another, denote H or alkyl having 1 to 12 C atoms,
m1 denotes 0, 1, 2, 3 or 4,
n1 denotes 1, 2, 3 or 4,
R* denotes P-Sp-, H, halogen, SF5, NO2, a carbon group or hydrocarbon group,
Q denotes a k-valent chiral group, which is optionally mono- or polysubstituted by L, and
k denotes 1, 2, 3, 4, 5 or 6,
and optionally with further liquid-crystalline compounds and/or additives.

### Claim 11 (depends on 8)

A liquid-crystal medium according to claim 8, wherein the polymerisable component B) comprises one or more polymerisable compounds of formula I or II
Ra-A1-(Z1-A2)m1-Rb I
(R*-(A1-Z1)m1)k-Q II
in which
Ra and Rb each, independently of one another, denote P-Sp-, H, L, or straight-chain or branched alkyl having 1 to 25 C atoms, in which one or more non-adjacent CH2 groups are optionally replaced, independently of one another, by —C(Rx)═C(Rx)—, —CC—, —N(Rx)—, —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 one or more H atoms are optionally replaced by F, Cl, Br, I, CN or P-Sp-, where at least one of the radicals Ra and Rb denotes P-Sp-,
Rx denotes P-Sp-, H, halogen, straight-chain, branched or cyclic alkyl having 1 to 25 C atoms, in which one or more non-adjacent CH2 groups are optionally replaced by —O—, —S—, —CO—, —OCO—, —O—CO—, —O—OCO—O— in such a way that O and/or S atoms are not linked directly to one another, and in which one or more H atoms are optionally replaced by F, Cl 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,
P on each occurrence, identically or differently, denotes a polymerisable group,
Sp on each occurrence, identically or differently, denotes a spacer group or a single bond,
A1 and A2 each, independently of one another, denote an aromatic, heteroaromatic, alicyclic or heterocyclic group, which may contain fused rings, and which is optionally mono- or polysubstituted by L,
Z1 on each occurrence, identically or differently, denotes —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—, —OCOO—CH═CH—, CR0R00 or a single bond,
L denotes P-Sp-, H, OH, CH2OH, halogen, SF5, NO2, a carbon group or hydrocarbon group,
R0 and R00 each, independently of one another, denote H or alkyl having 1 to 12 C atoms,
m1 denotes 0, 1, 2, 3 or 4,
n1 denotes 1, 2, 3 or 4,
R* denotes P-Sp-, H, halogen, SF5, NO2, a carbon group or hydrocarbon group,
Q denotes a k-valent chiral group, which is optionally mono- or polysubstituted by L, and
k denotes 1, 2, 3, 4, 5 or 6.

### Claim 12 (depends on 2)

A liquid-crystal display according to claim 2, wherein
R* denotes P-Sp-, H, L, or straight-chain or branched alkyl having 1 to 25 C atoms, in which one or more non-adjacent CH2 groups are optionally replaced, independently of one another, by —C(Rx)═C(Rx)—, —C≡C—, —N(Rx)—, —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 one or more H atoms are optionally replaced by F, Cl, Br, I, CN or P-Sp-, and
L denotes 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 1 to 25 C atoms, in which one or more H atoms are optionally replaced by F, Cl or P-Sp-.

### Claim 13 (depends on 9)

A liquid-crystal display according to claim 9, wherein
R* denotes P-Sp-, H, L, or straight-chain or branched alkyl having 1 to 25 C atoms, in which one or more non-adjacent CH2 groups are optionally replaced, independently of one another, by —C(Rx)═C(Rx)—, —CC—, —N(Rx)—, —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 one or more H atoms are optionally replaced by F, Cl, Br, I, CN or P-Sp-, and
L denotes 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 1 to 25 C atoms, in which one or more H atoms are optionally replaced by F, Cl or P-Sp-.

### Claim 14 (depends on 10)

A liquid-crystal display according to claim 10, wherein
R* denotes P-Sp-, H, L, or straight-chain or branched alkyl having 1 to 25 C atoms, in which one or more non-adjacent CH2 groups are optionally replaced, independently of one another, by —C(Rx)═C(Rx)—, —CC—, —N(Rx)—, —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 one or more H atoms are optionally replaced by F, Cl, Br, I, CN or P-Sp-, and
L denotes 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 1 to 25 C atoms, in which one or more H atoms are optionally replaced by F, Cl or P-Sp-.

### Claim 15 (depends on 11)

A liquid-crystal display according to claim 11, wherein
R* denotes P-Sp-, H, L, or straight-chain or branched alkyl having 1 to 25 C atoms, in which one or more non-adjacent CH2 groups are optionally replaced, independently of one another, by —C(Rx)═C(Rx)—, —CC—, —N(Rx)—, —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 one or more H atoms are optionally replaced by F, Cl, Br, I, CN or P-Sp-, and
L denotes 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 1 to 25 C atoms, in which one or more H atoms are optionally replaced by F, Cl or P-Sp-.