Cinnamic acid derivatives

Patent metadata

Field	Value
Publication number	US-10465115-B2
Application number	US-201616062942-A
Country	US
Kind code	B2
Filing date	Nov 18, 2016
Priority date	Dec 17, 2015
Publication date	Nov 5, 2019
Grant date	Nov 5, 2019

Abstract

The invention relates to cinnamic acid derivatives of formula S

wherein the radicals have the meaning indicated in claim 1,

to a process for their preparation and their use as self assembling photoalignment agent in liquid crystal mixtures. The invention further relates to a process for the fabrication of a liquid crystal (LC) display device with homogeneous alignment by photoaligning a liquid crystal mixture with positive or negative dielectric anisotropy comprising one or more compounds of formula S and optionally a polymerizable compound, to the liquid crystal mixture comprising the self assembling photoaligning agent and optionally the polymerizable compound and to the LC display produced by said process.

First claim

The invention claimed is:

1. A compound of formula S

wherein
R 11 and R 12 identically or differently denote P, P-Sp-, H, F, Cl, Br, I, —CN, —NO 2 , —NCO, —NCS, —OCN, —SCN, SF 5 or straight-chain or branched alkyl having 1 to 25 C atoms, in which, in addition, one or more non-adjacent CH 2 groups may each be replaced, independently of one another, by —C(R 0 ) ═C(R 00 )—, —C≡C—, —N(R 00 )—, —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, in addition, one or more H atoms may be replaced by F, Cl, Br, I, CN, P or P-Sp-,
P denotes a polymerisable group,
Sp,
Sp 11 , Sp 12 denote a spacer group or a single bond,
A 11 , A 12 and
A 13 on each occurrence, identically or differently, denote an aromatic, alicyclic or heterocyclic group, and which is unsubstituted, or mono- or polysubstituted by L,
Z 11 , Z 12 on each occurrence, identically or differently, denote —O—, —S—, —CO—, —CO—O—, —OCO—, —O—CO—O—, —OCH 2 —, —CH 2 O—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —(CH 2 ) n1 —, —CF 2 CH 2 —, —CH 2 CF 2 —, —(CF 2 ) n1 —, —CH═CH—, —CF═CF—, —C≡C—, —CH═CH—COO—, —OCO—CH═CH—, CR 0 R 00 or a single bond,
R 0 and R 00 each, independently of one another, denote H or alkyl having 1 to 12 C atoms,
n1 is 1, 2, 3 or 4,
m is 0, 1 or 2,
n is 0 or 1
p is 0 or 1
q is 0, 1 or 2
m+n+p+q is ≤4
r is 0, 1, 2 or 3,
s is 0, 1, 2, 3, or 4,
L P, P-Sp-, OH, CH 2 OH, F, Cl, Br, I, —CN, —NO 2 , —NCO, —NCS, —OCN, —SCN, —C(═O)N(R x ) 2 , —C(═O)Y 1 , —C(═O)R x , —N(R x ) 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, in addition, one or more H atoms may be replaced by F, Cl, or P-Sp-,
Y 1 denotes halogen,
R x denotes P, P-Sp-, H, halogen, straight-chain, branched or cyclic alkyl having 1 to 25 C atoms, in which, in addition, one or more non-adjacent CH 2 groups may be 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, in addition, one or more H atoms may 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,
G denotes OH or Si(OR 13 ) 3 ,
R 13 denotes straight chain or branched alkyl having 1 to 6 C atoms.

2. The compound of claim 1 selected from the following sub-formulae

wherein the radicals and parameters have the meaning indicated.

3. The compound of claim 1 wherein G denotes Si(OR 13 ) 3 .

4. The compound of claim 1 wherein G denotes OH.

5. A Liquid crystal mixture, characterised in that it comprises one or more compounds according to claim 1 .

6. The liquid crystal mixture according to claim 5 , characterised in that the concentration of the compounds of formula S is in the range of from 0.01 to 10% by weight.

7. The liquid crystal mixture according to claim 5 , characterised in that it additionally comprises one or more polymerisable compounds of formula P
P a -(Sp a ) s1 -A 2 -(Z a -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-cyclo-hexenylene and 4,4′-bicyclohexylene, wherein, in addition, one or more non-adjacent CH 2 groups may be replaced by —O— and/or —S— and wherein, in addition, one or more H atoms may be replaced by F,
b) the group consisting of 1,4-phenylene and 1,3-phenylene, wherein, in addition, one or two CH groups may be replaced by N and wherein, in addition, 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, in addition, be replaced by heteroatoms, preferably selected from:

where, in addition, one or more H atoms in these radicals may be replaced by L, and/or one or more double bonds may be replaced by single bonds, and/or one or more CH groups may be replaced by N,

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, in addition, 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 for R 0 above or denote Cl or CN.

8. The liquid crystal mixture according to claim 5 , characterised in that it comprises one or more compounds selected from the compounds of the formulae P10-1-1 and P10-1-2

wherein
n4 denotes an integer between 2 and 10.

9. The liquid crystal mixture according to claim 5 , characterised in that it has negative dielectric anisotropy.

10. The liquid crystal mixture of claim 9 , characterised in that it comprises one or more compounds selected from the following formulae:

wherein the individual radicals have the following meanings:
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, 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 liquid crysta

Assignees

• Merck Patent Gmbh

Inventors

• Adlem Kevin
• Davis Alex
• Arasi Hassan
• Sargent Joseph
• Tuffin Rachel
• Sage Ian Charles

Classifications

• C09K19/3402

  having oxygen as hetero atom (sugars C09K19/0422) · CPC title

• C09K19/2014

  containing additionally a linking group other than -COO- or -OCO-, e.g. -CH2-CH2-, -CH=CH-, -C=C-; containing at least one additional carbon atom in the chain containing -COO- or -OCO- groups, e.g. -(CH2)m-COO-(CH2)n- · CPC title

• C09K19/3066

  in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers · CPC title

• C09K2019/3416

  the heterocyclic ring being a four-membered ring, e.g. oxetane · CPC title

• G02F1/133788

  by light irradiation, e.g. linearly polarised light photo-polymerisation · CPC title