Photoalignment materials having improved adhesion

Patent metadata

Field	Value
Publication number	US-9475901-B2
Application number	US-95946710-A
Country	US
Kind code	B2
Filing date	Dec 3, 2010
Priority date	Dec 8, 2009
Publication date	Oct 25, 2016
Grant date	Oct 25, 2016

Abstract

The present disclosure provides for new photoalignment (co)polymer materials which demonstrate improved adhesion to a substrate. The (co)polymeric structure includes at least one photochemically active chromophore and at least one adhesion promoter group. Articles of manufacture, optical elements, ophthalmic elements and liquid crystal cells which include at least one photoalignment layer made from the photoalignment (co)polymer materials and methods for formation are also disclosed.

First claim

We claim:

1. A (co)polymer comprising:
a structure represented by the formula:

where:
each M a and M b is independently a residue of monomeric units of substituted or unsubstituted acryloyl units, wherein said acryloyl substituents are selected from the group consisting of C 1 -C 4 alkyl, phenyl, —O— and combinations thereof, substituted or unsubstituted styrene units, substituted or unsubstituted epoxy units, substituted or unsubstituted urethane units, substituted or unsubstituted polycarboxylic acid units, substituted or unsubstituted polyol units, substituted or unsubstituted polyamine units, and substituted or unsubstituted hydroxyalkanoic acid units; wherein said substituents are selected from the group consisting of C 1 -C 20 alkyl, C 1 -C 20 alkoxy, C 3 -C 10 cycloalkyl, C 1 -C 20 alkyl(C 1 -C 20 )alkoxy, halo(C 1 -C 20 )alkyl, heterocyclo(C 3 -C 10 )alkyl, haloaryl, halo(C 1 -C 20 )alkylaryl, C 1 -C 20 alkylaryl, C 1 -C 20 alkoxyaryl, aryl(C 1 -C 20 )alkyl, heteroaryl(C 1 -C 20 )alkyl, and combinations thereof;
L a and L b are spacer groups that are each independently selected from the group consisting of a single bond, —(CH 2 ) g —, —(CF 2 ) h —, —Si(Z′) 2 (CH 2 ) g —, —(Si(CH 3 ) 2 O) h —, —N(R)—, —C(R)═C(R)—, —C(R)═N—, —C(R′) 2 —C(R′) 2 —, —O—, —C(O)—, —C≡C—, —N═N—, —S—, —S(O)—, —S(O)(O)—, —(O)S(O)O—, —O(O)S(O)O—, straight-chain or branched C 1 -C 24 alkylene residue, arylene, C 3 -C 10 cycloalkylene, or various and various combinations thereof, wherein Z′ is independently, for each occurrence, hydrogen, C 1 -C 18 alkyl, C 3 -C 10 cycloalkyl or aryl; R is independently, for each occurrence, Z b , hydrogen, C 1 -C 18 alkyl, C 3 -C 10 cycloalkyl or aryl; R′ is independently, for each occurrence, Z b , C 1 -C 18 alkyl, C 3 -C 10 cycloalkyl or aryl; the C 1 -C 24 alkylene residue is mono-substituted by Z b , cyano, or halo, or poly-substituted by Z b or halo; “g” is independently, for each occurrence, from 1 to 20; and “h” is a whole number from 1 to 16 inclusive;
each Z a is independently a photochemically active chromophore selected from the group consisting of a dimerizable substituted or unsubstituted cinnamate, a dimerizable substituted or unsubstituted coumarin, a cis/trans isomerizable substituted or unsubstituted azo, and a substituted or unsubstituted aromatic ester capable of undergoing a Photo-Fries rearrangement; wherein said substituents are selected from the group consisting of C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 1 -C 20 alkoxy, C 1 -C 20 alkyl(C 1 -C 20 )alkoxy, C 1 -C 20 alkoxy(C 1 -C 20 )alkyl, aryl, heteroaryl, C 1 -C 20 alkylamino, di(C 1 -C 20 )alkyl amino, halogen, halo(C 1 -C 20 )alkyl, C 3 -C 10 cycloalkyl, heterocyclo(C 3 -C 10 )alkyl, carboxy, C 1 -C 20 alkylcarbonyl, C 1 -C 20 alkoxycarbonyl, aminocarbonyl, and combinations thereof;
each Z b is an adhesion promoter group independently selected from the group consisting of anhydride, isocyanato, blocked isocyanato, thioisocyanato, blocked thioisocyanato, organofunctional silane, organofunctional titanate, organofunctional zirconate, and epoxy; wherein each organofunctional group is independently selected from the group consisting of vinyl, allyl, vinyl-functional hydrocarbon radicals, allyl-functional hydrocarbon radicals, acryloyl-functional hydrocarbon radicals, methacryloyl-functional hydrocarbon radicals, styryl-functional hydrocarbon radicals, mercapto-functional hydrocarbon radicals or radicals, and combinations of such organofunctional groups, said hydrocarbon radicals being selected from the group consisting of C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 1 -C 20 alkoxy, C 1 -C 20 alkyl(C 1 -C 20 )alkoxy, C 1 -C 20 alkoxy(C 1 -C 20 )alkyl, aryl, heteroaryl, and combinations of such hydrocarbon radicals; and
“x” has a value of 0<x≦1, and “y” has a value of 0≦y<1, where x+y=1 and “n” has a value ranging from 10 to 10,000,
wherein when x=1, then at least one of L a and Z a is further substituted with at least one Z b adhesion promoter group, and
wherein said co-polymer further comprises a residue of at least one of a photochromic compound, a dichroic compound, a photochromic-dichroic compound, and a photosensitive material.

2. The (co)polymer of claim 1 , wherein the (co)polymer is in the form of a random copolymer, a block copolymer, a graft copolymer, a linear copolymer, a branched copolymer, a hyperbranched copolymer, a dendritic copolymer, or a star copolymer.

3. The (co)polymer of claim 1 , wherein each M a and M b is independently a residue of substituted or unsubstituted acryloyloxy units or substituted or unsubstituted methacryloyloxy units, and Z a is a photochemically active chromophore selected from the group consisting of a dimerizable substituted or unsubstituted cinnamate, and a dimerizable substituted or unsubstituted coumarin.

4. The (co)polymer of claim 1 , wherein the copolymer structure further comprises a residue of a substituted monomeric unit M c having the structure:

where
each M c is independently a residue of a monomeric unit selected from substituted or unsubstituted acryloyl units, wherein said acryloyl substituents are chosen selected from the group consisting of C 1 -C 4 alkyl, phenyl, —O— and combinations thereof, substituted or unsubstituted styrene units, substituted or unsubstituted epoxy units, substituted or unsubstituted urethane units, substituted or unsubstituted polycarboxylic acid units, substituted or unsubstituted polyol units, substituted or unsubstituted polyamine units, and substituted or unsubstituted hydroxyalkanoic acid units; wherein said substituents are selected from the group consisting of C 1 -C 20 alkyl, C 1 -C 20 alkoxy, C 3 -C 10 cycloalkyl, C 1 -C 20 alkyl(C 1 -C 20 )alkoxy, halo(C 1 -C 20 )alkyl, heterocyclo(C 3 -C 10 )alkyl, haloaryl, halo(C 1 -C 20 )alkylaryl, C 1 -C 20 alkylaryl, C 1 -C 20 alkoxyaryl, heteroaryl, aryl(C 1 -C 20 )alkyl, heteroaryl(C 1 -C 20 )alkyl, and combinations thereof;
each L c is a spacer group that is independently a single bond, —(CH 2 ) g —, —(CF 2 ) h —, —Si(Z′) 2 (CH 2 ) g —, or —(Si(CH 3 ) 2 O) h —, —N(R)—, —C(R)═C(R)—, —C(R)═N—, —C(R′) 2 —C(R′) 2 —, —O—, —C(O)—, —C≡C—, —N═N—, —S—, —S(O)—, —S(O)(O)—, —(O)S(O)O—, —O(O)S(O)O—, straight-chain or branched C 1 -C 24 alkylene residue, arylene, C 3 -C 10 cycloalkylene, or various combinations thereof;
Z c is a mesogen structure selected from the group consisting of a rigid straight rod-like liquid crystal group, a rigid bent rod-like liquid crystal group, and a rigid disc-like liquid crystal group; and
“z” has a value of 0<z<1 where x+y+z=1, wherein when y=0, then at least one of L a , Z a , L c and Z c is further substituted with at least one Z b adhesion promoter group.

5. A (co)polymer comprising:
a structure represented by the formula:

where:
each M a , M b , and M c is independently a residue of a monomeric unit selected from the group consisting of substituted or unsubstituted acryloyl units, wherein said acryloyl substituents are selected from the group consisting of C 1 -C 4 alkyl, phenyl, —O— and combinations thereof, substituted or unsubstituted styrene units, substituted or unsubstituted epoxy units, substituted or unsubstituted urethane units, substituted or unsubstituted polycarboxylic acid, substituted or unsubstituted polyol units, substituted or unsubstituted polyamine units, and substituted or unsubstituted hydroxyalkanoic acid units; wherein said substituents ar

Assignees

• Saha Gobinda
• Kumar Anil
• Transitions Optical Inc

Inventors

• Saha Gobinda
• Kumar Anil

Classifications

• C08F220/301

  and one oxygen in the alcohol moiety · CPC title

• C08F220/365

  containing further carboxylic moieties · CPC title

• C08F220/305

  and containing a polyether chain in the alcohol moiety · CPC title

• G02F1/133788

  by light irradiation, e.g. linearly polarised light photo-polymerisation · CPC title

• C09K19/56

  Aligning agents · CPC title