Polymerisable compounds and the use thereof in liquid-crystal displays

Patent metadata

Field	Value
Publication number	US-9938229-B2
Application number	US-201514812070-A
Country	US
Kind code	B2
Filing date	Jul 29, 2015
Priority date	Jul 30, 2014
Publication date	Apr 10, 2018
Grant date	Apr 10, 2018

Abstract

The present invention relates to polymerizable compounds, to processes and intermediates for the preparation thereof, to liquid-crystal (LC) media comprising them, and to the use of the polymerizable 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.

First claim

The invention claimed is:

1. A compound of formula I

in which
A 1 , A 2 denote, independently of each other, aryl or heteroaryl having 4 to 30 ring atoms, which is mono- or polycyclic and is optionally substituted,
R a , R b denote, independently of each other, P-Sp-, H, 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—, or —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, Cl or P-Sp-,
Sp denotes, on each occurrence identically or differently, a spacer group or a single bond,
P denotes, on each occurrence identically or differently, a polymerisable group selected from the group consisting of CH 2 ═CW 1 —CO—O—, CH 2 ═CH—O—, (CH 2 ═CH) 2 CH—O—CO—, (CH 2 ═CH) 2 CH—O—,

W 1 denotes H, F, Cl or CH 3 ,
W 2 denotes H or alkyl having 1 to 5 C atoms,
k 1 denotes 0 or 1, and
a, b denote, independently of each other, 0, 1 or 2,
wherein all the benzene groups in the compound of formula I are optionally substituted by one or two groups L,
wherein
L denotes P—, P-Sp-, F, Cl, —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 or heteroaryl having 5 to 20 ring atoms, or straight-chain or branched alkyl having 1 to 25 C atoms, in which one or more non-adjacent CH 2 groups are optionally each replaced, independently of one another, b —C(R 0 )═C(R 00 )—, —C≡C—, —N(R 0 )—, —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 one or more H atoms are optionally replaced by F, Cl, CN, P— or P-Sp-,
R x denotes H, F, Cl, CN, or a 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—, or —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, Cl, P— or P-Sp-,
R 0 and R 00 each, independently of one another, denote H or alkyl having 1 to 20 C atoms, and
Y 1 is halogen,
which compound of formula I contains exactly three polymerizable groups.

2. The compound of claim 1 , wherein A 1 and A 2 are each independently benzene or naphthalene, wherein each benzene is independently optionally substituted by one or two groups L, and each naphthalene is independently optionally substituted by one or more groups L, wherein
L denotes P—, P-Sp-, F, Cl, —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 or heteroaryl having 5 to 20 ring atoms, or straight-chain or branched alkyl having 1 to 25 C atoms, in which one or more non-adjacent CH 2 groups are optionally each replaced, independently of one another, by —C(R 0 )═C(R 00 )—, —C≡C—, —N(R 0 )—, —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 one or more H atoms are optionally replaced by F, Cl, CN, P— or P-Sp-,
R x denotes H, F, Cl, CN, or a 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—, or —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, Cl, P— or P-Sp-,
R 0 and R 00 each, independently of one another, denote H or alkyl having 1 to 20 C atoms, and
Y 1 is halogen.

3. The compound of claim 1 , which is one of the following formulae

wherein R a , R b , P and Sp are as defined for the compound of formula I, and the benzene rings are optionally substituted by one or two groups L,
wherein
L denotes P—, P-Sp-, F, Cl, —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 or heteroaryl having 5 to 20 ring atoms, or straight-chain or branched alkyl having 1 to 25 C atoms, in which one or more non-adjacent CH 2 groups are optionally each replaced, independently of one another, by —C(R 0 )═C(R 00 )—, —C≡C—, —N(R 0 )—, —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 one or more H atoms are optionally replaced by F, Cl, CN, P— or P-Sp-,
R x denotes H, F, Cl, CN, or a 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—, or —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, Cl, P— or P-Sp-,
R 0 and R 00 each, independently of one another, denote H or alkyl having 1 to 20 C atoms, and
Y 1 is halogen.

4. The compound of claim 1 , which is one of the following formulae

wherein P and Sp are as defined for the compound of formula I, and the benzene rings are optionally substituted by one or two groups L,
wherein
L denotes P—, P-Sp-, F, Cl, —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 or heteroaryl having 5 to 20 ring atoms, or straight-chain or branched alkyl having 1 to 25 C atoms, in which one or more non-adjacent CH 2 groups are optionally each replaced, independently of one another, by —C(R 0 )═C(R 00 )—, —C≡C—, —N(R 0 )—, —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 one or more H atoms are optionally replaced by F, Cl, CN, P— or P-Sp-,
R x denotes H, F, Cl, CN, or a 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—, or —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, Cl, P— or P-Sp-,
R 0 and R 00 each, independently of one another, denote H or alkyl having 1 to 20 C atoms, and
Y 1 is halogen.

5. The compound of claim 1 , which is one of the following formulae

wherein P 1 , P 2 and P 3 independently of each other have one of the meanings given for P for the compound of formula I, and Sp 1 , Sp 2 and Sp 3 independently of each other have one of the meanings given for Sp for the compound of formula I which is different from

Assignees

• Merck Patent Gmbh

Inventors

• Baron Eveline
• Vogt Julian
• Tong qiong
• Brocke Constanze
• Haas Helga
• Hahn Alexander

Classifications

• C07C69/65 Primary

  of unsaturated acids · CPC title

• C09K19/30

  containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings · CPC title

• C07C69/54 Primary

  Acrylic acid esters; Methacrylic acid esters · CPC title

• C09K2019/123

  Ph-Ph-Ph · CPC title

• C09K2019/3009

  Cy-Ph · CPC title