Birefringent polymer film with negative optical dispersion

Patent metadata

Field	Value
Publication number	US-RE46426-E
Application number	US-200814515011-A
Country	US
Kind code	E1
Filing date	Mar 4, 2008
Priority date	Mar 30, 2007
Publication date	Jun 6, 2017
Grant date	Jun 6, 2017

Abstract

The invention relates to a polymer film having negative optical dispersion, novel polymerisable compounds and liquid crystal (LC) materials for its preparation, and the use of the polymer film and novel compounds and materials in optical, electrooptical, electronic, semiconducting or luminescent components or devices.

First claim

The invention claimed is:

1. A polymer film with R 450 /R 550 <1, wherein R 450 is the optical on-axis retardation at a wavelength of 450 nm and R 550 is the optical on-axis retardation at a wavelength of 550 nm, said film being obtainable by polymerizing one or more polymerizable compounds, wherein said polymerizable compounds contain
two mesogenic groups comprising one or more non-aromatic rings,
one or more polymerizable groups attached to at least one of the mesogenic groups either directly or via spacer groups, and
a bridging group connecting the mesogenic groups, comprising one or more subgroups selected from pi-conjugated linear carbyl or hydrocarbyl groups, aromatic and heteroaromatic groups, and being linked to a sp 3 -hybridized C-atom or Si-atom in a non-aromatic ring of each mesogenic group.

2. The polymer film according to claim 1 , wherein the mesogenic groups are calamitic groups.

3. The polymer film according to claim 1 , wherein the mesogenic groups comprise more saturated rings than unsaturated or aromatic rings.

4. The polymer film according to claim 1 , wherein the bridging group is a subgroup selected from the group consisting of pi-conjugated linear groups, aromatic and heteroaromatic groups.

5. The polymer film according to claim 1 , wherein the bridging group is connected in axial position to a cyclohexylene or silanane ring comprised in the mesogenic group, which is optionally substituted and wherein one or more non-adjacent C-atoms are optionally replaced by Si and/or one or more non-adjacent CH 2 groups are optionally replaced by —O— and/or —S—.

6. The polymer film according to claim 1 , wherein the polymerizerable compounds are of the following formula

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 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 1,2 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, preferably 1, 2, 3, 4, 5 or 6,
A 1-4 are independently of each other non-aromatic carbocylic or heterocyclic groups and aromatic and heteroaromatic 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 1-4 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 , 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 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, and
Sp is a spacer group or a single bond.

7. The polymer film according to claim 1 , wherein the bridging group, is —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 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 C atoms, or straight chain or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy with 1 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 H or alkyl with 1-12 C atoms and X is halogen.

8. The polymer film according to claim 1 , characterized in that 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 is 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, and
Sp is a spacer group or a single bond.

9. The polymer film according to claim 1 , wherein the aromatic and non-aromatic groups, are trans-1,4-cyclohexylene and 1,4-phenylene that is optionally substituted with one or more groups L, and 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 1 to 12 C atoms, or straight chain or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy with 1 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 H or alkyl with 1-12 C atoms and X is halogen.

10. The polymer film according to claim 1 , wherein the mesogenic groups do not comprise more than one unsaturated or aromatic ring.

11. The polymer film according to claim 1 , wherein linkage bridging groups connecting the aromatic and non-aromatic cyclic groups in the mesogenic groups, are —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, are
R 0 , R 00 are independently of each other H or alkyl with 1 to 12 C-atoms, and
Y 1 and Y 2 are Y 1,2 are independently of each other H, F, Cl, CN or R 0 .

12. The polymer film according to claim 1 , wherein the polymerizable group, is CH 2 ═CW 1 —COO—, CH 2 ═CW 1 —CO—,

CH 2 ═CW 2 —(O) k1 —, CH 3 —CH═CH—O—,

Assignees

• Merck Patent Gmbh

Inventors

• Parri Owain Llyr
• Adlem Kevin
• Skjonnemand Karl
• Wilkes David

Classifications

• G02B5/3016

  involving passive liquid crystal elements (optical properties of liquid crystals G02F1/0063; polarising elements associated with active liquid crystal devices G02F1/133528) · CPC title

• C09K2019/0496

  the special bonding being a specific pi-conjugated group · CPC title

• C09K2019/3416

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

• G02B5/3083

  Birefringent or phase retarding elements (G02B5/3008, G02B5/3016 take precedence; systems for polarisation control G02B27/286; manufacturing phase modulating patterns by lithographic processes G03F7/001) · CPC title

• C09K2019/3422

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