Transitions Optical, Inc.

Ryan Stayshich

Robert W Walters

Zachary Smith

Anil Kumar

Meng He

Gobinda Saha

Darrin R Dabideen

Provided is a photochromic indolenaphthopyran compound having the skeletal structure of Formula (I): wherein Rand Reach independently have a steric bulk A, wherein at least one of Ror Rhas a steric bulk A of at least 0.6, Rand Reach independently have a Hammett σp value, and wherein the indolenaphthopyran compound has a calculated electronic steric factor of at least −3.3.

Indolonaphthopyrans

Provided is an article which transitions from a first state to a second state in response to actinic radiation. The article includes an indolenaphthopyran, wherein in the first state the article exhibits a percent transmission of greater than 80 percent, and in the second state the article exhibits a percent transmission of between 35 and 75 percent, and a τvalue of less than 20 percent. The article can be a photochromic article selected from ophthalmic articles, display articles, windows, mirrors, active liquid crystal cell articles, and passive liquid crystal cell articles.

Articles comprising indolenaphthopyrans

Provided is a photochromic indolenapthtopyran having the core skeletal structure of Formula (I): wherein Rand Rare each independently substituted or unsubstituted alkyloxy, substituted or unsubstituted aryloxy, substituted or unsubstituted alkylthio, substituted or unsubstituted arylthio, substituted or unsubstituted ether, substituted or unsubstituted thioether, amino, a nitrogen-containing heterocycle, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, —NHC(O)R, or —OC(O)R, wherein Ris substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted alkylthio, or substituted or unsubstituted arylthio; Ris selected from hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted heterocycloalkyl, allyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl; and B and B′ are each independently substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, wherein each substituted aryl or substituted heteroaryl is substituted with a group having a Hammett σvalue of greater than −0.50.

Indolenaphthopyrans

The present invention relates to silole and germole fused ring photochromic compounds represented, with some embodiments, by the following Formula (Ia), (Ia) With reference to Formula (Ia): M includes Si or Ge; Ring A and Ring B each independently include aryl or heteroaryl; and the photochromic compound is a thermally reversible photochromic compound. The present invention also relates to photochromic compositions and photochromic articles, such as photochromic ophthalmic articles that include one or more photochromic compounds represented, with some embodiments, by Formula (Ia).

Silole and germole fused ring photochromic compounds

Provided is a synthetic intermediate for the preparation of photochromic indolenaphthopyran compounds having the core skeletal structure of Formula (I): wherein m is 0 to 4, n is 0 to 4, Rand Rare each independently hydroxyl, cyano, (meth)acrylate, amino, halo, substituted or unsubstituted alkyl, boronic ester, boronic acid, polyether, polyester, polycarbonate, polyurethane, substituted or unsubstituted aryl, substituted or unsubstituted heterocycloaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted alkylthio, substituted or unsubstituted arylthio, ketone, aldehyde, ester, carboxylic acid, carboxylate, amide, carbonate, carbamate, urea, siloxane, alkoxysilane, or polysiloxane; Ris substituted or unsubstituted 2-pyridyl or substituted or unsubstituted 2-quinolyl; and Ris hydrogen, substituted or unsubstituted alkyl, alkoxymethyl, substituted or unsubstituted silyl, or acyl. Also provided is a process for producing an indolenaphthol compound which includes cyclizing the phenylnaphthol compound of Formula (I) in the presence of a catalyst. 

Method for preparing indolenaphthopyrans

The present invention relates to polymers that include residues of at least one monomer represented by the following Formula (I). With reference to Formula (I), at least one of E1 and E2 independently is, or is independently substituted with, at least one reactive group, such as a (meth)acryloyl group. Monomers represented by Formula (I) and monomer residues thereof have alignment properties, such as photoalignment properties. The present invention also relates to alignment layers that include such polymers, and articles of manufacture, such as optical elements, that include one or more such alignment layers. 

Alignment polymers

The present invention relates to compounds represented by the following Formula (I). With reference to Formula (I), at least one of Eand Eindependently is, or is independently substituted with, at least one reactive group, such as a (meth)acryloyl group. The compounds of the present invention can be used alone and/or in combination with polymers prepared from such compounds, such as to form or as one or more components of an alignment layer. 

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Pittsburgh, PA, United States of America

Ryan Stayshich