Polymerisable LC medium and polymer film with flat optical dispersion

Patent metadata

Field	Value
Publication number	US-11248171-B2
Application number	US-201716465631-A
Country	US
Kind code	B2
Filing date	Nov 28, 2017
Priority date	Dec 1, 2016
Publication date	Feb 15, 2022
Grant date	Feb 15, 2022

Abstract

The invention relates to a polymerisable LC medium with flat optical dispersion, a polymer film with flat optical dispersion obtainable from such a medium, and the use of the polymerisable LC medium and polymer film in optical, electro optical, electronic, semiconducting or luminescent components or devices.

First claim

The invention claimed is:

1. A polymerisable LC medium comprising:
one or more compounds of formula A in an amount of no more than 20% by weight,

wherein
P is independently of one another, a polymerisable group,
Sp is a spacer group or a single bond,
L a is, in case of multiple occurrence identically or differently F, Cl, CN, SCN, SF 5 or straight-chain or branched, optionally mono- or polyfluorinated alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, or alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms, or optionally halogenated alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy with 1 to 5 C atoms,
r is 0, 1, 2, 3 or 4,
and 10 to 15% by weight of one or more compounds of formula I,

wherein
U 1 and U 2 are independently of each other selected from

including their mirror images, wherein the rings U 1 and U 2 are each bonded to the group —(B) q — via the axial bond, and one or two non-adjacent CH 2 groups in these rings are optionally replaced by O and/or S, and the rings U 1 and U 2 are optionally substituted by one or more groups L,
Q 1 and Q 2 are independently of each other CH or SiH,
Q 3 is C or Si,
B is in each occurrence independently of one another —C≡—, —CY 1 ═CY 2 — or an optionally substituted aromatic or heteroaromatic group,
Y 1 and Y 2 are independently of each other H, F, Cl, CN or R 0 ,
q is an integer from 1 to 10,
A 1 to A 4 are independently of each other, in each occurrence selected from non-aromatic, aromatic or heteroaromatic carbocylic or heterocyclic groups, which are optionally substituted by one or more groups R 5 , and wherein each of -(A 1 -Z 1 ) m —U 1 —(Z 2 -A 2 ) n - and -(A 3 -Z 3 ) o —U 2 —(Z 4 -A 4 ) p - does not contain more aromatic groups than non-aromatic groups,
Z 1 to Z 4 are independently of each other, in each occurrence, —O—, —S—, —CO—, —COO—, —OCO—, —O—COO—, —CO—NR 0 —, —NR 0 —CO—, —NR 0 —CO—NR 0 —, —OCH 2 —, —CH 2 O—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH 2 CH 2 —, —(CH 2 ) 3 —, —(CH 2 ) 4 —, —CF 2 CH 2 —, —CH 2 CF 2 —, —CF 2 CF 2 —, —CH═CH—, —CY 1 ═CY 2 —, —CH═N—, —N═CH—, —N═N—, —CH═CR 0 —, —C≡C—, —CH═CH—COO—, —OCO—CH═CH—, CR 0 R 00 or a single bond,
R 0 and R 00 are independently of each other H or alkyl with 1 to 12 C-atoms,
m and n are independently of each other 0, 1, 2, 3 or 4,
and p are independently of each other 0, 1, 2, 3 or 4,
R 1 to R 5 are independently of each other identical or different groups selected from H, halogen, —CN, —NC, —NCO, —NCS, —OCN, —SCN, —C(═O)NR 0 R 00 , —C(═O)X 0 , —C(═O)R 0 , —NH 2 , —NR 0 R 00 , —SH, —SR 0 , —SO 3 H, —SO 2 R 0 , —OH, —NO 2 , —CF 3 , —SF 5 , P-Sp-, optionally substituted silyl, or carbyl or hydrocarbyl with 1 to 40 C atoms that is optionally substituted and optionally comprises one or more hetero atoms, or denote P or P-Sp-, or are substituted by P or P-Sp-, wherein the compounds comprise at least one group R 1-5 denoting or being substituted by P or P-Sp-,
P is a polymerizable group,
Sp is a spacer group or a single bond.

2. The polymerizable LC medium according to claim 1 , wherein the compounds of formula A are selected from the following sub formulae,

wherein the parameter P has one of the meanings as given above under claim 1 and x, y, z, are independently of each other 0 or identical or different integers from 1 to 12.

3. The polymerizable LC medium according to claim 1 , wherein the bridging group, or —(B) q — in formula I, is selected from —C≡C—, —C≡C—C≡C—, —C≡C—C≡C—C≡C—, —C≡C—C≡C—C≡C—C≡C—,

wherein
r is 0, 1, 2, 3 or 4, and
L is selected from P-Sp-, F, Cl, Br, I, —CN, —NO 2 , —NCO, —NCS, —OCN, —SCN, —C(═O)NR 0 R 00 , —C(═O)X, —C(═O)OR 0 , —C(═O)R 0 , —NR 0 R 00 , —OH, —SF 5 , optionally substituted silyl, aryl with 1 to 12, and straight chain or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy with 1 to 12, wherein one or more H atoms are optionally replaced by F or Cl, wherein R 0 and R 00 are as defined in claim 1 and X is halogen.

4. The polymerizable LC medium according to claim 1 , wherein the non-aromatic rings of the mesogenic groups where the bridging group is attached, or U 1 and U 2 in formula I, are selected from

wherein R 5 has one of the meanings as given above in claim 1 .

5. The polymerizable LC medium according to claim 1 , wherein the aromatic and non-aromatic groups, or A 1-4 in formula I, are selected from trans-1,4-cyclohexylene and 1,4-phenylene that is optionally substituted with one or more groups L,
where L is selected from P-Sp-, F, Cl, Br, I, —CN, —NO 2 , —NCO, —NCS, —OCN, —SCN, —C(═O)NR 0 R 00 , —C(═O)X, —C(═O)OR 0 , —C(═O)R 0 , —NR 0 R 00 , —OH, —SF 5 , optionally substituted silyl, aryl with 1 to 12, and straight chain or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy with 1 to 12, wherein one or more H atoms are optionally replaced by F or Cl, wherein R 0 and R 00 are as defined in claim 1 and X is halogen.

6. The polymerizable LC medium according to claim 1 , wherein the linkage groups connecting the aromatic and non-aromatic cyclic groups in the mesogenic groups, or Z 1-4 in formula I, are selected from —O—, —S—, —CO—, —COO—, —OCO—, —O—COO—, —CO—NR 0 —, —NR 0 —CO—, —NR 0 —CO—NR 0 —, —OCH 2 —, —CH 2 O—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH 2 CH 2 —, —(CH 2 ) 3 —, —(CH 2 ) 4 —, —CF 2 CH 2 —, —CH 2 CF 2 —, —CF 2 CF 2 —, —CH═CH—, —CY 1 ═CY 2 —, —CH═N—, —N═CH—, —N═N—, —CH═CR 0 —, —C≡C—, —CH═CH—COO—, —OCO—CH═CH—, CR 0 R 00 or a single bond, wherein R 0 , R 00 , Y 1 and Y 2 have the meanings given in claim 1 .

7. The polymerizable LC medium according to claim 1 , wherein the polymerisable compounds of formula I are selected from the following subformulae:

wherein R 1 to R 5 , A 1 to A 4 , Z 1 to Z 4 , B, m, n, o, p and q have the meanings given in claim 1 .

8. The polymerizable LC medium according to claim 1 , wherein the polymerizable compounds of formula I are selected from the following subformulae:

wherein Z has one

Assignees

• Merck Patent Gmbh

Inventors

• Beltran Gracia Eduardo
• Gardiner Iain
• Proctor Rebecca
• Mulcahy Stephen

Classifications

• C09K19/3857 Primary

  containing at least one asymmetric carbon atom · CPC title

• C08J2335/02

  Characterised by the use of homopolymers or copolymers of esters (C08J2335/06, C08J2335/08 take precedence) · CPC title

• G02F1/13363

  Birefringent elements, e.g. for optical compensation · CPC title

• C08J5/18

  Manufacture of films or sheets · CPC title

• C08F222/20

  Esters containing oxygen in addition to the carboxy oxygen · CPC title