Photoalignment materials having improved adhesion

Patent metadata

Field	Value
Publication number	US-10590220-B2
Application number	US-201615299846-A
Country	US
Kind code	B2
Filing date	Oct 21, 2016
Priority date	Dec 8, 2009
Publication date	Mar 17, 2020
Grant date	Mar 17, 2020

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

The invention claimed is:

1. An article of manufacture comprising
at least one photoalignable portion comprising:
a (co)polymer having a structure represented by the formula:

where:
each M a , M b , and M c are each independently residues 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, or
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, and heteroaryl(C 1 -C 20 )alkyl;
L a , L b , and L c are spacer groups that are each 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, 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 1 to 20, and “h” is a whole number from 1 to 16 inclusive;
each Z a is independently a photochemically active chromophore which is a dimerizable substituted or unsubstituted cinnamate, a dimerizable substituted or unsubstituted coumarin, a cis/trans isomerizable substituted or unsubstituted azo, a photochemically decomposable substituted or unsubstituted polyimide, or a substituted or unsubstituted aromatic ester capable of undergoing a Photo-Fries rearrangement;
each Z b is independently an adhesion promoter group which is hydroxy, carboxylic acid, anhydride, isocyanato, blocked isocyanato, thioisocyanato, blocked thioisocyanato, thio, organofunctional silane, organofunctional titanate, or organofunctional zirconate, wherein each organofunctional group is independently selected from the group consisting of vinyl, allyl, vinyl-functional hydrocarbon radicals, epoxy-functional hydrocarbon radicals, allyl-functional hydrocarbon radicals, acryloyl-functional hydrocarbon radicals, methacryloyl-functional hydrocarbon radicals, styryl-functional hydrocarbon radicals, mercapto-functional hydrocarbon 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; provided that when Z b is hydroxy or carboxylic acid, the (co)polymer further comprises at least one other adhesion promoter group;
each Z c is independently a mesogen structure selected from the group consisting of a rigid straight rod-like liquid crystal group, and a rigid bent rod-like liquid crystal group; and “x” has a value of 0<x≤1, “y” has a value of 0≤y<1, and “z” has a value of 0≤z<1 where x+y+z=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 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.

2. The article of manufacture of claim 1 , wherein the article is an active liquid crystal cell, a passive liquid crystal cell, an optical element, or an ophthalmic element.

3. An optical element comprising:
(i) a substrate; and
(ii) a first at least partial layer on at least a portion of a surface of the substrate, the layer comprising a (co)polymeric material having a structure represented by the formula:

where:
each M a , M b , and M c are each independently residues 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, or
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, and heteroaryl(C 1 -C 20 )alkyl;
L a , L b , and L c are spacer groups that are each 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, 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 1 to 20, and “h” is a whole number from 1 to 16 inclusive;
each Z a is independently a photochemically active chromophore which is a dimerizable substituted or unsubstituted cinnamate, a dimerizable substituted or unsubstituted coumarin, a cis/trans isomerizable substituted or unsubstituted azo, a photochemically decomposable substituted or unsubstituted polyimide, or a substituted or unsubstituted aromatic ester capable of undergoing a Photo-Fries rearrangement;
each Z b is independently an adhesion promoter group which is hydroxy, carboxylic acid, anhydride, isocyanato, blocked isocyanato, thioisocyanato, blocked thioisocyanato, thio, organofunctional silane, organofunctional titanate, or organofunctional zirconate, wherein each organofunctional group is independently selected from the group consisting of vinyl, allyl, vinyl-functional hydrocarbon radicals, epoxy-functional hydrocarbon radicals, allyl-functional hydrocarbon radicals, acryloyl-functional hydrocarbon radicals, methacryloyl-functional hydrocarbon radicals, styryl-functional hydrocarbon radicals, mercapto-functional hydrocarbon 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 alken

Assignees

• Transitions Optical Inc

Inventors

• Saha Gobinda
• Kumar Anil

Classifications

• C08F220/365

  containing further carboxylic moieties · CPC title

• G02F1/1337

  Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers · CPC title

• C08F220/62

  Monocarboxylic acids having ten or more carbon atoms; Derivatives thereof (copolymers of drying oils C08F242/00) · CPC title

• Y10T428/31931

  Polyene monomer-containing · CPC title

• C09K19/56

  Aligning agents · CPC title