Polymerisable LC medium and polymer film with negative optical dispersion

Patent metadata

Field	Value
Publication number	US-10435628-B2
Application number	US-201515501746-A
Country	US
Kind code	B2
Filing date	Jul 13, 2015
Priority date	Aug 4, 2014
Publication date	Oct 8, 2019
Grant date	Oct 8, 2019

Abstract

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

First claim

The invention claimed is:

1. A polymerizable liquid crystal medium comprising one or more compounds of formula A,

wherein
P is independently of one another, a polymerizable 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 a straight-chain or branched, unsubstituted or mono- or polyfluorinated, alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having up to 12 C atoms, or optionally halogenated alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy with up to 5 C atoms,
r is 0, 1, 2, 3 or 4,

wherein the amount of compounds of formula A in the medium as a whole is from 5 to 40 wt. %; and
one or more compounds of formula I,

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

including their mirror images, wherein the rings U 1 and U 2 are each bonded to the bridging group —(B) q - via the axial bond, and one or two non-adjacent CH 2 groups in these rings are each optionally replaced by O or S, and the rings U 1 and U 2 are optionally substituted by one or more groups L,

L is, in case of multiple occurrence identically or differently, 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 or heteroaryl with up to 12 C atoms, and straight chain or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy with up to 12 C atoms, wherein one or more H atoms are each optionally replaced by F or Cl,
X is halogen,
Q 1,2 are independently of each other CH or SiH,
Q 3 is C or Si,
B is in each occurrence independently of one another —C≡C-, —CY 1 ═CY 2 - or an optionally substituted aromatic or heteroaromatic group,
Y 1,2 are independently of each other H, F, Cl, CN or R 0 ,
q is an integer from 1 to 10,
A 1-4 are independently of each other selected from non-aromatic, aromatic or heteroaromatic carbocylic or heterocyclic groups, which are unsubstituted or 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 1-4 are independently of each other —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,
o and p are independently of each other 0, 1, 2, 3 or 4,
R 1-5 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, and 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, and
Sp is a spacer group or a single bond.

2. The polymerizable liquid crystal medium according to claim 1 , wherein compounds of formula A are selected from the following subformula,

wherein x, y, z, are independently of each other 0 or identical or different integers from 1 to 12.

3. The polymerizable liquid crystal medium according to claim 1 , wherein the bridging group —(B) q — 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,
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 up to 12 C atoms, and straight chain or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy with up to 12 C atoms, wherein one or more H atoms are each optionally replaced by F or Cl,
R 0 and R 00 are independently of each other H or alkyl with 1 to 12 C-atoms, and
X is halogen.

4. The polymerizable liquid crystal medium according to claim 1 , wherein the non-aromatic rings of the mesogenic groups U 1 and U 2 are selected from

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

5. The polymerizable liquid crystal medium according to claim 1 , wherein A 1-4 are trans-1,4-cyclohexylene or 1,4-phenylene, which in each case is unsubstituted or substituted with one or more groups L, wherein L is 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 up to 12 C atoms, or straight chain or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy with up to 12 C atoms, wherein one or more H atoms are optionally replaced by F or Cl, wherein R 0 and R 00 are independently of each other H or alkyl with 1 to 12 C-atoms, and X is halogen.

6. The polymerizable liquid crystal medium according to claim 1 , wherein Z 1-4 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 liquid crystal according to claim 1 , wherein the polymerizable compounds of formula I are selected from the following subformulae:

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

8. The polymerizable liquid crystal medium according claim 1 , characterized in that the polymerizable compounds of formula I are selected from the following subformulae:

Assignees

• Merck Patent Gmbh

Inventors

• Sargent Joseph
• Parri Owain Llyr
• Adlem Kevin
• Arasi Hassan

Classifications

• C09K2019/3422

  the heterocyclic ring being a six-membered ring · CPC title

• C09K2019/0448

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

• C08F2800/20

  as weight or mass percentages · CPC title

• C09K2019/3419

  Four-membered ring with oxygen(s), e.g. oxetane, in fused, bridged or spiro ring systems · CPC title

• C09K2219/03

  in the form of films, e.g. films after polymerisation of LC precursor · CPC title