Optically active poly(aryl)ethers containing optically pure spirobindane and indane moieties
AssigneeMolecular OptoElectronics Corporation
InventorsKwok Pong Chan, Kevin R. Stewart, Janet L. Gordon
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Abstract
Optically active poly(aryl)ether polymers prepared from monomers containing optically pure spirobiindane and/or indane moieties are disclosed. The chiral poly(aryl)ether polymers are of high molecular weight and exhibit high optical rotations. In addition, the polyethers are thermally stable at high temperatures and exhibit excellent hydrolytic resistance making them useful in high temperature processing applications, in the fabrication of optoelectronics devices, and as polarizing coatings and filters.
Claims22
An optically active poly(aryl)ether polymer comprising structural units of formulas (I), (II), and (III) ##STR18## wherein m is the mole fraction of structure (II), n is the mole fraction of structure (III), and the quantity 1-(m+n) is the mole fraction of structure (I);
- wherein m and n each independently have a value from 0 to about 0.99, and the sum of m and n is from 0 to about 0.99;
- A.sup.1 is selected from the group of optically active structural moieties having formulas (IVA), (IVB), (VA), or (VB) ##STR19## A.sup.2 and A.sup.3 are each independently a structural moiety selected from the group having formulas (IVA), (IVB), (VA), (VB), (VI), (VII), (VIII), (VIIIa), or (VIIb) ##STR20## wherein x is 0 or 1;
- wherein when A.sup.1 is (IVA) and A.sup.2 or A.sup.3 is (IVB);
- and when A.sup.1 is (IVB) and A.sup.2 or A.sup.3 is (IVA);
- and when A.sup.1 is (VA) and A.sup.2 or A.sup.3 is (VB);
- and when A.sup.1 is (VB) and A.sup.2 or A.sup.3 is (VA);
- then the mole fraction m or n of said structural units (II) or (III) corresponding to said A.sup.2 or A.sup.3 differs from the mole fraction (1-(m+n)) of said structural units (I) corresponding to said A.sup.1 ;
- Z.sup.2 is selected from the group of structural moieties having formulas (IX), (X), (XI), (XII), (XIII), or (XIV ##STR21## wherein when Z.sup.2 is a structural moiety having formula (XIII) or (XIV), then A.sup.2 and A.sup.3 may also each independently be a single bond, --O--, --S--, --SO.sub.2 --, --CO--, --C(CH.sub.3).sub.2 --, --C(CD.sub.3).sub.2 --, --C(CF.sub.3).sub.2 --, or a structural moiety having formula (VIIIc) ##STR22## wherein R.sup.3 is selected from the group of structural moieties having formulas (XIIIa), (XIIIb), (XIIIc), (XIIId), or (XIIIe) ##STR23## wherein y is 0 or 1;
- wherein R.sup.4 is selected from the group of structural moieties having formulas (XIVa), (XIVb), or (XIVc) ##STR24## wherein R.sup.5 is a single bond or is selected from the group of --O--, --S--, --SO.sub.2 --, --CO--, --C(CH.sub.3).sub.2 --, --C(CD.sub.3).sub.2 --, --C(CF.sub.3).sub.2 --, or from the group of structural moieties having formulas (IVA), (IVB), (VA), (VB), (VI), (VII), (VIII), (VIIIa), (VIIIb), or (VIIIc), except when m and n are both 0, then R.sup.1 is other than formula (IVA) when A.sup.1 is formula (IVB);
- other than formula (IVB) when A.sup.1 is formula (IVA);
- other than formula (VA) when A.sup.1 is formula (VB);
- and other than formula (VB) when A.sup.1 is formula (VA);
- wherein a is 0 except when said selected structural moiety Z.sup.2 has formula (XIII) or (XIV), then a is 1, and Z.sup.1 has structural formula (XIII') when Z.sup.2 has formula (XIII), and Z.sup.1 has structural formula (XIV') when Z.sup.2 has formula (XV) ##STR25## and wherein each R.sup.1 and R.sup.2 is independently hydrogen, deuterium, alkyl, cycloalkyl, alkenyl, cycloalkenyl, aryl, alkoxyaryl, alkylaryl, arylalkyl, alkoxy, alkoxyalkyl, aryloxyalkyl, haloalkyl, haloaryl, nitro, halogen, cyano, hydroxy, or deuterated equivalents thereof.
An optically active poly(aryl)ether polymer comprising an optically active structural moiety derived from an enantiomer of 6,6'-dihydroxy-3,3,3',3'-tetramethyl spirobiindane, said polymer having a glass transition temperature of at least 151.degree. C. or a melting point of at least 250.degree. C.
An optically active poly(aryl)ether polymer comprising an optically active structural moiety derived from an enantiomer of 5-hydroxy-3-(4-hydroxyphenyl)-1,1,3-trimethyl indane, said polymer having a glass transition temperature of at least 151.degree. C. or a melting point of at least 250.degree. C.
Dependencies are inferred from the claim text.