Polymerisable compounds and the use thereof in liquid-crystal displays

Patent metadata

Field	Value
Publication number	US-11299676-B2
Application number	US-201816651554-A
Country	US
Kind code	B2
Filing date	Sep 26, 2018
Priority date	Sep 29, 2017
Publication date	Apr 12, 2022
Grant date	Apr 12, 2022

Abstract

The present invention relates to a mixture comprising a not fully aromatic polymerisable compound and a polymerisable photoinitiator, to liquid-crystal (LC) media comprising them, and to 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.

First claim

The invention claimed is:

1. A mixture comprising one or more compounds of formula I and one or more compounds of formula II

wherein the individual radicals, independently of each other and on each occurrence identically or differently, have the following meanings
R 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 each be replaced by F, Cl, Br, I, CN, P or P-Sp-,
P a polymerizable group,
Sp a spacer group or a single bond,
A 1 , A 3 straight-chain, branched or cyclic alkylene with 1 to 20 C atoms, wherein one or more non-adjacent CH 2 -groups are optionally replaced by —CR 0 ═CR 00 —, —C≡C—, —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,
A 2 , A 4 arylene or heteroarylene having 5 to 20 ring atoms, which optionally contains fused rings, which are optionally substituted by one or more groups L or P-Sp-,
Z 1-4 —O—, —S—, —CO—, —CO—O—, —O—CO—, —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—, —CH═CF—, —CF═CH—, —C≡C—, —CH═CH—CO—O—, —O—CO—CH═CH—, —CH 2 —CH 2 —CO—O—, —O—CO—CH 2 —CH 2 —, —CR 0 R 00 —, or a single bond,
R 0 , R 00 H or alkyl having 1 to 12 C atoms,
L F, Cl, —CN, P-Sp- 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 —CR 0 ═CR 00 —, —C≡C—, —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 P-Sp-, F or Cl,
R 1 , R 2 straight-chain or branched alkyl with 1 to 6 C atoms,
R 3 OH or morpholine-1-yl,
a, b, c, d 0, 1, 2 or 3, with a+c≥1,
g 1, 2, 3 or 4,
n1 1, 2, 3 or 4,
r 0, 1, 2, 3 or 4,
p 1, 2 or 3, with p+r≤5,
and wherein in formula II in case of g≥2 the groups (P-Sp)p and —C(═O)—CR 1 R 2 R 3 are linked to different terminal benzene rings, and in case of g≥3 all benzene rings are connected with each other via para-positions.

2. The mixture according to claim 1 , wherein in formula I Z 1 , Z 2 , Z 3 and Z 4 are a single bond.

3. The mixture according to claim 1 , wherein in formula I A 1 and A 3 are trans-1,4-cyclohexylene which is optionally substituted by one or more groups L or P-Sp-, and A 2 and A 4 are selected from 1,4-phenylene, pyridine and thiophene which is optionally substituted by one or more groups L or P-Sp-.

4. The mixture according to claim 1 , wherein in formula I and II all groups Sp are a single bond.

5. The mixture according to claim 1 , wherein in formula I -(A 1 -Z 1 ) a -(A 2 -Z 2 ) b -(A 3 -Z 3 ) c -(A 4 -Z 4 ) d — is selected from the following formulae

wherein i is an integer from 1 to 12, and the cyclohexylene and benzene rings are optionally substituted by one or more groups L or P-Sp-.

6. The mixture according to claim 1 , wherein the compounds of formula I are selected from the following subformulae

wherein P, Sp and L have independently of each other, and on each occurrence identically or differently, one of the meanings given in claim 1 , i is an integer from 1 to 12 r is 0, 1, 2, 3 or 4, and s is 0, 1, 2 or 3.

7. The mixture according to claim 1 , wherein the compounds of formula II are selected from the following formulae

wherein P, Sp, L, R 1-3 and r have the meanings given in claim 1 , h is 0, 1 or 2, p1 is 0 or 1, p2 is 0, 1 or 2, with p1+p2≥1 and p1+p2+r≤5.

8. The mixture according to claim 7 , wherein in the compounds of formula II, IIA and IIB the group —C(═O)—CR 1 R 2 R 3 is selected from the following groups

wherein Me is methyl, the asterisk * denotes the linkage to the benzene ring in formula II, IIA or IIB, and P and Sp have the meanings given in claim 7 .

9. The mixture according to claim 7 , wherein the compounds of formula II, IIA and IIB are selected from the following formulae

wherein P, Sp, L, R 1-3 , r and h have the meanings given in claim 7 .

10. The mixture according to claim 9 , wherein the compounds of formula II, IIA, IIB, IIA1-IIA3 and IIB1-IIB5 are selected from the following subformulae

wherein P, Sp, L and r have the meanings given in claim 9 and Me is methyl.

11. A liquid crystal (LC) medium comprising one or more compounds of formula I and one or more compounds of formula II as defined in claim 1 .

12. The LC medium of claim 11 , wherein said medium comprises
a polymerizable component A) comprising one or more compounds of formula I and one or more compounds of formula II, and
a liquid-crystalline LC component B) comprising one or more mesogenic or liquid-crystalline compounds.

13. The LC medium of claim 11 , wherein said medium comprises one or more compounds of the formulae CY and/or PY:

in which a, b

R 1 , R 2 , Z x , and L 1-4 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 each 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,
L 1-4 each, independently

Assignees

• Merck Patent Gmbh

Inventors

• Tong qiong
• Ushakov Dmitry
• Haas Helga
• Gnauck Steffen
• Rachor Thorsten
• Schuepfer Sven
• Mundinger Simon

Classifications

• C09K19/3486

  the heterocyclic ring containing nitrogen and oxygen atoms · CPC title

• C09K2019/3004

  Cy-Cy · CPC title

• C09K2019/0448

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

• C09K2019/548

  stabilizing the alignment; Polymer stabilized alignment · CPC title

• C09K2019/122

  Ph-Ph · CPC title